Kingsway Financial Services (KFS) 10-Q 17 Jul 20 2020 Q1 Quarterly report Financial data

Document and Entity Information

Document and Entity Information Document - shares	3 Months Ended
	Mar. 31, 2020	Jul. 17, 2020
Document Information [Abstract]
Document Quarterly Report	true
Document Transition Report	false
Entity Registrant Name	KINGSWAY FINANCIAL SERVICES INC.
Entity Central Index Key	0001072627
Current Fiscal Year End Date	--12-31
Entity Interactive Data Current	Yes
Entity Filer Category	Accelerated Filer
Entity Small Business	true
Entity Emerging Growth Company	false
Entity Shell Company	false
Document Type	10-Q
Document Period End Date	Mar. 31, 2020
Document Fiscal Year Focus	2020
Document Fiscal Period Focus	Q1
Amendment Flag	false
Entity Common Stock, Shares Outstanding		22,711,069

Consolidated Balance Sheets

Consolidated Balance Sheets - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019
Investments:
Fixed maturities, at fair value (amortized cost of $15,065 and $22,136, respectively)	$ 15,247	$ 22,195
Equity investments, at fair value (cost of $2,895 and $2,895, respectively)	1,825	2,421
Limited liability investments	3,776	3,841
Limited liability investments, at fair value	30,986	29,078
Investments in private companies, at adjusted cost	1,364	2,035
Real estate investments, at fair value (cost of $10,225 and $10,225, respectively)	10,662	10,662
Other investments, at cost which approximates fair value	841	1,009
Short-term investments, at cost which approximates fair value	156	155
Total investments	64,857	71,396
Cash and cash equivalents	14,036	13,478
Restricted cash	17,891	12,183
Accrued investment income	562	562
Service fee receivable, net of allowance for doubtful accounts of $792 and $634, respectively	3,262	3,400
Other receivables, net of allowance for doubtful accounts of $201 and $201, respectively	11,739	14,013
Beginning balance, net	8,744	8,604
Property and equipment, net of accumulated depreciation of $21,596 and $20,503, respectively	98,011	99,064
Right-of-use asset	3,178	3,327
Goodwill	82,104	82,104
Intangible assets, net of accumulated amortization of $13,716 and $13,142, respectively	85,850	86,424
Other assets	4,855	5,068
Total Assets	395,089	399,623
Liabilities:
Accrued expenses and other liabilities	27,266	26,993
Income taxes payable	2,805	2,758
Deferred service fees	56,219	56,252
Unpaid loss and loss adjustment expenses	1,691	1,774
Bank loans	8,727	9,240
Notes payable	193,418	194,634
Subordinated debt, at fair value	40,387	54,655
Lease liability	3,392	3,529
Net deferred income tax liabilities	29,146	29,015
Total Liabilities	363,051	378,850
Redeemable Class A preferred stock, no par value; 1,000,000 and 1,000,000 authorized at March 31, 2020 and December 31, 2019, respectively; 182,876 and 222,876 issued and outstanding at March 31, 2020 and December 31, 2019, respectively; redemption amount of $6,400 and $7,696 at March 31, 2020 and December 31, 2019, respectively	5,815	6,819
Shareholders' Equity:
Common stock, no par value; 50,000,000 and 50,000,000 authorized at March 31, 2020 and December 31, 2019, respectively; 22,211,069 and 21,866,959 issued and outstanding at March 31, 20120 and December 31, 2019, respectively	0	0
Additional paid-in capital	355,067	354,101
Treasury stock, at cost; 247,450 and 247,450 outstanding at March 31, 2020 and December 31, 2019, respectively	(492)	(492)
Accumulated deficit	(389,196)	(388,082)
Accumulated other comprehensive income	47,078	35,347
Shareholders' equity attributable to common shareholders	12,457	874
Noncontrolling interests in consolidated subsidiaries	13,766	13,080
Total Shareholders' Equity	26,223	13,954
Total Liabilities, Class A preferred stock and Shareholders' Equity	$ 395,089	$ 399,623

Consolidated Balance Sheets (Pa

Consolidated Balance Sheets (Parenthetical) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019
Assets
Fixed maturities, cost	$ 15,065	$ 22,136
Equity investments, cost	2,895	2,895
Real estate investments, cost	10,225	10,225
Premiums receivable, allowance for doubtful accounts	0	0
Other receivables, allowance for doubtful accounts	201	201
Service fee receivable, allowance for doubtful accounts	792	634
Property and equipment, accumulated depreciation	21,596	20,503
Intangible assets accumulated amortization	$ 13,716	$ 13,142
Liabilities:
Preferred stock authorized (in shares)	1,000,000	1,000,000
Preferred stock issued (in shares)	182,876	222,876
Preferred stock outstanding (in shares)	182,876	222,876
Redemption amount	$ 6,400	$ 7,696
Shareholders' Equity:
Common stock authorized (in shares)	50,000,000	50,000,000
Common stock issued (in shares)	22,211,069	21,866,959
Common stock outstanding (in shares)	22,211,069	21,866,959
Treasury stock (in shares)	247,450	247,450

Consolidated Statements of Oper

Consolidated Statements of Operations - USD ($) shares in Thousands, $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Revenues:
Service fee and commission income	$ 11,186	$ 9,815
Rental income	3,341	3,341
Other income	142	145
Total revenues	14,669	13,301
Operating expenses:
Claims authorized on vehicle service agreements	2,380	1,887
Loss and loss adjustment expenses	13	107
Commissions	1,303	918
Cost of services sold	403	1,359
General and administrative expenses	10,693	8,402
Leased real estate segment interest expense	1,499	1,527
Total operating expenses	16,291	14,200
Operating loss	(1,622)	(899)
Other revenues (expenses), net:
Net investment income	719	699
Net realized gains	208	315
(Loss) gain on change in fair value of equity investments	(597)	78
Gain on change in fair value of limited liability investments, at fair value	1,899	4,265
Net change in unrealized (loss) gain on private company investments	(670)	19
Other-than-temporary impairment loss	(117)	(75)
Non-operating other income	39	154
Interest expense not allocated to segments	(2,153)	(2,102)
Amortization of intangible assets	(574)	(521)
Gain on change in fair value of debt	2,645	576
Equity in net loss of investee	0	(33)
Total other revenues, net	1,399	3,375
(Loss) income before income tax expense (benefit)	(223)	2,476
Income tax expense (benefit)	170	(713)
Net (loss) income	(393)	3,189
Less: net income attributable to noncontrolling interests in consolidated subsidiaries	721	211
Less: dividends on preferred stock	377	246
Net (loss) income attributable to common shareholders	$ (1,491)	$ 2,732
(Loss) earnings per share – net (loss) income attributable to common shareholders:
Basic (in dollars per share)	$ (0.07)	$ 0.13
Diluted (in dollars per share)	$ (0.07)	$ 0.13
Weighted-average shares outstanding (in ‘000s):
Basic (in shares)	22,069	21,841
Diluted (in shares)	22,069	21,841

Consolidated Statements of Comp

Consolidated Statements of Comprehensive Income - USD ($) $ in Thousands		3 Months Ended
		Mar. 31, 2020	Mar. 31, 2019
Statement of Comprehensive Income [Abstract]
Net (loss) income		$ (393)	$ 3,189
Unrealized gains on available-for-sale investments:
Unrealized gains arising during the period	[1]	55	111
Reclassification adjustment for amounts included in net income	[1]	61	(6)
Change in fair value of debt attributable to instrument-specific credit risk	[1]	11,623	(945)
Other comprehensive income (loss)	[1]	11,739	(840)
Comprehensive income		11,346	2,349
Less: comprehensive income attributable to noncontrolling interests in consolidated subsidiaries		729	217
Comprehensive income attributable to common shareholders		$ 10,617	$ 2,132
[1]	Net of income tax expense (benefit) of $0 and $0 for the three months ended March 31, 2020 and March 31, 2019, respectively.

