UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D. C. 20549

FORM 10-Q

(Mark One)


☒			QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the quarterly period ended ~~June 30, 2022~~March 31, 2023


☐			TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the transition period from to

Commission File Number 1-12043

OPPENHEIMER HOLDINGS INC.

(Exact name of registrant as specified in its charter)


Delaware			98-0080034
(State or other jurisdiction of incorporation or organization)			(I.R.S. Employer Identification No.)

85 Broad Street

New York, NY 10004

(Address of principal executive offices) (Zip Code)

(212) 668-8000

(Registrant's telephone number, including area code)

(Former name, former address and former fiscal year, if changed since last report)

Securities registered pursuant to Section 12(b) of the Act:


Title of each class	Trading Symbol	Name of each exchange on which registered
Class A non-voting common stock	OPY	The New York Stock Exchange

Indicate by check mark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days. Yes ☒ No ☐

Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit such files). Yes ☒ No ☐

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitions of "large accelerated filer", "accelerated filer", "smaller reporting company", and "emerging growth company" in Rule 12b-2 of the Exchange Act. (Check one):

Large accelerated filer

☐

Accelerated Filer

☒

Non-accelerated filer

☐

Smaller reporting company

☐

Emerging growth company

☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act). Yes ☐ No ☒

The number of shares of the Company's Class A non-voting common stock and Class B voting common stock (being the only classes of common stock of the Company) outstanding on ~~July 29, 2022~~April 28, 2023 was ~~11,251,930~~10,955,723 and 99,665 shares, respectively.

Table of Contents

OPPENHEIMER HOLDINGS INC.

INDEX TO QUARTERLY REPORT ON FORM 10-Q



		Page No.
PART I	FINANCIAL INFORMATION
Item 1.	Financial Statements (unaudited)
	Condensed Consolidated Balance Sheets as of ~~June~~M arch 3 01 , ~~2022~~202 3 and December 31, ~~2021~~202 2	3
	Condensed Consolidated Income Statements for the three ~~and six~~ months ended ~~June~~March 3 01 , ~~2022~~202 3 and ~~2021~~20 2 2	4
	Condensed Consolidated Statements of Comprehensive Income for the three ~~and six~~ months ended ~~June~~March 3 01 , ~~2022~~202 3 and ~~2021~~202 2	5
	Condensed Consolidated Statements of Changes in Stockholders' Equity and Redeemable Noncontrolling Interests for the three ~~and six~~ months ended ~~June~~March 3 01 , ~~2022~~202 3 and ~~2021~~20 2 2	6
	Condensed Consolidated Statements of Cash Flows for the ~~six~~three months ended ~~June~~March 3 01 , ~~2022~~202 3 and ~~2021~~202 2	7
	Notes to Condensed Consolidated Financial Statements	8
Item 2.	Management's Discussion and Analysis of Financial Condition and Results of Operations	4037
Item 3.	Quantitative and Qualitative Disclosures About Market Risk	5450
Item 4.	Controls and Procedures	5451
PART II	OTHER INFORMATION
Item 1.	Legal Proceedings	5552
Item 1A.	Risk Factors	5654
Item 2.	Unregistered Sales of Equity Securities and Use of Proceeds	5654
Item 6.	Exhibits	5755
	Signatures	5856

Table of Contents

PART I. FINANCIAL INFORMATION

Item 1. FINANCIAL STATEMENTS (UNAUDITED)

OPPENHEIMER HOLDINGS INC.

CONDENSED CONSOLIDATED BALANCE SHEETS (unaudited)


(Expressed in thousands, except number of shares and per share amounts)	(Expressed in thousands, except number of shares and per share amounts)	June 30, 2022		December 31, 2021 (1)		(Expressed in thousands, except number of shares and per share amounts)	March 31, 2023		December 31, 2022
ASSETS	ASSETS					ASSETS
Cash and cash equivalents	Cash and cash equivalents	$	36,606	$	213,759	Cash and cash equivalents	$	30,320	$	112,433
Deposits with clearing organizations	Deposits with clearing organizations	99,568		66,968		Deposits with clearing organizations	69,305		77,691
Restricted cash	Restricted cash	127,875		127,765		Restricted cash	25,581		25,534
Receivable from brokers, dealers and clearing organizations	Receivable from brokers, dealers and clearing organizations	167,898		169,902		Receivable from brokers, dealers and clearing organizations	361,039		206,077
Receivable from customers, net of allowance for credit losses of $3,400 ($3,326 in 2021)		1,288,079		1,221,450
Receivable from customers, net of allowance for credit losses of $347 ($350 in 2022)						Receivable from customers, net of allowance for credit losses of $347 ($350 in 2022)	1,054,316		1,202,764
Income tax receivable	Income tax receivable	9,161		—		Income tax receivable	5,374		—
Securities purchased under agreements to resell		—		935
Securities owned, including amounts pledged of $316,605 ($266,428 in 2021), at fair value		621,272		634,504

Securities owned, including amounts pledged of $337,810 ($175,724 in 2022), at fair value						Securities owned, including amounts pledged of $337,810 ($175,724 in 2022), at fair value	762,154		498,594
Notes receivable, net	Notes receivable, net	59,099		53,983		Notes receivable, net	63,649		57,495
Furniture, equipment and leasehold improvements, net of accumulated depreciation of $96,203 ($92,785 in 2021)		26,537		28,036
Right-of-use lease assets, net of accumulated amortization of $74,164 ($76,462 in 2021)		146,057		150,121
Furniture, equipment and leasehold improvements, net of accumulated depreciation of $98,662 ($97,751 in 2022)						Furniture, equipment and leasehold improvements, net of accumulated depreciation of $98,662 ($97,751 in 2022)	38,398		36,742
Right-of-use lease assets, net of accumulated amortization of $86,943 ($82,449 in 2022)						Right-of-use lease assets, net of accumulated amortization of $86,943 ($82,449 in 2022)	152,773		142,630
Goodwill	Goodwill	137,889		137,889		Goodwill	137,889		137,889
Intangible assets	Intangible assets	32,100		32,100		Intangible assets	32,100		32,100
Other assets	Other assets	168,440		205,838		Other assets	187,309		184,443
Total assets	Total assets	$	2,920,581	$	3,043,250	Total assets	$	2,920,207	$	2,714,392
LIABILITIES AND STOCKHOLDERS' EQUITY	LIABILITIES AND STOCKHOLDERS' EQUITY					LIABILITIES AND STOCKHOLDERS' EQUITY
Liabilities	Liabilities					Liabilities
Drafts payable	Drafts payable	$	10,020	$	—	Drafts payable	$	18,024	$	—
Bank call loans	Bank call loans	$	177,300	$	69,500	Bank call loans	19,300		—
Payable to brokers, dealers and clearing organizations	Payable to brokers, dealers and clearing organizations	388,467		422,057		Payable to brokers, dealers and clearing organizations	635,970		550,006
Payable to customers	Payable to customers	419,315		456,958		Payable to customers	458,588		456,475
Securities sold under agreements to repurchase	Securities sold under agreements to repurchase	170,968		277,322		Securities sold under agreements to repurchase	280,436		161,009
Securities sold but not yet purchased, at fair value	Securities sold but not yet purchased, at fair value	254,652		71,958		Securities sold but not yet purchased, at fair value	110,657		52,768
Accrued compensation	Accrued compensation	173,287		342,125		Accrued compensation	155,984		239,136
Income tax payable	Income tax payable	—		13,536		Income tax payable	4,232		4,130
Accounts payable and other liabilities	Accounts payable and other liabilities	58,336		76,655		Accounts payable and other liabilities	68,250		102,202
Lease liabilities	Lease liabilities	187,531		192,019		Lease liabilities	193,350		182,570
Senior secured notes, net of debt issuance costs of $800 ($926 in 2021)		124,200		124,074
Deferred tax liabilities, net of deferred tax assets of $46,229 ($54,957 in 2021)		47,372		44,016
Senior secured notes, net of debt issuance costs of $556 ($616 in 2022)						Senior secured notes, net of debt issuance costs of $556 ($616 in 2022)	112,494		113,434
Deferred tax liabilities, net of deferred tax assets of $52,957 ($55,628 in 2022)						Deferred tax liabilities, net of deferred tax assets of $52,957 ($55,628 in 2022)	36,507		32,241
Total liabilities	Total liabilities	2,011,448		2,090,220		Total liabilities	2,093,792		1,893,971
Commitments and contingencies (note 14)		0		0
Commitments and contingencies (Note 14)						Commitments and contingencies (Note 14)
Redeemable noncontrolling interests	Redeemable noncontrolling interests	127,765		127,765		Redeemable noncontrolling interests	25,557		25,466
Stockholders' equity	Stockholders' equity					Stockholders' equity
Common stock ($0.001 par value per share): Class A: shares authorized: 50,000,000; shares issued and outstanding: 11,270,944 and 12,447,036 as of June 30, 2022 and December 31, 2021, respectively Class B: shares authorized, issued and outstanding: 99,665 as of June 30, 2022 and December 31, 2021		11		13
Additional paid-In capital		35,461		78,032
Common stock ($0.001 par value per share): Class A: shares authorized: 50,000,000; shares issued and outstanding: 10,975,723 and 10,868,556 as of March 31, 2023 and December 31, 2022, respectively Class B: shares authorized, issued and outstanding: 99,665 as of March 31, 2023 and December 31, 2022						Common stock ($0.001 par value per share): Class A: shares authorized: 50,000,000; shares issued and outstanding: 10,975,723 and 10,868,556 as of March 31, 2023 and December 31, 2022, respectively Class B: shares authorized, issued and outstanding: 99,665 as of March 31, 2023 and December 31, 2022	11		11
Additional paid-in capital						Additional paid-in capital	22,374		28,628
Retained earnings	Retained earnings	742,614		740,926		Retained earnings	777,121		764,178
Accumulated other comprehensive income	Accumulated other comprehensive income	1,573		4,225		Accumulated other comprehensive income	919		1,416
Total Oppenheimer Holdings Inc. stockholders' equity	Total Oppenheimer Holdings Inc. stockholders' equity	779,659		823,196		Total Oppenheimer Holdings Inc. stockholders' equity	800,425		794,233
Noncontrolling interest (Note 2)	Noncontrolling interest (Note 2)	1,709		2,069		Noncontrolling interest (Note 2)	433		722
Total Stockholders' equity	Total Stockholders' equity	781,368		825,265		Total Stockholders' equity	800,858		794,955
Total Liabilities, Redeemable Noncontrolling Interests and Stockholders' Equity	Total Liabilities, Redeemable Noncontrolling Interests and Stockholders' Equity	$	2,920,581	$	3,043,250	Total Liabilities, Redeemable Noncontrolling Interests and Stockholders' Equity	$	2,920,207	$	2,714,392

The accompanying notes are an integral part of these condensed consolidated financial statements.

~~(1)~~ ~~Certain prior period reported amounts were reclassified to conform to the current period presentation, see Note 2.~~

Table of Contents

OPPENHEIMER HOLDINGS INC.

CONDENSED CONSOLIDATED INCOME STATEMENTS (unaudited)


		For the Three Months Ended June 30,				For the Six Months Ended June 30,					For the Three Months Ended March 31,
(Expressed in thousands, except number of shares and per share amounts)	(Expressed in thousands, except number of shares and per share amounts)	2022		2021		2022		2021		(Expressed in thousands, except number of shares and per share amounts)	2023		2022
REVENUE	REVENUE									REVENUE
Commissions	Commissions	$	94,378	$	96,171	$	192,699	$	209,642	Commissions	$	86,697	$	98,321
Advisory fees	Advisory fees	107,405		111,152		223,171		215,648		Advisory fees	100,544		115,766
Investment banking	Investment banking	16,653		104,742		55,123		229,243		Investment banking	37,965		38,470
Bank deposit sweep income	Bank deposit sweep income	14,845		3,712		19,199		7,720		Bank deposit sweep income	48,909		4,354
Interest	Interest	11,789		8,909		21,306		17,575		Interest	24,941		9,517
Principal transactions, net	Principal transactions, net	1,258		6,305		3,622		17,170		Principal transactions, net	13,490		2,364
Other	Other	(9,106)		9,302		(11,870)		16,577		Other	9,133		(2,764)
Total revenue	Total revenue	237,222		340,293		503,250		713,575		Total revenue	321,679		266,028
EXPENSES	EXPENSES									EXPENSES
Compensation and related expenses	Compensation and related expenses	177,979		231,140		364,010		486,741		Compensation and related expenses	206,292		186,031
Communications and technology	Communications and technology	20,896		19,172		42,481		39,779		Communications and technology	22,440		21,585
Occupancy and equipment costs	Occupancy and equipment costs	14,554		15,225		29,244		30,407		Occupancy and equipment costs	15,901		14,690
Clearing and exchange fees	Clearing and exchange fees	6,242		5,155		12,218		11,430		Clearing and exchange fees	6,263		5,976
Interest	Interest	3,628		2,448		6,140		5,095		Interest	13,142		2,512
Other	Other	20,092		23,985		41,113		44,828		Other	38,592		21,021
Total expenses	Total expenses	243,391		297,125		495,206		618,280		Total expenses	302,630		251,815

Pre-tax income (loss)		(6,169)		43,168		8,044		95,295
Income taxes provision (benefit)		(1,449)		12,009		2,986		25,478
Net income (loss)		$	(4,720)	$	31,159	$	5,058	$	69,817
Pre-tax income										Pre-tax income	19,049		14,213
Income taxes provision										Income taxes provision	4,585		4,435
Net income										Net income	$	14,464	$	9,778

Net income (loss) attributable to noncontrolling interest, net of tax	Net income (loss) attributable to noncontrolling interest, net of tax	(846)		—		(360)		—		Net income (loss) attributable to noncontrolling interest, net of tax	(153)		486
Net income (loss) attributable to Oppenheimer Holdings Inc.		$	(3,874)	$	31,159	$	5,418	$	69,817
Net income attributable to Oppenheimer Holdings Inc.										Net income attributable to Oppenheimer Holdings Inc.	$	14,617	$	9,292

Earnings (Loss) per share attributable to Oppenheimer Holdings Inc.
Earnings per share attributable to Oppenheimer Holdings Inc.										Earnings per share attributable to Oppenheimer Holdings Inc.
Basic	Basic	$	(0.32)	$	2.46	$	0.44	$	5.53	Basic	$	1.32	$	0.75
Diluted	Diluted	$	(0.32)	$	2.28	$	0.41	$	5.17	Diluted	$	1.22	$	0.69

Weighted average shares outstanding	Weighted average shares outstanding									Weighted average shares outstanding
Basic	Basic	11,980,115		12,689,191		12,222,527		12,634,464		Basic	11,092,603		12,467,632
Diluted	Diluted	11,980,115		13,681,146		13,141,538		13,495,589		Diluted	11,963,492		13,499,334

Period end shares outstanding	Period end shares outstanding	11,370,609		12,692,311		11,370,609		12,692,311		Period end shares outstanding	11,075,388		12,255,839

The accompanying notes are an integral part of these condensed consolidated financial statements.

Table of Contents

OPPENHEIMER HOLDINGS INC.

CONDENSED CONSOLIDATED STATEMENTS OF COMPREHENSIVE INCOME (unaudited)

For the Three Months Ended
June 30, For the Six Months Ended
June 30,
(Expressed in thousands) 2022 2021 2022 2021
Net income (loss) $ (4,720) $ 31,159 $ 5,058 $ 69,817
Other comprehensive income (loss), net of tax
Currency translation adjustment (2,038) 537 (2,652) (299)
Comprehensive income (loss) $ (6,758) $ 31,696 2,406 69,518
Less net income (loss) attributable to noncontrolling interests (846) — (360) —
Comprehensive income (loss) attributable to Oppenheimer Holdings Inc. $ (5,912) $ 31,696 $ 2,766 $ 69,518



	For the Three Months Ended March 31,
(Expressed in thousands)	2023		2022
Net income	$	14,464	$	9,778
Other comprehensive income, net of tax
Currency translation adjustment	(497)		(614)
Comprehensive income	$	13,967	$	9,164
Less net income (loss) attributable to noncontrolling interests	(153)		486
Comprehensive income attributable to Oppenheimer Holdings Inc.	$	14,120	$	8,678

The accompanying notes are an integral part of these condensed consolidated financial statements.

Table of Contents

OPPENHEIMER HOLDINGS INC.

CONDENSED CONSOLIDATED STATEMENTS OF CHANGES IN STOCKHOLDERS' EQUITY AND REDEEMABLE NONCONTROLLING INTERESTS (unaudited)


		For the Three Months Ended (1) June 30,				For the Six Months Ended (1) June 30,					For the Three Months Ended March 31,
(Expressed in thousands, except per share amount)	(Expressed in thousands, except per share amount)	2022		2021		2022		2021		(Expressed in thousands, except per share amount)	2023		2022 (1)
Common stock ($0.001 par value per share)	Common stock ($0.001 par value per share)									Common stock ($0.001 par value per share)
Beginning Balance	Beginning Balance	$	12	$	13	$	12	$	13	Beginning Balance	$	11	$	13
Issuance of Class A non-voting common stock	Issuance of Class A non-voting common stock	—		0		0		0		Issuance of Class A non-voting common stock	—		—
Repurchase of Class A non-voting common stock for cancellation	Repurchase of Class A non-voting common stock for cancellation	(1)		—		(1)		—		Repurchase of Class A non-voting common stock for cancellation	—		(1)
Ending Balance	Ending Balance	11		13		11		13		Ending Balance	11		12
Additional paid-in capital	Additional paid-in capital									Additional paid-in capital
Balance at beginning of period	Balance at beginning of period	62,446		78,557		78,034		80,801		Balance at beginning of period	28,628		78,033
Issuance of Class A non-voting common stock	Issuance of Class A non-voting common stock	—		188		2,344		3,996		Issuance of Class A non-voting common stock	5,488		2,344
Repurchase of Class A non-voting common stock for cancellation	Repurchase of Class A non-voting common stock for cancellation	(30,217)		—		(46,375)		—		Repurchase of Class A non-voting common stock for cancellation	(3,687)		(16,158)

Share-based expense	Share-based expense	3,232		2,759		6,053		5,219		Share-based expense	3,293		2,821
Vested employee share plan awards	Vested employee share plan awards	—		(352)		(4,595)		(8,864)		Vested employee share plan awards	(11,319)		(4,595)

Change in redemption value of redeemable non-controlling interests										Change in redemption value of redeemable non-controlling interests	(29)		—
Balance at end of period	Balance at end of period	35,461		81,152		35,461		81,152		Balance at end of period	22,374		62,445
Retained earnings	Retained earnings									Retained earnings
Balance at beginning of period	Balance at beginning of period	748,323		638,558		740,926		601,406		Balance at beginning of period	764,178		740,926
Net income (loss) (2)		(3,874)		31,159		5,418		69,817

Net income (2)										Net income (2)	14,617		9,292
Dividends paid	Dividends paid	(1,835)		(1,524)		(3,730)		(3,030)		Dividends paid	(1,674)		(1,895)

Balance at end of period	Balance at end of period	742,614		668,193		742,614		668,193		Balance at end of period	777,121		748,323
Accumulated other comprehensive income	Accumulated other comprehensive income									Accumulated other comprehensive income
Balance at beginning of period	Balance at beginning of period	3,611		2,612		4,225		3,448		Balance at beginning of period	1,416		4,225
Currency translation adjustment	Currency translation adjustment	(2,038)		537		(2,652)		(299)		Currency translation adjustment	(497)		(614)
Balance at end of period	Balance at end of period	1,573		3,149		1,573		3,149		Balance at end of period	919		3,611
Total Oppenheimer Holdings Inc. stockholders' equity	Total Oppenheimer Holdings Inc. stockholders' equity	$	779,659	$	752,507	$	779,659	$	752,507	Total Oppenheimer Holdings Inc. stockholders' equity	$	800,425	$	814,391
Noncontrolling interest	Noncontrolling interest									Noncontrolling interest
Balance at beginning of period	Balance at beginning of period	2,555		—		2,069		—		Balance at beginning of period	722		2,069

Net income (loss) attributable to noncontrolling interest	Net income (loss) attributable to noncontrolling interest	(846)		—		(360)		—		Net income (loss) attributable to noncontrolling interest	(153)		486

Change in redemption value of redeemable non-controlling interests										Change in redemption value of redeemable non-controlling interests	(136)		—
Balance at end of period	Balance at end of period	1,709		—		1,709		—		Balance at end of period	433		2,555
Total stockholders' equity	Total stockholders' equity	$	781,368	$	752,507	$	781,368	$	752,507	Total stockholders' equity	$	800,858	$	816,946
Redeemable noncontrolling Interests
Redeemable Noncontrolling Interests										Redeemable Noncontrolling Interests
Balance at beginning of period	Balance at beginning of period	127,765		—		127,765		—		Balance at beginning of period	25,466		127,765
Contributions during the year		—		—		—		—
Redemption of redeemable noncontrolling interests										Redemption of redeemable noncontrolling interests	(74)		—
Change in redemption value of redeemable noncontrolling interests										Change in redemption value of redeemable noncontrolling interests	165		—
Balance at end of period	Balance at end of period	$	127,765	$	—	$	127,765	$	—	Balance at end of period	$	25,557	$	127,765

Dividends paid per share	Dividends paid per share	$	0.15	$	0.12	$	0.30	$	0.24	Dividends paid per share	$	0.15	$	0.15

(1) Certain prior period reported amounts were reclassified to conform to the current period presentation, see Note 2.
(1) Certain prior period reported amounts were reclassified to conform to the current period presentation, See Note 2.										(1) Certain prior period reported amounts were reclassified to conform to the current period presentation, See Note 2.
(2) Attributable to Oppenheimer Holdings Inc.

The accompanying notes are an integral part of these condensed consolidated financial statements.

Table of Contents

OPPENHEIMER HOLDINGS INC.

CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS (unaudited)

FOR THE ~~SIX~~THREE MONTHS ENDED ~~JUNE 30,~~MARCH 31,


(Expressed in thousands)	(Expressed in thousands)	2022		2021		(Expressed in thousands)	2023		2022
Cash flows from operating activities	Cash flows from operating activities					Cash flows from operating activities
Net income	Net income	$	5,058	$	69,817	Net income	$	14,464	$	9,778
Adjustments to reconcile net income to net cash (used in)/provided by operating activities
Adjustments to reconcile net income to net cash used in operating activities						Adjustments to reconcile net income to net cash used in operating activities
Non-cash items included in net income:	Non-cash items included in net income:					Non-cash items included in net income:
Depreciation and amortization of furniture, equipment and leasehold improvements	Depreciation and amortization of furniture, equipment and leasehold improvements	3,806		3,945		Depreciation and amortization of furniture, equipment and leasehold improvements	1,875		1,996
Deferred income taxes	Deferred income taxes	3,026		(3,320)		Deferred income taxes	4,562		3,162
Amortization of notes receivable	Amortization of notes receivable	6,995		6,677		Amortization of notes receivable	3,612		3,735
Amortization of debt issuance costs	Amortization of debt issuance costs	126		125		Amortization of debt issuance costs	56		63

Provision for credit losses		94		3,008
Write-off of debt issuance costs						Write-off of debt issuance costs	5		—
Provision for (reversal of) credit losses						Provision for (reversal of) credit losses	(4)		5
Share-based compensation	Share-based compensation	(2,589)		26,133		Share-based compensation	2,000		2,910
Amortization of right-of-use lease assets	Amortization of right-of-use lease assets	13,170		13,008		Amortization of right-of-use lease assets	6,843		6,570

Gain on repurchase of senior secured notes						Gain on repurchase of senior secured notes	(51)		—
Decrease (increase) in operating assets:	Decrease (increase) in operating assets:					Decrease (increase) in operating assets:
Deposits with clearing organizations	Deposits with clearing organizations	(32,600)		1,579		Deposits with clearing organizations	8,386		(34,403)
Receivable from brokers, dealers and clearing organizations	Receivable from brokers, dealers and clearing organizations	2,004		(31,950)		Receivable from brokers, dealers and clearing organizations	(154,962)		(39,535)
Receivable from customers	Receivable from customers	(66,723)		(117,313)		Receivable from customers	148,452		(39,860)

Income tax receivable						Income tax receivable	(5,374)		—
Securities purchased under agreements to resell	Securities purchased under agreements to resell	935		—		Securities purchased under agreements to resell	—		935
Securities owned	Securities owned	13,232		66,455		Securities owned	(263,560)		(54,542)
Notes receivable	Notes receivable	(12,111)		(12,635)		Notes receivable	(9,766)		(7,631)
Other assets	Other assets	24,394		96,652		Other assets	(3,918)		29,708
Increase (decrease) in operating liabilities:	Increase (decrease) in operating liabilities:					Increase (decrease) in operating liabilities:
Drafts payable	Drafts payable	10,020		17,133		Drafts payable	18,024		—
Payable to brokers, dealers and clearing organizations	Payable to brokers, dealers and clearing organizations	(33,590)		89,235		Payable to brokers, dealers and clearing organizations	85,964		(102,554)
Payable to customers	Payable to customers	(37,643)		(40,629)		Payable to customers	2,113		50,030
Securities sold under agreements to repurchase	Securities sold under agreements to repurchase	(106,354)		(110,837)		Securities sold under agreements to repurchase	119,427		203,829
Securities sold but not yet purchased	Securities sold but not yet purchased	182,694		(13,333)		Securities sold but not yet purchased	57,889		25,413
Accrued compensation	Accrued compensation	(160,196)		(40,906)		Accrued compensation	(81,859)		(226,483)

Income tax payable						Income tax payable	102		(378)
Accounts payable and other liabilities	Accounts payable and other liabilities	(45,119)		(2,704)		Accounts payable and other liabilities	(40,403)		15,106
Cash (used in)/provided by operating activities		(231,371)		20,140
Cash used in operating activities						Cash used in operating activities	(86,123)		(152,146)
Cash flows from investing activities	Cash flows from investing activities					Cash flows from investing activities
Purchase of furniture, equipment and leasehold improvements	Purchase of furniture, equipment and leasehold improvements	(2,307)		(6,739)		Purchase of furniture, equipment and leasehold improvements	(3,531)		(2,490)

Proceeds from the settlement of Company-owned life insurance	Proceeds from the settlement of Company-owned life insurance	1,191		1,308		Proceeds from the settlement of Company-owned life insurance	555		—
Cash used in investing activities	Cash used in investing activities	(1,116)		(5,431)		Cash used in investing activities	(2,976)		(2,490)
Cash flows from financing activities	Cash flows from financing activities					Cash flows from financing activities
Cash dividends paid on Class A non-voting and Class B voting common stock	Cash dividends paid on Class A non-voting and Class B voting common stock	(3,730)		(3,030)		Cash dividends paid on Class A non-voting and Class B voting common stock	(1,674)		(1,895)

Repurchase of Class A non-voting common stock for cancellation	Repurchase of Class A non-voting common stock for cancellation	(46,375)		—		Repurchase of Class A non-voting common stock for cancellation	(3,687)		(16,158)
Payments for employee taxes withheld related to vested share-based awards	Payments for employee taxes withheld related to vested share-based awards	(2,251)		(4,883)		Payments for employee taxes withheld related to vested share-based awards	(5,832)		(2,251)

Redemption of redeemable noncontrolling interests						Redemption of redeemable noncontrolling interests	(74)		—

Repurchase of senior secured notes						Repurchase of senior secured notes	(1,000)		—

Debt issuance costs		—		(22)

Increase/(decrease) in bank call loans, net		107,800		(2,400)
Increase in bank call loans, net						Increase in bank call loans, net	19,300		8,650
Cash provided by/(used in) financing activities	Cash provided by/(used in) financing activities	55,444		(10,335)		Cash provided by/(used in) financing activities	7,033		(11,654)
Net (decrease)/increase in cash, cash equivalents and restricted cash		(177,043)		4,374
Net decrease in cash, cash equivalents and restricted cash						Net decrease in cash, cash equivalents and restricted cash	(82,066)		(166,290)
Cash, cash equivalents and restricted cash, beginning of period	Cash, cash equivalents and restricted cash, beginning of period	341,524		35,424		Cash, cash equivalents and restricted cash, beginning of period	137,967		341,524
Cash, cash equivalents and restricted cash, end of period	Cash, cash equivalents and restricted cash, end of period	$	164,481	$	39,798	Cash, cash equivalents and restricted cash, end of period	$	55,901	$	175,234

Reconciliation of cash, cash equivalents and restricted cash within the condensed consolidated balance sheets:	Reconciliation of cash, cash equivalents and restricted cash within the condensed consolidated balance sheets:	2022		2021		Reconciliation of cash, cash equivalents and restricted cash within the condensed consolidated balance sheets:	2023		2022
Cash and cash equivalents	Cash and cash equivalents	$	36,606	$	39,798	Cash and cash equivalents	$	30,320	$	47,453
Restricted cash	Restricted cash	127,875		—		Restricted cash	25,581		127,781
Total cash, cash equivalents and restricted cash	Total cash, cash equivalents and restricted cash	$	164,481	$	39,798	Total cash, cash equivalents and restricted cash	$	55,901	$	175,234

Schedule of non-cash financing activities	Schedule of non-cash financing activities					Schedule of non-cash financing activities
Employee share plan issuance	Employee share plan issuance	$	3,809	$	6,513	Employee share plan issuance	$	8,805	$	3,809

Supplemental disclosure of cash flow information	Supplemental disclosure of cash flow information					Supplemental disclosure of cash flow information
Cash paid during the period for interest	Cash paid during the period for interest	$	5,776	$	5,277	Cash paid during the period for interest	$	14,261	$	4,135
Cash paid during the period for income taxes, net	Cash paid during the period for income taxes, net	$	22,750	$	34,994	Cash paid during the period for income taxes, net	$	4,238	$	1,675

The accompanying notes are an integral part of these condensed consolidated financial statements.