Consolidated Statements of Co_2

Consolidated Statements of Comprehensive Income (Parenthetical) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Statement of Comprehensive Income [Abstract]
Other comprehensive income (loss), tax	$ 0	$ 0

Consolidated Statements of Shar

Consolidated Statements of Shareholders' Equity - USD ($) $ in Thousands	Total		Shareholders' Equity Attributable to Common Shareholders	Common Stock	Additional Paid-in Capital	Treasury Stock	Accumulated Deficit	Accumulated Other Comprehensive Income (Loss)	Noncontrolling Interests in Consolidated Subsidiaries
Balance, beginning of period (in shares) at Dec. 31, 2018				21,787,728
Balance, beginning of period at Dec. 31, 2018	$ 24,258		$ 12,462	$ 0	$ 353,890	$ 0	$ (382,196)	$ 40,768	$ 11,796
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Vesting of restricted stock awards, net of share settlements for tax withholdings (in shares)				79,231
Net (loss) income	3,189		2,978				2,978		211
Preferred stock dividends	(246)		(246)		(246)
Other comprehensive (loss) income	(840)	[1]	(846)					(846)	6
Stock-based compensation, net of forfeitures	242		242		242
Balance, end of period (in shares) at Mar. 31, 2019				21,866,959
Balance, end of period at Mar. 31, 2019	$ 26,603		14,590	$ 0	353,886	0	(379,218)	39,922	12,013
Balance, beginning of period (in shares) at Dec. 31, 2019	21,866,959			21,866,959
Balance, beginning of period at Dec. 31, 2019	$ 13,954		874	$ 0	354,101	(492)	(388,082)	35,347	13,080
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Vesting of restricted stock awards, net of share settlements for tax withholdings (in shares)				94,110
Conversion of redeemable Class A preferred stock to common stock (in shares)				250,000
Conversion of redeemable Class A preferred stock to common stock	1,381		1,381		1,381
Net (loss) income	(393)		(1,114)				(1,114)		721
Preferred stock dividends	(377)		(377)		(377)
Distributions to noncontrolling interest holders	(43)								(43)
Other comprehensive (loss) income	11,739	[1]	11,731					11,731	8
Stock-based compensation, net of forfeitures	$ (38)		(38)		(38)
Balance, end of period (in shares) at Mar. 31, 2020	22,211,069			22,211,069
Balance, end of period at Mar. 31, 2020	$ 26,223		$ 12,457	$ 0	$ 355,067	$ (492)	$ (389,196)	$ 47,078	$ 13,766
[1]	Net of income tax expense (benefit) of $0 and $0 for the three months ended March 31, 2020 and March 31, 2019, respectively.

Consolidated Statements of Cash

Consolidated Statements of Cash Flows - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Operating activities:
Net (loss) income	$ (393)	$ 3,189
Adjustments to reconcile net (loss) income to net cash provided by (used in) operating activities:
Equity in net loss of investee	0	33
Equity in net (income) loss of limited liability investments	(23)	18
Depreciation and amortization expense	1,667	1,606
Stock-based compensation (benefit) expense, net of forfeitures	(38)	242
Net realized gains	(208)	(315)
Loss (gain) on change in fair value of equity investments	597	(78)
Gain on change in fair value of limited liability investments, at fair value	1,899	4,265
Net change in unrealized loss (gain) on private company investments	670	(19)
Gain on change in fair value of debt	(2,645)	(576)
Deferred income taxes, adjusted for Geminus liabilities assumed	131	(849)
Other-than-temporary impairment loss	117	75
Amortization of fixed maturities premiums and discounts	31	6
Amortization of note payable premium	(225)	(231)
Service fee receivable, net, adjusted for Geminus assets acquired	138	(1,071)
Other receivables, net, adjusted for Geminus assets acquired	2,274	(783)
Deferred acquisition costs, net	(140)	(316)
Unpaid loss and loss adjustment expenses	(83)	(634)
Deferred service fees, adjusted for Geminus liabilities assumed	(33)	1,749
Other, net, adjusted for Geminus assets acquired and liabilities assumed	675	(708)
Net cash provided by (used in) operating activities	613	(2,927)
Investing activities:
Proceeds from sales and maturities of fixed maturities	8,646	2,694
Purchases of fixed maturities	(1,549)	(6,104)
Net proceeds from limited liability investments	87	0
Net proceeds from limited liability investments, at fair value	77	249
Net proceeds from investments in private companies	60	249
Net proceeds from other investments	52	1,335
Net (purchases of) proceeds from short-term investments	(1)	7
Acquisition of business, net of cash acquired	0	(4,321)
Net purchases of property and equipment, adjusted for Geminus assets acquired	(40)	(16)
Net cash provided by (used in) investing activities	7,332	(5,907)
Financing activities:
Distributions to noncontrolling interest holders	(43)	0
Taxes paid related to net share settlements of restricted stock awards	(83)	(89)
Principal proceeds from bank loan, net of debt issuance costs of $981	0	9,019
Principal payments on bank loans	(562)	(250)
Principal payments on notes payable	(991)	(894)
Net cash (used in) provided by financing activities	(1,679)	7,786
Net increase (decrease) in cash and cash equivalents and restricted cash	6,266	(1,048)
Cash and cash equivalents and restricted cash at beginning of period	31,927	30,530
Cash and cash equivalents and restricted cash at end of period	$ 25,661	$ 31,578

Consolidated Statements of Ca_2

Consolidated Statements of Cash Flows (Parenthetical) $ in Thousands	3 Months Ended
	Mar. 31, 2019USD ($)
Statement of Cash Flows [Abstract]
Principal proceeds from bank loan, debt issuance costs	$ 981

BASIS OF PRESENTATION

BASIS OF PRESENTATION	3 Months Ended
	Mar. 31, 2020
Organization, Consolidation and Presentation of Financial Statements [Abstract]
BASIS OF PRESENTATION	BASIS OF PRESENTATION The accompanying unaudited consolidated interim financial statements have been prepared in accordance with accounting principles generally accepted in the United States of America ("U.S. GAAP") for interim financial information and with the instructions to Form 10-Q and Article 10 of Regulation S-X. Accordingly, they do not include all of the information and notes required by U.S. GAAP for complete financial statements of the Company. In the opinion of management, all adjustments necessary for a fair presentation have been included and are of a normal recurring nature. Interim results are not necessarily indicative of the results that may be expected for the year. The accompanying unaudited consolidated interim financial statements and footnotes should be read in conjunction with the audited consolidated financial statements and footnotes included within our Annual Report on Form 10-K (" 2019 Annual Report") for the year ended December 31, 2019 . The unaudited consolidated interim financial statements include the accounts of the Company and its subsidiaries, as well as certain variable interest entities as further described in Note 6, "Variable Interest Entities," to the consolidated financial statements in the 2019 Annual Report. All material intercompany transactions and balances have been eliminated in consolidation. The preparation of consolidated financial statements in accordance with U.S. GAAP requires management to make estimates and assumptions that affect the reported amounts and classifications of assets and liabilities, revenues and expenses, and the related disclosures of contingent assets and liabilities in the consolidated financial statements and accompanying notes. Actual results could differ from these estimates. Estimates and their underlying assumptions are reviewed on an ongoing basis. Changes in estimates are recorded in the accounting period in which they are determined. The critical accounting estimates and assumptions in the accompanying unaudited consolidated interim financial statements include the provision for unpaid loss and loss adjustment expenses; valuation of fixed maturities and equity investments; impairment assessment of investments; valuation of limited liability investments, at fair value; valuation of real estate investments; valuation of deferred income taxes; valuation of mandatorily redeemable preferred stock; valuation and impairment assessment of intangible assets; goodwill recoverability; deferred acquisition costs; fair value assumptions for subordinated debt obligations; fair value assumptions for warrant liability; and revenue recognition. The fair values of the Company's investments in fixed maturities and equity investments, limited liability investments, at fair value, real estate investments, subordinated debt and warrant liability are estimated using a fair value hierarchy to categorize the inputs it uses in valuation techniques. Fair values for other investments approximate their unpaid principal balance. The carrying amounts reported in the consolidated balance sheets approximate fair values for cash and cash equivalents, restricted cash, short-term investments and certain other assets and other liabilities because of their short-term nature. The Company's financial results contained herein are reported in U.S. dollars unless otherwise indicated.

BUSINESS

BUSINESS	3 Months Ended
	Mar. 31, 2020
Organization, Consolidation and Presentation of Financial Statements [Abstract]
BUSINESS	BUSINESS Kingsway Financial Services Inc. (the "Company" or "Kingsway") was incorporated under the Business Corporations Act (Ontario) on September 19, 1989. Effective December 31, 2018, the Company changed its jurisdiction of incorporation from the province of Ontario, Canada, to the State of Delaware. Kingsway is a holding company with operating subsidiaries located in the United States. The Company owns or controls subsidiaries primarily in the extended warranty, asset management and real estate industries.

SUMMARY OF SIGNIFICANT ACCOUNTI

SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES	12 Months Ended
	Dec. 31, 2019
Accounting Policies [Abstract]
SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES	SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES Except as set forth below there have been no material changes to our significant accounting policies as reported in our 2019 Annual Report. Holding Company Liquidity The Company's Extended Warranty subsidiaries fund their obligations primarily through service fee and commission income. The Company's Leased Real Estate subsidiary funds its obligations through rental income. The Company's insurance subsidiaries fund their obligations primarily through investment income and maturities in the investments portfolios. The liquidity of the holding company is managed separately from its subsidiaries. The obligations of the holding company primarily consist of holding company operating expenses; transaction-related expenses; investments; and any other extraordinary demands on the holding company. Actions available to the holding company to increase liquidity in order to meet its obligations include the sale of passive investments; sale of subsidiaries; issuance of debt or equity securities; distributions from the Company’s Extended Warranty subsidiaries, subject to certain restrictions; and giving notice to its Trust Preferred trustees of its intention to exercise its voluntary right to defer interest payments for up to 20 quarters on the six subsidiary trusts of the Company’s subordinated debt, which right the Company exercised during the third quarter of 2018. Dividends from the Leased Real Estate segment are not generally considered a source of liquidity for the holding company, except upon the occurrence of certain events that would trigger payment of service fees. There can be no assurance as to the timing of the occurrence, or the resulting outcome, from one of these events. The holding company’s liquidity, defined as the amount of cash in the bank accounts of Kingsway Financial Services Inc. and Kingsway America Inc., was $4.0 million and $2.3 million at March 31, 2020 and December 31, 2019 , respectively, which excludes future actions available to the holding company that could be taken to increase liquidity and reflects approximately nine months of operating cash outflows. These amounts are reflected in the cash and cash equivalents of $14.0 million and $13.5 million reported at March 31, 2020 and December 31, 2019 , respectively, on the Company’s consolidated balance sheets. The cash and cash equivalents and restricted cash other than the holding company’s liquidity represent restricted and unrestricted cash held by Kingsway Amigo Insurance Company ("Amigo"), Kingsway Reinsurance Corporation and the Company’s Extended Warranty and Leased Real Estate segments. As of March 31, 2020 and June 30, 2020, there are 182,876 shares of the Company’s Class A Preferred Stock (the "Preferred Shares"), issued and outstanding. Any outstanding Preferred Shares would be required to be redeemed by the Company on April 1, 2021 ("Redemption Date") at a redemption value of $6.7 million (assuming all current outstanding Preferred Shares would be redeemed), if the Company has sufficient legally available funds to do so. Additionally, the Company has exercised its right to defer payment of interest on its outstanding subordinated debt ("trust preferred securities") and, because of the deferral which totaled $10.4 million at March 31, 2020, the Company is prohibited from redeeming any shares of its capital stock while payment of interest on the trust preferred securities is being deferred. If, as of April 1, 2021, the Company was required to pay both the deferred interest on the trust preferred securities and redeem all the Preferred Shares currently outstanding, then the Company currently projects that it would not have sufficient legally available funds to do so. However, the Company would be prohibited from doing so under Delaware law and, as such, (a) the interest estimated to be $14.9 million on March 31, 2021 on the trust preferred securities would remain on deferral as permitted under the indentures and (b) in accordance with Delaware law the Preferred Shares would not be redeemed on the Redemption Date (with a redemption value of $6.7 million ) and would instead remain outstanding and continue to accrue dividends until such time as the Company has sufficient legally available funds to redeem the Preferred Shares and is not otherwise prohibited from doing so. In such a situation, the Company would continue to operate in the ordinary course. The Company notes there are several variables to consider in such a situation, and management is currently exploring the following opportunities: negotiating with the holders of the Preferred Shares with respect to the Redemption Date and/or other key provisions, raising additional funds through capital market transactions, as well as the Company’s continued strategy of working to monetize its non-core investments while attempting to maximize the tradeoff between liquidity and value received. The Company also notes that the conversion of any Preferred Shares that might occur prior to April 1, 2021 would impact its analysis as of April 1, 2021. Based on the Company’s current business plan and revenue prospects, existing cash, cash equivalents, investment balances and anticipated cash flows from operations are expected to be sufficient to meet the Company’s working capital and operating expenditure requirements, excluding the cash that may be required to redeem the Preferred Shares and deferred interest on its trust preferred securities, for the next twelve months. However, the Company’s assessment could also be affected by various risks and uncertainties, including, but not limited to, the effects of the COVID-19 pandemic.

RECENTLY ISSUED ACCOUNTING STAN

RECENTLY ISSUED ACCOUNTING STANDARDS	3 Months Ended
	Mar. 31, 2020
Accounting Policies [Abstract]
RECENTLY ISSUED ACCOUNTING STANDARDS	RECENTLY ISSUED ACCOUNTING STANDARDS (a) Adoption of New Accounting Standards: Effective January 1, 2020, the Company adopted ASU 2017-04, Intangibles - Goodwill and Other (Topic 350): Simplifying the Test for Goodwill Impairment ("ASU 2017-04"). ASU 2017-04 was issued to simplify the subsequent measurement of goodwill. This update changes the impairment test by requiring an entity to compare the fair value of a reporting unit with its carrying amount as opposed to comparing the carrying amount of goodwill with its implied fair value. The adoption of ASU 2017-04 did not have an impact on the Company's consolidated financial statements. Effective January 1, 2020, the Company adopted ASU 2018-17, Consolidation (Topic 810): Targeted Improvements to Related Party Guidance for Variable Interest Entities ("ASU 2018-17"). Among other things, ASU 2018-17 changes how all entities that apply the variable interest entity ("VIE") guidance evaluate decision making fees. Under ASU 2018-17, when an entity determines whether a decision-making fee is a variable interest, it considers indirect interests held through related parties under common control on a proportionate basis rather than in their entirety. The new approach is consistent with how indirect interests held by related parties under common control are evaluated when determining whether a reporting entity is the primary beneficiary of a VIE. The adoption of ASU 2018-17 did not have an impact on the Company's consolidated financial statements. Effective January 1, 2020, the Company adopted ASU 2018-13, Fair Value Measurements (Topic 820): Disclosure Framework - Changes to the Disclosure Requirements for Fair Value Measurement ("ASU 2018-13"). ASU 2018-13 modifies the disclosure requirements for assets and liabilities measured at fair value. The requirements to disclose the amount of and reasons for transfers between Level 1 and Level 2 of the fair value hierarchy, the policy for timing of transfers between levels and the valuation processes for Level 3 fair value measurements have all been removed. However, the changes in unrealized gains and losses included in other comprehensive income for recurring Level 3 fair value measurements held at the end of the reporting period must be disclosed along with the range and weighted average of significant unobservable inputs used to develop Level 3 fair value measurements (or other quantitative information if it is more reasonable). Finally, for investments measured at net asset value, the requirements have been modified so that the timing of liquidation and the date when restrictions from redemption might lapse are only disclosed if the investee has communicated the timing to the entity or announced the timing publicly. As the amendments are only disclosure related, the effect of adoption did not have a material impact on the Company's consolidated financial statements. (b) Accounting Standards Not Yet Adopted: In June 2016, the Financial Accounting Standards Board ("FASB") issued ASU 2016-13, Financial Instruments-Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments ("ASU 2016-13"). ASU 2016-13 replaces the current incurred loss model used to measure impairment losses with an expected loss model for trade, reinsurance, and other receivables as well as financial instruments measured at amortized cost. ASU 2016-13 will require a financial asset measured at amortized cost, including reinsurance balances recoverable, to be presented at the net amount expected to be collected by means of an allowance for credit losses that runs through net loss. Credit losses relating to available-for-sale debt securities will also be recorded through an allowance for credit losses. However, the amendments would limit the amount of the allowance to the amount by which fair value is below amortized cost. The measurement of credit losses on available-for-sale investments is similar under current GAAP, but the update requires the use of the allowance account through which amounts can be reversed, rather than through irreversible write-downs. On November 15, 2019, the FASB issued ASU 2019-10, which (1) provides a framework to stagger effective dates for future major accounting standards and (2) amends the effective dates for certain major new accounting standards to give implementation relief to certain types of entities. Specifically, per ASU 2019-10 the Company would adopt ASU 2016-13 beginning January 1, 2023, as the Company is considered to be a smaller reporting company. The Company is currently evaluating ASU 2016-13 to determine the potential impact that adopting this standard will have on its consolidated financial statements.