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

1. Organization

Oppenheimer Holdings Inc. ("OPY" or the "Parent") is incorporated under the laws of the State of Delaware. The condensed consolidated financial statements include the accounts of OPY and its consolidated subsidiaries (together, the "Company"). Oppenheimer Holdings Inc., through its operating subsidiaries, is a leading middle market investment bank and full service broker-dealer that is engaged in a broad range of activities in the financial services industry, including retail securities brokerage, institutional sales and trading, investment banking (corporate and public finance), equity and fixed income research, market-making, trust services, and investment advisory and asset management services.

The Company is headquartered in New York and has 9192 retail branch offices in 25 states located throughout the United States and offices in Puerto Rico, Tel Aviv, Israel, Hong Kong, China, London, England, St. Helier, Isle of Jersey, Munich, Germany, Portugal and Geneva, Switzerland as well as institutional businesses located in London, Tel Aviv, and Hong Kong. The principal subsidiaries of OPY are Oppenheimer & Co. Inc. ("Oppenheimer"), a registered broker-dealer in securities and investment adviser under the Investment Advisers Act of 1940; Oppenheimer Asset Management Inc. ("OAM") and its wholly-owned subsidiary, Oppenheimer Investment Management LLC, both registered investment advisers under the Investment Advisers Act of 1940; Oppenheimer Trust Company of Delaware ("Oppenheimer Trust"), a limited purpose trust company that provides fiduciary services such as trust and estate administration and investment management; OPY Credit Corp., which ~~offers~~from time to time may offer syndication as well as trading of issued corporate loans; Oppenheimer Europe Ltd., based in the United Kingdom, with offices in the Isle of Jersey, Portugal, Germany, and Switzerland, which provides institutional equities and fixed income brokerage and corporate finance and is regulated by the Financial Conduct Authority; ~~and~~ Oppenheimer Investments Asia Limited, based in Hong Kong, China, which provides fixed income and equities brokerage services to institutional investors and is regulated by the Securities and Futures ~~Commission.~~

~~Oppenheimer owns Freedom Investments, Inc. ("Freedom"), a registered broker dealer in securities, which provides discount brokerage services,~~Commission; and Oppenheimer Israel ~~(OPCO)~~ Ltd., based in Tel Aviv, Israel, which ~~is engaged in offering~~provides investment services in the State of ~~Israel. Oppenheimer holds a trading permit on~~Israel and operates subject to the ~~New York Stock Exchange.~~authority of the Israel Securities Authority.

2. Summary of significant accounting policies and estimates

Basis of Presentation

The accompanying condensed consolidated financial statements of the Company have been prepared pursuant to the rules and regulations of the U.S. Securities and Exchange Commission (the "SEC") regarding interim financial reporting. Accordingly, they do not include all of the information and notes required by accounting principles generally accepted in the United States of America ("U.S. GAAP") ~~for complete financial statements~~ and should be read in conjunction with the audited consolidated financial statements and notes thereto included in the Company's Annual Report on Form 10-K for the year ended December 31, ~~2021~~2022 (the "Form 10-K"). The accompanying condensed consolidated balance sheet data was derived from the audited consolidated financial statements but does not include all disclosures required by U.S. GAAP for annual financial statement purposes. The accompanying condensed consolidated financial statements reflect all adjustments that are, in the opinion of management, necessary for a fair presentation of the financial position, results of operations and cash flows for the interim periods presented. Preparing financial statements requires management to make estimates and assumptions that affect the amounts that are reported in the financial statements and the accompanying disclosures. Although these estimates are based on management's knowledge of current events and actions that the Company may undertake in the future, actual results may differ materially from the estimates. The condensed consolidated results of operations for the three-month ~~and six-month~~ period ended ~~June 30, 2022~~March 31, 2023 are not necessarily indicative of the results to be expected for any future interim or annual period.

Reclassification

Effective ~~this quarter,~~June 30, 2022, the Company reclassified certain stockholders' equity amounts on the condensed consolidated balance sheet and condensed consolidated statements of changes in stockholders' ~~equity.~~equity and redeemable noncontrolling interests. The reclassification included separately presenting the par value of common ~~stocks,~~stock, and combining previously disclosed share capital and contributed capital amounts in the currently reported additional paid-in capital amount. The reclassification had no impact on previously reported total stockholders’ equity amounts.


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Oppenheimer Acquisition Corp. I

On October 26, 2021, ~~Oppenheimer~~OPY Acquisition Corp. I (“OHAA”) consummated its $126.5 million initial public offering (the “OHAA IPO”). OHAA is a special purpose acquisition company, incorporated in Delaware for the purpose of entering into a merger, share exchange, asset acquisition, stock purchase, recapitalization, reorganization or other similar business combination with one or more businesses or entities (a “Business Combination”). ~~Oppenheimer~~OPY Acquisition LLC I (the “Sponsor”), a Delaware series limited liability company and the Company’s subsidiary, is the sponsor of OHAA. The Company and its employees control OHAA through the Sponsor’s ownership of Class A founder shares of OHAA. As a result, both OHAA and the Sponsor are ~~consolidated~~recorded in the ~~Company’s~~Company's consolidated financial statements.

~~Funds~~Upon IPO completion, funds totaling $127.8 million, including proceeds from the OHAA IPO of $126.5 million and $1.3 million in investment from the Sponsor, are held in a trust account until the earlier of (i) the completion of a Business Combination or (ii) ten business days after April 29, 2023, 18 months from the closing of the OHAA IPO (“Combination Period”)., pursuant to OHAA's certificate of incorporation. The cash held in the trust account is recorded in “Restricted Cash” on the ~~condensed~~ consolidated balance sheet.

Transaction costs, which consisted of a net underwriting fee of $2.5 million and $0.5 million of other offering costs, were charged ~~during the fourth quarter of 2021~~ against the gross proceeds of the OHAA IPO consistent with SEC Staff Accounting Bulletin (SAB) Topic 5.

On December 20, 2022, OHAA’s stockholders approved an amendment to its certificate of incorporation that was filed with the Delaware Secretary of State on December 22, 2022 which extends the deadline by which it must complete its initial business combination from April 29, 2023 to October 30, 2023.In connection with its proposal to amend its certificate of incorporation, OHAA was required to give its Class A stockholders the opportunity to redeem their shares of Class A common stock.Of the 12,650,000 shares of Class A common stock that were outstanding, a total of 10,170,490 shares exercised their redemption rights. As of March 31, 2023, $25.6 million remained in the trust account that is recorded within “Restricted Cash” on the condensed consolidated balance sheet.

“Redeemable noncontrolling interests” of ~~$127.8~~$25.6 million associated with the publicly held OHAA Class A ordinary shares are recorded on the Company’s condensed consolidated balance sheet as of ~~June 30, 2022~~March 31, 2023 at redemption value and classified as temporary equity in accordance with Financial Accounting Standards Board (“FASB”) Accounting Standards Codification (“ASC”) Topic 480 “Distinguishing Liabilities from Equity”. Changes in redemption value are recognized immediately as they occur and will adjust the carrying value of redeemable noncontrolling interests to equal the redemption value at the end of each reporting period. Increases or decreases in the carrying amount of redeemable noncontrolling interests ~~shall~~will be affected by charges to additional paid-in-capital and noncontrolling interests attributable to certain members of the Sponsor on a pro rata ownership basis.

The public warrants and private warrants exercisable for OHAA Class A ordinary shares that were issued in connection with the OHAA IPO (the “OHAA Warrants”) qualify for equity accounting treatment under FASB ASC Topic 815.

Oppenheimer Principal Investments LLC

Oppenheimer Principal Investments LLC ("OPI") is a Delaware special purpose "Series" limited liability company formed in December 2020 and designed to retain and reward talented employees of the Company, primarily in connection with the deployment of Company capital into successful private market investments, and also in connection with the Company's receipt of non-cash compensation from investment banking assignments. OPI is designed to promote alignment of Company, client and employee interests as they relate to profitable investment opportunities. This program acts as an incentive for senior employees to identify attractive private investments for the Company and its clients, and as a retention tool for key employees of the Company. OPI treats its members as partners for tax purposes generally and with respect to the separate Series formed to participate in (i) the incentive fees generated by successful client investments in the Company's Private Market Opportunities program, or (ii) principal investments made by the Company or a portion of the gains thereon, either through the outright purchase of an investment or consideration earned in lieu of an investment banking fee or other transaction fee. Employees who become members of a Series receive a "profit interest", as that term is used in ~~IRS~~Internal Revenue Service (“IRS”) regulations, and receive an allocation of capital appreciation of the investment held by the particular Series that exceeds a threshold amount established for each Series. Participating employees are also subject to vesting and forfeiture requirements for each Series investment. ~~The~~ Vested profit interests are accounted for as compensation expense under FASB Topic ASC 710. Additionally, the


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Company’s policy is to consolidate those entities where it owns the majority voting interests. The Company owns the majority voting interest of OPI through Oppenheimer Alternative Investment Management (“OAIM”), the managing member of OPI and a subsidiary of OAM. Pursuant to the Company’s policy for consolidation, the Company consolidates OPI.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

~~Noncontrolling Interests~~See Note 10 for details.

Noncontrolling interests represents ownership interests in the Sponsor of OHAA, OHAA Class A founder and Class A ordinary shares held by management and employees of the Company, as well as OHAA Class B shares held by directors and officers of OHAA and an employee of the Company. Noncontrolling interests also include publicly held warrants to purchase OHAA Class A ordinary shares. ~~Additionally,~~

For the three months ended March 31, 2023 and March 31, 2022, the net income (loss) attributed to noncontrolling interests ~~includes the profits allocated to employees who have profit interests in OPI's Series.~~was (net of taxes) $153,000 and ($486,000), respectively.

Restricted Cash

Restricted cash represents OHAA deposits held in trust as indicated above.

3. Financial Instruments - Credit Losses

~~The Company follows ASU 2016-13,~~Under ASC 326 "Financial Instruments - Credit ~~Losses (Topic 326): Measurement of Credit Losses on Financial Instruments". The~~Losses", the Company can elect to use an approach to measure the allowance for credit losses using the fair value of collateral where the borrower is required to, and reasonably expected to, continually adjust and replenish the amount of collateral securing the instrument to reflect changes in the fair value of such collateral. The Company has elected to use this approach for securities borrowed, margin loans, and reverse repurchase agreements. No material historical losses have been reported on these assets. See note 9 for details.

As of ~~June 30, 2022,~~March 31, 2023, the Company had ~~$59.1~~$63.6 million of notes receivable ($~~54.0~~57.5 million as of December 31, ~~2021)~~2022). Notes receivable represent recruiting and retention payments generally in the form of upfront loans to financial advisors and key revenue producers as part of the Company's overall growth strategy. These notes generally amortize over a service period of 3 to 10 years from the initial date of the note or based on productivity levels of the respective employees. All such notes are contingent on the employees' continued employment with the Company. The unforgiven portion of the notes becomes due on demand in the event the employee departs during the service period. At this point, any uncollected portion of the notes is reclassified into a defaulted notes category.

The allowance for uncollectibles is a valuation account that is deducted from the amortized cost basis of the defaulted notes balance to present the net amount expected to be collected. Balances are charged-off against the allowance when management deems the amount to be uncollectible.

The Company reserves 100% of the uncollected balance of defaulted notes which are five years and older and applies an expected loss rate to the remaining balance. The expected loss rate is based on historical collection rates of defaulted notes. The expected loss rate is adjusted for changes in market conditions such as changes in unemployment rates, changes in interest rates and other relevant factors. For the three months ~~and six months~~ ended ~~June 30, 2022,~~March 31, 2023, no adjustments were made to the expected loss rates. The Company will continuously monitor the effect of these factors on the expected loss rate and adjust it as necessary.

The allowance is measured on a pool basis as the Company has determined that the entire defaulted portion of notes receivable has similar risk characteristics.

As of ~~June 30, 2022,~~March 31, 2023, the uncollected balance of defaulted notes was ~~$7.4~~$6.1 million and the allowance for uncollectibles was ~~$5.1~~$4.1 million. The allowance for uncollectibles consisted of ~~$3.4~~$2.7 million related to defaulted notes balances (five years and older) and ~~$1.7~~$1.4 million related to defaulted notes balances (under five years).


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

The following table presents the disaggregation of defaulted notes by year of default as of ~~June 30, 2022:~~March 31, 2023:


(Expressed in thousands)	(Expressed in thousands)			(Expressed in thousands)
		As of June 30, 2022			As of March 31, 2023

2023				2023	$	521
2022	2022	$	578	2022	288
2021	2021	2,332		2021	1,937
2020	2020	568		2020	423
2019	2019	356		2019	330
2018		138
2017 and prior		3,452
2018 and prior				2018 and prior	2,639
Total	Total	$	7,424	Total	$	6,138

The following table presents activity in the allowance for uncollectibles of defaulted notes for the three ~~and six~~ months ended

~~June 30, 2022~~March 31, 2023 and ~~2021:~~2022:


(Expressed in thousands)	(Expressed in thousands)									(Expressed in thousands)
		For the Three Months Ended June 30,				For the Six Months Ended June 30					For the Three Months Ended March 31
		2022		2021		2022		2021				2023		2022
Beginning balance	Beginning balance	$	5,247	$	4,766	$	4,923	$	4,234	Beginning balance		$	4,327	$	4,923
Additions and other adjustments	Additions and other adjustments	(141)		(65)		183		467		Additions and other adjustments		(276)		324
Ending balance	Ending balance	$	5,106	$	4,701	$	5,106	$	4,701	Ending balance		$	4,051	$	5,247

4. Leases

The Company ~~and its subsidiaries have~~has operating leases for office space and equipment expiring at various dates through 2034. The Company leases its corporate headquarters at 85 Broad Street, New York, New York which houses its executive management team and many administrative functions for the firm as well as its research, trading, investment banking, and asset management divisions and an office in Troy, Michigan, which among other things, houses its payroll and human resources departments. In addition, the Company has 9192 retail branch offices in the United States as well as offices in London, England, St. Helier, Isle of Jersey, Geneva, Switzerland, Munich, Germany, Tel Aviv, Israel and Hong Kong, China.

The Company is constantly assessing its needs for office space and, on a rolling basis, has many leases that expire in any given year.

~~The majority~~Substantially all of the leases are held by the Company's subsidiary, Viner Finance Inc., which is a consolidated subsidiary and 100% owned by the Company.

Leases with an initial term of 12 months or less are not recorded on the balance sheet; the Company recognizes lease expense for these leases on a straight-line basis over the lease term. Most leases include an option to renew and the exercise of lease renewal options is at the Company's sole discretion. The Company did not include the renewal options as part of the right of use assets and liabilities.

The depreciable life of assets and leasehold improvements is limited by the expected lease term. The Company's lease agreements do not contain any material residual value guarantees or material restrictive covenants.


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

As of ~~June 30, 2022,~~March 31, 2023, the Company had right-of-use operating lease assets of ~~$146.1~~$152.8 million (net of accumulated amortization of ~~$74.2~~$86.9 million) which are comprised of real estate leases of ~~$143.3~~$149.7 million (net of accumulated amortization of ~~$71.8~~$84.6 million) and equipment leases of ~~$2.8~~$3.1 million (net of accumulated amortization of ~~$2.4~~$2.3 million). As of ~~June 30, 2022,~~March 31, 2023, the Company had operating lease liabilities of ~~$187.5~~$193.4 million which are comprised of real estate lease liabilities of ~~$184.8~~$190.3 million and equipment lease liabilities of ~~$2.7~~$3.1 million. The Company had no finance leases ~~or embedded leases~~ as of ~~June 30, 2022.~~March 31, 2023.

As most of the Company's leases do not provide an implicit rate, the Company uses the incremental borrowing rate based on the information available at commencement date in determining the present value of lease payments. The Company used the incremental borrowing rate on January 1, 2019 for operating leases that commenced prior to that date. The Company used the incremental borrowing rate as of the lease commencement date for the operating leases that commenced subsequent to January 1, 2019.

The following table presents the weighted average lease term and weighted average discount rate for the Company's operating leases as of ~~June 30, 2022~~March 31, 2023 and December 31, ~~2021,~~2022, respectively:


		As of			As of
		June 30, 2022	December 31, 2021		March 31, 2023	December 31, 2022

Weighted average remaining lease term (in years)	Weighted average remaining lease term (in years)	7.06	7.38	Weighted average remaining lease term (in years)	6.94	6.82
Weighted average discount rate	Weighted average discount rate	6.81%	6.89%	Weighted average discount rate	7.03%	6.66%

The following table presents operating lease costs recognized for the three ~~and six~~ months ended ~~June 30,~~March 31, 2023 and March 31, 2022, ~~and June 30, 2021,~~ respectively, which are included in occupancy and equipment costs on the condensed consolidated income statements:


(Expressed in thousands)	(Expressed in thousands)									(Expressed in thousands)
		For the Three Months Ended June 30,				For the Six Months Ended June 30,					For the Three Months Ended March 31,
		2022		2021		2022		2021			2023		2022
Operating lease costs:	Operating lease costs:									Operating lease costs:
Real estate leases - Right-of-use lease asset amortization	Real estate leases - Right-of-use lease asset amortization	$	6,189	$	6,062	$	12,346	$	12,118	Real estate leases - Right-of-use lease asset amortization	$	6,439	$	6,157
Real estate leases - Interest expense	Real estate leases - Interest expense	3,267		3,607		6,623		7,203		Real estate leases - Interest expense	3,209		3,356
Equipment leases - Right-of-use lease asset amortization	Equipment leases - Right-of-use lease asset amortization	410		445		824		890		Equipment leases - Right-of-use lease asset amortization	422		414
Equipment leases - Interest expense	Equipment leases - Interest expense	35		37		67		76		Equipment leases - Interest expense	46		32

The maturities of lease liabilities as of ~~June 30, 2022~~March 31, 2023 and December 31, ~~2021~~2022 are as follows:


(Expressed in thousands)	(Expressed in thousands)					(Expressed in thousands)
		As of					As of
		June 30, 2022		December 31, 2021			March 31, 2023		December 31, 2022
2022		$	21,196	$	41,696
2023	2023	40,578		38,477		2023	$	32,656	$	42,343
2024	2024	35,700		33,573		2024	41,070		38,018
2025	2025	29,902		27,703		2025	35,007		31,684
2026	2026	28,368		26,342		2026	32,706		29,671
After 2026		81,723		78,593
2027						2027	31,258		28,178
After 2027						After 2027	73,181		58,146
Total lease payments	Total lease payments	$	237,467	$	246,384	Total lease payments	$	245,878	$	228,040
Less interest	Less interest	(49,936)		(54,365)		Less interest	(52,528)		(45,470)
Present value of lease liabilities	Present value of lease liabilities	$	187,531	$	192,019	Present value of lease liabilities	$	193,350	$	182,570

As of March 31, 2023, the Company had $20.3 million of additional real estate operating leases that have not yet commenced ($40.2 million as of December 31, 2022).


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

~~As of June 30, 2022, the Company had $33.2 million of additional operating leases that have not yet commenced ($16.2 million as of December 31, 2021).~~

5. Revenue from contracts with customers

Revenue from contracts with customers is recognized when, or as, the Company satisfies its performance obligations by transferring the promised goods or services to customers. A good or service is transferred to a customer when, or as, the customer obtains control of that good or service. A performance obligation may be satisfied over time or at a point in time. Revenue from a performance obligation satisfied over time is recognized by measuring the Company's progress in satisfying the performance obligation in a manner that depicts the transfer of the goods or services to the customer. Revenue from a performance obligation satisfied at a point in time is recognized at the point in time that the Company determines the customer obtains control over the promised good or service.

The amount of revenue recognized reflects the consideration to which the Company expects to be entitled in exchange for those promised goods or services (i.e., the "transaction price"). In determining the transaction price, the Company considers multiple factors, including the effects of variable consideration. Variable consideration is included in the transaction price only to the extent it is probable that a significant reversal in the amount of cumulative revenue recognized will not occur when the uncertainties with respect to the amount are resolved. In determining when to include variable consideration in the transaction price, the Company considers the range of possible outcomes, the predictive value of its past experiences, the time period during which uncertainties are expected to be resolved and the amount of consideration that is susceptible to factors outside of the Company's influence, such as market volatility or the judgment and actions of third parties.

The Company earns revenue from contracts with customers and other sources (principal transactions, interest and other). The following provides detailed information on the recognition of the Company's revenue from contracts with customers:

Commissions

Commissions from Sales and Trading — The Company earns commission revenue by executing, settling and clearing transactions with clients primarily in exchange-traded and over-the-counter corporate equity and debt securities, money market instruments and exchange-traded options and futures contracts. A substantial portion of the Company's revenue is derived from commissions from private clients through accounts with transaction-based pricing. Trade execution and clearing services, when provided together, represent a single performance obligation, as the services are not separately identifiable in the context of the contract. Commission revenue associated with combined trade execution and clearing services, as well as trade execution services on a standalone basis, isare recognized at a point in time on trade date when the performance obligation is satisfied.

Commission revenue is generally paid on settlement date, which is generally two business days after trade date for equity securities and corporate bond transactions and one day for government securities, options and commodities transactions. The Company records a receivable on the trade date and receives a payment on the settlement date.

Mutual Fund Income — The Company earns mutual fund income for sales and distribution of mutual fund shares, which consists of a fixed fee amount and a variable amount. The Company recognizes mutual fund income at a point in time on the trade date when the performance obligation is satisfied which is when the mutual fund interest is sold to the investor. The ongoing distribution fees for distributing investment products from mutual fund companies are generally considered variable consideration because they are based on the value of AUM and are uncertain on trade date. The Company recognizes distribution fees over the investment period as the amounts become known and the portion recognized in the current period may relate to distribution services performed in prior periods. Mutual fund income is generally received within 90 days.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Advisory Fees

The Company earns management and performance (or incentive) fees in connection with the advisory and asset management services it provides to various types of funds, asset-based programs and investment vehicles through its subsidiaries. Management fees are generally based on the account value at the valuation date per the respective asset management agreements and are recognized over time as the customer receives the benefits of the services evenly throughout the term of the contract. Performance fees are recognized when the return on client AUM exceeds a specified benchmark return or as other performance targets over a 12-month measurement period are met. Performance fees are considered variable and they are recognized at a point in time as they are subject to fluctuation and/or are contingent on a future event over the measurement


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

period and are not subject to adjustment once the measurement period ends. Such fees are computed as of the fund's year-end when the measurement period ends and generally are recorded as earned in the fourth quarter of the Company's fiscal year. Both management and performance fees are generally received within 90 days.

Investment Banking

The Company earns underwriting revenues by providing capital raising solutions for corporate clients through initial public offerings, follow-on offerings, equity-linked offerings, private investments in public entities, and private placements. Underwriting revenues are recognized at a point in time on trade date, as the client obtains the control and benefit of the capital markets offering at that ~~point.~~time. These fees are generally received within 90 days after the transactions are completed. Transaction-related expenses, primarily consisting of legal, travel and other costs directly associated with the transaction, are deferred and recognized in the same period as the related investment banking transaction revenue. Underwriting revenues and related expenses are presented gross on the condensed consolidated income statements.

Revenue from financial advisory services includes fees generated in connection with mergers, acquisitions, and restructuring transactions. Such revenue and fees are primarily recorded at a point in time when services for the ~~transactions are~~performance obligations have been completed and income is reasonably determinable, generally as set forth under the terms of the engagement. Payment for advisory services is generally due upon completion of the transaction or milestone. Retainer fees and fees earned from certain advisory services are recognized ratably over the service period as the customer receives the benefit of the services throughout the term of the contracts, and such fees are collected based on the terms of the contracts.

Bank Deposit Sweep Income

Bank deposit sweep income consists of revenue earned from the FDIC-insured bank deposit program. Under this program, client funds are swept into deposit accounts at participating banks and are eligible for FDIC deposit insurance up to FDIC standard maximum deposit insurance amounts. Fees are earned over time and are generally received within 30 days.

Disaggregation of Revenue

The following presents the Company's revenue from contracts with customers disaggregated by major business activity and other sources of revenue for the three months ended March 31, 2023 and 2022:


(Expressed in thousands)	For the Three Months Ended March 31, 2023
	Reportable Segments
	Private Client		Asset Management		Capital Markets		Corporate/Other		Total
Revenue from contracts with customers:
Commissions from sales and trading	$	38,924	$	—	$	40,047	$	6	$	78,977
Mutual fund and insurance income	7,712		—		4		4		7,720
Advisory fees	76,583		23,954		—		7		100,544
Investment banking - capital markets	1,787		—		8,241		—		10,028
Investment banking - advisory	—		—		27,937		—		27,937
Bank deposit sweep income	48,909		—		—		—		48,909
Other	3,993		—		506		97		4,596
Total revenue from contracts with customers	177,908		23,954		76,735		114		278,711
Other sources of revenue:
Interest	20,579		—		3,029		1,333		24,941
Principal transactions, net	1,049		—		10,404		2,037		13,490
Other	3,885		5		114		533		4,537
Total other sources of revenue	25,513		5		13,547		3,903		42,968
Total revenue	$	203,421	$	23,959	$	90,282	$	4,017	$	321,679


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)


(Expressed in thousands)	For the Three Months Ended March 31, 2022
	Reportable Segments
	Private Client		Asset Management		Capital Markets		Corporate/Other		Total
Revenue from contracts with customers:
Commissions from sales and trading	$	43,355	$	—	$	46,636	$	11	$	90,002
Mutual fund and insurance income	8,322		—		5		(8)		8,319
Advisory fees	88,527		27,113		117		9		115,766
Investment banking - capital markets	3,306		—		13,224		—		16,530
Investment banking - advisory	35		—		21,905		—		21,940
Bank deposit sweep income	4,354		—				—		4,354
Other	2,837		—		318		122		3,277
Total revenue from contracts with customers	150,736		27,113		82,205		134		260,188
Other sources of revenue:
Interest	8,147		—		1,293		77		9,517
Principal transactions, net	(1,933)		—		1,516		2,781		2,364
Other	(6,103)		4		37		21		(6,041)
Total other sources of revenue	111		4		2,846		2,879		5,840
Total revenue	$	150,847	$	27,117	$	85,051	$	3,013	$	266,028

~~Disaggregation~~Contract Assets and Liabilities

The timing of ~~Revenue~~the Company's revenue recognition may differ from the timing of payment by its customers. The Company records contract assets when payment is due from a client conditioned on future performance or the occurrence of other events. Alternatively, when payment precedes the provision of the related services, the Company records deferred revenue until the performance obligations are satisfied.