ACQUISITION AND DISCONTINUED OP

ACQUISITION AND DISCONTINUED OPERATIONS	3 Months Ended
	Mar. 31, 2020
Business Combinations [Abstract]
ACQUISITION AND DISCONTINUED OPERATIONS	ACQUISITION AND DISCONTINUED OPERATIONS (a) Acquisition Geminus Holdings Company, Inc.: On March 1, 2019, the Company acquired 100% of the outstanding shares of Geminus Holding Company, Inc. ("Geminus") for cash consideration of $8.4 million , comprised of $7.7 million of cash and an installment payable to the seller of $0.7 million due February 15, 2020. The payable to seller was paid in full by February 15, 2020. As further discussed in Note 20 , " Segmented Information ," Geminus is included in the Extended Warranty segment. Geminus is a specialty, full-service provider of vehicle service agreements and other finance and insurance products to used car buyers around the country. Geminus, headquartered in Wilkes-Barre, Pennsylvania, has been creating, marketing and administering these products on high-mileage used cars through its subsidiaries, The Penn Warranty Corporation ("Penn") and Prime Auto Care, Inc. ("Prime"), since 1988. Penn and Prime distribute these products via independent used car dealerships and franchised car dealerships, respectively. This acquisition allows the Company to grow its portfolio of warranty companies and further expand into the vehicle service agreement business. This acquisition was accounted for as a business combination using the acquisition method of accounting. The purchase price was allocated to the assets acquired and liabilities assumed based upon their estimated fair values at the date of acquisition. Goodwill of $7.4 million was recognized, and $5.7 million of separately identifiable intangible assets were recognized resulting from the valuations of acquired customer relationships and trade names. Refer to Note 9 , " Intangible Assets ," for further disclosure of the intangible assets related to this acquisition. The goodwill represents the premium paid over the fair value of the net tangible and intangible assets acquired, which the Company paid to grow its portfolio of warranty companies and acquire an assembled workforce. The goodwill is not deductible for tax purposes. The following table summarizes the estimated fair values of the assets acquired and liabilities assumed at the date of acquisition: (in thousands) March 1, 2019 Investments $ 4,405 Cash and cash equivalents 755 Restricted cash 2,650 Accrued investment income 32 Service fee receivable 513 Other receivables 12 Property and equipment, net 79 Goodwill 7,445 Intangible assets not subject to amortization - trade names 1,974 Intangible asset subject to amortization - customer relationships 3,732 Other assets 620 Total assets $ 22,217 Accrued expenses and other liabilities $ 2,018 Income taxes payable 1 Deferred service fees 10,564 Net deferred income tax liabilities 1,263 Total liabilities $ 13,846 Purchase price $ 8,371 The consolidated statements of operations include the earnings of Geminus from the date of acquisition. From the date of acquisition through March 31, 2019 , Geminus earned revenue of $0.9 million and net income of $0.6 million . (b) Discontinued Operations Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company: On July 16, 2018, the Company announced it had entered into a definitive agreement to sell its non-standard automobile insurance companies Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company (collectively "Mendota"). On October 18, 2018, the Company completed the previously announced sale of Mendota. As a result of this announcement, Mendota, which was previously disclosed as part of the Insurance Underwriting segment, has been classified as a discontinued operation, and the results of their operations are reported separately for all periods presented. The Company recognized a loss on disposal of Mendota of zero for the three months ended March 31, 2020 and March 31, 2019 . The Company recognized a loss on disposal of Mendota of $1.5 million for the year ended December 31, 2019 . The final aggregate purchase price of $28.6 million was redeployed primarily to acquire equity investments, limited liability investments, limited liability investment, at fair value and other investments, which were owned by Mendota at the time of the closing, and to fund $5.0 million into an escrow account to be used to satisfy potential indemnity obligations under the definitive stock purchase agreement. As part of the transaction, the Company will indemnify the buyer for any loss and loss adjustment expenses with respect to open claims and certain specified claims in excess of Mendota's carried unpaid loss and loss adjustment expenses at June 30, 2018. The maximum obligation to the Company with respect to the open claims is $2.5 million . There is no maximum obligation to the Company with respect to the specified claims. During the first quarter of 2019, Mendota settled one of the two specified claims for $0.5 million , resulting in no loss to the Company. During the fourth quarter of 2019, Mendota notified the Company that Mendota had entered into an agreement to settle the remaining specified claim for $1.6 million . Net of expenses, the Company recorded a loss of $1.5 million related to the settlement of the remaining specified claim, which is reported as loss on disposal of discontinued operations in the consolidated statement of operations for the year ended December 31, 2019 . The $1.6 million settlement was funded from the $5.0 million escrow account, and the $3.4 million remaining in the escrow account was released to the Company during the first quarter of 2020 consistent with the terms of the escrow agreement.

ACQUISITION AND DISCONTINUES OP

ACQUISITION AND DISCONTINUES OPERATIONS	3 Months Ended
	Mar. 31, 2020
Business Combinations [Abstract]
ACQUISITION AND DISCONTINUED OPERATIONS	ACQUISITION AND DISCONTINUED OPERATIONS (a) Acquisition Geminus Holdings Company, Inc.: On March 1, 2019, the Company acquired 100% of the outstanding shares of Geminus Holding Company, Inc. ("Geminus") for cash consideration of $8.4 million , comprised of $7.7 million of cash and an installment payable to the seller of $0.7 million due February 15, 2020. The payable to seller was paid in full by February 15, 2020. As further discussed in Note 20 , " Segmented Information ," Geminus is included in the Extended Warranty segment. Geminus is a specialty, full-service provider of vehicle service agreements and other finance and insurance products to used car buyers around the country. Geminus, headquartered in Wilkes-Barre, Pennsylvania, has been creating, marketing and administering these products on high-mileage used cars through its subsidiaries, The Penn Warranty Corporation ("Penn") and Prime Auto Care, Inc. ("Prime"), since 1988. Penn and Prime distribute these products via independent used car dealerships and franchised car dealerships, respectively. This acquisition allows the Company to grow its portfolio of warranty companies and further expand into the vehicle service agreement business. This acquisition was accounted for as a business combination using the acquisition method of accounting. The purchase price was allocated to the assets acquired and liabilities assumed based upon their estimated fair values at the date of acquisition. Goodwill of $7.4 million was recognized, and $5.7 million of separately identifiable intangible assets were recognized resulting from the valuations of acquired customer relationships and trade names. Refer to Note 9 , " Intangible Assets ," for further disclosure of the intangible assets related to this acquisition. The goodwill represents the premium paid over the fair value of the net tangible and intangible assets acquired, which the Company paid to grow its portfolio of warranty companies and acquire an assembled workforce. The goodwill is not deductible for tax purposes. The following table summarizes the estimated fair values of the assets acquired and liabilities assumed at the date of acquisition: (in thousands) March 1, 2019 Investments $ 4,405 Cash and cash equivalents 755 Restricted cash 2,650 Accrued investment income 32 Service fee receivable 513 Other receivables 12 Property and equipment, net 79 Goodwill 7,445 Intangible assets not subject to amortization - trade names 1,974 Intangible asset subject to amortization - customer relationships 3,732 Other assets 620 Total assets $ 22,217 Accrued expenses and other liabilities $ 2,018 Income taxes payable 1 Deferred service fees 10,564 Net deferred income tax liabilities 1,263 Total liabilities $ 13,846 Purchase price $ 8,371 The consolidated statements of operations include the earnings of Geminus from the date of acquisition. From the date of acquisition through March 31, 2019 , Geminus earned revenue of $0.9 million and net income of $0.6 million . (b) Discontinued Operations Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company: On July 16, 2018, the Company announced it had entered into a definitive agreement to sell its non-standard automobile insurance companies Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company (collectively "Mendota"). On October 18, 2018, the Company completed the previously announced sale of Mendota. As a result of this announcement, Mendota, which was previously disclosed as part of the Insurance Underwriting segment, has been classified as a discontinued operation, and the results of their operations are reported separately for all periods presented. The Company recognized a loss on disposal of Mendota of zero for the three months ended March 31, 2020 and March 31, 2019 . The Company recognized a loss on disposal of Mendota of $1.5 million for the year ended December 31, 2019 . The final aggregate purchase price of $28.6 million was redeployed primarily to acquire equity investments, limited liability investments, limited liability investment, at fair value and other investments, which were owned by Mendota at the time of the closing, and to fund $5.0 million into an escrow account to be used to satisfy potential indemnity obligations under the definitive stock purchase agreement. As part of the transaction, the Company will indemnify the buyer for any loss and loss adjustment expenses with respect to open claims and certain specified claims in excess of Mendota's carried unpaid loss and loss adjustment expenses at June 30, 2018. The maximum obligation to the Company with respect to the open claims is $2.5 million . There is no maximum obligation to the Company with respect to the specified claims. During the first quarter of 2019, Mendota settled one of the two specified claims for $0.5 million , resulting in no loss to the Company. During the fourth quarter of 2019, Mendota notified the Company that Mendota had entered into an agreement to settle the remaining specified claim for $1.6 million . Net of expenses, the Company recorded a loss of $1.5 million related to the settlement of the remaining specified claim, which is reported as loss on disposal of discontinued operations in the consolidated statement of operations for the year ended December 31, 2019 . The $1.6 million settlement was funded from the $5.0 million escrow account, and the $3.4 million remaining in the escrow account was released to the Company during the first quarter of 2020 consistent with the terms of the escrow agreement.

INVESTMENTS

INVESTMENTS	3 Months Ended
	Mar. 31, 2020
Investments [Abstract]
INVESTMENTS	INVESTMENTS The amortized cost, gross unrealized gains and losses, and estimated fair value of the Company's available-for-sale investments at March 31, 2020 and December 31, 2019 are summarized in the tables shown below: (in thousands) March 31, 2020 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 5,503 $ 126 $ — $ 5,629 States, municipalities and political subdivisions 600 3 — 603 Mortgage-backed 4,009 48 3 4,054 Corporate 4,953 22 14 4,961 Total fixed maturities $ 15,065 $ 199 $ 17 $ 15,247 (in thousands) December 31, 2019 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 13,246 $ 74 $ 4 $ 13,316 States, municipalities and political subdivisions 601 — 1 600 Mortgage-backed 2,951 2 14 2,939 Corporate 5,338 8 6 5,340 Total fixed maturities $ 22,136 $ 84 $ 25 $ 22,195 The table below summarizes the Company's fixed maturities at March 31, 2020 by contractual maturity periods. Actual results may differ as issuers may have the right to call or prepay obligations, with or without penalties, prior to the contractual maturity of these obligations. (in thousands) March 31, 2020 Amortized Cost Estimated Fair Value Due in one year or less $ 4,166 $ 4,183 Due after one year through five years 9,530 9,676 Due after five years through ten years 538 549 Due after ten years 831 839 Total $ 15,065 $ 15,247 The following tables highlight the aggregate unrealized loss position, by security type, of available-for-sale investments in unrealized loss positions as of March 31, 2020 and December 31, 2019 . The tables segregate the holdings based on the period of time the investments have been continuously held in unrealized loss positions. (in thousands) March 31, 2020 Less than 12 Months Greater than 12 Months Total Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Fixed maturities: States, municipalities and political subdivisions $ 100 $ — $ — $ — $ 100 $ — Mortgage-backed 354 3 149 — 503 3 Corporate 1,176 12 199 2 1,375 14 Total fixed maturities $ 1,630 $ 15 $ 348 $ 2 $ 1,978 $ 17 (in thousands) December 31, 2019 Less than 12 Months Greater than 12 Months Total Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Fixed maturities: U.S. government, government agencies and authorities $ 305 $ — $ 1,002 $ 4 $ 1,307 $ 4 States, municipalities and political subdivisions — — 453 1 453 1 Mortgage-backed 1,063 1 1,271 13 2,334 14 Corporate 2,495 4 526 2 3,021 6 Total fixed maturities $ 3,863 $ 5 $ 3,252 $ 20 $ 7,115 $ 25 There are approximately 14 and 48 individual available-for-sale investments that were in unrealized loss positions as of March 31, 2020 and December 31, 2019 , respectively. The establishment of an other-than-temporary impairment on an investment requires a number of judgments and estimates. The Company performs a quarterly analysis of the individual investments to determine if declines in market value are other-than-temporary. The analysis includes some or all of the following procedures as deemed appropriate by the Company: • identifying all unrealized loss positions that have existed for at least six months; • identifying other circumstances management believes may affect the recoverability of the unrealized loss positions; • obtaining a valuation analysis from third-party investment managers regarding the intrinsic value of these investments based on their knowledge and experience together with market-based valuation techniques; • reviewing the trading range of certain investments over the preceding calendar period; • assessing if declines in market value are other-than-temporary for debt instruments based on the investment grade credit ratings from third-party rating agencies; • assessing if declines in market value are other-than-temporary for any debt instrument with a non-investment grade credit rating based on the continuity of its debt service record; • determining the necessary provision for declines in market value that are considered other-than-temporary based on the analyses performed; and • assessing the Company's ability and intent to hold these investments at least until any potential investment impairment is recovered. The risks and uncertainties inherent in the assessment methodology used to determine declines in market value that are other-than-temporary include, but may not be limited to, the following: • the opinions of professional investment managers could be incorrect; • the past trading patterns of individual investments may not reflect future valuation trends; • the credit ratings assigned by independent credit rating agencies may be incorrect due to unforeseen or unknown facts related to a company's financial situation; and • the debt service pattern of non-investment grade instruments may not reflect future debt service capabilities and may not reflect a company's unknown underlying financial problems. As a result of the analysis performed by the Company to determine declines in market value that are other-than-temporary, the Company recorded write-downs of $0.1 million and zero for other-than-temporary impairment related to other investments for the three months ended March 31, 2020 and March 31, 2019 , respectively, and zero and $0.1 million for other-than-temporary impairment related to limited liability investments for the three months ended March 31, 2020 and March 31, 2019 , respectively. There were no write-downs recorded for other-than-temporary impairments related to available-for sale investments for the three months ended March 31, 2020 and March 31, 2019 , respectively. The Company has reviewed currently available information regarding investments with estimated fair values less than their carrying amounts and believes these unrealized losses are not other-than-temporary and are primarily due to temporary market and sector-related factors rather than to issuer-specific factors. The Company does not intend to sell those investments, and it is not likely it will be required to sell those investments before recovery of its amortized cost. The Company does not have any exposure to subprime mortgage-backed investments. Limited liability investments include investments in limited liability companies and limited partnerships. The Company's interests in these investments are not deemed minor and, therefore, are accounted for under the equity method of accounting. The most recently available financial statements are used in applying the equity method. The difference between the end of the reporting period of the limited liability entities and that of the Company is no more than three months. As of March 31, 2020 and December 31, 2019 , the carrying value of limited liability investments totaled $3.8 million and $3.8 million , respectively. Income or loss from limited liability investments is recognized based on the Company's share of the earnings of the limited liability entities and is included in net investment income in the consolidated statements of operations. At March 31, 2020 , the Company has no unfunded commitments related to limited liability investments. Limited liability investments, at fair value represents the underlying investments of the Company’s consolidated entities Net Lease Investment Grade Portfolio LLC ("Net Lease") and Argo Holdings Fund I, LLC ("Argo Holdings"). Prior to the fourth quarter of 2019, limited liability investments, at fair value included the Company's investment in 1347 Investors LLC ("1347 Investors"). The fair value of the Company's investment in 1347 Investors was calculated based on a model that distributed the net equity of 1347 Investors to all classes of membership interests. The model used quoted market prices and significant market observable inputs. The most significant input to the model was the observed stock price of Limbach Holdings, Inc. ("Limbach") common stock. During the fourth quarter of 2019, the Company’s investment in 1347 Investors was dissolved, which resulted in the Company holding shares of Limbach common stock directly. Through the first quarter of 2020, the Limbach common stock price has declined, which has resulted in a loss on change in fair value of $0.6 million . As of March 31, 2020 and December 31, 2019 , the carrying value of the Company's limited liability investments, at fair value was $31.0 million and $29.1 million , respectively. The Company recorded no impairments related to limited liability investments, at fair value for the three months ended March 31, 2020 and March 31, 2019 . At March 31, 2020 , the Company has no unfunded commitments to fund limited liability investments, at fair value. Investments in private companies consist of convertible preferred stocks and notes in privately owned companies and investments in limited liability companies in which the Company’s interests are deemed minor. The Company's investments in private companies do not have readily determinable fair values. The Company has elected to record investments in private companies at cost, adjusted for observable price changes and impairments. As of March 31, 2020 and December 31, 2019 , the carrying value of the Company's investments in private companies totaled $1.4 million and $2.0 million , respectively. For the three months ended March 31, 2020 and March 31, 2019 , the Company recorded adjustments of zero and less than $0.1 million , respectively, to adjust the fair value of certain investments in private companies for observable price changes, which are included in net change in unrealized (loss) gain on private company investments in the consolidated statements of operations. The Company performs a quarterly impairment analysis of its investments in private companies. The analysis includes some or all of the following procedures as deemed appropriate by the Company: • the opinions of external investment and portfolio managers; • the financial condition and prospects of the investee; • recent operating trends and forecasted performance of the investee; • current market conditions in the geographic area or industry in which the investee operates; • changes in credit ratings; and • changes in the regulatory environment. As a result of the analysis performed, the Company recorded impairments related to investments in private companies of $0.7 million and zero for the three months ended March 31, 2020 and March 31, 2019 , respectively, which are included in net change in unrealized (loss) gain on private company investments in the consolidated statements of operations. The impairment recorded for the three months ended March 31, 2020 is a result of the impact of COVID-19 on the investment's underlying business. Real estate investments are reported at fair value. As of March 31, 2020 and December 31, 2019 , the carrying value of the Company's real estate investments totaled $10.7 million . Other investments include collateral loans and are reported at their unpaid principal balance. As of March 31, 2020 and December 31, 2019 , the carrying value of other investments totaled $0.8 million and $1.0 million , respectively. Net investment income for the three months ended March 31, 2020 and March 31, 2019 is comprised as follows: (in thousands) Three months ended March 31, 2020 2019 Investment income: Interest from fixed maturities $ 102 $ 73 Dividends 45 58 Income (loss) from limited liability investments 23 (18 ) Income from limited liability investments, at fair value 234 235 Income from real estate investments 200 200 Other 127 178 Gross investment income 731 726 Investment expenses (12 ) (27 ) Net investment income $ 719 $ 699 Gross realized gains and losses on available-for-sale investments, limited liability investments, limited liability investments, at fair value and investments in private companies for the three months ended March 31, 2020 and March 31, 2019 are comprised as follows: (in thousands) Three months ended March 31, 2020 2019 Gross realized gains $ 208 $ 315 Gross realized losses — — Net realized gains gains $ 208 $ 315 (Loss) gain on change in fair value of equity investments for the three months ended March 31, 2020 and March 31, 2019 is comprised as follows: (in thousands) Three months ended March 31, 2020 2019 Net losses recognized on equity investments sold during the period $ — $ — Change in unrealized (losses) gains on equity investments held at end of the period (597 ) 78 (Loss) gain on change in fair value of equity investments $ (597 ) $ 78 Short-term investments and fixed maturities with an estimated fair value of $0.2 million at March 31, 2020 and December 31, 2019 , were on deposit with state and provincial regulatory authorities. The Company also has restricted cash of $17.9 million and $12.2 million at March 31, 2020 and December 31, 2019 , respectively. Included in restricted cash are (i) zero and $1.1 million at March 31, 2020 and December 31, 2019 , respectively, held in escrow as part of the transaction to sell Mendota; (ii) $15.3 million and $8.6 million at March 31, 2020 and December 31, 2019 , respectively, held as deposits by IWS Acquisition Corporation ("IWS"), Professional Warranty Service Corporation ("PWSC"), and Geminus; (iii) $2.0 million and $1.9 million at March 31, 2020 and December 31, 2019 , respectively, on deposit with state and provincial regulatory authorities; and (iv) $0.6 million at March 31, 2020 and December 31, 2019 , pledged to third-parties as deposits or to collateralize liabilities. Collateral pledging transactions are conducted under terms that are common and customary to standard collateral pledging and are subject to the Company's standard risk management controls. Impact of COVID-19 on Investments As discussed in Note 24 , " Subsequent Events ," in March 2020 the outbreak of COVID-19 caused by a novel strain of the coronavirus was recognized as a pandemic by the World Health Organization, and the outbreak has become increasingly widespread in the United States, including in the markets in which we operate. The COVID-19 outbreak has had a notable impact on general economic conditions, including but not limited to the temporary closures of many businesses; "shelter in place" and other governmental regulations; and reduced consumer spending due to both job losses and other effects attributable to COVID-19. There remain many unknowns. The Company continues to assess the impact that the COVID-19 pandemic may have on the value of its various investments, which could result in future material decreases in the underlying investment values. Such decreases may be considered temporary or could be deemed to be other-than-temporary, and management may be required to record write-downs of the related investments in future reporting periods.