The Company had receivables related to revenue from contracts with customers of $28.6 million and $32.8 million at March 31, 2023 and December 31, 2022, respectively. The Company had no significant impairments related to these receivables during the three months ended March 31, 2023.

Deferred revenue relates to IRA fees received annually in advance on customers' IRA accounts managed by the Company and retainer fees and other fees earned from certain advisory transactions where the performance obligations have not yet been satisfied. Total deferred revenue was $1,701,000 and $900,000 at March 31, 2023 and December 31, 2022, respectively.

The following presents the Company's contract assets and deferred revenue balances from contracts with customers, ~~disaggregated by major business activity~~which are included in other assets and other ~~sources of revenue for~~liabilities, respectively, on the ~~three and six months ended June 30, 2022 and 2021:~~

(Expressed in thousands) For the Three Months Ended June 30, 2022
Reportable Segments
Private Client Asset Management Capital Markets Corporate/Other Total
Revenue from contracts with customers:
Commissions from sales and trading $ 38,108 0 $ 48,425 $ 6 $ 86,539
Mutual fund and insurance income 7,808 0 1 30 7,839
Advisory fees 83,085 24,311 — 9 107,405
Investment banking - capital markets 2,359 0 6,010 — 8,369
Investment banking - advisory — 0 8,284 — 8,284
Bank deposit sweep income 14,845 0 — — 14,845
Other 4,807 — 479 66 5,352
Total revenue from contracts with customers 151,012 24,311 63,199 111 238,633
Other sources of revenue:
Interest 10,369 0 1,392 28 11,789
Principal transactions, net (2,233) 0 6,564 (3,073) 1,258
Other (14,677) 4 119 96 (14,458)
Total other sources of revenue (6,541) 4 8,075 (2,949) (1,411)
Total revenue $ 144,471 $ 24,315 $ 71,274 $ (2,838) $ 237,222

(Expressed in thousands) For the Three Months Ended June 30, 2021
Reportable Segments
Private Client Asset Management Capital Markets Corporate/Other Total
Revenue from contracts with customers:
Commissions from sales and trading $ 44,510 $ — $ 42,407 $ 4 $ 86,921
Mutual fund and insurance income 9,243 — 2 5 9,250
Advisory fees 85,598 25,541 — 13 111,152
Investment banking - capital markets 5,770 — 48,208 — 53,978
Investment banking - advisory 250 — 50,514 — 50,764
Bank deposit sweep income 3,712 — — — 3,712
Other 4,474 — 202 19 4,695
Total revenue from contracts with customers 153,557 25,541 141,333 41 320,472
Other sources of revenue:
Interest 7,235 — 1,666 8 8,909
Principal transactions, net 1,546 — 4,878 (119) 6,305
Other 4,525 3 68 11 4,607
Total other sources of revenue 13,306 3 6,612 (100) 19,821
Total revenue $ 166,863 $ 25,544 $ 147,945 $ (59) $ 340,293

condensed consolidated balance sheet:


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

(Expressed in thousands) For the Six Months Ended June 30, 2022
Reportable Segments
Private Client Asset Management Capital Markets Corporate/Other Total
Revenue from contracts with customers:
Commissions from sales and trading $ 81,463 $ — 95,061 17 $ 176,541
Mutual fund and insurance income 16,130 — 6 22 16,158
Advisory fees 171,613 51,424 117 17 223,171
Investment banking - capital markets 5,665 — 19,234 — 24,899
Investment banking - advisory 35 — 30,189 — 30,224
Bank deposit sweep income 19,199 — — — 19,199
Other 7,642 — 797 188 8,627
Total revenue from contracts with customers 301,747 51,424 145,404 244 498,819
Other sources of revenue:
Interest 18,517 — 2,685 104 21,306
Principal transactions, net (4,166) — 8,080 (292) 3,622
Other (20,780) 8 156 119 (20,497)
Total other sources of revenue (6,429) 8 10,921 (69) 4,431
Total revenue $ 295,318 $ 51,432 $ 156,325 $ 175 $ 503,250

(Expressed in thousands) For the Six Months Ended June 30, 2021
Reportable Segments
Private Client Asset Management Capital Markets Corporate/Other Total
Revenue from contracts with customers:
Commissions from sales and trading $ 92,908 $ — $ 98,207 $ 1 $ 191,116
Mutual fund and insurance income 18,441 — 4 81 18,526
Advisory fees 165,852 49,768 3 25 215,648
Investment banking - capital markets 14,280 — 128,277 — 142,557
Investment banking - advisory 250 — 86,436 — 86,686
Bank deposit sweep income 7,720 — — — 7,720
Other 7,594 — 761 33 8,388
Total revenue from contracts with customers 307,045 49,768 313,688 140 670,641
Other sources of revenue:
Interest 13,711 — 3,818 46 17,575
Principal transactions, net 2,176 — 13,832 1,162 17,170
Other 7,954 6 206 23 8,189
Total other sources of revenue 23,841 6 17,856 1,231 42,934
Total revenue $ 330,886 $ 49,774 $ 331,544 $ 1,371 $ 713,575

~~Contract Balances~~

The timing of the Company's revenue recognition may differ from the timing of payment by its customers. The Company records receivables when revenue is recognized prior to payment and it has an unconditional right to payment. Alternatively, when payment precedes the provision of the related services, the Company records deferred revenue until the performance obligations are satisfied.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

The Company had receivables related to revenue from contracts with customers of $25.1 million and $37.2 million at June 30, 2022 and December 31, 2021, respectively. The Company had no significant impairments related to these receivables during the three months ended June 30, 2022.

Deferred revenue relates to IRA fees received annually in advance on customers' IRA accounts and retainer fees and other fees earned from certain advisory transactions where the performance obligations have not yet been satisfied. Total deferred revenue was $2.0 million and $235,000 at June 30, 2022 and December 31, 2021, respectively.

The following presents the Company's contract assets and deferred revenue balances from contracts with customers, which are included in other assets and other liabilities, respectively, on the condensed consolidated balance sheet:


(Expressed in thousands)	(Expressed in thousands)	As of				(Expressed in thousands)	As of
		June 30, 2022		December 31, 2021			March 31, 2023		December 31, 2022
Contract assets (receivables):	Contract assets (receivables):					Contract assets (receivables):
Commission (1)	Commission (1)	$	3,912	$	2,886	Commission (1)	$	3,475	$	3,533
Mutual fund income (2)	Mutual fund income (2)	5,636		6,205		Mutual fund income (2)	5,225		4,993
Advisory fees (3)	Advisory fees (3)	3,909		4,546		Advisory fees (3)	7,084		5,368
Bank deposit sweep income (4)	Bank deposit sweep income (4)	4,258		595		Bank deposit sweep income (4)	7,182		9,057
Investment banking fees (5)	Investment banking fees (5)	4,418		17,765		Investment banking fees (5)	180		5,136
Other	Other	2,975		5,195		Other	5,427		4,686
Total contract assets	Total contract assets	$	25,108	$	37,192	Total contract assets	$	28,573	$	32,773
Deferred revenue (payables):	Deferred revenue (payables):					Deferred revenue (payables):
Investment banking fees (6)	Investment banking fees (6)	$	481	$	235	Investment banking fees (6)	$	945	$	900
IRA fees (7)	IRA fees (7)	1,529		—		IRA fees (7)	756		—
Total deferred revenue	Total deferred revenue	$	2,010	$	235	Total deferred revenue	$	1,701	$	900

(1)Commission recorded on trade date but not yet settled.

(2)Mutual fund income earned but not yet received.

(3)Management and performance fees earned but not yet received.

(4)Fees earned from FDIC-insured bank deposit program but not yet received.

(5)Underwriting revenue and advisory fees earned but not yet ~~received.~~received, including certain receivables.

(6)Retainer fees and fees received from certain advisory transactions where the performance

obligations have not yet been satisfied.

(7) Fee received in advance on an annual basis.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

6. Earnings per share

Basic earnings per share are computed by dividing net income over the weighted average number of shares of Class A non-voting common stock ("Class A Stock") and Class B voting common stock ("Class B Stock") outstanding. Diluted earnings per share includes the weighted average number of shares of Class A Stock and Class B Stock outstanding and options to purchase Class A Stock and unvested restricted stock awards of Class A Stock using the treasury stock method.

Earnings per share have been calculated as follows:


(Expressed in thousands, except number of shares and per share amounts)	(Expressed in thousands, except number of shares and per share amounts)									(Expressed in thousands, except number of shares and per share amounts)
		For the Three Months Ended June 30,				For the Six Months Ended June 30,					For the Three Months Ended March 31,
		2022		2021		2022		2021				2023		2022
Basic weighted average number of shares outstanding	Basic weighted average number of shares outstanding	11,980,115		12,689,191		12,222,527		12,634,464		Basic weighted average number of shares outstanding		11,092,603		12,467,632
Net dilutive effect of share-based awards, treasury stock method (1)	Net dilutive effect of share-based awards, treasury stock method (1)	—		991,955		919,011		861,125		Net dilutive effect of share-based awards, treasury stock method (1)		870,889		1,031,702
Diluted weighted average number of shares outstanding	Diluted weighted average number of shares outstanding	11,980,115		13,681,146		13,141,538		13,495,589		Diluted weighted average number of shares outstanding		11,963,492		13,499,334

Net income (loss) attributable to Oppenheimer Holdings Inc.		$	(3,874)	$	31,159	$	5,418	$	69,817
Net income attributable to Oppenheimer Holdings Inc.										Net income attributable to Oppenheimer Holdings Inc.		$	14,617	$	9,292

Earnings (Loss) per share attributable to Oppenheimer Holdings Inc.
Earnings per share attributable to Oppenheimer Holdings Inc.										Earnings per share attributable to Oppenheimer Holdings Inc.
Basic	Basic	$	(0.32)	$	2.46	$	0.44	$	5.53	Basic		$	1.32	$	0.75
Diluted	Diluted	$	(0.32)	$	2.28	$	0.41	$	5.17	Diluted		$	1.22	$	0.69

(1) For the three months ended June 30, 2022, the diluted net loss per share computation did not include the anti-dilutive effect of 1,267,733 shares of Class A Stock granted under share-based compensation arrangements. For the six months ended June 30, 2022,March 31, 2023, the diluted net income per share computation did not include the anti-dilutive effect of ~~4,100~~282,360 shares of Class A Stock granted under share-based compensation arrangements. For the three ~~and six~~ months ended ~~June 30, 2021,~~March 31, 2022, there was no Class A Stock granted under share-based compensation arrangements that was anti-dilutive.

~~7. Receivable from and payable to brokers, dealers and clearing organizations~~

(Expressed in thousands)
As of
June 30, 2022 December 31, 2021
Receivable from brokers, dealers and clearing organizations consists of:
Securities borrowed $ 79,038 $ 99,752
Receivable from brokers 42,255 39,716
Securities failed to deliver 26,705 9,212
Clearing organizations 19,355 19,518
Other 545 1,704
Total $ 167,898 $ 169,902
Payable to brokers, dealers and clearing organizations consists of:
Securities loaned $ 281,407 $ 244,223
Securities failed to receive 50,028 6,457
Payable to brokers 3,357 2,077
Clearing organizations and other (1)
53,675 169,300
Total $ 388,467 $ 422,057

~~(1) The balances are primarily related to a trade/settlement date adjustment for U.S. Government Securities.~~

1816


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

7. Receivable from and payable to brokers, dealers and clearing organizations


(Expressed in thousands)
	As of
	March 31, 2023		December 31, 2022
Receivable from brokers, dealers and clearing organizations consisting of:
Securities borrowed	$	256,508	$	127,817
Receivable from brokers	72,942		49,125
Clearing organizations and other	19,101		20,036
Securities failed to deliver	12,488		9,099

Total	$	361,039	$	206,077
Payable to brokers, dealers and clearing organizations consisting of:
Securities loaned	$	368,101	$	320,843
Securities failed to receive	10,105		62,646
Payable to brokers	226		123
Clearing organizations and other (1)	257,538		166,394
Total	$	635,970	$	550,006

(1) The balances are primarily related to a trade/settlement date adjustment for U.S. Government Securities.

8. Fair value measurements

Securities owned, securities sold but not yet purchased, investments and derivative contracts are carried at fair value with changes in fair value recognized in earnings each period.

Valuation Techniques

A description of the valuation techniques applied, and inputs used in measuring the fair value of the Company's financial instruments, is as follows:

U.S. Government Obligations

U.S. Treasury securities are valued using quoted market prices obtained from active market makers and inter-dealer brokers.

U.S. Agency Obligations

U.S. agency securities consist of agency issued debt securities and mortgage pass-through securities. Non-callable agency issued debt securities are generally valued using quoted market ~~prices.~~prices, quoted market prices for comparable securities or discounted cash flow models. Callable agency issued debt securities are valued by benchmarking model-derived prices to quoted market prices and trade data for identical or comparable securities. The fair value of mortgage pass-through securities ~~are~~is model driven with respect to spreads of the comparable to-be-announced ("TBA") security.

Sovereign Obligations

The fair value of sovereign obligations is determined based on quoted market prices when available or a valuation model that generally utilizes interest rate yield curves and credit spreads as inputs.

Corporate Debt and Other Obligations

The fair value of corporate bonds is estimated using recent transactions, broker quotations and bond spread information.

Mortgage and Other Asset-Backed Securities


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

The Company values non-agency securities collateralized by home equity and various other types of collateral based on external pricing and spread data provided by independent pricing services. When specific external pricing is not observable, the valuation is based on yields and spreads for comparable bonds.

Municipal Obligations

The fair value of municipal obligations is estimated using recently executed transactions, broker quotations, and bond spread information.

Convertible Bonds

The fair value of convertible bonds is estimated using recently executed transactions and dollar-neutral price quotations, where observable. When observable price quotations are not available, fair value is determined based on cash flow models using yield curves and bond spreads as key inputs.

Corporate Equities

Equity securities and options are generally valued based on quoted prices from the exchange or market where traded. To the extent quoted prices are not available, fair values are generally derived using bid/ask spreads.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Auction Rate Securities ("ARS")

Background

In February 2010, Oppenheimer finalized settlements with each of the New York Attorney General's office ~~("NYAG")~~ and the Massachusetts Securities Division ~~("MSD" and, together with the NYAG,~~(collectively, the "Regulators") concluding proceedings by the Regulators concerning Oppenheimer's marketing and sale of ARS. Pursuant to the settlements with the Regulators, Oppenheimer agreed to extend offers to repurchase ARS from certain of its clients. As of September 30, 2021, the Company had completed its ARS purchase obligations related to the settlements with the Regulators. In addition to the settlements with the Regulators, Oppenheimer had also reached settlements of and received adverse awards in legal proceedings with various clients where the Company was obligated to purchase ARS. As of ~~June 30, 2022,~~March 31, 2023, the Company no longer had any obligations to purchase ARS from such legal settlements or adverse awards.

As of ~~June 30, 2022,~~March 31, 2023, the Company owned ~~$32.0~~$31.8 million of ARS. This amount represents the unredeemed or unsold amount that the Company holds as a result of ARS buybacks pursuant to the settlements with the Regulators and legal settlements and awards referred to above.

Valuation

The Company’s ARS owned referred to above have, for the most part, been subject to issuer tender offers. The Company has valued the ARS securities owned at the tender offer price and categorized them in Level 3 of the fair value hierarchy due to the illiquid nature of the securities and the period of time since the last tender offer. The fair value of ARS is particularly sensitive to movements in interest rates. However, an increase or decrease in short-term interest rates may or may not result in a higher or lower tender offer in the future or the tender offer price may not provide a reasonable estimate of the fair value of the securities. In such cases, other valuation techniques might be necessary.

As of ~~June 30, 2022,~~March 31, 2023, the Company had a valuation ~~adjustment~~allowance totaling $5.2 million relating to ARS owned (which is included as a reduction to securities owned on the condensed consolidated balance sheet).

Investments

In its role as general partner in certain hedge funds and private equity funds, the Company, through its subsidiaries, holds direct investments in such funds. The Company uses the net asset value of the underlying fund as a basis for estimating the fair value of its investment.


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

The following table provides information about the Company's investments in Company-sponsored funds as of ~~June 30, 2022:~~March 31, 2023:


(Expressed in thousands)	(Expressed in thousands)							(Expressed in thousands)
		Fair Value		Unfunded Commitments		Redemption Frequency	Redemption Notice Period		Fair Value		Unfunded Commitments		Redemption Frequency	Redemption Notice Period
Hedge funds (1)	Hedge funds (1)	$	700	$	—	Quarterly - Annually	30 - 120 Days	Hedge funds (1)	$	554	$	—	Quarterly - Annually	30 - 120 Days
Private equity funds (2)	Private equity funds (2)	8,960		3,075		N/A	N/A	Private equity funds (2)	12,747		2,893		N/A	N/A
		$	9,660	$	3,075				$	13,301	$	2,893

(1) Includes investments in hedge funds and hedge fund of funds that pursue long/short, event-driven, and activist strategies

(2) Includes private equity funds and private equity fund of funds with diversified portfolios focusing on but not limited to

technology companies, venture capital and global natural resources


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

The following table provides information about the Company's investments in Company-sponsored funds as of December 31, ~~2021:~~2022:


(Expressed in thousands)	(Expressed in thousands)							(Expressed in thousands)
		Fair Value		Unfunded Commitments		Redemption Frequency	Redemption Notice Period		Fair Value		Unfunded Commitments		Redemption Frequency	Redemption Notice Period
Hedge funds (1)	Hedge funds (1)	$	900	$	—	Quarterly - Annually	30 - 120 Days	Hedge funds (1)	$	574	$	—	Quarterly - Annually	30 - 120 Days
Private equity funds (2)	Private equity funds (2)	4,621		4,035		N/A	N/A	Private equity funds (2)	8,221		3,018		N/A	N/A
		$	5,521	$	4,035				$	8,795	$	3,018

(1) Includes investments in hedge funds and hedge fund of funds that pursue long/short, event-driven, and activist strategies.

(2) Includes private equity funds and private equity fund of funds with diversified portfolios focusing on but not limited to technology companies, venture capital and global natural resources.

During 2020, the Company made an investment in a financial technologies firm. The Company elected the fair value option for this investment and it is included in other assets on the condensed consolidated balance sheet. The Company determined the fair value of the investment based on an implied market-multiple approach and observable market data, including comparable company transactions. As of ~~June 30, 2022,~~March 31, 2023, the fair value of the investment was ~~$4.6~~$6.0 million and was categorized in Level 2 of the fair value hierarchy.

Assets and Liabilities Measured at Fair Value

The Company's assets and liabilities, recorded at fair value on a recurring basis as of ~~June 30, 2022,~~March 31, 2023, and December 31, ~~2021,~~2022, have been categorized based upon the above fair value hierarchy as follows:


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Assets and liabilities measured at fair value on a recurring basis as of ~~June 30, 2022~~March 31, 2023:


(Expressed in thousands)	(Expressed in thousands)									(Expressed in thousands)
		Fair Value Measurements as of June 30, 2022									Fair Value Measurements as of March 31, 2023
		Level 1		Level 2		Level 3		Total			Level 1		Level 2		Level 3		Total
Assets	Assets									Assets

Deposits with clearing organizations	Deposits with clearing organizations	$	41,189	$	—	$	—	$	41,189	Deposits with clearing organizations	$	25,211	$	—	$	—	$	25,211
Securities owned:	Securities owned:									Securities owned:
U.S. Treasury securities	U.S. Treasury securities	367,425		—		—		367,425		U.S. Treasury securities	618,227		—		—		618,227
U.S. Agency securities	U.S. Agency securities	—		5,538		—		5,538		U.S. Agency securities	—		7,994		—		7,994
Sovereign obligations		—		452		—		452

Corporate debt and other obligations	Corporate debt and other obligations	—		9,382		—		9,382		Corporate debt and other obligations	—		4,591		—		4,591
Mortgage and other asset-backed securities	Mortgage and other asset-backed securities	—		2,084		—		2,084		Mortgage and other asset-backed securities	—		2,741		—		2,741
Municipal obligations	Municipal obligations	—		162,530		—		162,530		Municipal obligations	—		38,183		—		38,183
Convertible bonds	Convertible bonds	—		14,557		—		14,557		Convertible bonds	—		29,812		—		29,812
Corporate equities	Corporate equities	27,013		—		—		27,013		Corporate equities	27,311		—		—		27,311
Money markets	Money markets	314		—		—		314		Money markets	—		1,519		—		1,519
Auction rate securities	Auction rate securities	—		—		31,977		31,977		Auction rate securities	—		—		31,776		31,776
Securities owned, at fair value	Securities owned, at fair value	394,752		194,543		31,977		621,272		Securities owned, at fair value	645,538		84,840		31,776		762,154
Investments (1)	Investments (1)	—		9,150		—		9,150		Investments (1)	5,242		9,794		—		15,036

TBAs										TBAs	—		21		—		21

Derivative contracts, total										Derivative contracts, total	—		21		—		21
Total	Total	$	435,941	$	203,693	$	31,977	$	671,611	Total	$	675,991	$	94,655	$	31,776	$	802,422
Liabilities	Liabilities									Liabilities
Securities sold but not yet purchased:	Securities sold but not yet purchased:									Securities sold but not yet purchased:
U.S. Treasury securities	U.S. Treasury securities	$	233,450	$	—	$	—	$	233,450	U.S. Treasury securities	$	82,387	$	—	$	—	$	82,387
U.S. Agency securities	U.S. Agency securities	—		3		—		3		U.S. Agency securities	—		2		—		2

Corporate debt and other obligations	Corporate debt and other obligations	—		4,867		—		4,867		Corporate debt and other obligations	—		208		—		208

Convertible bonds	Convertible bonds	—		5,900		—		5,900		Convertible bonds	—		13,732		—		13,732
Corporate equities	Corporate equities	10,431		—		—		10,431		Corporate equities	14,328		—		—		14,328

Securities sold but not yet purchased, at fair value	Securities sold but not yet purchased, at fair value	243,881		10,771		—		254,652		Securities sold but not yet purchased, at fair value	96,715		13,942		—		110,657

Derivative contracts:	Derivative contracts:									Derivative contracts:
Futures	Futures	371		—		—		371		Futures	51		—		—		51

TBAs	TBAs	—		3		—		3		TBAs	—		19		—		19

Derivative contracts, total	Derivative contracts, total	371		3		—		374		Derivative contracts, total	51		19		—		70
Total	Total	$	244,252	$	10,774	$	—	$	255,026	Total	$	96,766	$	13,961	$	—	$	110,727

(1) Included in other assets on the condensed consolidated balance sheet.

2220


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Assets and liabilities measured at fair value on a recurring basis as of December 31, ~~2021:~~2022:


(Expressed in thousands)	(Expressed in thousands)									(Expressed in thousands)
		Fair Value Measurements as of December 31, 2021									Fair Value Measurements as of December 31, 2022
		Level 1		Level 2		Level 3		Total			Level 1		Level 2		Level 3		Total
Assets	Assets									Assets

Deposits with clearing organizations	Deposits with clearing organizations	$	29,083	$	—	$	—	$	29,083	Deposits with clearing organizations	$	24,937	$	—	$	—	$	24,937
Securities owned:	Securities owned:									Securities owned:
U.S. Treasury securities	U.S. Treasury securities	505,875		—		—		505,875		U.S. Treasury securities	362,815		—		—		362,815
U.S. Agency securities	U.S. Agency securities	—		5,622		—		5,622		U.S. Agency securities	—		6,012		—		6,012
Sovereign obligations	Sovereign obligations	—		1,494		—		1,494		Sovereign obligations	—		9,502		—		9,502
Corporate debt and other obligations	Corporate debt and other obligations	—		8,111		—		8,111		Corporate debt and other obligations	—		9,844		—		9,844
Mortgage and other asset-backed securities	Mortgage and other asset-backed securities	—		3,889		—		3,889		Mortgage and other asset-backed securities	—		1,882		—		1,882
Municipal obligations	Municipal obligations	—		18,520		—		18,520		Municipal obligations	—		30,126		—		30,126
Convertible bonds	Convertible bonds	—		13,778		—		13,778		Convertible bonds	—		21,800		—		21,800
Corporate equities	Corporate equities	45,380		—		—		45,380		Corporate equities	24,837		—		—		24,837
Money markets	Money markets	31		—		—		31		Money markets	—		—		—		—
Auction rate securities	Auction rate securities	—		—		31,804		31,804		Auction rate securities	—		—		31,776		31,776
Securities owned, at fair value	Securities owned, at fair value	551,286		51,414		31,804		634,504		Securities owned, at fair value	387,652		79,166		31,776		498,594
Investments (1)	Investments (1)	—		12,970		—		12,970		Investments (1)	—		7,068		—		7,068

Derivative contracts:	Derivative contracts:									Derivative contracts:
TBAs	TBAs	—		92		—		92		TBAs	—		1,762		—		1,762

Total	Total	$	580,369	$	64,476	$	31,804	$	676,649	Total	$	412,589	$	87,996	$	31,776	$	532,361
Liabilities	Liabilities									Liabilities
Securities sold but not yet purchased:	Securities sold but not yet purchased:									Securities sold but not yet purchased:
U.S. Treasury securities	U.S. Treasury securities	$	42,298	$	—	$	—	$	42,298	U.S. Treasury securities	$	25,006	$	—	$	—	$	25,006
U.S. Agency securities	U.S. Agency securities	—		4		—		4		U.S. Agency securities	—		3		—		3

Corporate debt and other obligations	Corporate debt and other obligations	—		2,515		—		2,515		Corporate debt and other obligations	—		2,905		—		2,905

Convertible bonds	Convertible bonds	—		8,462		—		8,462		Convertible bonds	—		4,428		—		4,428
Corporate equities	Corporate equities	18,679		—		—		18,679		Corporate equities	11,378		—		—		11,378

Securities sold but not yet purchased, at fair value	Securities sold but not yet purchased, at fair value	60,977		10,981		—		71,958		Securities sold but not yet purchased, at fair value	36,384		16,384		—		52,768

Derivative contracts:	Derivative contracts:									Derivative contracts:
Futures	Futures	287		—		—		287		Futures	44		—		—		44

TBAs	TBAs	—		81		—		81		TBAs	—		1,761		—		1,761

Derivative contracts, total	Derivative contracts, total	287		81		—		368		Derivative contracts, total	44		1,761		—		1,805
Total	Total	$	61,264	$	11,062	$	—	$	72,326	Total	$	36,428	$	18,145	$	—	$	54,573

(1) Included in other assets on the condensed consolidated balance sheet.

2321


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

The following tables present changes in Level 3 assets and liabilities measured at fair value on a recurring basis for the three ~~and six~~ months ended ~~June 30, 2022~~March 31, 2023 and ~~2021:~~2022:

(Expressed in thousands)
Level 3 Assets and Liabilities
For the Three Months Ended June 30, 2022
Total Realized
Beginning and Unrealized Purchases Sales and Transfers Ending
Balance Losses and Issuances Settlements In (Out) Balance
Assets
Auction rate securities (1)
$ 31,804 $ (27) $ 200 $ — $ — $ 31,977

~~(1) Represents auction rate securities that failed in the auction rate market.~~


(Expressed in thousands)	(Expressed in thousands)													(Expressed in thousands)
		Level 3 Assets and Liabilities													Level 3 Assets and Liabilities
		For the Three Months Ended June 30, 2021													For the Three Months Ended March 31, 2023
				Total Realized													Total Realized
		Beginning		and Unrealized		Purchases		Sales and		Transfers		Ending			Beginning		and Unrealized		Purchases		Sales and		Transfers		Ending
		Balance		Gains (Losses)(3)(4)		and Issuances		Settlements		In (Out)		Balance			Balance		Losses		and Issuances		Settlements		In (Out)		Balance
Assets	Assets													Assets
Auction rate securities (1)	Auction rate securities (1)	$	31,470	$	2	$	—	$	(50)	$	—	$	31,422	Auction rate securities (1)	$	31,776	$	—	$	—	$	—	$	—	$	31,776

Liabilities	Liabilities													Liabilities
ARS Purchase Commitments (2)	ARS Purchase Commitments (2)	65		(1)		—		—		—		66		ARS Purchase Commitments (2)	—		—		—		—		—		—

(1) Represents auction rate securities that failed in the auction rate market.

(2) Represents the difference in principal and fair value for auction rate securities purchase commitments outstanding at the end of the period.

~~(3) Included in principal transactions in the condensed consolidated income statement.~~

~~(4) Unrealized gains are attributable to assets or liabilities that are still held at the reporting date.~~

Level 3 Assets and Liabilities
For the Six Months Ended June 30, 2022
Total Realized
Beginning and Unrealized Purchases Sales and Transfers Ending
Balance Losses and Issuances Settlements In (Out) Balance
Assets
Auction rate securities (1)
$ 31,804 $ (27) $ 200 $ — $ — $ 31,977

~~1) Represents auction rate securities that failed in the auction rate market.~~


(Expressed in thousands)														(Expressed in thousands)
		Level 3 Assets and Liabilities													Level 3 Assets and Liabilities
		For the Six Months Ended June 30, 2021													For the Three Months Ended March 31, 2022
				Total Realized													Total Realized
		Beginning		and Unrealized		Purchases		Sales and		Transfers		Ending			Beginning		and Unrealized		Purchases		Sales and		Transfers		Ending
		Balance		Losses(3)(4)		and Issuances		Settlements		In (Out)		Balance			Balance		Losses		and Issuances		Settlements		In (Out)		Balance
Assets	Assets													Assets
Auction rate securities (1)	Auction rate securities (1)	$	30,701	$	(129)	$	1,875	$	(1,025)	$	—	$	31,422	Auction rate securities (1)	$	31,804	$	—	$	—	$	—	$	—	$	31,804

Liabilities	Liabilities													Liabilities
ARS Purchase Commitments (2)	ARS Purchase Commitments (2)	195		(1)		—		(130)		—		66		ARS Purchase Commitments (2)	—		—		—		—		—		—

(1) Represents auction rate securities that failed in the auction rate market.

(2) Represents the difference in principal and fair value for auction rate securities purchase commitments outstanding at the end of the period.

~~(3) Included in principal transactions in the condensed consolidated income statement.~~

~~(4) Unrealized losses are attributable to assets or liabilities that are still held at the reporting date.~~


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Financial Instruments Not Measured at Fair Value

The table below presents the carrying value, fair value and fair value hierarchy category of certain financial instruments that are not measured at fair value on the condensed consolidated balance sheets. The table below excludes non-financial assets and liabilities (e.g., furniture, equipment and leasehold improvements, and accrued compensation).

The carrying value of financial instruments not measured at fair value categorized in the fair value hierarchy as Level 1 or Level 2 (e.g., cash and receivables from customers) approximates fair value because of the relatively short-term nature of the underlying assets. The fair value of the Company's senior secured notes, categorized in Level 2 of the fair value hierarchy, is based on quoted prices from the market in which the notes trade.

~~Assets and liabilities not measured at fair value as of June 30, 2022:~~

(Expressed in thousands) Fair Value Measurement: Assets
Carrying Value Level 1 Level 2 Level 3 Total
Cash $ 36,606 $ 36,606 $ — $ — $ 36,606
Restricted cash 127,875 127,875 — — 127,875
Deposits with clearing organization 58,379 58,379 — — 58,379
Receivable from brokers, dealers and clearing organizations:
Securities borrowed 79,038 — 79,038 — 79,038
Receivables from brokers 42,255 — 42,255 — 42,255
Securities failed to deliver 26,705 — 26,705 — 26,705
Clearing organizations 19,355 — 19,355 — 19,355
Other 548 — 548 — 548
167,901 — 167,901 — 167,901
Receivable from customers 1,288,079 — 1,288,079 — 1,288,079
Notes receivable, net 59,099 — 59,099 — 59,099
Investments (1)
78,246 — 78,246 — 78,246

~~(1) Included in other assets on the condensed consolidated balance sheet.~~

(Expressed in thousands) Fair Value Measurement: Liabilities
Carrying Value Level 1 Level 2 Level 3 Total
Drafts payable $ 10,020 $ 10,020 $ — $ — $ 10,020
Bank call loans $ 177,300 $ — $ 177,300 $ — $ 177,300
Payables to brokers, dealers and clearing organizations:
Securities loaned 281,407 — 281,407 — 281,407
Payable to brokers 3,357 — 3,357 — 3,357
Securities failed to receive 50,028 — 50,028 — 50,028
Other 53,304 — 53,304 — 53,304
388,096 — 388,096 — 388,096
Payables to customers 419,315 — 419,315 — 419,315
Securities sold under agreements to repurchase 170,968 — 170,968 — 170,968
Senior secured notes 125,000 — 125,213 — 125,213

2522


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Assets and liabilities not measured at fair value as of March 31, 2023:


(Expressed in thousands)			Fair Value Measurement: Assets
	Carrying Value		Level 1		Level 2		Level 3		Total
Cash	$	30,320	$	30,320	$	—	$	—	$	30,320
Restricted cash	25,581		25,581		—		—		25,581
Deposits with clearing organization	44,094		44,094		—		—		44,094
Receivable from brokers, dealers and clearing organizations:
Securities borrowed	256,508		—		256,508		—		256,508
Receivables from brokers	72,942		—		72,942		—		72,942
Securities failed to deliver	12,488		—		12,488		—		12,488
Clearing organizations and other	19,099		—		19,099		—		19,099

	361,037		—		361,037		—		361,037
Receivable from customers	1,054,316		—		1,054,316		—		1,054,316

Notes receivable, net	63,649		—		63,649		—		63,649
Investments (1)	83,302		—		83,302		—		83,302

(1) Included in other assets on the condensed consolidated balance sheet.


(Expressed in thousands)			Fair Value Measurement: Liabilities
	Carrying Value		Level 1		Level 2		Level 3		Total
Drafts payable	$	18,024	$	18,024	$	—	$	—	$	18,024
Bank call loans	$	19,300	$	—	$	19,300	$	—	$	19,300
Payables to brokers, dealers and clearing organizations:
Securities loaned	368,101		—		368,101		—		368,101
Payable to brokers	226		—		226		—		226
Securities failed to receive	10,105		—		10,105		—		10,105
Clearing organization and other	257,487		—		257,487		—		257,487
	635,919		—		635,919		—		635,919
Payables to customers	458,588		—		458,588		—		458,588
Securities sold under agreements to repurchase	280,436		—		280,436		—		280,436
Senior secured notes	113,050		—		105,986		—		105,986

Assets and liabilities not measured at fair value as of December 31, ~~2021:~~2022:

(Expressed in thousands) Fair Value Measurement: Assets
Carrying Value Level 1 Level 2 Level 3 Total
Cash $ 213,759 $ 213,759 $ — $ — $ 213,759
Restricted cash 127,765 127,765 — — 127,765
Deposits with clearing organization 37,885 37,885 — — 37,885
Receivable from brokers, dealers and clearing organizations:
Securities borrowed 99,752 — 99,752 — 99,752
Receivables from brokers 39,716 — 39,716 — 39,716
Securities failed to deliver 9,212 — 9,212 — 9,212
Clearing organizations 19,518 — 19,518 — 19,518
Other 1,693 — 1,693 — 1,693
169,891 — 169,891 — 169,891
Receivable from customers 1,221,450 — 1,221,450 — 1,221,450
Securities purchased under agreements to resell 935 — 935 — 935
Notes receivable, net 53,983 — 53,983 — 53,983
Investments (1)
99,169 — 99,169 — 99,169


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)


(Expressed in thousands)			Fair Value Measurement: Assets
	Carrying Value		Level 1		Level 2		Level 3		Total
Cash	$	112,433	$	112,433	$	—	$	—	$	112,433
Restricted cash	25,534		25,534		—		—		25,534
Deposits with clearing organization	52,754		52,754		—		—		52,754
Receivable from brokers, dealers and clearing organizations:
Securities borrowed	127,817		—		127,817		—		127,817
Receivables from brokers	49,125		—		49,125		—		49,125
Securities failed to deliver	9,099		—		9,099		—		9,099
Clearing organizations	20,035		—		20,035		—		20,035
Other	—		—		—		—		—
	206,076		—		206,076		—		206,076
Receivable from customers	1,202,764		—		1,202,764		—		1,202,764
Securities purchased under agreements to resell	—		—		—		—		—
Notes receivable, net	57,495		—		57,495		—		57,495
Investments (1)	79,322		—		79,322		—		79,322

(1) Included in other assets on the condensed consolidated balance sheet.


(Expressed in thousands)	(Expressed in thousands)			Fair Value Measurement: Liabilities								(Expressed in thousands)			Fair Value Measurement: Liabilities
		Carrying Value		Level 1		Level 2		Level 3		Total			Carrying Value		Level 1		Level 2		Level 3		Total

Bank call loans	Bank call loans	$	69,500	$	—	$	69,500	$	—	$	69,500	Bank call loans	$	—	$	—	$	—	$	—	$	—
Payables to brokers, dealers and clearing organizations:	Payables to brokers, dealers and clearing organizations:											Payables to brokers, dealers and clearing organizations:
Securities loaned	Securities loaned	244,223		—		244,223		—		244,223		Securities loaned	320,843		—		320,843		—		320,843
Payable to brokers	Payable to brokers	2,077		—		2,077		—		2,077		Payable to brokers	123		—		123		—		123
Securities failed to receive	Securities failed to receive	6,457		—		6,457		—		6,457		Securities failed to receive	62,646		—		62,646		—		62,646
Other	Other	169,013		—		169,013		—		169,013		Other	166,350		—		166,350		—		166,350
		421,770		—		421,770		—		421,770			549,962		—		549,962		—		549,962
Payables to customers	Payables to customers	456,958		—		456,958		—		456,958		Payables to customers	456,475		—		456,475		—		456,475
Securities sold under agreements to repurchase	Securities sold under agreements to repurchase	277,322		—		277,322		—		277,322		Securities sold under agreements to repurchase	161,009		—		161,009		—		161,009
Senior secured notes	Senior secured notes	125,000		—		131,094		—		131,094		Senior secured notes	114,050		—		113,233		—		113,233

Fair Value Option

The Company elected the fair value option for securities sold under agreements to repurchase ("repurchase agreements") and securities purchased under agreements to resell ("reverse repurchase agreements") that do not settle overnight or have an open settlement date. The Company has elected the fair value option for these instruments to reflect more accurately market and economic events in its earnings and to mitigate a potential mismatch in earnings caused by using different measurement attributes (i.e. fair value versus carrying value) for certain assets and liabilities. As of ~~June 30, 2022,~~March 31, 2023, the Company ~~did not have any~~had no repurchase agreements and reverse repurchase agreements that do not settle overnight or have an open settlement date.

Derivative Instruments and Hedging Activities

The Company transacts, on a limited basis, in exchange traded and over-the-counter derivatives for both asset and liability management as well as for trading and investment purposes. Risks managed using derivative instruments include interest rate risk and, to a lesser extent, foreign exchange risk. All derivative instruments are measured at fair value and are recognized as either assets or liabilities on the condensed consolidated balance sheet.

Foreign exchange hedges


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

risk and, to a lesser extent, foreign exchange risk. All derivative instruments are measured at fair value and are recognized as either assets or liabilities on the condensed consolidated balance sheet.

~~Foreign exchange hedges~~

From time to time, the Company also utilizes forward and options contracts to hedge the foreign currency risk associated with compensation obligations to Oppenheimer Israel (OPCO) Ltd. employees denominated in New Israeli Shekel ("NIS"). Such hedges have not been designated as accounting hedges. Unrealized gains and losses on foreign exchange forward contracts are recorded in other assets or other liabilities on the condensed consolidated balance sheet and other income in the condensed consolidated income statement.

Derivatives used for trading and investment purposes

Futures contracts represent commitments to purchase or sell securities or other commodities at a future date and at a specified price. Market risk exists with respect to these instruments. Notional or contractual amounts are used to express the volume of these transactions and do not represent the amounts potentially subject to market risk. The Company uses futures contracts, including U.S. Treasury notes, Federal Funds, General Collateral futures, and Eurodollar contracts primarily as an economic hedge of interest rate risk associated with government trading activities. Unrealized gains and losses on futures contracts are recorded on the condensed consolidated balance sheet in payable to brokers, dealers and clearing organizations and in the condensed consolidated income statement as principal transactions revenue, net.

To-be-announced securities

The Company also transacts in pass-through mortgage-backed securities eligible to be sold in the TBA market as economic hedges against mortgage-backed securities that it owns or has sold but not yet purchased. TBAs provide for the forward or delayed delivery of the underlying instrument with settlement up to 180 days. The contractual or notional amounts related to these financial instruments reflect the volume of activity and do not reflect the amounts at risk. Net unrealized gains and losses on TBAs are recorded on the condensed consolidated balance sheet in receivable from brokers, dealers and clearing organizations or payable to brokers, dealers and clearing organizations and in the condensed consolidated income statement as principal transactions revenue, net.

The notional amounts and fair values of the Company's derivatives as of ~~June 30, 2022~~March 31, 2023 and December 31, ~~2021~~2022 by product were as follows:


(Expressed in thousands)	(Expressed in thousands)						(Expressed in thousands)
		Fair Value of Derivative Instruments as of June 30, 2022						Fair Value of Derivative Instruments as of March 31, 2023
		Description	Notional		Fair Value			Description	Notional		Fair Value
Assets:	Assets:						Assets:
Derivatives not designated as hedging instruments (1)	Derivatives not designated as hedging instruments (1)						Derivatives not designated as hedging instruments (1)
Other contracts	Other contracts	TBAs	$	3,842	$	—	Other contracts	TBAs	$	1,227	$	21
		Forward reverse repurchase agreements	123,350		—			Forward reverse repurchase agreements	15,000		—

			$	127,192	$	—			$	16,227	$	21
Liabilities:	Liabilities:						Liabilities:
Derivatives not designated as hedging instruments (1)	Derivatives not designated as hedging instruments (1)						Derivatives not designated as hedging instruments (1)
Commodity contracts	Commodity contracts	Futures	$	1,175,600	$	371	Commodity contracts	Futures	$	3,880,000	$	51

Other contracts	Other contracts	TBAs	3,842		3		Other contracts	TBAs	1,277		19

			$	1,179,442	$	374			$	3,881,277	$	70

(1)See "Derivative Instruments and Hedging Activities" above for a description of derivative financial instruments. Such derivative instruments are not subject to master netting agreements, thus the related amounts are not offset.

2725


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)


(Expressed in thousands)	(Expressed in thousands)						(Expressed in thousands)
		Fair Value of Derivative Instruments as of December 31, 2021						Fair Value of Derivative Instruments as of December 31, 2022
		Description	Notional		Fair Value			Description	Notional		Fair Value
Assets:	Assets:						Assets:
Derivatives not designated as hedging instruments (1)	Derivatives not designated as hedging instruments (1)						Derivatives not designated as hedging instruments (1)
Other contracts	Other contracts	TBAs	$	14,300	$	92	Other contracts	TBAs	$	1,775	$	1,762
								Forward reverse repurchase agreements	15,000		—
								Other	275		$	—
			$	14,300	$	92			$	17,050	$	1,762
Liabilities:	Liabilities:						Liabilities:
Derivatives not designated as hedging instruments (1)	Derivatives not designated as hedging instruments (1)						Derivatives not designated as hedging instruments (1)
Commodity contracts	Commodity contracts	Futures	$	3,520,000	$	287	Commodity contracts	Futures	$	1,912,500	$	44

Other contracts	Other contracts	TBAs	14,300		81		Other contracts	TBAs	1,775		1,761

			$	3,534,300	$	368			$	1,914,275	$	1,805

The following table presents the location and fair value amounts of the Company's derivative instruments and their effect in the condensed consolidated income statements for the three ~~and six~~ months ended ~~June 30, 2022~~March 31, 2023 and ~~2021:~~2022:

(Expressed in thousands)

The Effect of Derivative Instruments in the Income Statement

For the Three Months Ended ~~June 30, 2022~~March 31, 2023

Recognized in Income on Derivatives
(pre-tax)

Types

Description

Location

Net Gain/(Loss)

Commodity contracts

Futures

Principal transactions revenue, net

~~1,328~~210

Other contracts

Foreign exchange forward contracts

Other revenue

~~(20)~~(1)

Other contracts

TBAs

Principal transactions revenue, net

~~(6)~~2

~~1,302~~211

(Expressed in thousands)

The Effect of Derivative Instruments in the Income Statement

For the Three Months Ended ~~June 30, 2021~~

Recognized in Income on Derivatives
(pre-tax)

~~Types~~

~~Description~~

~~Location~~

~~Net Gain/(Loss)~~

~~Commodity contracts~~

~~Futures~~

~~Principal transactions revenue, net~~

~~(525)~~

~~Other contracts~~

~~Foreign exchange forward contracts~~

~~Other revenue~~

~~(8)~~

~~TBAs~~

~~Principal transactions revenue, net~~

~~Purchase commitments~~

~~Principal transactions revenue, net~~

~~(490)~~

~~ARS purchase commitments~~

~~Principal transactions revenue, net~~

~~(1)~~

~~(1,010)~~


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

~~The Effect of Derivative Instruments in the Income Statement~~

~~For the Six Months Ended June 30,~~March 31, 2022

Recognized in Income on Derivatives
(pre-tax)

Types

Description

Location

Net ~~Gain/(Loss)~~Gain

Commodity contracts

Futures

Principal transactions revenue, net

~~3,519~~2,191

Other contracts

~~Foreign exchange forward contracts~~

~~Other revenue~~

~~(20)~~

TBAs

Principal transactions revenue, net

5663

~~3,555~~

~~(Expressed in thousands)~~

~~The Effect of Derivative Instruments in the Income Statement~~

~~For the Six Months Ended June 30, 2021~~

Recognized in Income on Derivatives
(pre-tax)

~~Types~~

~~Description~~

~~Location~~

~~Net Gain/(Loss)~~

~~Commodity contracts~~

~~Futures~~

~~Principal transactions revenue~~

~~495~~

~~Other contracts~~

~~Foreign exchange forward contracts~~

~~Other revenue~~

~~(8)~~

~~TBAs~~

~~Principal transactions revenue~~

~~Purchase commitments~~

~~Principal transactions revenue~~

~~(490)~~

~~ARS purchase commitments~~

~~Principal transactions revenue~~

~~(1)~~

472,254

9. Collateralized transactions

The Company enters into collateralized borrowing and lending transactions in order to meet customers' needs and earn interest rate spreads, obtain securities for settlement and finance trading inventory positions. Under these transactions, the Company either receives or provides collateral, including U.S. Government and Agency, asset-backed, corporate debt, equity, and non-U.S. Government and Agency securities.


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

The Company obtains short-term borrowings primarily through bank call loans. Bank call loans are generally payable on demand and bear interest at various rates. As of ~~June 30, 2022,~~March 31, 2023, the outstanding balance of bank call loans was ~~$177.3~~$19.3 million ~~($69.5 million~~(zero as of December 31, ~~2021)~~2022). Such loans with commercial banks were collateralized by the Company's securities and customer securities with market values of approximately ~~$55.9~~$23.9 million and ~~$145.0~~$1.0 million, respectively.

As of ~~June 30, 2022,~~March 31, 2023, the Company had approximately ~~$1.7~~$1.6 billion of customer securities under customer margin loans that are available to be pledged, of which the Company has re-pledged approximately ~~$236.3~~$256.1 million under securities loan agreements.

As of ~~June 30, 2022,~~March 31, 2023, the Company had pledged ~~$518.5~~$271.5 million of customer securities directly with the Options Clearing Corporation to secure obligations and margin requirements under option contracts written by customers.

As of ~~June 30, 2022,~~March 31, 2023, the Company had no outstanding letters of credit.

The Company enters into reverse repurchase agreements, repurchase agreements, securities borrowed and securities loaned transactions in order to, among other things, acquire securities to cover short positions and settle other securities obligations, so as to accommodate customers' needs and to finance the Company's inventory positions. Except as described below, repurchase and reverse repurchase agreements, principally involving U.S. Government and Agency securities, are carried at amounts at which the securities subsequently will be resold or reacquired as specified in the respective agreements and include accrued interest.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Repurchase agreements and reverse repurchase agreements are presented on a net-by-counterparty basis, when the repurchase agreements and reverse repurchase agreements are executed with the same counterparty, have the same explicit settlement date, are executed in accordance with a master netting arrangement, the securities underlying the repurchase agreements and reverse repurchase agreements exist in "book entry" form and certain other requirements are met.

The following table presents a disaggregation of the gross obligation by the class of collateral pledged and the remaining contractual maturity of the repurchase agreements and securities loaned transactions as of ~~June 30, 2022:~~March 31, 2023:


(Expressed in thousands)
	Overnight and Open
Repurchase agreements:
U.S. Government and Agency securities	$	~~411,713~~310,490
Securities loaned:
Equity securities	~~281,407~~368,101
Gross amount of recognized liabilities for repurchase agreements and securities loaned	$	~~693,120~~678,591

The following tables present the gross amounts and the offsetting amounts of reverse repurchase agreements, repurchase agreements, securities borrowed and securities loaned transactions as of ~~June 30, 2022~~March 31, 2023 and December 31, ~~2021:~~2022:


As of June 30, 2022
As of March 31, 2023														As of March 31, 2023
(Expressed in thousands)	(Expressed in thousands)							Gross Amounts Not Offset on the Balance Sheet						(Expressed in thousands)							Gross Amounts Not Offset on the Balance Sheet
		Gross Amounts of Recognized Assets		Gross Amounts Offset on the Balance Sheet		Net Amounts of Assets Presented on the Balance Sheet		Financial Instruments		Cash Collateral Received		Net Amount			Gross Amounts of Recognized Assets		Gross Amounts Offset on the Balance Sheet		Net Amounts of Assets Presented on the Balance Sheet		Financial Instruments		Cash Collateral Received		Net Amount
Reverse repurchase agreements	Reverse repurchase agreements	$	240,745	$	(240,745)	$	—	$	—	$	—	$	—	Reverse repurchase agreements	$	30,054	$	(30,054)	$	—	$	—	$	—	$	—
Securities borrowed (1)	Securities borrowed (1)	79,038		—		79,038		(78,758)		—		280		Securities borrowed (1)	256,508		—		256,508		(254,639)		—		1,869
Total	Total	$	319,783	$	(240,745)	$	79,038	$	(78,758)	$	—	$	280	Total	$	286,562	$	(30,054)	$	256,508	$	(254,639)	$	—	$	1,869

(1)Included in receivable from brokers, dealers and clearing organizations on the condensed consolidated balance sheet.

Gross Amounts Not Offset
on the Balance Sheet
Gross
Amounts of
Recognized
Liabilities Gross
Amounts
Offset on the Balance Sheet Net Amounts
of Liabilities
Presented on
the Balance
Sheet Financial
Instruments Cash
Collateral
Pledged Net Amount
Repurchase agreements $ 411,713 $ (240,745) $ 170,968 $ (170,691) $ — $ 277
Securities loaned (2)
281,407 — 281,407 (266,801) — 14,606
Total $ 693,120 $ (240,745) $ 452,375 $ (437,492) $ — $ 14,883

~~(2)Included in payable to brokers, dealers and clearing organizations on the condensed consolidated balance sheet.~~

3027


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)


							Gross Amounts Not Offset on the Balance Sheet
	Gross Amounts of Recognized Liabilities		Gross Amounts Offset on the Balance Sheet		Net Amounts of Liabilities Presented on the Balance Sheet		Financial Instruments		Cash Collateral Pledged		Net Amount
Repurchase agreements	$	310,490	$	(30,054)	$	280,436	$	(278,404)	$	—	$	2,032
Securities loaned (2)	368,101		—		368,101		(363,484)		—		4,617
Total	$	678,591	$	(30,054)	$	648,537	$	(641,888)	$	—	$	6,649

(2)Included in payable to brokers, dealers and clearing organizations on the condensed consolidated balance sheet.


As of December 31, 2021
As of December 31, 2022														As of December 31, 2022
(Expressed in thousands)	(Expressed in thousands)							Gross Amounts Not Offset on the Balance Sheet						(Expressed in thousands)							Gross Amounts Not Offset on the Balance Sheet
		Gross Amounts of Recognized Assets		Gross Amounts Offset on the Balance Sheet		Net Amounts of Assets Presented on the Balance Sheet		Financial Instruments		Cash Collateral Received		Net Amount			Gross Amounts of Recognized Assets		Gross Amounts Offset on the Balance Sheet		Net Amounts of Assets Presented on the Balance Sheet		Financial Instruments		Cash Collateral Received		Net Amount
Reverse repurchase agreements	Reverse repurchase agreements	$	30,406	$	(29,471)	$	935	$	—	$	—	$	935	Reverse repurchase agreements	$	28,012	$	(28,012)	$	—	$	—	$	—	$	—
Securities borrowed (1)	Securities borrowed (1)	99,752		—		99,752		(96,929)		—		2,823		Securities borrowed (1)	127,817		—		127,817		(127,365)		—		452
Total	Total	$	130,158	$	(29,471)	$	100,687	$	(96,929)	$	—	$	3,758	Total	$	155,829	$	(28,012)	$	127,817	$	(127,365)	$	—	$	452

(1)Included in receivable from brokers, dealers and clearing organizations on the condensed consolidated balance sheet.

Gross Amounts Not Offset
on the Balance Sheet
Gross
Amounts of
Recognized
Liabilities Gross
Amounts
Offset on the Balance Sheet Net Amounts
of Liabilities
Presented on
the Balance
Sheet Financial
Instruments Cash
Collateral
Pledged Net Amount
Repurchase agreements $ 306,793 $ (29,471) $ 277,322 $ (276,992) $ — $ 330
Securities loaned (2)
244,223 — 244,223 (236,597) — 7,626
Total $ 551,016 $ (29,471) $ 521,545 $ (513,589) $ — $ 7,956


							Gross Amounts Not Offset on the Balance Sheet
	Gross Amounts of Recognized Liabilities		Gross Amounts Offset on the Balance Sheet		Net Amounts of Liabilities Presented on the Balance Sheet		Financial Instruments		Cash Collateral Pledged		Net Amount
Repurchase agreements	$	189,021	$	(28,012)	$	161,009	$	(157,981)	$	—	$	3,028
Securities loaned (2)	320,843		—		320,843		(308,535)		—		12,308
Total	$	509,864	$	(28,012)	$	481,852	$	(466,516)	$	—	$	15,336

(2)Included in payable to brokers, dealers and clearing organizations on the condensed consolidated balance sheet.

The Company ~~elected~~elects the fair value option for those repurchase agreements and reverse repurchase agreements that do not settle overnight or have an open settlement date. As of ~~June 30, 2022,~~March 31, 2023, the Company did not have any repurchase agreements orand reverse repurchase agreements that do not settle overnight or have an open settlement date.

The Company receives collateral in connection with securities borrowed and reverse repurchase agreement transactions and customer margin loans. Under many agreements, the Company is permitted to sell or re-pledge the securities received (e.g., use the securities to enter into securities lending transactions, or deliver to counterparties to cover short positions). As of ~~June 30, 2022,~~March 31, 2023, the fair value of securities received as collateral under securities borrowed transactions and reverse repurchase agreements was ~~$76.1~~$255.4 million ($~~96.4~~124.1 million as of December 31, ~~2021)~~2022) and ~~$240.9~~$30.1 million ($~~307.3~~28.0 million as of December 31, ~~2021)~~2022), respectively, of which the Company has sold and re-pledged approximately ~~$31.6~~$106.3 million ($~~29.4~~39.4 million as of December 31, ~~2021)~~2022) under securities loaned transactions and ~~$240.9~~$30.1 million under repurchase agreements ($~~307.3~~28.0 million as of December 31, ~~2021)~~2022).

The Company pledges certain of its securities owned for securities lending and repurchase agreements and to collateralize bank call loan transactions. The carrying value of pledged securities owned that can be sold or re-pledged by the counterparty was ~~$316.6~~


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

$337.8 million, as presented on the face of the condensed consolidated balance sheet as of ~~June 30, 2022~~March 31, 2023 ($~~266.4~~175.7 million as of December 31, ~~2021)~~2022).