INVESTMENT IN INVESTEE

INVESTMENT IN INVESTEE	12 Months Ended
	Dec. 31, 2019
Equity Method Investments and Joint Ventures [Abstract]
INVESTMENT IN INVESTEE	INVESTMENT IN INVESTEE The Company formerly held an investment in the common stock of Itasca Capital Ltd. ("ICL") that was recorded as investment in investee in the consolidated balance sheets. During the fourth quarter of 2019, the Company sold its remaining investment in the common stock of ICL. See Note 22 (b), " Related Parties ," for more information. For the three months ended March 31, 2019 , equity in net loss of investee was less than $0.1 million .

DEFERRED ACQUISITION COSTS

DEFERRED ACQUISITION COSTS	12 Months Ended
	Dec. 31, 2019
Deferred Policy Acquisition Costs Disclosures [Abstract]
DEFERRED ACQUISITION COSTS	DEFERRED ACQUISITION COSTS Deferred acquisition costs consist primarily of commissions and agency expenses incurred related to successful efforts to acquire vehicle service agreements and are amortized over the period in which the related revenues are earned in accordance with ASC 606, Revenue from Contracts with Customers . The components of deferred acquisition costs and the related amortization expense for the three months ended March 31, 2020 and March 31, 2019 are comprised as follows: (in thousands) Three months ended March 31, 2020 2019 Beginning balance, net $ 8,604 $ 6,904 Additions 1,096 1,201 Amortization (956 ) (885 ) Balance at March 31, net $ 8,744 $ 7,220

INTANGIBLE ASSETS

INTANGIBLE ASSETS	3 Months Ended
	Mar. 31, 2020
Goodwill and Intangible Assets Disclosure [Abstract]
INTANGIBLE ASSETS	INTANGIBLE ASSETS Intangible assets at March 31, 2020 and December 31, 2019 are comprised as follows: (in thousands) March 31, 2020 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 3,628 $ 1,290 Vehicle service agreements in-force 3,680 3,680 — Customer relationships 12,646 6,044 6,602 In-place lease 1,125 234 891 Non-compete 266 130 136 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Trade names 3,264 — 3,264 Total $ 99,566 $ 13,716 $ 85,850 (in thousands) December 31, 2019 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 3,505 $ 1,413 Vehicle service agreements in-force 3,680 3,680 — Customer relationships 12,646 5,622 7,024 In-place lease 1,125 218 907 Non-compete 266 117 149 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Trade names 3,264 — 3,264 Total $ 99,566 $ 13,142 $ 86,424 As further discussed in Note 5 , " Acquisition and Discontinued Operations ," during the first quarter of 2019, the Company recorded $5.7 million of separately identifiable intangible assets, related to acquired customer relationships and trade names, as part of the acquisition of Geminus. The customer relationships intangible asset of $3.7 million is being amortized over ten years based on the pattern in which the economic benefits of the intangible asset are expected to be consumed. The trade name intangible assets of $2.0 million are deemed to have indefinite useful lives and are not amortized. The Company's other intangible assets with definite useful lives are amortized either based on the patterns in which the economic benefits of the intangible assets are expected to be consumed or using the straight-line method over their estimated useful lives, which range from 5 to 18 years. Amortization of intangible assets was $0.6 million and $0.5 million for the three months ended March 31, 2020 and March 31, 2019 , respectively. The tenant relationship and trade names intangible assets have indefinite useful lives and are not amortized. No impairment charges were recorded during the three months ended March 31, 2020 and March 31, 2019 .