The Company manages credit exposure arising from repurchase and reverse repurchase agreements by, in appropriate circumstances, entering into master netting agreements and collateral arrangements with counterparties that provide the Company, in the event of a customer default, the right to liquidate securities and the right to offset a counterparty's rights and obligations. The Company manages market risk of repurchase agreements and securities loaned by monitoring the market value of collateral held and the market value of securities receivable from others. It is the Company's policy to request and obtain additional collateral when exposure to loss exists. In the event the counterparty is unable to meet its contractual obligation to return the securities, the Company may be exposed to off-balance sheet risk of acquiring securities at prevailing market prices.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Credit Concentrations

Credit concentrations may arise from trading, investing, underwriting and financing activities and may be impacted by changes in economic, industry or political factors. In the normal course of business, the Company may be exposed to credit risk in the event customers, counterparties including other brokers and dealers, issuers, banks, depositories or clearing organizations are unable to fulfill their contractual obligations. The Company seeks to mitigate these risks by actively monitoring exposures and obtaining collateral as deemed appropriate. Included in receivable from brokers, dealers and clearing organizations as of ~~June 30, 2022~~March 31, 2023 were receivables from 3five major U.S. broker-dealers totaling approximately ~~$61.7~~$192.1 million.

The Company is obligated to settle transactions with brokers and other financial institutions even if its clients fail to meet their obligations to the Company. Clients are required to complete their transactions on the settlement date, generally one to two business days after the trade date. If clients do not fulfill their contractual obligations, the Company may incur losses. The Company has clearing/participating arrangements with the National Securities Clearing Corporation, the Fixed Income Clearing Corporation ("FICC"), R.J. O'Brien & Associates (commodities transactions), Mortgage-Backed Securities Division (a division of FICC), and others. With respect to its business in reverse repurchase and repurchase agreements, substantially all open contracts as of ~~June 30, 2022~~March 31, 2023 are with the FICC. In addition, the Company clears its non-U.S. international equities business carried on by Oppenheimer Europe Ltd. through Global Prime Partners, Ltd, a global clearing financial institution located in United Kingdom. The clearing organizations have the right to charge the Company for losses that result from a client's failure to fulfill its contractual obligations. Accordingly, the Company has credit exposures with these clearing brokers. The clearing brokers can re-hypothecate the securities held on behalf of the Company. As the right to charge the Company has no maximum amount and applies to all trades executed through the clearing brokers, the Company believes there is no maximum amount assignable to this right. As of ~~June 30, 2022,~~March 31, 2023, the Company had recorded no liabilities with regard to this right. The Company's policy is to monitor the credit standing of the clearing brokers and banks with which it conducts business.

10. Variable interest entities ("VIEs")

The Company's policy is to consolidate all subsidiaries in which it has a controlling financial interest, as well as any VIEs where the Company is deemed to be the primary beneficiary when it has the power to make the decisions that most significantly affect the economic performance of the VIE and has the obligation to absorb significant losses or the right to receive benefits that could potentially be significant to the VIE.

The Company serves as general partner of hedge funds and private equity funds that were established for the purpose ofproviding alternative investments to both its institutional and qualified retail clients. The Company's investment in andadditional capital commitments to these hedge funds and private equity funds are considered variable interests. TheCompany'sadditionalcapitalcommitmentsaresubjecttocallatalaterdateandarelimitedtotheamountcommitted.

The Company assesses whether it is the primary beneficiary of the hedge funds and private equity funds in which it holds a variable interest in the form of general and limited partner interests. In each instance, the Company has determined that it is not the primary beneficiary and therefore need not consolidate the hedge funds or private equity funds. The subsidiaries' general and limited partnership interests and additional capital commitments represent ~~the Company's~~their maximum exposure to loss. The subsidiaries' general partnership and limited partnership interests are included in other assets on the condensed consolidated balance sheet. As of March 31, 2023, the Company did not have any hedge funds and private equity funds that are VIEs.

~~In addition, the~~


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

The Company serves as general partner of ~~the Sponsor~~Oppenheimer Acquisition LLC I and Oppenheimer Acquisition LLC II (the "Sponsors"). They are sponsors of ~~2 Special Purpose Acquisition Companies, respectively,~~two special purpose acquisition companies, OHAA and Oppenheimer Acquisition Corp. II ~~(together, the~~(the "SPACs”), that are seeking to effect a transaction which could be in the form of a merger, capital stock exchange, asset acquisition, stock purchase, reorganization or similar business combination with one or more businesses. The Sponsors and the SPACs are consolidated ~~VIEs~~VIE's as the Company is the primary beneficiary.

On October 26, 2021, OHAA consummated its $126.5 million IPO. The Company and its employees control OHAA through the Sponsor's ownership of Class A founder shares of OHAA. As a result, both OHAA and ~~such~~the Sponsor are consolidated in the Company’s financial statements.

In addition, OPI was formed in December 2020 and designed to retain and reward talented employees of the Company, primarily in connection with the deployment of Company capital into successful private market investments, and also in connection with the Company's receipt of non-cash compensation from investment banking assignments. OPI is designed to promote alignment of Company, client and employee interests as they relate to profitable investment opportunities. This program acts as an incentive for senior employees to identify attractive private investments for the Company and its clients, and as a retention tool for key employees of the Company. The Company owns the majority voting interest and control of OPI through Oppenheimer Alternative Investment Management (“OAIM”), the managing member of OPI and a subsidiary of OAM. OPI is a consolidated VIE as the Company is the primary beneficiary.

The following table sets forth the total assets and liabilities of VIEs consolidated on our condensed consolidated balance sheet:


(Expressed in thousands)
	As of March 31,
	2023		2022
Asset
Cash and cash equivalents	$	5,810	$	1,633
Restricted Cash	25,581		127,781
Other Assets	730		680
Total Assets	$	32,121	$	130,094
Liabilities
Other Liabilities	859		63
Total Liabilities	$	859	$	63

11. Long-term debt


(Expressed in thousands)
Issued	Maturity Date	March 31, 2023		December 31, 2022
5.50% Senior Secured Notes	10/1/2025	$	113,050	$	114,050
Unamortized Debt Issuance Cost		(556)		(616)
		$	112,494	$	113,434

5.50% Senior Secured Notes due 2025 (the "Notes")


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

~~The following table sets forth the total assets and liabilities of VIEs consolidated on our condensed consolidated balance sheet:~~

(Expressed in thousands)
As of June 30,
2022 2021
Asset
  Cash and cash equivalents $ 1,458 $ —
  Restricted Cash 127,875 —
  Other Assets 568 —
       Total Assets $ 129,901 $ —
Liabilities
  Other Liabilities 123 —
       Total Liabilities $ 123 $ —

~~11. Long-term debt~~

(Expressed in thousands)
Issued Maturity Date June 30, 2022 December 31, 2021
5.50% Senior Secured Notes 10/1/2025 $ 125,000 $ 125,000
Unamortized Debt Issuance Cost (800) (926)
$ 124,200 $ 124,074

~~5.50% Senior Secured Notes due 2025 (the "Notes")~~

On September 22, 2020, in a private offering, the Company issued $125.0 million aggregate principal amount of 5.50% Senior Secured Notes due 2025 (the "Unregistered Notes") under an ~~Indenture~~indenture at an issue price of 100% of the principal amount. Interest on the Unregistered Notes is payable semi-annually on April 1st and October 1st. The Company used the net proceeds from the offering of the Unregistered Notes, along with cash on hand, to redeem in full our 6.75% Senior Secured Notes due July 1, 2022 (the "Old Notes") in the principal amount of $150.0 million (the Company held $1.4 million in treasury for a net outstanding amount of $148.6 million), and pay all related fees and expenses in relation thereto.

On November 23, 2020, we completed an exchange offer in which we exchanged 99.8% of the Unregistered Notes for a like principal amount of Notes with identical terms, except that such new ~~notes~~Notes have been registered under the Securities Act of 1933, as amended (the "Securities Act"). We did not receive any proceeds in the exchange offer. The Notes will mature on October 1, 2025 and bear interest at a rate of 5.50% per annum, payable semiannually on April 1st and October 1st, respectively, of each year.

The Parent used the net proceeds from the offering of the Notes, along with cash on hand, to redeem in full its Old Notes, in the principal amount of $150.0 million (the Parent held $1.4 million in treasury for a net outstanding amount of $148.6 million), and pay all related fees and expenses in relation thereto. The cost to issue the Notes was $3.1 million, of which $1.9 million was paid to its subsidiary, Oppenheimer, ~~& Co Inc.,~~ who served as the initial purchaser of the offering, and was eliminated in consolidation. The remaining $1.2 million was capitalized and is amortized over the term of the Notes.

The Company has repurchased and may continue to seek to repurchase its Notes from time to time through, as applicable, tender offers, open market purchases, privately negotiated transactions or otherwise. Such repurchases, if any, will depend on a number of factors, including, but not limited to, the Company’s priorities for the use of cash, price, market and economic conditions, its liquidity requirements, and legal and contractual restrictions. During the first quarter of 2023, the Company repurchased and cancelled $1.0 million aggregate principal amount of its Notes in the open market. As of March 31, 2023, $113.05 million aggregate principal amount of the Notes remain outstanding.

The indenture governing the Notes contains covenants which place restrictions on the incurrence of indebtedness, the payment of dividends, the repurchase of equity, the sale of assets, the issuance of guarantees, mergers and acquisitions and the granting of liens. These covenants are subject to a number of important exceptions and qualifications. These exceptions and qualifications include, among other things, a variety of provisions that are intended to allow the Company to continue to conduct its brokerage operations in the ordinary course of business. In addition, certain of the covenants will be suspended upon the Parent attaining an investment grade debt rating for the Notes from both S&P Global Ratings and Moody’s Investors Service, Inc.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Pursuant to the indenture, the following covenants apply to the Parent and its restricted subsidiaries, but generally do not apply, or apply only in part, to its Regulated Subsidiaries (as defined):

•limitation on indebtedness and issuances of preferred stock, which restricts the Parent’s ability to incur additional indebtedness or to issue preferred stock;

•limitation on restricted payments, which generally restricts the Parent’s ability to declare certain dividends or distributions, repurchase its capital stock or make certain investments;

•limitation on dividends and other payment restrictions affecting restricted subsidiaries or Regulated Subsidiaries, which generally limits the ability of certain of the Parent’s subsidiaries to pay dividends or make other transfers;

•limitation on future Subsidiary Guarantors (as hereinafter defined), which prohibits certain of the Parent’s subsidiaries from guaranteeing its indebtedness or indebtedness of any restricted subsidiary unless the Notes are comparably guaranteed;

•limitation on transactions with shareholders and affiliates, which generally requires transactions among the Parent’s affiliated entities to be conducted on an arm’s-length basis;

•limitation on liens, which generally prohibits the Parent and its restricted subsidiaries from granting liens unless the Notes are comparably secured; and

•limitation on asset sales, which generally prohibits the Parent and certain of its subsidiaries from selling assets or certain securities or property of significant subsidiaries.


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

The indenture also provides for events of default which, if any of them occurs, would permit or require the principal of and accrued interest on the Notes to become or to be declared due and payable. As of ~~June 30, 2022,~~March 31, 2023, the Parent was in compliance with all of its covenants.

The Notes are jointly and severally and fully and unconditionally guaranteed on a senior secured basis by the Subsidiary Guarantors and future subsidiaries are required to guarantee the Notes pursuant to the indenture. The Notes are secured by a first-priority security interest in substantially all of the Parent’s and the Subsidiary Guarantors’ existing and future tangible and intangible assets, subject to certain exceptions and permitted liens.

Interest expense on the Notes for the three ~~and six~~ months ended ~~June 30, 2022~~March 31, 2023 was ~~$1.7 million and $3.4 million, respectively.~~$1.6 million. Interest expense on the Notes for the three ~~and six~~ months ended ~~June 30, 2021~~March 31, 2022 was $1.7 ~~million and $3.4 million, respectively.~~million.

12. Income taxes

The effective income tax rate for the three ~~and six~~ months ended ~~June 30, 2022~~March 31, 2023 was ~~23.5% and 37.1% respectively,~~24.1%, compared with ~~27.8% and 26.7%~~31.2% for the three ~~and six~~ months ended ~~June 30, 2021~~March 31, 2022 and reflects the Company's annual estimate of the statutory federal and state tax rates adjusted for certain discrete items. The effective tax rate for the ~~second~~first quarter of ~~2022~~2023 was ~~negatively~~positively impacted by ~~valuation allowance on the Company's foreign operations whereas the effective tax rate for the second quarter of 2021 was impacted by unfavorable~~favorable permanent items.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

13. ~~Stockholder's~~Stockholders' Equity

The Company's authorized shares ~~authorized consists~~consist of (a) 50,000,000 shares of Preferred Stock, par value $0.001 per share; (b) 50,000,000 shares of Class A Stock, par value $0.001 per share; and (c) 99,665 shares of Class B Stock, par value $0.001 per share. No Preferred Stock has been issued. 99,665 shares of Class B Stock have been issued and are outstanding.

The Class A Stock and the Class B Stock are equal in all respects except that the Class A Stock is non-voting.

The following table reflects changes in the number of shares of Class A Stock outstanding for the periods indicated:


		For the Three Months Ended June 30,		For the Six Months Ended June 30,			For the Three Months Ended March 31,
		2022	2021	2022	2021			2023	2022
Class A Stock outstanding, beginning of period	Class A Stock outstanding, beginning of period	12,156,174	12,586,043	12,447,036	12,381,778	Class A Stock outstanding, beginning of period		10,868,556	12,447,036
Issued pursuant to share-based compensation plans	Issued pursuant to share-based compensation plans	—	6,603	86,451	210,868	Issued pursuant to share-based compensation plans		202,222	86,451
Repurchased and canceled pursuant to the stock buy-back	Repurchased and canceled pursuant to the stock buy-back	(885,230)	—	(1,262,543)	—	Repurchased and canceled pursuant to the stock buy-back		(95,055)	(377,313)
Class A Stock outstanding, end of period	Class A Stock outstanding, end of period	11,270,944	12,592,646	11,270,944	12,592,646	Class A Stock outstanding, end of period		10,975,723	12,156,174

Stock buy-back

On May 15, 2020, the Company announced that its Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 530,000 shares of the Company's Class A Stock, representing approximately 4.2% of its 12,636,523 then issued and outstanding shares of Class A Stock. This authorization supplemented the 98,625 shares that remained authorized and available under the Company's previous share repurchase program for a total of 628,625 shares authorized and available for repurchase at May 15, 2020.

On February 28, 2022, the Company announced that its Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 518,000 shares of the Company's Class A Stock, representing approximately 4.2% of its 12,322,073 then issued and outstanding shares of Class A Stock. This authorization supplemented the 12,407 shares that remained authorized and available under the Company's previous share repurchase program for a total of 530,407 shares authorized and available for repurchase at February 28, 2022.

On May 24, 2022, the Company announced that its Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 550,000 shares of the Company's Class A Stock, representing approximately 4.6% of its 11,863,559 then issued and outstanding shares of Class A Stock. This authorization supplemented the 71,893 shares that remained


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

authorized and available under the Company's previous share repurchase program for a total of 621,893 shares authorized and available for repurchase at May 24, 2022.

On July 29, 2022, the Company's Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 536,500 shares of the Company's Class A Stock, representing approximately 4.8% of its 11,251,930 then issued and outstanding shares of Class A Stock. This authorization supplemented the 4,278 shares that remained authorized and available under the Company's previous share repurchase program for a total of 540,778 shares authorized.

On December 13, 2022, the Company's Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 543,000 shares of the Company's Class A Stock, representing approximately 5.0% of its 10,867,660 then issued and outstanding shares of Class A Stock. This authorization supplemented the 144,034 shares that remained authorized and available under the Company's previous share repurchase program for a total of 687,034 shares authorized.

During the three months ended ~~June 30, 2022,~~March 31, 2023, the Company purchased and canceled an aggregate of ~~885,230~~95,055 shares of Class A Stock for a total consideration of ~~$30.2~~$3.7 million ($~~34.13~~38.79 per share) under this program. During the ~~six~~three months ended ~~June 30,~~March 31, 2022, the Company purchased and canceled an aggregate of ~~1,262,543~~377,313 shares of Class A Stock for a total consideration of ~~$46.4~~$16.2 million ($~~36.73~~42.82 per share) under this program. ~~During the three and six months ended June 30, 2021, the Company did not purchase or cancel any Class A Stock under this program.~~ As of ~~June 30, 2022, 29,278~~March 31, 2023, 591,979 shares remained available to be purchased under the share repurchase program.

The Company repurchases shares from time to time in the open market at the prevailing open market price using cash on hand, in compliance with the applicable rules and regulations of the New York Stock Exchange and federal and state securities laws and the terms of the Company's Notes. All shares purchased will be canceled. The share repurchase program is expected to continue indefinitely. The timing and amounts of any purchases will be based on market conditions and other factors including price, regulatory requirements and capital availability. The share repurchase program does not obligate the Company to repurchase any dollar amount or number of shares of Class A Stock. Depending on market conditions and other factors, these repurchases may be commenced or suspended from time to time without prior notice.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

14. Contingencies

Many aspects of the Company's business involve substantial risks of liability. In the normal course of business, the Company has been named as defendant or co-defendant in various legal actions, including arbitrations, class actions and other litigation, creating substantial exposure and periodic expenses. Certain of the actual or threatened legal matters include claims for substantial compensatory and/or punitive damages or claims for indeterminate amounts of damages. These proceedings arise primarily from securities brokerage, asset management and investment banking activities. The Company is also involved, from time to time, in other reviews, investigations and proceedings (both formal and informal) by governmental and self-regulatory agencies regarding the Company's business, which may result in expenses, adverse judgments, settlements, fines, penalties, injunctions or other relief. The investigations include inquiries from the SEC, the Financial Industry Regulatory Authority ("FINRA") and various state regulators.

The Company accrues for estimated loss contingencies related to legal and regulatory matters within Other Expenses in the consolidated income statement when available information indicates that it is probable a liability had been incurred and the Company can reasonably estimate the amount of that loss. In many proceedings, however, it is inherently difficult to determine whether any loss is probable or even possible or to estimate the amount of any loss. In addition, even where a loss is possible or an exposure to loss exists in excess of the liability already accrued with respect to a previously recognized loss contingency, it is often not possible to reasonably estimate the size of the possible loss or range of loss or possible additional losses or range of additional losses.

For certain legal and regulatory proceedings, the Company cannot reasonably estimate such losses, particularly for proceedings that are in their early stages of development or where plaintiffs seek substantial, indeterminate or special damages. Counsel may be required to review, analyze and resolve numerous issues, including through potentially lengthy discovery and determination of important factual matters, and by addressing novel or unsettled legal questions relevant to the proceedings in question, before the Company can reasonably estimate a loss or range of loss or additional loss for the proceeding. Even after lengthy review


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

and analysis, the Company, in many legal and regulatory proceedings, may not be able to reasonably estimate possible losses or range of ~~loss.~~losses.

For certain other legal and regulatory proceedings, the Company can estimate possible losses, or range of loss in excess of amounts accrued, but does not believe, based on current knowledge and after consultation with counsel, that such losses individually, or in the aggregate, will have a material adverse effect on the Company's ~~condensed~~ consolidated financial statements as a whole.

For legal and regulatory proceedings where there is at least a reasonable possibility that a loss or an additional loss may be incurred, the Company estimates a range of aggregate loss in excess of amounts accrued of $0up to ~~$41.3 million as of June 30, 2022.~~$33 million. This estimated aggregate range is based upon currently available information for those legal proceedings in which the Company is involved, where the Company can make an estimate for such losses. For certain cases, the Company does not believe that it can make an estimate. The foregoing aggregate estimate is based on various factors, including the varying stages of the proceedings (including the fact that some are currently in preliminary stages), the numerous yet-unresolved issues in many of the proceedings and the attendant uncertainty of the various potential outcomes of such proceedings. Accordingly, the Company's estimate will change from time to time, and actual losses may be more than the current estimate.

OnBeginning on or about August 31, 2021, Oppenheimer was named as a ~~complaint~~respondent in a class action entitled 6694 Dawson Blvd, LLC, Individually and on Behalf of a Class of Similarly Situated Persons v. Oppenheimer & Co. Inc., James Wallace Woods, Michael J. Mooney, Britt Wright, William V. Conn, Jr., Conn & Co. Tax Practice, LLC, Conn & Company Consulting, LLC and Kathleen Lloyd, wasthirty-nine arbitrations, many containing multiple claimants, each filed ~~in the U.S. District Court for the Northern District of Georgia. Plaintiff purports~~before FINRA, relating to ~~represent a class of investors~~those claimants’ purported investment in Horizon Private Equity, III, LLC (“Horizon”). Horizon is alleged to be a fraudulent scheme involving, among others, a former Oppenheimer employee John Woods. John Woods left Oppenheimer’s employ in 2016 and ~~plaintiff is~~Oppenheimer never received a complaint or question from any of the investors prior to the Securities and Exchange Commission (“SEC”) bringing a complaint against Woods and his co-conspirators in 2021. Each investor who was an Oppenheimer client, signed a document acknowledging that Horizon was not an approved Oppenheimer product. Over a protracted period of time, Woods made multiple false statements to Oppenheimer, to regulators and to a state court. The claimants are seeking ~~unspecified~~ damages ~~sounding in~~based on a number of legal theories, including, without limitation, violations of ~~the Georgia RICO statute,~~various state and federal statutes, breach of fiduciary duty, procurement of breach of fiduciary duty, negligent misrepresentation, aiding and abetting fraud, and unjust ~~enrichment, punitive damages and attorneys’ fees. Plaintiff does~~enrichment. Claimants do not allege Oppenheimer received any of the funds invested in Horizon, but rather that Oppenheimer’s purported failure to properly supervise its employees allowed the alleged scheme to occur and continue. ~~On November 22, 2021, Oppenheimer filed~~The twenty-two individual arbitrations still pending claim specific monetary damages allege losses of approximately $24.0 million in the aggregate while a ~~motion to dismiss the complaint on a number of grounds. The motion to dismiss was fully briefed on January 17, 2022, and the Court heard oral argument on the motion on June 21, 2022.~~few others claim unspecified damages. Oppenheimer believes ~~the~~these claims to be without merit and intends to ~~vigorously~~ defend itself vigorously against ~~the claims made in this action.~~


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

these claims.

~~In addition~~As previously reported Oppenheimer’s motion to vacate the arbitration award in Donald Robinson, Timothy and Sharon Padden, Rhett Rainey, Kelly A. Rainey Trust, Toucan Holdings LP, Robert Goodman, Robert Daniel Burgner, Individually and as Trustee of the Burgner Family Charitable Remainder Trust, Douglas Kasemeier, Wesley Callaway, and Billy Loveless v. Oppenheimer & Co. Inc. (the “Robinson Arbitration”) was denied on January 30, 2023. However, on March 27, 2023, the Court entered a consent judgment vacating the award in Robinson Arbitration pursuant to the ~~class action described~~parties’ request in connection with their settlement of the ~~preceding paragraph~~matter. Oppenheimer has ~~also~~settled, or settled in principle or an award has been ~~named as a respondent~~rendered in~~NaN arbitrations, many containing multiple claimants, each filed before FINRA, relating to investments made by formerOppenheimer clients who invested in Horizon. Claimants allege many~~ seventeen of the ~~causes of action alleged in~~Horizon related arbitrations, including the ~~class actiondescribed~~in~~theprecedingparagraph.~~Robinson Arbitration,with approximately fifty-seven individual complainants. The~~arbitrationsclaimingspecificmonetarydamagesallegedamages~~of~~approximately~~

~~$41.3 million in the~~ aggregate ~~while others claim unspecified damages.Oppenheimer believes these claims to be without meritandintendsto defend itselfvigorously againsttheseclaims.~~settlement payments for those total approximately $58.0 million.

On June 30, 2022, the Company received a "Wells Notice" from the SEC requesting that Oppenheimer make a written submission to the SEC to explain why Oppenheimer should not be charged with violations of Section 15c2-12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and ~~Rule15c2-12~~Rule 15c2-12 thereunder as well as Municipal Securities Rulemaking Board Rules G-17 and G-27 in relation to its sales of municipal notes pursuant to an exemption from continuing disclosure contained in Rule 15c2-12. AsOn September 13, 2022, the SEC filed a ~~result~~complaint against Oppenheimer in the United States District Court for the Southern District of New York (the “Court") alleging that Oppenheimer violated Section 15B(c)(1) of the ~~foregoing the Company believes the SEC may institute an administrative proceeding against Oppenheimer~~Exchange Act and Rule 15c2-12 thereunder as well as Municipal Securities Rulemaking Board Rules G-17 and G-27 for not having fully complied with the exemption from the continuing disclosure obligations under Rule 15c2-12. The SEC asked the Court to enter an order enjoining Oppenheimer from violating the above referenced rules and requiring it to disgorge approximately $1.9 million plus interest. The Company believes such claim to be without merit and intends to vigorously defend itself against ~~any~~ such claim.


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

15. Regulatory requirements

The Company's U.S. broker dealer subsidiaries, Oppenheimer and Freedom, are subject to the uniform net capital requirements of the SEC under Rule 15c3-1 (the "Rule") promulgated under the ~~Securities~~ Exchange ~~Act of 1934, as amended (the "Exchange Act").~~Act. Oppenheimer computes its net capital requirements under the alternative method provided for in the Rule which requires that Oppenheimer maintain net capital equal to 2two percent of aggregate customer-related debit items, as defined in SEC Rule 15c3-3. As of ~~June 30, 2022,~~March 31, 2023, the net capital of Oppenheimer as calculated under the Rule was ~~$435.6~~$440.0 million or ~~27.53%~~39.98% of Oppenheimer's aggregate debit items. This was ~~$404~~$418.0 million in excess of the minimum required net capital at that date. Freedom computes its net capital requirement under the basic method provided for in the Rule, which requires that Freedom maintain net capital equal to the greater of $100,000 or 6-2/3% of aggregate indebtedness, as defined.

As of ~~June 30, 2022,~~March 31, 2023, Freedom had net capital of ~~$4.4~~$4.3 million, which was ~~$4.3~~$4.2 million in excess of the $100,000 required to be maintained at that date.

As of ~~June 30, 2022,~~March 31, 2023, the capital required and held under the FCA’s Investment Firms’ Prudential Regime (“IFPR”) for Oppenheimer Europe Ltd. was as follows:

•Common Equity Tier 1 ratio ~~130%~~110% (required 56.0%);

•Tier 1 Capital ratio ~~130%~~110% (required 75.0%); and

•Total Capital ratio ~~174%~~147% (required 100.0%).

Effective January 2022, IFPR changed its minimum capital requirement, which is now sterling 750,000 (previously it was Euro 730,000). Capital ratios are now expressed differently, but are effectively unchanged when comparing performance to required regulatory minimums. As of ~~June 30, 2022,~~March 31, 2023, Oppenheimer Europe Ltd. iswas in compliance with its regulatory requirements.

As of ~~June 30, 2022,~~March 31, 2023, the regulatory capital of Oppenheimer Investments Asia Limited was ~~$4.8~~$4.9 million, which was ~~$4.4~~$4.5 million in excess of the ~~$382,297~~$382,172 required to be maintained on that date. Oppenheimer Investments Asia Limited computes its regulatory capital pursuant to the requirements of the Securities and Futures Commission of Hong Kong. As of ~~June 30, 2022,~~March 31, 2023, Oppenheimer Investment Asia Limited iswas in compliance with its regulatory requirements.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

16. Segment information

The Company has determined its reportable segments based on the Company's method of internal reporting, which disaggregates its retail business by branch and its proprietary and investment banking businesses by product. The Company evaluates the performance of its segments and allocates resources to them based upon profitability.

The Company's reportable segments are:

Private Client — includes commissions and a proportionate amount of fee income earned on assets under management ("AUM"), net interest earnings on client margin loans and cash balances, fees from money market funds, custodian fees, net contributions from stock loan activities and financing activities, and direct expenses associated with this ~~segment.~~segment; and

Asset Management — includes a proportionate amount of fee income earned on AUM from investment management services of Oppenheimer Asset Management Inc. Oppenheimer's asset management divisions employ various programs to manage client assets either in individual accounts or in funds, and includes direct expenses associated with this segment; and

Capital Markets — includes investment banking, institutional equities sales, trading, and research, taxable fixed income sales, trading, and research, public finance and municipal trading, as well as the Company's operations in the United Kingdom, Hong Kong and Israel, and direct expenses associated with this segment.

The Company does not allocate costs associated with certain infrastructure support groups that are centrally managed for its reportable segments. These areas include, but are not limited to, legal, compliance, operations, accounting, and internal audit.


Table of Contents
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Costs associated with these groups are separately reported in a Corporate/Other category and primarily include compensation and benefits.

The table below presents information about the reported revenue and pre-tax income (loss) of the Company for the three ~~and six~~ months ended ~~June 30, 2022~~March 31, 2023 and ~~2021.~~2022. Asset information by reportable segment is not reported since the Company does not produce such information for internal use by the chief operating decision maker.

(Expressed in thousands)
For the Three Months Ended
June 30, For the Six Months Ended
June 30,
2022 2021 2022 2021
Revenue
Private client (1)
$ 144,471 $ 166,863 $ 295,318 $ 330,886
Asset management (1)
24,315 25,544 51,432 49,774
Capital markets 71,274 147,945 156,325 331,544
Corporate/Other (2,838) (59) 175 1,371
Total $ 237,222 $ 340,293 $ 503,250 $ 713,575
Pre-Tax Income (Loss)
Private client (1)
$ 38,800 $ 21,673 $ 62,946 $ 45,936
Asset management (1)
8,120 8,638 17,594 16,191
Capital markets (17,935) 39,373 (16,769) 89,364
Corporate/Other (35,154) (26,516) (55,727) (56,196)
Total $ (6,169) $ 43,168 $ 8,044 $ 95,295


(Expressed in thousands)
	For the Three Months Ended March 31,
	2023		2022
Revenue
Private client (1)	$	203,421	$	150,847
Asset management (1)	23,959		27,117
Capital markets	90,282		85,051
Corporate/Other	4,017		3,013
Total	$	321,679	$	266,028
Pre-Tax Income (Loss)
Private client (1)	$	54,456	$	24,146
Asset management (1)	6,481		9,474
Capital markets	(15,477)		1,166
Corporate/Other	(26,411)		(20,573)
Total	$	19,049	$	14,213

(1)Clients investing in the OAM advisory program are charged fees based on the value of AUM.

Advisory fees are allocated 10.0% to the Asset Management and 90.0% to the Private Client segments.


~~Table of Contents~~
OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited)

Revenue, classified by the major geographic areas in which it was earned, for the three ~~and six~~ months ended ~~June 30,~~March 31, 2023 and 2022 ~~and 2021~~ was:


(Expressed in thousands)	(Expressed in thousands)									(Expressed in thousands)
		For the Three Months Ended June 30,				For the Six Months Ended June 30,					For the Three Months Ended March 31,
		2022		2021		2022		2021			2023		2022
Americas	Americas	$	225,500	$	326,485	$	477,410	$	683,192	Americas	$	309,789	$	251,910
Europe/Middle East	Europe/Middle East	10,474		12,501		22,451		27,911		Europe/Middle East	10,860		11,977
Asia	Asia	1,248		1,307		3,389		2,472		Asia	1,030		2,141
Total	Total	$	237,222	$	340,293	$	503,250	$	713,575	Total	$	321,679	$	266,028

17. Subsequent events

On ~~July 29, 2022,~~April 28, 2023, the Company announced a quarterly dividend in the amount of $0.15 per share, payable on ~~August~~May 26, ~~2022~~2023 to holders of Class A Stock and Class B Stock of record on ~~August~~May 12, ~~2022.~~

On July 28, 2022, the Company's Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 536,500 shares of the Company's Class A Stock, representing approximately 4.8% of its 11,251,930 then issued and outstanding shares of Class A Stock. This authorization supplemented the 4,278 shares that remained authorized and available under the Company's previous share repurchase program for a total of 540,778 shares authorized.2023.

3936

Table of Contents

Item 2. MANAGEMENT'S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS

BACKGROUND

The condensed consolidated financial statements include the accounts of Oppenheimer Holdings Inc. and its consolidated subsidiaries (together, the "Company", "Firm", "Parent", "we", "our" or "us"). The Company's condensed consolidated financial statements have been prepared in accordance with accounting principles generally accepted in the United States of America. The following discussion should be read in conjunction with the condensed consolidated financial statements and notes thereto which appear elsewhere in this quarterly report.

Oppenheimer Holdings Inc., through its operating subsidiaries, is a leading middle market investment bank and full service broker-dealer that is engaged in a broad range of activities in the securities industry, including retail securities brokerage, institutional sales and trading, market-making, research, investment banking (both corporate and public finance), investment advisory and asset management services and trust services. Its principal subsidiaries are Oppenheimer & Co. Inc. ("Oppenheimer") and Oppenheimer Asset Management Inc. ("OAM"). As of ~~June 30, 2022,~~March 31, 2023, we provided our services from 9192 offices in 25 states located throughout the United States and offices in Puerto Rico, Tel Aviv, Israel, Hong Kong, China, London, England, St. Helier, Isle of Jersey, Munich, Germany, Portugal and Geneva, Switzerland. ~~Client assets under administration ("CAUA") as of June 30, 2022 totaled $104.0 billion.~~ The Company provides investment advisory services through OAM and Oppenheimer Investment Management LLC ("OIM") and Oppenheimer's financial advisor directed programs. At ~~June 30, 2022,~~March 31, 2023, client assets under management ("AUM") totaled ~~$37.1~~$39.3 billion. AUM includes the total market value of client investments in discretionary and non-discretionary advisory programs as well as the net asset value of private placements of alternative investments offered by and held by clients of the firm. Client assets under administration ("CAUA") as of March 31, 2023 totaled $108.9 billion. CAUA includes AUM and the other assets for which the firm provides services. We also provide trust services and products through Oppenheimer Trust Company of Delaware and discount brokerage services through Freedom Investments, Inc. ("Freedom"). Through OPY Credit Corp., from time to time we may offer syndication as well as trading of issued syndicated corporate loans. At ~~June 30, 2022,~~March 31, 2023, the Company employed ~~2,913~~2,916 employees ~~(2,866~~(2,876 full-time and 4740 part-time), of whom ~~990~~959 were financial advisors.

Outlook

We are focused on growing our private client and asset management businesses through strategic additions of experienced financial advisors in our existing branch system and employment of experienced money management personnel in our asset management business as well as deploying our capital for expansion through targeted acquisitions. We are increasingly creating and investing in private market opportunities on our own behalf and on behalf of qualified clients. We are also focused on opportunities in our capital market businesses where we can employ experienced personnel and/or small units that will improve our ability to attract institutional clients in both equities and fixed income without significantly raising our risk profile. We are continuously reviewing ways in which we can increase security around our data and our platform as the risks of cybercrime increase. In investment banking, we are committed to ~~grow~~growing our footprint by adding experienced bankers within our existing industry practices as well as new industry ~~exposure~~practices where we believe we can be successful.

We continuously invest in and improve our technology platform to support client service and to remain competitive, while continuously managing expenses. The Company's long-term growth plan is to continue to expand existing offices by hiring experienced professionals as well as expand through the purchase of operating branch offices from other broker-dealers or the opening of new branch offices in attractive locations, and to continue to grow and develop the existing trading, investment banking, investment advisory and other divisions. We are committed to continuing to improve our capabilities to ensure compliance with industry regulations, support client service and expand our wealth management and capital markets capabilities. We recognize the importance of compliance with applicable regulatory requirements and are committed to performing rigorous and ongoing assessments of our compliance and risk management effort, and investing in people and programs, while providing a platform with first class investment programs and services.

The Company is also reviewing its full service business model to determine the opportunities available to build or acquire closely related businesses in areas where others have shown some success. Equally important is the search for viable acquisition candidates. Our long-term intention is to pursue growth by acquisition where we can find a comfortable match in terms of corporate goals and personnel at a price that would provide our shareholders with incremental value. We review potential acquisition opportunities from time to time with the aim of fulfilling the Company's strategic goals, while evaluating and managing our existing businesses. In addition, the Company may from

Table of Contents

time to time make minority private investments out of excess capital in allied or unrelated businesses with the goal of either syndicating the investment to eligible clients or retaining ownership because we believe them to be an attractive investment.

~~Table of Contents~~

Impact of Interest Rates

~~The~~During the first quarter of 2023, the Federal Reserve ("FED") remained committed to tightening monetary policy as a means of combating inflation. While modest decreases in key inflationary measures such as the Consumer Price Index demonstrated that the rate increases implemented throughout 2022 were beginning to have their intended impact, unexpectedly strong job growth and consumer spending data led the FED to conclude that further short-term rate increases were necessary. As a result, the FED increased the ~~FED Funds Rate~~Federal funds rate by ~~25bps~~50 basis point to a target range of 4.75% to 5.00% during the three months ended March 31, 2023. However, the smaller nature (25 basis point) of both first quarter 2023 rate increases balances the FED’s intention not to ‘over-tighten,’ while also acknowledging that a contraction in ~~March 2022, 50bps~~bank lending in ~~May 2022, 75bps in June 2022~~light of the Silicon Valley Bank and ~~75bps in July 2022.~~Signature Bank failures will likely help ease inflation. As a result of ~~recent increased rate of inflation, it is likely that interest rates will continue to increase from~~ the ~~record low levels of recent years. In addition,~~banking failures, the FED has ~~announced~~signaled that it will ~~reduce its balance sheet as~~proceed with both prudence and patience in determining whether additional rate increases are warranted when it ~~allows maturing bonds to runoff without re-investing~~meets in May 2023.

The unexpected failure of two commercial banks (Silicon Valley Bank and Signature Bank) during the ~~proceeds.~~quarter, resulted from the rapid increase in interest rates during 2022 and the consequential impact on the value of fixed income investments by these banks and many others. The increases in ~~interest~~ rates, ~~if and when they take place will be favorable to the Company’s interest-based revenues. These changes in policy~~which are intended to reduce inflation, ~~and~~ are also likely to ~~also~~ reduce economic activity possibly leading to a ~~recession.~~recession in the coming months. These factors have already reduced customer confidence and are likely to continue to reduce discretionary spending, increase volatility in financial markets, and reduce revenues the Company derives from commissions and possibly from fees based on the value of client assets managed by the Company should equity prices decline. The increases in the Federal funds rate are favorable to the Company's interest-based revenue. However, increases in interest rates will increase fees the Company earns from FDIC-insured deposits of clients through a program offered by the ~~Company.~~Company, though such increases may be offset to some extent if the cash sweep balances decrease as clients seek higher-yielding investments. These rate increases will also increase the rates the Company charges on margin balances and have a positive impact on our earnings. However, such increases while bringing down inflationary pressures may also prove detrimental to economic activity and thereby to financial markets in general. The impact of rate increases seems likely to increase volatility in financial markets, decrease the value of fixed income investments and impact equity share prices.

Ukraine War

In February 2022, without provocation, Russia invaded Ukraine. The war has lasted longer than previously anticipated, and it seems likely it will last for an extended period of time as the Ukrainians continue to be more successful than initially expected at turning back Russian forces and as NATO and other countries supply the Ukrainians with armaments and supplies. The European Union and the United States have imposed broad-based sanctions and impounded financial assets of Russia, its companies and various notable Russian individuals. The impact of the sanctions ~~has been~~initially was to significantly increase the price of hydrocarbons and the ~~costs~~cost of various agricultural products produced by both Russia and ~~Ukraine to disrupt~~Ukraine. In addition, the disruption of supplies for those products ~~which~~ has further increased inflationary pressures in Europe as well as the rest of the ~~world.~~world and has led to significant cutbacks in economic activity due to anticipated shortages of natural gas in the winter period due to actions taken by Russia and OPEC. It has also had the indirect effect of lowering consumer confidence and consumer spending in Europe, all of which could have an adverse impact on financial markets in Europe as well as the U.S. and, thus on our business. However, that impact has largely abated and the equity markets have performed quite well in early 2023 as they continue to try to discern the likely direction of the world economy as it is impacted by these crosscurrents.

~~CORONAVIRUS DISEASE 2019 ("~~COVID-19 ~~PANDEMIC")~~

PANDEMIC

The Company continues to monitor the effects of the COVID-19 pandemic both on a national level as well as regionally and locally and is responding accordingly. In addition, we continue to provide frequent communications to clients, employees, and regulators regarding the impact of COVID-19 on our business. We have adopted enhanced cleaning practices and other health protocols in our offices, taken measures to limit business travel and have practices in place to mandate that employees who may have been exposed to COVID-19, or show any relevant symptoms, self-quarantine. In early March 2020, the Company executed on its Business Continuity Plan whereby the vast majority of our employees began to work remotely with only "essential" employees reporting to our offices. We accomplished this by significantly expanding the use of technology infrastructure that facilitates remote operations. Our ability to avoid significant business disruptions is reliant on the continued ability to support our employees that continue to work remotely. To date, there have been no significant disruptions to our business or control processes as a result of ~~this dispersion of employees. Given~~COVID. Since the surge in COVID-19 cases related to the Omicron variant and its offspring, some employees from our home office and branch locations continue to work remotely. We anticipate more employees returning to offices once the risks associated with the COVID-19 subside while maintaining flexible work arrangements for our employees in keeping with the change in expectations and work habits that have developed during the past two yearsdirect impact of the ~~pandemic. In recent months,~~virus has been substantially reduced, we have seen increased attendance at the workplace as local regulations have been loosened, hospital visits reduced and a larger portion of the population vaccinated. The aftermath of the pandemic has continued to produce lower office attendance than pre-pandemic and had an ongoing impact on attitudes surrounding work-life balance. Some employees from our home office and branch locations continue to work remotely at least part of each week but the efforts continue to encourage office attendance. There can be no assurance at this time that ~~these~~ improvements in attendance will continue and we continue to closely monitor the ~~situation.~~long term impact and to adjust our office footprints as real estate leases expire.

EXECUTIVE SUMMARY

Macroeconomic factors drove lower results for the second quarter. While the economy continued to grow and unemployment remained at a record low level, waning consumer confidence, driven by high inflation and rising interest rates, created significantly higher volatility and markedly lower valuations in both equity and fixed income markets. The profitable results for the quarter reflect ~~the significant downturn~~our ability to continue supporting and advising our clients and prudently managing our business in ~~equity capital market issuance, which had an out-sized impact on~~all types of markets. Due to a combination of macroeconomic factors and turmoil within the Company, compared to the prior year. By quarter’s end, interest rates reached the highest levels since 2018 and higher mortgage rates were already impacting construction and home sales. While the Company’s pipeline of potential future banking business remains strong, the closing of the window for IPOs and secondary offerings, and the closing down of the SPAC market, dramatically reduced capital markets revenues for the second quarter of 2022 compared to the second quarter of 2021. Higher interest rates and the beginning of quantitative tightening reduced bond issuances across markets, but particularly impacted the high yield and emerging markets as spreads off U.S Treasuries widened dramatically during the quarter. These factors reduced revenues from capital markets (down 52%) for the quarter.

4138

Table of Contents

~~Wealth Management continued~~regional banking industry, the equity and fixed income markets were volatile during the first quarter of the year. Convinced that Federal Reserve ("FED") tightening would soon end, the equity markets rallied to ~~deliver solid results driven~~start the year. However, unexpected bank failures created large uninsured bank deposit withdrawals at certain regional banks that led to the fear of a broader bank contagion. Early action by ~~continued high levels~~the regulators to provide liquidity to banks seems to have dramatically slowed the move of ~~assets under management but below recent all-time highs. The continued performance~~funds into money market funds and short-term government securities. While the Company did not have any direct exposures to the failed institutions, the events caused a reaction in equity and fixed income markets, impacted portfolio turnover and our transaction-based revenues. Rising interest rates and fear of ~~our Wealth Management business~~a recession significantly limited issuers' access to capital, resulting in markedly lower investment banking revenues associated with new equity issuances and ~~the increase in~~secondary offerings. Strong M&A advisory fees ~~from our FDIC program~~and trading revenues offset some of the ~~impact of lower revenue from capital markets as~~weakness seen in the IPO market.

Our Wealth Management business continues to perform well, as its revenue mix has benefited from the ~~increase in operating costs reflecting~~rising interest rate environment. Income from our FDIC-insured bank deposit program and interest income on margin loans approached record quarterly levels as a result of the inflationary environment, with the Firm showing a loss for the period. Declines in the Company’s share price and equity prices in general had an outsized impact on the costs associated with deferred compensation plans and share awardsFED’s 50 basis point rate increase during the ~~period.~~quarter. These revenue increases were partially offset by lower valuations in client portfolios, which drove decreased fee income.

Despite the ~~unfavorable environment,~~volatility and market stress seen in the first quarter, the Company ~~still maintains the strongest~~continues to maintain a strong balance sheet with capital near its historic highs and ample levels of liquidity. During the ~~highest capital level in its history. The~~first quarter, the Company took advantage of the lower level of its share price to purchase ~~885,230~~95,055 shares ~~(7%~~(approximately 1%) of its Class A non-voting common ~~shares~~stock at an average price of ~~$34.13~~$38.79 per share in the open market under its share repurchase program. This resulted in 10,975,723 shares of Class A non-voting common stock remaining outstanding at March 31, 2023. We remain confident in the resiliency of our platform and our ability ~~to continue~~ to provide essential investment services to our clients.

RESULTS OF OPERATIONS

The Company reported net ~~loss~~income of ~~$3.9~~$14.6 million or ~~$(0.32)~~$1.32 basic earnings per share for the ~~second~~first quarter of ~~2022, a decrease of 112.4%,~~2023, compared with net income of ~~$31.2~~$9.3 million or ~~$2.46~~$0.75 basic earnings per share for the ~~second~~first quarter of ~~2021.~~2022. Revenue for the ~~second~~first quarter of ~~2022~~2023 was ~~$237.2~~$321.7 million, ~~a decrease~~an increase of ~~30.3%~~20.9% compared to revenue of ~~$340.3~~$266.0 million for the ~~second~~first quarter of ~~2021.~~2022.


(Expressed in thousands, except Per Share Amounts or otherwise indicated)	(Expressed in thousands, except Per Share Amounts or otherwise indicated)								(Expressed in thousands, except Per Share Amounts or otherwise indicated)
		2Q-2022		2Q-2021		Change		% Change		1Q-2023		1Q-2022		Change		% Change
Revenue	Revenue	$	237,222	$	340,293	$	(103,071)	(30.3)	Revenue	$	321,679	$	266,028	$	55,651	20.9
Compensation expense	Compensation expense	$	177,979	$	231,140	$	(53,161)	(23.0)	Compensation expense	$	206,292	$	186,031	$	20,261	10.9
Non-compensation expense	Non-compensation expense	$	65,412	$	65,985	$	(573)	(0.9)	Non-compensation expense	$	96,338	$	65,784	$	30,554	46.4
Pre-Tax Income (Loss)		$	(6,169)	$	43,168	$	(49,337)	(114.3)
Income Taxes Provision (Benefit)		$	(1,449)	$	12,009	$	(13,458)	(112.1)
Net Income (Loss) (1)		$	(3,874)	$	31,159	$	(35,033)	(112.4)
Pre-Tax Income									Pre-Tax Income	$	19,049	$	14,213	$	4,836	34.0
Income Taxes Provision									Income Taxes Provision	$	4,585	$	4,435	$	150	3.4
Net Income (1)									Net Income (1)	$	14,617	$	9,292	$	5,325	57.3

Earnings (Loss) per share (basic) (1)		$	(0.32)	$	2.46	$	(2.78)	(113.0)
Earnings (Loss) per share (diluted) (1)		$	(0.32)	$	2.28	$	(2.60)	(114.0)
Earnings per share (basic) (1)									Earnings per share (basic) (1)	$	1.32	$	0.75	$	0.57	76.0
Earnings per share (diluted) (1)									Earnings per share (diluted) (1)	$	1.22	$	0.69	$	0.53	76.8

Book Value Per Share	Book Value Per Share	$	68.57	$	59.29	$	9.28	15.7	Book Value Per Share	$	72.27	$	66.45	$	5.82	8.8
Tangible Book Value Per Share (2)	Tangible Book Value Per Share (2)	$	53.62	$	45.90	$	7.72	16.8	Tangible Book Value Per Share (2)	$	56.92	$	52.58	$	4.34	8.3
Class A Shares Outstanding									Class A Shares Outstanding	10,975,723		12,156,174		(1,180,451)		(9.7)

CAUA ($ billions)		$	104.0	$	117.3	$	(13.3)	(11.3)
AUA ($ billions)									AUA ($ billions)	$	108.9	$	117.2	$	(8.3)	(7.1)
AUM ($ billions)	AUM ($ billions)	$	37.1	$	43.7	$	(6.6)	(15.1)	AUM ($ billions)	$	39.3	$	42.7	$	(3.4)	(8.0)
(1) Attributable to Oppenheimer Holdings Inc.	(1) Attributable to Oppenheimer Holdings Inc.								(1) Attributable to Oppenheimer Holdings Inc.
(2) Represents book value less goodwill and intangible assets divided by number of shares outstanding.	(2) Represents book value less goodwill and intangible assets divided by number of shares outstanding.								(2) Represents book value less goodwill and intangible assets divided by number of shares outstanding.

Table of Contents

Highlights

•~~Client assets~~Gross revenue, net income, and earnings per share for the first quarter of 2023 primarily reflected increases in our interest sensitive revenues, growth in M&A advisory fees and stronger sales and trading revenues partially offset by lower activity levels and valuations in client portfolios.

•Assets under administration and under management were both at reduced levels at ~~June 30, 2022 and also down from the first quarter of 2022 as well as~~March 31, 2023 when compared with the same period last year.

•~~Reduced second~~Non-compensation expenses increased from the prior year quarter ~~2022 gross revenue, net~~largely due to higher interest expense and legal costs.

•Near record revenues in the Private Client segment are largely attributed to higher bank deposit sweep income and ~~earnings per share reflected a significant decline in industry-wide activity, and lower net~~margin interest revenue, ~~in underwriting, trading and M&A fees.~~which benefited from higher short-term interest rates.

•The Company repurchased ~~885,230~~95,055 shares of Class A non-voting common stock during the ~~second~~first quarter of ~~2022~~2023 under its previously announced ~~buy-back plan~~share repurchase program, or 7%approximately 1% of shares outstanding at year-end ~~2021, bringing the total shares purchased during the first 6 months of 2022 to 1,262,543.~~2022.

•Book value and tangible book value per share ~~reached record levels at June 30, 2022~~increased from the prior year period largely as a result of share ~~buybacks.~~repurchases and positive earnings.

~~Table of Contents~~

BUSINESS SEGMENTS

The table below presents information about the reported revenue and pre-tax income (loss) of the Company's reportable business segments for the three ~~and six~~ months ended ~~June 30, 2022~~March 31, 2023 and ~~2021:~~2022:


(Expressed in thousands)	(Expressed in thousands)											(Expressed in thousands)
		For the Three Months Ended June 30,					For the Six Months Ended June 30,						For the Three Months Ended March 31,
		2022		2021		% Change	2022		2021		% Change			2023		2022		% Change
Revenue	Revenue											Revenue
Private Client	Private Client	$	144,471	$	166,863	(13.4)	$	295,318	$	330,886	(10.7)	Private Client		$	203,421	$	150,847	34.9
Asset Management	Asset Management	24,315		25,544		(4.8)	51,432		49,774		3.3	Asset Management		23,959		27,117		(11.6)
Capital Markets	Capital Markets	71,274		147,945		(51.8)	156,325		331,544		(52.8)	Capital Markets		90,282		85,051		6.2
Corporate/Other	Corporate/Other	(2,838)		(59)		4,710.2	175		1,371		(87.2)	Corporate/Other		4,017		3,013		33.3
Total	Total	$	237,222	$	340,293	(30.3)	$	503,250	$	713,575	(29.5)	Total		$	321,679	$	266,028	20.9

Pre-Tax Income (Loss)	Pre-Tax Income (Loss)											Pre-Tax Income (Loss)
Private Client	Private Client	$	38,800	$	21,673	79.0	$	62,946	$	45,936	37.0	Private Client		$	54,456	$	24,146	125.5
Asset Management	Asset Management	8,120		8,638		(6.0)	17,594		16,191		8.7	Asset Management		6,481		9,474		(31.6)
Capital Markets	Capital Markets	(17,935)		39,373		*	(16,769)		89,364		*	Capital Markets		(15,477)		1,166		*
Corporate/Other	Corporate/Other	(35,154)		(26,516)		32.6	(55,727)		(56,196)		(0.8)	Corporate/Other		(26,411)		(20,573)		28.4
Total	Total	$	(6,169)	$	43,168	(114.3)	$	8,044	$	95,295	(91.6)	Total		$	19,049	$	14,213	34.0

*Percentage not meaningful

Table of Contents

Private Client

Private Client reported revenue for the current quarter of ~~$144.5~~$203.4 million, ~~13.4% lower when~~34.9% higher compared with a year ago mostly due to ~~lower commissions as well as decreases in the cash surrender value of Company-owned life insurance policies, partially offset by~~ an increase in bank deposit sweep income and margin interest income driven by higher ~~average margin balances.~~short-term interest rates. Pre-tax income of ~~$38.8~~$54.5 million in the current quarter resulted in a pre-tax profit margin of ~~26.9%~~26.8%. Financial advisor headcount at the end of the current quarter was ~~990~~959 compared to ~~1,004~~993 at the end of the ~~second~~first quarter of 2022.

~~2021.~~

('000s, except Financial advisor headcount or otherwise indicated)
2Q-2022 2Q-2021 Change % Change
Revenue $ 144,471 $ 166,863 $ (22,392) (13.4)
Retail commissions $ 45,916 $ 53,753 $ (7,837) (14.6)
Advisory fee revenue $ 83,085 $ 85,598 $ (2,513) (2.9)
Bank deposit sweep income $ 14,845 $ 3,712 $ 11,133 300
Interest $ 10,369 $ 7,235 $ 3,134 43.3
Other $ (9,744) $ 16,565 $ (26,309) *
Total Expenses $ 105,671 $ 145,190 $ (39,519) (27.2)
Compensation $ 77,342 $ 117,564 $ (40,222) (34.2)
Non-compensation $ 28,329 $ 27,626 $ 703 2.5
Pre-tax Income $ 38,800 $ 21,673 $ 17,127 79.0
Compensation Ratio 53.5 % 70.5 % (1,700) (24.1)
Non-compensation Ratio 19.6 % 16.6 % 300 18.1
Pre-tax Margin 26.9 % 13.0 % 13.9 % 106.9
Client Asset Under Administration (billions) $ 104.0 $ 117.3 $ (13.3) (11.3)
Cash Sweep Balances (billions) $ 7.5 $ 7.3 $ 0.2 26.0

*Percentage not meaningful

~~Table of Contents~~


('000s, except Financial advisor headcount or otherwise indicated)
	1Q-2023			1Q-2022			Change			% Change
Revenue	$	203,421		$	150,847		$	52,574		34.9
Retail commissions	$	46,636		$	51,677		$	(5,041)		(9.8)
Advisory fee revenue	$	76,583		$	88,527		$	(11,944)		(13.5)
Bank deposit sweep income	$	48,909		$	4,354		$	44,555		1,023
Interest	$	20,579		$	8,147		$	12,432		152.6
Other	$	10,714		$	(1,858)		$	12,572		*

Total Expenses	$	148,965		$	126,701		$	22,264		17.6
Compensation	$	95,074		$	99,855		$	(4,781)		(4.8)
Non-compensation	$	53,891		$	26,846		$	27,045		100.7

Pre-tax Income	$	54,456		$	24,146		$	30,310		125.5

Compensation Ratio	46.7		%	66.2		%	(1,950)			(29.5)
Non-compensation Ratio	26.5		%	17.8		%	870			48.9
Pre-tax Margin	26.8		%	16.0		%	10.8		%	67.5

Asset Under Administration (billions)	$	108.9		$	117.2		$	(8.3)		(7.1)
Cash Sweep Balances (billions)	$	4.4		$	8.1		$	(3.7)		(45.7)

*Percentage not meaningful

•Retail commissions decreased ~~14.6%~~9.8% from a year ago primarily due to ~~a decrease in~~lower client activity ~~compared to the significantly elevated levels from a year ago.~~in volatile markets.