PROPERTY AND EQUIPMENT

PROPERTY AND EQUIPMENT	3 Months Ended
	Mar. 31, 2020
Property, Plant and Equipment [Abstract]
PROPERTY AND EQUIPMENT	PROPERTY AND EQUIPMENT Property and equipment at March 31, 2020 and December 31, 2019 are comprised as follows: (in thousands) March 31, 2020 Total Property and Equipment Cost Accumulated Depreciation Carrying Value Land $ 21,120 $ — $ 21,120 Site improvements 91,308 15,328 75,980 Buildings 580 54 526 Leasehold improvements 159 111 48 Furniture and equipment 1,127 1,019 108 Computer hardware 5,313 5,084 229 Total $ 119,607 $ 21,596 $ 98,011 (in thousands) December 31, 2019 Total Property and Equipment Cost Accumulated Depreciation Carrying Value Land $ 21,120 $ — $ 21,120 Site improvements 91,308 14,295 77,013 Buildings 580 50 530 Leasehold improvements 156 109 47 Furniture and equipment 1,121 1,010 111 Computer hardware 5,282 5,039 243 Total $ 119,567 $ 20,503 $ 99,064

VEHICLE SERVICE AGREEMENT LIABI

VEHICLE SERVICE AGREEMENT LIABILITY	12 Months Ended
	Dec. 31, 2019
Guarantees and Product Warranties [Abstract]
VEHICLE SERVICE AGREEMENT LIABILITY	VEHICLE SERVICE AGREEMENT LIABILITY Vehicle service agreement fees include the fees collected to cover the costs of future automobile mechanical breakdown claims and the associated administration of those claims. Vehicle service agreement fees are initially recorded as deferred service fees. On a quarterly basis, the Company compares the remaining deferred service fees balance to the estimated amount of expected future claims under the vehicle service agreement contracts and records an additional accrual if the deferred service fees balance is less than expected future claims costs. In certain jurisdictions the Company is required to refund to a customer a pro-rata share of the vehicle service agreement fees if a customer cancels the agreement prior to the end of the term. Depending on the jurisdiction, the Company may be entitled to deduct from the refund a cancellation fee and/or amounts for claims incurred prior to cancellation. While refunds vary depending on the term and type of product offered, historically refunds have averaged 9% to 13% of the original amount of the vehicle service agreement fee. Revenues recorded by the Company are net of refunds and the associated refund liability is included in accrued expenses and other liabilities. The Company estimates refunds based on the actual historical refund rates by warranty type taking into consideration current observable refund trends in estimating the expected amount of future customer refunds to be paid at each reporting period. A reconciliation of the changes in the vehicle service agreement liability, including deferred service fees related to vehicle service agreements, as of March 31, 2020 and March 31, 2019 were as follows: (in thousands) March 31, 2020 March 31, 2019 Balance at January 1, net $ 51,723 $ 43,734 Vehicle service agreement liability acquired during the year related to the purchase of Geminus — 10,792 Gross service fees for vehicle service agreements sold 4,666 6,055 Recognition of service fees on vehicle service agreements (5,701 ) (5,367 ) Liability for claims authorized on vehicle service agreements 2,380 1,887 Payments of claims authorized on vehicle service agreements (1,475 ) (970 ) Re-estimation of deferred service fees (121 ) (148 ) Balance at March 31, net $ 51,472 $ 55,983 The vehicle service agreement liability is presented as components of deferred services fees and accrued expenses and other liabilities in the consolidated balance sheets as follows: (in thousands) March 31, December 31, 2020 2019 Deferred service fees $ 50,946 $ 51,226 Accrued expenses and other liabilities 526 497 Balance at end of period, net $ 51,472 $ 51,723

UNPAID LOSS AND LOSS ADJUSTMENT

UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES	12 Months Ended
	Dec. 31, 2019
Insurance [Abstract]
UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES	UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES The establishment of the provision for unpaid loss and loss adjustment expenses is based on known facts and interpretation of circumstances and is, therefore, a complex and dynamic process influenced by a large variety of factors. These factors include the Company's experience with similar cases and historical trends involving loss payment patterns, pending levels of unpaid loss and loss adjustment expenses, product mix or concentration, loss severity and loss frequency patterns. Other factors include the continually evolving and changing regulatory and legal environment; actuarial studies; professional experience and expertise of the Company's claims departments' personnel and independent adjusters retained to handle individual claims; the quality of the data used for projection purposes; existing claims management practices including claims-handling and settlement practices; the effect of inflationary trends on future loss settlement costs; court decisions; economic conditions; and public attitudes. Consequently, the process of determining the provision for unpaid loss and loss adjustment expenses necessarily involves risks that the actual loss and loss adjustment expenses incurred by the Company will deviate, perhaps materially, from the estimates recorded. The Company's evaluation of the adequacy of unpaid loss and loss adjustment expenses includes a re-estimation of the liability for unpaid loss and loss adjustment expenses relating to each preceding financial year compared to the liability that was previously established. The results of this comparison and the changes in the provision for unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of March 31, 2020 and March 31, 2019 were as follows: (in thousands) March 31, 2020 March 31, 2019 Balance at beginning of period, gross $ 1,774 $ 2,073 Less reinsurance recoverable related to unpaid loss and loss adjustment expenses — — Balance at beginning of period, net 1,774 2,073 Incurred related to: Current year — — Prior years 13 107 Paid related to: Current year — — Prior years (96 ) (741 ) Balance at end of period, net 1,691 1,439 Plus reinsurance recoverable related to unpaid loss and loss adjustment expenses — — Balance at end of period, gross $ 1,691 $ 1,439 The Company reported unfavorable development on unpaid loss and loss adjustment expenses of less than $0.1 million and $0.1 million for the three months ended March 31, 2020 and March 31, 2019 , respectively. The unfavorable development for the three months ended March 31, 2020 and March 31, 2019 was related to an increase in loss adjustment expenses at Amigo.