•Advisory fees decreased ~~2.9%~~13.5% due to lower valuations of assets under management.

•Bank deposit sweep income increased ~~$11.1~~$44.6 million ~~or 300%~~ from a year ago due to ~~higher balances and~~ higher short-term interest rates.

•Interest revenue approached a record high and increased ~~43.3%~~152.6% from a year ago due to higher short-term interest ~~rates and higher average margin balances.~~rates.

•Other revenue ~~decreased~~increased primarily due to ~~decreases~~increases in the cash surrender value of Company-owned life insurance policies ~~during the current period compared to increases~~, which fluctuates based on changes in ~~the~~fair value of ~~those policies in~~ the ~~same period last year.~~policies' underlying investments.

•Compensation expenses decreased ~~34.2%~~4.8% from a year ago primarily due to decreased ~~production, and decreased share-based and deferred compensation costs.~~production.

•Non-compensation expenses increased ~~2.5%~~100.7% from a year ago primarily due to higher interest ~~travel~~expense and legal ~~expenses, offset by a decrease in allowance for credit losses.~~costs.

Asset Management

Asset Management reported revenue for the current quarter of ~~$24.3~~$24.0 million, ~~4.8%~~11.6% lower compared with a year ago. Pre-tax income was ~~$8.1~~$6.5 million, a decrease of ~~6.0%~~31.6% compared with the prior year period.

('000s unless otherwise indicated) 2Q-2022 2Q-2021 Change % Change
Revenue $ 24,315 $ 25,544 $ (1,229) (4.8)
Advisory fee revenue $ 24,311 $ 25,541 $ (1,230) (4.8)
Other $ 4 $ 3 $ 1 100.0
Total Expenses $ 16,195 $ 16,906 $ (711) (4.2)
Compensation $ 6,697 $ 6,261 $ 436 7.0
Non-compensation $ 9,498 $ 10,645 $ (1,147) (10.8)
Pre-tax Income $ 8,120 $ 8,638 $ (518) (6.0)
Compensation Ratio 27.5 % 24.5 % 300 12.2
Non-compensation Ratio 39.1 % 41.7 % (260) (6.2)
Pre-tax Margin 33.4 % 33.8 % — % —
AUM (billions) $ 37.1 $ 43.7 $ (6.6) (15.1)

Table of Contents


('000s unless otherwise indicated)	1Q-2023			1Q-2022			Change			% Change
Revenue	$	23,959		$	27,117		$	(3,158)		(11.6)
Advisory fee revenue	$	23,954		$	27,113		$	(3,159)		(11.7)
Other	$	5		$	4		$	1		25.0

Total Expenses	$	17,478		$	17,643		$	(165)		(0.9)
Compensation	$	7,615		$	7,086		$	529		7.5
Non-compensation	$	9,863		$	10,557		$	(694)		(6.6)

Pre-tax Income	$	6,481		$	9,474		$	(2,993)		(31.6)

Compensation Ratio	31.8		%	26.1		%	570			21.8
Non-compensation Ratio	41.2		%	38.9		%	230			5.9
Pre-tax Margin	27.1		%	34.9		%	(7.8)		%	(22.3)

AUM (billions)	$	39.3		$	42.7		$	(3.4)		(8.0)

•Advisory fee revenue decreased ~~4.8%~~11.7% due to reduced management fees resulting from the lower net value of assets under ~~management during the second quarter of 2022 compared with~~ ~~the second quarter of 2021.~~management.

•AUM ~~was~~were at a reduced levels of ~~$37.1~~$39.3 billion at ~~June 30, 2022,~~March 31, 2023, which is the basis for advisory fee billings for ~~July 2022.~~April 2023.

•The decrease in AUM was comprised of lower asset values of ~~$6.0~~$3.1 billion on existing client holdings and a net distribution of assets of ~~$0.6~~$0.3 billion.

•Compensation expenses were up ~~7.0%~~7.5% from a year ago which was primarily ~~due~~related to increases in ~~fixed~~incentive compensation.

•Non-compensation expenses were down ~~10.8%~~6.6% when compared to the prior year period mostly due to lower external portfolio ~~manager expense.~~management costs which is directly related to the decrease in AUM, partially offset by higher travel-related expenses.

~~Table of Contents~~

The following table provides a breakdown of the change in assets under management for the three months ended ~~June 30, 2022:~~March 31, 2023:


(Expressed in millions)	(Expressed in millions)																			(Expressed in millions)
		For the Three Months Ended June 30, 2022
		Beginning Balance												Appreciation (Depreciation)				Ending Balance					For the Three Months Ended March 31, 2023
Fund Type	Fund Type			Contributions				Redemptions/Profit Distribution								Fund Type				Beginning Balance				Contributions			Redemptions/Profit Distribution			Appreciation (Depreciation)			Ending Balance
Traditional (1)	Traditional (1)			$	35,991			$	1,407			$	(1,998)			$	(4,181)				$	31,219	Traditional (1)		$	31,413		$	2,418		$	(1,619)		$	1,485		$	33,697
Institutional Fixed Income (2)	Institutional Fixed Income (2)	839				14				(24)				(34)				795		Institutional Fixed Income (2)			835			3			(17)			20			841
Alternative Investments:	Alternative Investments:																			Alternative Investments:
Hedge funds (3)	Hedge funds (3)	3,843				61				(16)				(639)				3,249		Hedge funds (3)			3,041			25			(131)			311			3,246
Private Equity Funds (4)	Private Equity Funds (4)	1,663				23				(39)				(206)				1,441		Private Equity Funds (4)			1,152			72			(4)			(32)			1,188
Portfolio Enhancement Program (5)	Portfolio Enhancement Program (5)	367				6				(7)				—				366		Portfolio Enhancement Program (5)			352			—			(20)			—			332
		$	42,703			$	1,511			$	(2,084)			$	(5,060)			$	37,070				$	36,793		$	2,518		$	(1,791)		$	1,784		$	39,304

(1)Traditional investments include ~~third~~first party advisory programs, Oppenheimer financial adviser managed advisory programs and Oppenheimer Asset Management taxable and tax-exempt portfolio management strategies.

(2)Institutional fixed income provides solutions to institutional investors including: Taft-Hartley Funds,

Public Pension Funds, Corporate Pension Funds, and Foundations and Endowments.

(3) Hedge funds represent single manager hedge fund strategies in areas including hedged equity,

technology and financial services, and multi-manager and multi-strategy fund of funds.

Table of Contents

(4)Private equity funds represent private equity fund of funds including portfolios focused on natural resources and related assets.

(5)The portfolio enhancement program sells uncovered, out-of-money puts and calls on the S&P 500 Index. The program is intended to be market neutral and uncorrelated to the index. Valuation is based on collateral requirements for a series of contracts representing the investment strategy.

~~Table of Contents~~

Capital Markets

Capital Markets reported revenue for the current quarter of ~~$71.3~~$90.3 million, ~~51.8% lower~~6.2% higher when compared with the prior year period. Pre-tax loss was ~~$17.9~~$15.5 million compared with ~~the~~ pre-tax income of ~~$39.4~~$1.2 million ~~in the prior~~a year ~~period.~~ago.

('000s) 2Q-2022 2Q-2021 Change % Change
Revenues $ 71,274 $ 147,945 $ (76,671) (51.8)
Investment Banking $ 14,699 $ 99,045 $ (84,346) (85.2)
Advisory fees $ 8,284 $ 50,515 $ (42,231) (83.6)
Equities underwriting $ 2,751 $ 39,371 $ (36,620) (93.0)
Fixed income underwriting $ 3,259 $ 8,835 $ (5,576) (63.1)
Other $ 405 $ 324 $ 81 25.0
Sales and Trading $ 55,978 $ 48,630 $ 7,348 15.1
Equities $ 37,126 $ 30,218 $ 6,908 22.9
Fixed Income $ 18,852 $ 18,412 $ 440 2.4
Other $ 597 $ 270 $ 327 121.1
Total Expenses $ 89,209 $ 108,572 $ (19,363) (17.8)
Compensation $ 67,172 $ 85,663 $ (18,491) (21.6)
Non-compensation $ 22,037 $ 22,909 $ (872) (3.8)
Pre-tax Income (Loss) $ (17,935) $ 39,373 $ (57,308) *
Compensation Ratio 94.2 % 57.9 % 3,630 62.7
Non-compensation Ratio 30.9 % 15.5 % 1,540 99.4
Pre-tax Margin (25.2) % 26.6 % (51.8) % *

*Percentage not meaningful


('000s)	1Q-2023			1Q-2022			Change			% Change
Revenues	$	90,282		$	85,051		$	5,231		6.2

Investment Banking	$	36,281		$	32,975		$	3,306		10.0
Advisory fees	$	27,937		$	21,905		$	6,032		27.5
Equities underwriting	$	7,343		$	11,236		$	(3,893)		(34.6)
Fixed income underwriting	$	897		$	1,987		$	(1,090)		(54.9)
Other	$	104		$	(2,153)		$	2,257		*

Sales and Trading	$	53,379		$	51,603		$	1,776		3.4
Equities	$	31,686		$	35,928		$	(4,242)		(11.8)
Fixed Income	$	21,693		$	15,675		$	6,018		38.4

Other	$	622		$	473		$	149		31.5

Total Expenses	$	105,759		$	83,885		$	21,874		26.1
Compensation	$	76,796		$	60,223		$	16,573		27.5
Non-compensation	$	28,963		$	23,662		$	5,301		22.4

Pre-tax Income (Loss)	$	(15,477)		$	1,166		$	(16,643)		*

Compensation Ratio	85.1		%	70.8		%	1,430			20.2
Non-compensation Ratio	32.1		%	27.8		%	430			15.5
Pre-tax Margin	(17.1)		%	1.4		%	(18.5)		%	*
*Percentage not meaningful

•Advisory fees earned from investment banking activities ~~decreased 83.6%~~increased 27.5% compared with a year ~~ago. The high advisory fees from the prior year period were driven by large completed~~ago due to an increase in M&A ~~transactions in healthcare, technology, and consumer products.~~transactions.

•Equity underwriting fees decreased ~~93.0%~~34.6% compared with a year ago due to a ~~significant decrease~~continued market slowdown in equity ~~underwriting activity in the healthcare~~IPOs and ~~technology sectors, particularly for~~secondary offerings, including SPAC ~~issuances to access the public markets.~~issuances.

•Fixed income underwriting fees were down ~~63.1%~~54.9% compared with a year ago primarily driven by ~~a decrease in public finance issuances and emerging market debt~~lower deal volumes during the ~~second~~first quarter of ~~2022.~~2023.

•Equities sales and trading revenue ~~increased 22.9%~~decreased 11.8% compared with a year ago due to ~~a marked increase in volatility~~reduced volumes in the equities market compared to the levels in the prior year period.

•Fixed ~~Income~~income sales and trading revenues increased ~~by 2.4% compared with a year ago.~~

•~~Compensation expenses decreased 21.6%~~38.4% compared with a year ago primarily due to ~~decreased~~both an increase in trading income attributable to wider spreads and also increased activity due to high volatility during the period.

•Compensation expenses increased 27.5% compared with a year ago primarily due to opportunistic hiring and increased incentive compensation.

•Non-compensation expenses were ~~3.8% lower~~22.4% higher than a year ago primarily due to ~~a decrease in underwriting expenses, partially offset by~~ an increase in ~~business travel and entertainment expenses.~~interest expense in financing inventories.

4643

Table of Contents

CRITICAL ACCOUNTING POLICIES

The Company's condensed consolidated financial statements have been prepared in accordance with accounting principles generally accepted in the United States of America. Reference is also made to the Company's condensed consolidated financial statements and notes thereto found in its Annual Report on Form 10-K for the year ended December 31, ~~2021.~~2022.

The Company's accounting policies are essential to understanding and interpreting the financial results reported on the condensed consolidated financial statements. The significant accounting policies used in the preparation of the Company's condensed consolidated financial statements are summarized in note 2 to those statements and the notes thereto found in the Company's Annual Report on Form 10-K for the year ended December 31, ~~2021.~~2022. Certain of those policies are considered to be particularly important to the presentation of the Company's financial results because they require management to make difficult, complex or subjective judgments, often as a result of matters that are inherently uncertain.

During the three months ended ~~June 30, 2022,~~March 31, 2023, there were no material changes to matters discussed under the heading "Critical Accounting Polices" in Part II, Item 7 of the Company's Annual Report on Form 10-K for the year ended December 31, ~~2021.~~2022.

LIQUIDITY AND CAPITAL RESOURCES

At ~~June 30, 2022,~~March 31, 2023, total assets ~~decreased~~increased by ~~4.0%~~7.6% from December 31, ~~2021.~~2022. The Company satisfies its need for short-term financing from internally generated funds and collateralized and uncollateralized borrowings, consisting primarily of bank call loans, stock loans, and uncommitted lines of credit. We finance our trading in government securities through the use of securities sold under repurchase agreements. We met our longer-term capital needs through the issuance of the 5.50% Senior Secured Notes due 2025 (see "Senior Secured Notes" below). Oppenheimer has arrangements with banks for borrowings on a fully collateralized basis. The amount of Oppenheimer's bank borrowings fluctuates in response to changes in the level of the Company's securities inventories and customer margin debt, changes in notes receivable from employees, investment in furniture, equipment and leasehold improvements, and changes in stock loan balances and financing through repurchase agreements. At ~~June 30, 2022,~~March 31, 2023, the Company had bank call loans of ~~$177.3~~$19.3 million compared to ~~$69.5 million~~zero at December 31, ~~2021.~~2022. The Company also has some availability of short-term bank financing on an unsecured basis.

The Company's overseas subsidiaries, Oppenheimer Europe Ltd. and Oppenheimer Investments Asia Limited, are subject to local regulatory capital requirements that restrict our ability to utilize their capital for other purposes.

The regulatory capital requirements for Oppenheimer Europe Ltd. and Oppenheimer Investments Asia Limited were ~~$5.2~~$5.1 million and ~~$382,297,~~$382,172, respectively, at ~~June 30, 2022.~~March 31, 2023. The liquid assets at Oppenheimer Europe Ltd. are primarily comprised of cash deposits in bank accounts.

The liquid assets at Oppenheimer Investments Asia Limited are primarily comprised of investments in U.S. Treasuries and cash deposits in bank accounts. Any transfer of these liquid assets from Oppenheimer Europe Ltd. and Oppenheimer Investments Asia Limited to the Company or its other subsidiaries would be limited by regulatory capital requirements.

The Company permanently reinvests eligible earnings of its foreign subsidiaries and, accordingly, does not accrue any U.S. income taxes that would arise if these earnings were repatriated. The unrecognized deferred tax liability associated with the outside basis difference of its foreign subsidiaries is estimated at ~~$3.5~~$3.6 million for those subsidiaries. We have continued to reinvest permanently the excess earnings of Oppenheimer Israel (OPCO) Ltd. in its own business and in the businesses in Europe and Asia to support business initiatives in those regions. We will continue to review our historical treatment of these earnings to determine whether our historical practice will continue or whether a change is warranted. The Company has been assessing the impact that the administration’s proposed increased corporate tax proposals will have on its operations, cash flows and financial condition, although changes during this fiscal year seem increasingly unlikely.

~~Table of Contents~~

Senior Secured Notes

On September 22, 2020, in a private offering, we issued $125.0 million aggregate principal amount of 5.50% Senior Secured Notes due 2025 (the "Unregistered Notes") under an indenture at an issue price of 100% of the principal

amount. Interest on the Unregistered Notes is payable semi-annually on April 1st and October 1st. We used the net proceeds from the offering of the Unregistered Notes, along with cash on hand, to redeem in full our 6.75% Senior

Secured Notes due July 1, 2022 in the principal amount of $150.0 million (the Company held $1.4 million in treasury for a net outstanding amount of $148.6 million), and pay all related fees and expenses related thereto. On November 23, 2020, we completed an exchange offer in which we exchanged 99.8% of our Unregistered Notes for a like principal

Table of Contents

amount of notes with identical terms (the "Notes"), except that such new ~~notes~~Notes have been registered under the Securities Act. We did not receive any proceeds in the exchange offer. See note 11 to the condensed consolidated financial statements appearing in Item 1 for further discussion.

During the fourth quarter of 2022, the Company repurchased and subsequently cancelled $10.95 million of the Notes, recognizing a small extinguishment gain. As of December 31, 2022, $114.05 million aggregate principal amount of the Notes remains outstanding.

During the first quarter of 2023, the Company repurchased and subsequently cancelled $1.0 million of the Notes, recognizing a small extinguishment gain. As of March 31, 2023, $113.05 million aggregate principal amount of the Notes remains outstanding.

The Notes are jointly and severally and fully and unconditionally guaranteed on a senior secured basis by E.A. Viner International Co. and Viner Finance Inc. (together, the "Subsidiary Guarantors"), unless released as described below. Each of the Subsidiary Guarantors is 100% owned by the Parent. The indenture for the Notes contains covenants with restrictions which are discussed in note 11.

The guarantees are senior secured obligations of each Subsidiary Guarantor. The guarantees rank:

•effectively senior in right of payment to all unsecured and unsubordinated obligations of such guarantor, to the extent of the value of the collateral owned by such Subsidiary Guarantor (and, to the extent of any unsecured remainder after payment of the value of the collateral, rank equally in right of payment with such unsecured and unsubordinated indebtedness of such Subsidiary Guarantor);

•senior in right of payment to any subordinated debt of such guarantor; and

•secured on a first-priority basis by the collateral, subject to certain exceptions and permitted liens, and it is intended that pari passu lien indebtedness, if any, will be secured on an equal and ratable basis.

Each subsidiary guarantee is limited so that it does not constitute a fraudulent conveyance under applicable law, which may reduce the subsidiary’s obligations under the guarantee. There are no externally imposed restrictions on transfers of assets between the Company and its subsidiaries.

Each Subsidiary Guarantor will be automatically and unconditionally released and discharged upon the sale, exchange or transfer of the capital stock of a Subsidiary Guarantor and the Subsidiary Guarantor ceasing to be a direct or indirect subsidiary of the Parent if such sale does not constitute an asset sale under the indenture for the Notes or does not constitute an asset sale effected in compliance with the asset sale and merger covenants of the indenture for the Notes; a Subsidiary Guarantor being dissolved or liquidated; a Subsidiary Guarantor being designated unrestricted in compliance with the applicable provisions of the Notes; or the exercise by the Parent of its legal defeasance option or covenant defeasance option or the discharge of the Parent's obligations under the indenture for the Notes in accordance with the terms of such indenture.

The following tables present the results of operations for the ~~six~~three months ended ~~June 30, 2022~~March 31, 2023 and the balance sheet at ~~June 30, 2022~~March 31, 2023 for the Parent and Subsidiary Guarantors.

~~Table of Contents~~



(Expressed in thousands)	As of
	~~June 30, 2022~~March 31, 2023
Total Assets	$	~~1,995,212~~2,057,254
Due From Non-Guarantor Subsidiary	~~17,971~~15,454
Total Liabilities	~~535,145~~546,772
Due To ~~Non-guarantor~~Non-Guarantor Subsidiary	~~1,895~~11,628

	For the ~~Six~~Three Months Ended
	~~June 30, 2022~~March 31, 2023
Total Revenue	$	~~4,976~~2,661
Pre-Tax Income (Loss)	~~(448)~~55
Net Income (Loss)	~~(577)~~(176)

On June 17, 2021, S&P upgraded the Company's Corporate Family rating and rating on the Unregistered Notes from 'B+' with a stable outlook to 'BB-' with a stable outlook. On August 23, 2021, Moody’s upgraded the Company's Corporate Family rating and the rating on the Unregistered Notes from “B1” with a stable outlook to “Ba3” with a stable outlook.

Table of Contents

Liquidity

For the most part, the Company's assets consist of cash and cash equivalents and assets that it can readily convert into cash. The receivable from brokers, dealers and clearing organizations represents deposits for securities borrowed transactions, margin deposits and current transactions awaiting settlement. The receivable from customers represents margin balances and amounts due on transactions awaiting settlement. Our receivables are, for the most part, collateralized by marketable securities. Our collateral maintenance policies and procedures are designed to limit our exposure to credit risk. Securities owned, with the exception of the ARS, are mainly comprised of actively trading readily marketable securities. We issued ~~$5.1~~$10.8 million in forgivable notes (which are inherently illiquid) to employees for the three months ended ~~June 30, 2022~~March 31, 2023 ($~~7.0~~7.7 million for the three months ended ~~June 30, 2021)~~March 31, 2022) as upfront or backend inducements to commence or continue employment as the case may be. The amount of funds allocated to such inducements will vary with hiring activity.

We satisfy our need for short-term liquidity from internally generated funds, collateralized and uncollateralized bank borrowings, stock loans and repurchase agreements. Bank borrowings are, in most cases, collateralized by Firm and customer securities.

We obtain short-term borrowings primarily through bank call loans. Bank call loans are generally payable on demand and bear interest at various rates. At ~~June 30, 2022,~~March 31, 2023, the Company had ~~$177.3~~$19.3 million of bank call loans ~~($69.5 million~~(zero at December 31, ~~2021)~~2022). The average daily bank loan outstanding for the three ~~and six~~ months ended ~~June 30, 2022~~March 31, 2023 was ~~$111.5~~$57.5 million ~~and $99.40 million, respectively~~ ($~~88.9 million and $69.7~~87.1 million for the three ~~and six~~ months ended ~~June 30, 2021)~~March 31, 2022). The largest daily bank loans outstanding for ~~both of~~ the three ~~and six~~ months ended ~~June 30, 2022~~March 31, 2023 was ~~$226.6~~$167.3 million ($~~148.1~~190.2 million for ~~both of~~ the three ~~and six~~ months ended ~~June 30, 2021)~~March 31, 2022).

At ~~June 30, 2022,~~March 31, 2023, securities loan balances totaled ~~$281.4~~$368.1 million ($~~244.2~~320.8 million at December 31, ~~2021~~2022 and ~~$267.5~~$300.3 million at ~~June 30, 2021)~~March 31, 2022). The average daily securities loan balance outstanding for the three ~~and six~~ months ended ~~June 30, 2022~~March 31, 2023 was ~~$269.6~~$341.4 million ~~and $286.9 million, respectively~~ ($~~280.8 million and $271.7~~304.1 million for the three ~~and six~~ months ended ~~June 30, 2021)~~March 31, 2022). The largest daily stock loan balance for the three ~~and six~~ months ended ~~June 30, 2022~~March 31, 2023 was ~~$302.9~~$388.4 million ~~and $350.1 million, respectively~~ ($~~314.0~~350.1 million for both of the three ~~and six~~ months ended ~~June 30, 2021)~~March 31, 2022).

We finance our government trading operations through the use of securities purchased under reverse repurchase agreements and repurchase agreements. Except as described below, repurchase and reverse repurchase agreements, primarily involving government and agency securities, are carried at amounts at which securities subsequently will be resold or reacquired as specified in the respective agreements and include accrued interest.

~~Table of Contents~~

Repurchase and reverse repurchase agreements are presented on a net-by-counterparty basis, when the repurchase and reverse repurchase agreements are executed with the same counterparty, have the same explicit settlement date, are executed in accordance with a master netting arrangement, the securities underlying the repurchase and reverse repurchase agreements exist in "book entry" form and certain other requirements are met.

Certain of our repurchase agreements and reverse repurchase agreements are carried at fair value as a result of the Company's fair value option election. We elected the fair value option for those repurchase agreements and reverse repurchase agreements that do not settle overnight or have an open settlement date. We have elected the fair value option for these instruments to more accurately reflect market and economic events in our earnings and to mitigate a potential imbalance in earnings caused by using different measurement attributes (i.e. fair value versus carrying value) for certain assets and liabilities. At ~~June 30, 2022,~~March 31, 2023, we did not have any repurchase agreements and reverse repurchase agreements that did not settle overnight or have an open settlement date.

At ~~June 30, 2022,~~March 31, 2023, the gross balances of reverse repurchase agreements and repurchase agreements were ~~$240.7~~$30.1 million and ~~$411.7~~$310.5 million, respectively. The average daily balance of reverse repurchase agreements and repurchase agreements on a gross basis for the three months ended ~~June 30, 2022~~March 31, 2023 was ~~$146.9~~$179.0 million and ~~$291.8~~$283.1 million, respectively ($~~91.4~~132.4 million and ~~$356.8~~$443.5 million, respectively, for the three months ended ~~June 30, 2021)~~March 31, 2022). The largest amount of reverse repurchase agreements and repurchase agreements outstanding on a gross basis during the three months ended ~~June 30, 2022~~March 31, 2023 was ~~$435.7~~$506.4 million and ~~$540.1~~$634.9 million, respectively ($~~327.6~~462.5 million and ~~$496.9~~$644.1 million, respectively, for the three months ended ~~June 30, 2021)~~March 31, 2022).

Liquidity Management

We manage our liquidity to meet our current obligations and upcoming liquidity needs as well as to ensure compliance with regulatory requirements. Our liquidity needs may be affected by market conditions, increased inventory positions,

Table of Contents

business expansion and other unanticipated occurrences. In the event that existing financial resources do not satisfy our liquidity needs, we may have to seek additional external financing. The availability of such additional external financing may depend on market factors outside our control.

We have Company-owned life insurance policies which are utilized to fund certain non-qualified deferred compensation plans. Certain policies which could provide additional liquidity if needed had a cash surrender value of ~~$74.4~~$79.1 million as of ~~June 30, 2022.~~March 31, 2023.

We regularly review our sources of liquidity and financing and conduct internal stress analysis to determine the impact on the Company of events that could remove sources of liquidity or financing and to plan actions the Company could take in the case of such an eventuality. ~~Our reviews~~Recent bank failures did not result in reducing the availability of funding or any disruption in the Company’s business. Should such disruption occur in the future we have ~~resulted in~~ plans that we believe would result in a reduction of assets through liquidation that would significantly reduce the Company's need for external financing.

Our primary long-term cash requirements include ~~$124.2~~$112.5 million principal outstanding as of ~~June 30, 2022~~March 31, 2023 under our Senior Secured Notes (due in 2025) and ~~$187.5~~$193.4 million of operating lease obligations. The total cash requirement for interest expense related to the Notes and operating lease obligations is estimated to be approximately ~~$9.7~~$14.2 million for the ~~2022 year.~~remainder of 2023.

Funding Risk

(Expressed in thousands)
For the Six Months Ended June 30,
2022 2021
Cash (used in)/provided by operating activities $ (231,371) $ 20,140
Cash used in investing activities (1,116) (5,431)
Cash provided by/(used in) financing activities 55,444 (10,335)
Net (decrease)/increase in cash, cash equivalents and restricted cash $ (177,043) $ 4,374

~~Table of Contents~~


(Expressed in thousands)
	For the Three Months Ended March 31,
	2023		2022
Cash used in operating activities	$	(86,123)	$	(152,146)
Cash used in investing activities	(2,976)		(2,490)
Cash provided by/(used in) financing activities	7,033		(11,654)
Net decrease in cash, cash equivalents and restricted cash	$	(82,066)	$	(166,290)

Management believes that funds from operations, combined with our capital base and available credit facilities, are sufficient for our liquidity needs for the foreseeable future. Under some circumstances, banks including those on whom we rely may back away from providing funding to the securities industry. Such a development might impact our ability to finance our day-to-day activities or increase the costs to acquire funding. We may or may not be able to pass such increased funding costs on to our clients.

During periods of high volatility, we have seen increased calls for deposits of collateral to offset perceived risk between the Company's settlement liability to industry clearinghouses such as the Options Clearing Corporation (“OCC”) and National Securities Clearing Corp. (“NSCC”) as well as more stringent collateral arrangements with our bank lenders. All such requirements have been and will be met in the ordinary course with available collateral.

CYBERSECURITY

For many years, we have sought to maintain the security of our clients' data, limit access to our data processing environment, and protect our data processing facilities. See "Risk Factors — Cybersecurity – Security breaches of our technology systems, or those of our clients or other ~~third-party~~first-party vendors we rely on, could subject us to significant liability and harm our reputation" as further described in Part I, Item 1A of the Company's Annual Report on Form 10-K for the year ended December 31, ~~2021.~~2022. Recent examples of vulnerabilities of other companies and the government that have resulted in loss of client data and fraudulent activities by both domestic and foreign actors have caused us to continuously review our security policies and procedures and to take additional actions to protect our network and our information. The commencement of hostilities between Ukraine and Russia has resulted in increased attacks on the infrastructure of data processing facilities around the world and heightened awareness of potential vulnerabilities including ~~those~~the compliance of ~~the~~ Company.

Given the importance of the protection of client data, regulators have developed increased oversight of cybersecurity planning and protections that broker-dealers and other financial service providers have implemented. Such planning and protection are subject to the SEC's and FINRA's oversight and examination on a periodic or targeted basis. We expect that regulatory oversight will intensify, as a result of publicly announced data breaches by other organizations involving

Table of Contents

tens of millions of items of personally identifiable information. We continue to implement protections and adopt procedures to address the risks posed by the current information technology environment. The Company has significantly increased the resources dedicated to this effort and believes that further increases may be required in the future, in anticipation of increases in the sophistication and persistency of such attacks. There can be no guarantee that our cybersecurity efforts will be successful in discovering or preventing a security breach.

~~Table of Contents~~

REGULATORY MATTERS AND DEVELOPMENTS

Regulation Best Interest (U.S.)

On June 5, 2019, the SEC adopted Regulation Best Interest (“Reg BI”) as Rule 15l-1 under the Exchange Act. Reg BI imposes a federal standard of conduct on registered broker-dealers and their associated persons when dealing with retail clients and requires that a broker-dealer and its representatives act in the best interest of clients and not place its own interests ahead of the customer’s interests. Reg BI does not define the term “best interest” but instead sets forth four distinct obligations, disclosure, care, conflict of interest and compliance, that a broker-dealer must satisfy in each transaction. Compliance with Reg BI became required on June 30, 2020. In addition to adopting Reg BI, the SEC adopted rules (i) requiring broker-dealers and investment advisers to provide a written relationship summary to each client, and (ii) clarifying certain interpretations under the Investment Advisers Act of 1940 including but not limited to when a broker-dealer's activity is considered “solely incidental” to its broker-dealer business and is, therefore, not considered investment advisory activity (collectively, the “Reg BI Rules”).

Reg BI requires enhanced documentation for recommendations of securities transactions to broker-dealer retail clients as well as the cessation of certain practices and limitations on certain kinds of transactions previously conducted in the normal course of business. The rules and processes required under Reg BI limit revenue and involve increased costs, including, but not limited to, compliance costs associated with enhanced technology as well as increased litigation costs. The Company made significant structural, technological and operational changes to our business practices to comply with the requirements of the Reg BI Rules and it is likely that additional changes may be necessary to continue to comply as more experience with the Reg BI Rules is gained. Regulators have commenced in-depth reviews of the industry’s compliance with the requirements of Reg BI, including that of the Company.

On December 18, 2020, the DOL published its final prohibited transaction exemption (“PTE”) addressing investment advice fiduciaries byof ERISA plans and IRAs. Similar to the proposal the DOL released in June of 2020, the final exemption takes a principles-based (rather than a prescriptive) approach to resolving conflicts that arise under ERISA when an investment advice fiduciary, its affiliate or a related party is paid certain types of compensation (such as commissions, trailing fees or revenue- sharing) or engages in certain principal transactions. The final exemption should provide a new and more flexible approach to ERISA compliance for certain types of transactions, which financial institutions may choose to utilize in place of other existing exemptions. Like the proposal (but in contrast to the precursor rule the DOL finalized in April 2016 that the U.S. Court of Appeals for the Fifth Circuit later vacated in June 2018), the final exemption does not materially change the scope of fiduciary activities under ERISA, with the exception of including certain rollover-related advice as fiduciary advice. The effective date for compliance with the PTE was February 1, 2022. The Company believes many of the steps taken by the Company to achieve compliance with the Reg BI Rules will enable the Company to comply with the PTE. The Company implemented certain additional processes to accompany the actions taken to comply with the Reg BI Rules in order to ensure full compliance with the PTE.

Regulatory Environment

See the discussion of the regulatory environment in which we operate and the impact on our operations of certain rules and regulations in Item 1 “Business - Regulation” in the Company's Annual Report on Form 10-K for the year ended December 31, ~~2021~~2022 for additional information.

Oppenheimer and many of its affiliates are each subject to various regulatory capital requirements. As of ~~June 30, 2022,~~March 31, 2023, all of our active regulated domestic and international subsidiaries had net capital in excess of minimum requirements. See note 15 to the condensed consolidated financial statements in Item 1 for further information on regulatory capital requirements.

Other Regulatory Matters

Since August 2021, Oppenheimer has been responding to information requests from the SEC’s Division of Enforcement relating to a former Oppenheimer financial advisor and his relationship with registered investment adviser, Southport Capital and its affiliates.

Table of Contents

On June 30, 2022, the Company received a "Wells Notice" from the SEC requesting that Oppenheimer make a written submission to the SEC to explain why Oppenheimer should not be charged with violations of Section 15c2-12 of the Exchange Act and ~~Rule15c2-12~~Rule 15c2-12 thereunder as well as Municipal Securities Rulemaking Board Rules G-17 and G-27 in relation to its sales of municipal notes pursuant to an exemption from continuing disclosure contained in Rule 15c2-12.

~~Table~~ On September 13, 2022, the SEC filed a complaint against Oppenheimer in the United States District Court for the Southern District of ~~Contents~~

~~As a result~~New York (the "Court") alleging that Oppenheimer violated Section 15B(c)(1) of the ~~foregoing the Company believes the SEC may institute an administrative proceeding against Oppenheimer~~Exchange Act and Rule 15c2-12 thereunder as well as Municipal Securities Rulemaking Board Rules G-17 and G-27 for not having fully complied with the exemption from the continuing disclosure obligations under Rule 15c2-12. The SEC asked the Court to enter an order enjoining Oppenheimer from violating the above referenced rules and requiring it to disgorge approximately $1.9 million plus interest. The Company believes such claim to be without merit and intends to vigorously defend itself against any such claim.

On November 18, 2022, the Company received an information request from the SEC requesting information relating to the use of text messaging and similar forms of electronic communications by employees of the Company and whether those communications were properly retained by the Company as part of its records preservation requirements relating to the broker-dealer or investment adviser business activities of the Company. The Company has submitted multiple responses to the information request and continues to cooperate with the SEC inquiry.

The SEC has under consideration a number of rules that are believed will change the operation of the equity markets and may disrupt and/or remove liquidity from the markets as well as significant rule proposals relating to cybersecurity, climate change and investment advisory custodial practices. The Company continues to monitor these developments and cannot currently determine what, if any, impact they may have on its business.

FACTORS AFFECTING "FORWARD-LOOKING STATEMENTS"

From time to time, the Company may publish or make oral statements that constitute “forward-looking statements” under the Private Securities Litigation Reform Act of 1995 which provides a safe harbor for forward-looking statements. These forward-looking statements may relate to such matters as anticipated financial performance, future revenues, earnings, liabilities or expenses, business prospects, projected ventures, new products, anticipated market performance, and similar matters. The Company cautions readers that a variety of factors could cause the Company’s actual results to differ materially from the anticipated results or other expectations expressed in the Company’s forward-looking statements. These risks and uncertainties, many of which are beyond the Company’s control, include, but are not limited to: (i) transaction volume in the securities markets, (ii) the volatility of the securities markets, (iii) fluctuations in interest rates, (iv) changes in regulatory requirements that could affect the cost and method of doing business, (v) general economic conditions, both domestic and international, including inflation, recession, and changes in consumer confidence and spending, (vi) competition from existing financial institutions, new entrants and other participants in the securities markets and financial services industry, (vii) potential cybersecurity threats and attacks, (viii) legal developments affecting the litigation experience of the securities industry and the Company, (ix) changes in foreign, federal and state tax laws that could affect the popularity of products sold by the Company or impose taxes on securities transactions, (x) the adoption and implementation of the SEC’s “Regulation Best Interest” and other regulations adopted in recent years, (xi) war, terrorist acts and nuclear confrontation as well as political unrest, including events relating to Russia's invasion of Ukraine and related Western sanctions, (xii) the Company’s ability to achieve its business plan, (xiii) the effects of the economy on the Company’s ability to find and maintain financing options and liquidity, (xiv) credit, operational, legal and regulatory risks, (xv) risks related to foreign operations, including those in the United Kingdom which may be affected by Britain’s January 2020 exit from the EU (“Brexit”), and economic uncertainty in the UK, EU and elsewhere, (xvi) the effect of technological innovation on the financial services industry and securities business, (xvii) risks related to election results, Congressional gridlock, political and social unrest, government shutdowns and investigations, trade wars, bank failures, changes in or uncertainty surrounding regulation, and the potential for default by the U.S. government on the nation's debt, (xviii) risks related to changes in capital requirements under international standards that may cause banks to back away from providing funding to the securities industry, and (xix) risks related to the severity and duration of the COVID-19 Pandemic, the COVID-19 Pandemic’s impact on the U.S. and global economies including supply chain disruptions, and Federal, state and local governmental responses to the COVID-19 Pandemic. There can be no assurance that the Company has correctly or completely identified and assessed all of the factors affecting the Company's business. See “Risk Factors” in Part I, Item 1A of the Company’s Quarterly Report on Form 10-Q for the quarter ended March 31, 2023 and Annual Report on Form 10-K for the year ended December 31, ~~2021.~~2022.

5349

Table of Contents

Item 3. QUANTITATIVE AND QUALITATIVE DISCLOSURES ABOUT MARKET RISK

During the ~~six~~three months ended ~~June 30, 2022,~~March 31, 2023, there were no material changes to the information contained in Part II, Item 7A of the Company's Annual Report on Form 10-K for the year ended December 31, ~~2021.~~

2022.

Table of Contents

Item 4. CONTROLS AND PROCEDURES

The Company carried out an evaluation, under the supervision and with the participation of management, including the Chief Executive Officer and ~~Interim~~ Chief Financial Officer, of the effectiveness of the design and operation of its disclosure controls and procedures pursuant to Rule 13a–15(e) of the Exchange Act. Based on this evaluation, the Company's Chief Executive Officer and ~~Interim~~ Chief Financial Officer concluded that the Company's disclosure controls and procedures were effective as of the end of the period covered by this report.

Management, including the Chief Executive Officer and ~~Interim~~ Chief Financial Officer, does not expect that the Company's disclosure controls and procedures or its internal controls will prevent all error and all fraud. A control system, no matter how well conceived and operated, can provide only reasonable, not absolute, assurance that the objectives of the control system are met. Further, the design of a control system must reflect the fact that there are resource constraints and the benefits of controls must be considered relative to their costs. Because of the inherent limitations in all control systems, no evaluation of controls can provide absolute assurance that all control issues and instances of fraud, if any, within the Company have been detected. These inherent limitations include, but are not limited to, the realities that judgments in decision-making can be faulty and that breakdowns can occur because of a simple error or omission. Additionally, controls can be circumvented by the individual acts of some persons, by collusion of two or more people, or by management override of the control. The design of any system of controls also is based, in part, upon certain assumptions about the likelihood of future events and there can be no assurance that any design will succeed in achieving its stated goals under all potential future conditions; over time, controls may become inadequate because of changes in conditions or the degree of compliance with the policies or procedures may deteriorate. Because of the inherent limitations in a cost–effective control system, misstatements due to error or fraud may occur and not be detected.

The Company confirms that its management, including its Chief Executive Officer and its ~~Interim~~ Chief Financial Officer, concluded that the Company's disclosure controls and procedures are effective to ensure that the information required to be disclosed by the Company in its reports filed under the Exchange Act is recorded, processed, summarized and reported within the time periods specified in the rules and forms of the SEC.

Changes in Internal Control over Financial Reporting

There have been no changes in the Company's internal controls over financial reporting (as defined in Rule 13a-15(f) of the Exchange Act) during the ~~six~~three months ended ~~June 30, 2022~~March 31, 2023 that have materially affected, or are reasonably likely to materially affect, the Company's internal controls over financial reporting.

5451

Table of Contents

PART II. OTHER INFORMATION

Item 1. LEGAL PROCEEDINGS

Many aspects of the Company's business involve substantial risks of liability. In the normal course of business, the Company has been ~~the subject of customer complaints and has been~~ named as a defendant or co-defendant in various ~~lawsuits or~~legal actions, including arbitrations, class actions and other litigation, creating substantial ~~exposure. The Company is also involved from time to time in certain governmental~~exposure and ~~self-regulatory agency investigations and proceedings.~~periodic expenses. Certain of the actual or threatened legal matters include claims for substantial compensatory and/or punitive damages or claims for indeterminate amounts of damages. These proceedings arise primarily from securities brokerage, asset management and investment banking activities. The Company is also involved, from time to time, in other reviews, investigations and proceedings (both formal and informal) by governmental and self-regulatory agencies regarding the Company's business, which may result in expenses, adverse judgments, settlements, fines, penalties, injunctions or other relief. The investigations include inquiries from the SEC, the Financial Industry Regulatory ~~investigations~~Authority ("FINRA") and various state regulators.

The Company accrues for estimated loss contingencies related to legal and regulatory matters within Other Expenses in the ~~financial services industry may include investigations by multiple regulators~~consolidated income statement when available information indicates that it is probable a liability had been incurred and the Company can reasonably estimate the amount of ~~matters involving~~that loss. In many proceedings, however, it is inherently difficult to determine whether any loss is probable or even possible or to estimate the ~~same~~amount of any loss. In addition, even where a loss is possible or ~~similar underlying facts~~an exposure to loss exists in excess of the liability already accrued with respect to a previously recognized loss contingency, it is often not possible to reasonably estimate the size of the possible loss or range of loss or possible additional losses or range of additional losses.

For certain legal and regulatory proceedings, the Company cannot reasonably estimate such losses, particularly for proceedings that are in their early stages of development or where plaintiffs seek substantial, ~~penalties, fines~~indeterminate or special damages. Counsel may be required to review, analyze and resolve numerous issues, including through potentially lengthy discovery and determination of important factual matters, and by addressing novel or unsettled legal questions relevant to the proceedings in question, before the Company can reasonably estimate a loss or range of loss or additional loss for the proceeding. Even after lengthy review and analysis, the Company, in many legal and regulatory proceedings, may not be able to reasonably estimate possible losses or range of losses.

For certain other ~~monetary relief.~~

~~While~~legal and regulatory proceedings, the ~~ultimate resolution~~Company can estimate possible losses, or range of ~~routine pending litigation, regulatory~~loss in excess of amounts accrued, but does not believe, based on current knowledge and ~~other matters cannot be currently determined, in the opinion of management,~~ after consultation with ~~legal~~ counsel, that such losses individually, or in the ~~Company does not believe that the resolution of these matters~~aggregate, will have a material adverse effect on its condensed consolidated balance sheet and statement of cash flows. However, the Company's results of operations could be materially affected during any period if liabilities in that period differ from prior estimates.

~~Notwithstanding the foregoing, multiple adverse results in arbitrations, litigations or regulatory proceedings currently filed or to be filed against the Company, could~~ have a material adverse effect on the Company's ~~results of operations and~~consolidated financial ~~condition, including its cash position.~~statements as a whole.

~~The materiality of~~

For legal and regulatory matters to the Company's future operating results depends on the level of future results of operations as well as the timing and ultimate outcome of such legal and regulatory matters. See "Management's Discussion and Analysis of Financial Condition and Results of Operations - Factors Affecting 'Forward-Looking Statements'" in Part I, Item 2.

In accordance with applicable accounting guidance, the Company establishes reserves for litigation and regulatory matters when those matters present loss contingencies that are both probable and reasonably estimable. When loss contingencies are not both probable and reasonably estimable, the Company does not establish reserves. In some of the matters described below, loss contingencies are not probable and reasonably estimable in the view of management and, accordingly, the Company has not established reserves for those matters. For legal or regulatory proceedings where there is at least a reasonable possibility that a loss or an additional loss may be incurred, the Company estimates a range of aggregate loss in excess of amounts accrued of $0up to ~~$41.3~~$35 million. This estimated aggregate range is based upon currently available information for those legal proceedings in which the Company is involved, where the Company can make an estimate for such ~~losses can be made.~~losses. For certain cases, the Company does not believe that it can make an estimate. The foregoing aggregate estimate is based on various factors, including the varying stages of the proceedings (including the fact that some are currently in preliminary stages), the numerous yet-unresolved issues in many of the proceedings and the attendant uncertainty of the various potential outcomes of such proceedings. Accordingly, the Company's estimate will change from time to time, and actual losses may be ~~materially~~ more than the current estimate.

OnBeginning on or about August 31, 2021, Oppenheimer was named as a ~~complaint~~respondent in a class action entitled 6694 Dawson Blvd, LLC, Individually and on Behalf of a Class of Similarly Situated Persons v. Oppenheimer & Co. Inc., James Wallace Woods, Michael J. Mooney, Britt Wright, William V. Conn, Jr., Conn & Co. Tax Practice, LLC, Conn & Company Consulting, LLC and Kathleen Lloyd, wasthirty-nine arbitrations, many containing multiple claimants, each filed ~~in the U.S. District Court for the Northern District of Georgia. Plaintiff purports~~before FINRA, relating to ~~represent a class of investors~~those claimants’ purported investment in Horizon Private Equity, III, LLC (“Horizon”). Horizon is alleged to be a fraudulent scheme involving, among others, a former Oppenheimer employee John Woods. John Woods left Oppenheimer’s employ in 2016 and ~~plaintiff is~~Oppenheimer never received a complaint or question from any of the investors prior to the Securities and Exchange Commission (“SEC”) bringing a complaint against Woods and his co-conspirators in 2021. Each investor, who was an Oppenheimer client, signed a document acknowledging that Horizon was not an approved Oppenheimer product. Over a protracted period of time, Woods made multiple false statements to Oppenheimer, to regulators and to a state court. The claimants are seeking ~~unspecified~~ damages ~~sounding in~~based on a number of legal theories, including, without limitation, violations of ~~the Georgia RICO statute,~~various state and federal statutes, breach of fiduciary duty, procurement of breach of fiduciary duty, negligent misrepresentation, aiding and abetting fraud, and unjust ~~enrichment, punitive damages and attorneys’ fees. Plaintiff does~~enrichment. Claimants do not allege Oppenheimer received any of the funds invested in Horizon, but rather that Oppenheimer’s purported failure to properly supervise its employees allowed the alleged scheme to occur and continue. ~~On November 22, 2021, Oppenheimer filed a motion to dismiss the complaint on a number of grounds.~~ The motion to dismiss was fully briefed on January 17, 2022, and the Court heard oral argument on the motion on June 21, 2022. Oppenheimer believes the claims to be without merit and intends to vigorously defend itself against the claims made in this action.

~~In addition to the class action described in the preceding paragraph Oppenheimer has also been named as a respondent in twenty-four~~twenty-two arbitrations many containing multiple claimants, each filed before FINRA, relating to investments made by former Oppenheimer clients who invested in Horizon. Claimants allege many of the causes of action alleged in the class action described in the preceding paragraph. The arbitrations claimingstill pending claim specific monetary damages and allege ~~damages~~losses of approximately ~~$41.3~~$24 million in the aggregate while a few others claim unspecified damages. Oppenheimer believes these claims to be without merit and intends to defend itself vigorously against these claims.

Table of Contents

As previously reported Oppenheimer’s motion to vacate the arbitration award in Donald Robinson, Timothy and Sharon Padden, Rhett Rainey, Kelly A. Rainey Trust, Toucan Holdings LP, Robert Goodman, Robert Daniel Burgner, Individually and as Trustee of the Burgner Family Charitable Remainder Trust, Douglas Kasemeier, Wesley Callaway, and Billy Loveless v. Oppenheimer & Co. Inc. (the “Robinson Arbitration”) was denied on January 30, 2023. However, on March 27, 2023, the court entered a consent judgment vacating the award in the Robinson Arbitration pursuant to the parties’ request in connection with their settlement of the matter. Oppenheimer has settled, or settled in principle or an award has been rendered in seventeen of the Horizon related arbitrations, including the Robinson Arbitration,with approximately fifty-seven individual complainants. The aggregate settlement payments for those total approximately $58 million.

On June 30, 2022, the Company received a "Wells Notice" from the SEC requesting that Oppenheimer make a written submission to the SEC to explain why Oppenheimer should not be charged with violations of Section 15c2-12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and Rule 15c2-12 thereunder as well as Municipal Securities Rulemaking Board Rules G-17 and G-27 in relation to its sales of municipal notes pursuant to an exemption from continuing disclosure contained in Rule 15c2-12. On September 13, 2022, the SEC filed a complaint against Oppenheimer in the United States District Court for the Southern District of New York (the “Court") alleging that Oppenheimer violated Section 15B(c)(1) of the Exchange Act and Rule 15c2-12 thereunder as well as Municipal Securities Rulemaking Board Rules G-17 and G-27 for not having fully complied with the exemption from the continuing disclosure obligations under Rule 15c2-12. The SEC asked the Court to enter an order enjoining Oppenheimer from violating the above referenced rules and requiring it to disgorge approximately $1.9 million plus interest. The Company believes such claim to be without merit and intends to vigorously defend itself against such claim.

Table of Contents

Item 1A. RISK FACTORS

During the ~~six~~three months ended ~~June 30, 2022,~~March 31, 2023, there were no material changes to the information contained in Part I, Item 1A of the Company's Annual Report on Form 10-K for the year ended December 31, ~~2021.~~2022. The following addition amends our risk factors previously included within the Company’s Annual Report on Form 10-K for the year-ended December 31, 2022:

Sudden changes in market conditions or other macroeconomic factors may adversely impact our business, financial condition and operating results

Economic and market conditions will continue to have an impact on our financial condition and results of operations since the Company’s financial performance is largely correlated with the overall health of our economy and financial market activity.The unexpected failure of two commercial banks (Silicon Valley Bank and Signature Bank) during the quarter-ended March 31, 2023 raised concerns about institutions with concentrated exposure to certain types of depositors in the same industry as well as those with large unrealized losses in their investment security holdings.While the Company does not have any direct exposure to Silicon Valley Bank or Signature Bank, our cash is held with various third-party financial institutions.In particular, a substantial majority of our cash is held with a large, global systemically important bank, often in balances that exceed the current FDIC insurance limits. If the banks that we hold our deposits with enter receivership or become insolvent, we may be prevented from accessing our cash and cash equivalents in excess of FDIC insured limits. While such an event would be harmful to our financial condition, it is highly unlikely, given the normal size of such deposits, that such an event would be harmful to our overall financial condition.

Item 2. Unregistered Sales of Equity Securities and Use of Proceeds

(a) During the ~~second~~first quarter of ~~2022,~~2023, the Company ~~did not issue any~~issued 202,222 shares of Class A Stock pursuant to the Company's share-based compensation plans to employees of the ~~Company.~~Company for no cash consideration. Such issuances were exempt

from registration pursuant to Section 4(a)(2) of the Securities Act.

(b) Not applicable.

(a) (b) (c) (d)
Period Total number of shares purchased Average price paid per share Total number of shares purchased as part of publicly announced plans or programs
Maximum number of shares that may yet be purchased under the plans or programs (4)
April 1 - 30, 2022 (1) (2)
24,518 $43.83 24,518 339,990
May 1 - 31, 2022 (3)
346,051 $32.84 346,051 543,939
June 1 - 30, 2022 514,661 $34.54 514,661 29,278
Q2 2022 Total 885,230 $34.13 885,230 29,278
(1) On May 15, 2020, the Company announced that its Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 530,000 shares of the Company's Class A Stock.
(2) On February 28, 2022, the Company announced that its Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 518,000 shares of the Company's Class A Stock.
(3) On May 24, 2022, the Company announced that its Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 550,000 shares of the Company's Class A Stock.
(4) None of the foregoing authorizations are subject to expiration.


	(a)	(b)	(c)	(d)
Period	Total number of shares purchased	Average price paid per share	Total number of shares purchased as part of publicly announced plans or programs	Maximum number of shares that may yet be purchased under the plans or programs (1)

January 1 - 31, 2023	—	$—	—	687,034
February 1 - 28, 2023	—	$—	—	687,034
March 1 - 31, 2023	95,055	$38.79	95,055	591,979
Q1 2023 Total	95,055	$38.79	95,055	591,979


(1) None of the foregoing authorizations is subject to expiration.

5654

Table of Contents

Item 6. EXHIBITS


31.1			Certification of Albert G. Lowenthal

31.2			Certification of ~~Salvatore F. Agosta~~Brad M. Watkins

32			Certification of Albert G. Lowenthal and ~~Salvatore F. Agosta~~Brad M. Watkins

101			Interactive data files pursuant to Rule 405 of Regulation S-T (unaudited): (i) the Condensed Consolidated Balance Sheets as of ~~June 30, 2022~~March 31, 2023 and December 31, ~~2021,~~2022, (ii) the Condensed Consolidated Income Statements for the three ~~and six~~ months ended ~~June 30,~~March 31, 2023 and 2022, ~~and 2021,~~ (iii) the Condensed Consolidated Statements of Comprehensive Income for the three ~~and six~~ months ended ~~June 30, 2021~~March 31, 2023 and 2022, (iv) the Condensed Consolidated Statements of Changes in Stockholders' Equity and Redeemable Noncontrolling Interests for the three ~~and six~~ months ended ~~June 30, 2021~~March 31, 2023 and 2022, (v) the Condensed Consolidated Statements of Cash Flows for the ~~six~~three months ended ~~June 30, 2021~~March 31, 2023 and 2022, and (vi) the notes to the Condensed Consolidated Financial Statements.*

*			This information is furnished and not filed for purposes of Sections 11 and 12 of the Securities Act of 1933 and Section 18 of the Securities Exchange Act of 1934.

5755

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned, thereunto duly authorized, in the City of New York, State of New York, on the ~~29th~~28th day of ~~July 2022.~~April, 2023.


OPPENHEIMER HOLDINGS INC.

BY: /s/ Albert G. Lowenthal
Albert G. Lowenthal, Chairman and Chief Executive Officer
(Principal Executive Officer)

BY: /s/ ~~Salvatore F. Agosta~~Brad M. Watkins
~~Salvatore F. Agosta, Interim~~Brad M. Watkins, Chief Financial Officer
(Principal Financial and Accounting Officer)

5856


(Expressed in thousands)	For the Six Months Ended June 30, 2022
	Reportable Segments
	Private Client		Asset Management		Capital Markets		Corporate/Other		Total
Revenue from contracts with customers:
Commissions from sales and trading	$	81,463	$	—	95,061		17		$	176,541
Mutual fund and insurance income	16,130		—		6		22		16,158
Advisory fees	171,613		51,424		117		17		223,171
Investment banking - capital markets	5,665		—		19,234		—		24,899
Investment banking - advisory	35		—		30,189		—		30,224
Bank deposit sweep income	19,199		—		—		—		19,199
Other	7,642		—		797		188		8,627
Total revenue from contracts with customers	301,747		51,424		145,404		244		498,819
Other sources of revenue:
Interest	18,517		—		2,685		104		21,306
Principal transactions, net	(4,166)		—		8,080		(292)		3,622
Other	(20,780)		8		156		119		(20,497)
Total other sources of revenue	(6,429)		8		10,921		(69)		4,431
Total revenue	$	295,318	$	51,432	$	156,325	$	175	$	503,250


(Expressed in thousands)
	As of June 30,
	2022		2021
Asset
Cash and cash equivalents	$	1,458	$	—
Restricted Cash	127,875		—
Other Assets	568		—
Total Assets	$	129,901	$	—
Liabilities
Other Liabilities	123		—
Total Liabilities	$	123	$	—