DEBT

DEBT	3 Months Ended
	Mar. 31, 2020
Debt Disclosure [Abstract]
DEBT	DEBT Debt consists of the following instruments at March 31, 2020 and December 31, 2019 : (in thousands) March 31, 2020 December 31, 2019 Principal Carrying Value Fair Value Principal Carrying Value Fair Value Bank loans: PWSC Loan $ — $ — $ — $ 437 $ 437 $ 435 KWH Loan 9,500 8,727 10,966 9,625 8,803 11,820 Total bank loans 9,500 8,727 10,966 10,062 9,240 12,255 Notes payable: Mortgage 168,938 177,192 182,941 169,818 178,297 182,265 Flower Note 7,226 7,226 7,890 7,337 7,337 8,071 Net Lease Note 9,000 9,000 8,785 9,000 9,000 9,396 Total notes payable 185,164 193,418 199,616 186,155 194,634 199,732 Subordinated debt 90,500 40,387 40,387 90,500 54,655 54,655 Total $ 285,164 $ 242,532 $ 250,969 $ 286,717 $ 258,529 $ 266,642 Subordinated debt mentioned above consists of the following trust preferred debt instruments: Issuer Principal (in thousands) Issue date Interest Redemption date Kingsway CT Statutory Trust I $ 15,000 12/4/2002 annual interest rate equal to LIBOR, plus 4.00% payable quarterly 12/4/2032 Kingsway CT Statutory Trust II $ 17,500 5/15/2003 annual interest rate equal to LIBOR, plus 4.10% payable quarterly 5/15/2033 Kingsway CT Statutory Trust III $ 20,000 10/29/2003 annual interest rate equal to LIBOR, plus 3.95% payable quarterly 10/29/2033 Kingsway DE Statutory Trust III $ 15,000 5/22/2003 annual interest rate equal to LIBOR, plus 4.20% payable quarterly 5/22/2033 Kingsway DE Statutory Trust IV $ 10,000 9/30/2003 annual interest rate equal to LIBOR, plus 3.85% payable quarterly 9/30/2033 Kingsway DE Statutory Trust VI $ 13,000 12/16/2003 annual interest rate equal to LIBOR, plus 4.00% payable quarterly 1/8/2034 (a) Bank loans: As part of the acquisition of PWSC on October 12, 2017, the Company borrowed a principal amount of $5.0 million from a bank at a fixed interest rate of 5.0% (the "PWSC Loan"). The carrying value of the PWSC Loan represents its unpaid principal balance. The fair value of the PWSC Loan disclosed in the table above is derived from quoted market prices of B and B minus rated industrial bonds with similar maturities. The PWSC Loan was scheduled to mature on October 12, 2022; however, the remaining principal was fully repaid on January 30, 2020. As part of the acquisition of Geminus on March 1, 2019, the Company formed Kingsway Warranty Holdings LLC ("KWH") and contributed IWS and Trinity Warranty Solutions LLC (Trinity") to KWH, which then borrowed a principal amount of $10.0 million from a bank at an annual interest rate equal to LIBOR, having a floor of 2.00% , plus 9.25% (the "KWH Loan"), using most of the proceeds to acquire Geminus. The KWH Loan matures on March 1, 2024. As part of the KWH Loan, KWH also issued warrants (the "KWH Warrants") to the lender exercisable to purchase an aggregate 1.25% membership interest in KWH. The Company allocated $0.4 million of the KWH loan proceeds to a liability, recorded as part of accrued expenses and other liabilities in the consolidated balance sheets, to reflect the estimated fair value of the KWH Warrants, as the warrants contain a put right exercisable by the holder. Changes in the estimated fair value of the KWH Warrants are recorded in the consolidated statements of operations. The Company also recorded as a discount to the carrying value of the KWH Loan issuance costs of $1.0 million specifically related to the KWH Loan. The KWH Loan is carried in the consolidated balance sheets at its amortized cost, which reflects the quarterly pay-down of principal as well as the amortization of the discount using the effective interest rate method. The fair value of the KWH Loan disclosed in the table above is derived from quoted market prices of BB minus rated industrial bonds with similar maturities. The KWH Loan is secured by certain of the equity interests and assets of KWH and its subsidiaries. (b) Notes payable: As part of the acquisition of CMC Industries, Inc. ("CMC") in July 2016, the Company assumed a mortgage, which is recorded as note payable in the consolidated balance sheets ("the Mortgage"). The Mortgage is nonrecourse indebtedness with respect to CMC and its subsidiaries, and the Mortgage is not, nor will it be, guaranteed by Kingsway or its affiliates. The Mortgage was recorded at its estimated fair value of $191.7 million , which included the unpaid principal amount of $180.0 million as of the date of acquisition plus a premium of $11.7 million . The Mortgage matures on May 15, 2034 and has a fixed interest rate of 4.07% . The Mortgage is carried in the consolidated balance sheets at its amortized cost, which reflects the monthly pay-down of principal as well as the amortization of the premium using the effective interest rate method. The fair value of the Mortgage disclosed in the table above is derived from quoted market prices of A-rated industrial bonds with similar maturities. On January 5, 2015, Flower Portfolio 001, LLC ("Flower") assumed a $9.2 million mortgage in conjunction with the purchase of investment real estate properties, which is recorded as note payable in the consolidated balance sheets ("the Flower Note"). The Flower Note requires monthly payments of principal and interest and is secured by certain investments of Flower. The Flower Note matures on December 10, 2031 and has a fixed interest rate of 4.81% . The carrying value of the Flower Note at March 31, 2020 of $7.2 million represents its unpaid principal balance. The fair value of the Flower Note disclosed in the table above is derived from quoted market prices of A and BBB plus rated industrial bonds with similar maturities. On October 15, 2015, Net Lease assumed a $9.0 million mezzanine debt in conjunction with the purchase of investment real estate properties, which is recorded as note payable in the consolidated balance sheets ("the Net Lease Note"). The Net Lease Note requires monthly payments of interest and is secured by certain investments of Net Lease. The Net Lease Note matures on November 1, 2020 and has a fixed interest rate of 10.25% . The carrying value of the Net Lease Note at March 31, 2020 of $9.0 million represents its unpaid principal balance. The fair value of the Net Lease Note disclosed in the table above is derived from quoted market prices of B and B minus rated industrial bonds with similar maturities. Net Lease is exploring alternatives given that the Net Lease Note matures later this year and has commenced discussions with various parties. (c) Subordinated debt: Between December 4, 2002 and December 16, 2003, six subsidiary trusts of the Company issued $90.5 million of 30-year capital securities to third-parties in separate private transactions. In each instance, a corresponding floating rate junior subordinated deferrable interest debenture was then issued by KAI to the trust in exchange for the proceeds from the private sale. The floating rate debentures bear interest at the rate of the London interbank offered interest rate for three-month U.S. dollar deposits ("LIBOR"), plus spreads ranging from 3.85% to 4.20% . The Company has the right to call each of these securities at par value any time after five years from their issuance until their maturity. The subordinated debt is carried in the consolidated balance sheets at fair value. See Note 21 , " Fair Value of Financial Instruments ," for further discussion of the subordinated debt. Of the $14.3 million decrease in fair value of the Company’s subordinated debt between December 31, 2019 and March 31, 2020 , $11.6 million is reported as change in fair value of debt attributable to instrument-specific credit risk in the Company's consolidated statements of comprehensive income and $2.6 million reported as gain on change in fair value of debt in the Company’s consolidated statements of operations. During the third quarter of 2018, the Company gave notice to its Trust Preferred trustees of its intention to exercise its voluntary right to defer interest payments for up to 20 quarters, pursuant to the contractual terms of its outstanding Trust Preferred indentures, which permit interest deferral. This action does not constitute a default under the Company's Trust Preferred indentures or any of its other debt indentures. At March 31, 2020 , deferred interest payable of $10.4 million is included in accrued expenses and other liabilities in the consolidated balance sheets. The agreements governing our subordinated debt contain a number of covenants that, among other things, restrict the Company’s ability to incur additional indebtedness, make dividends and distributions, and make certain payments in respect of the Company’s outstanding securities. Pursuant to indentures governing the Company’s subordinated debt, the Company is obligated to deliver audited financial statements for certain of its subsidiaries as of and for the year ended December 31, 2019. Due to the delay in filing its 2019 Annual Report, the Company has been unable to meet this obligation, the failure of which could be declared an event of default under the respective indentures. As of the date of the filing of this report on Form 10-Q for the three months ended March 31, 2020 , none of the trustees responsible for administering any of our outstanding debt has declared an event of default, if required by the applicable indenture, notified us of an intent to accelerate any portion of the outstanding debt or charge default interest thereon, or pursued any other remedies available to it. Were any of these trustees to declare an event of default, the Company would have a period of time to cure the default. Now that the Company has filed its 2019 Annual Report, the Company expects to be in a position to deliver to the trustees the requisite audited financial statements for certain of its subsidiaries as of and for the year ended December 31, 2019.

LEASES

LEASES	3 Months Ended
	Mar. 31, 2020
Leases [Abstract]
LEASES	LEASES The Company adopted ASU 2016-02 on January 1, 2019 using the modified retrospective adoption method. The adoption resulted in an increase of the ROU assets of approximately $2.7 million and lease liabilities of $2.9 million . The difference of $0.2 million relates to straight-line rent accruals and lease incentive liabilities that were reclassified to ROU assets for operating leases. Lessee Leases Operating lease costs and variable lease costs included in selling and administrative costs for the three months ended March 31, 2020 were $0.2 million and de minimis, respectively. The annual maturities of lease liabilities as of March 31, 2020 were as follows: (in thousands) Lease Commitments 2020 $ 549 2021 802 2022 824 2023 624 2024 550 2025 and thereafter 546 Total undiscounted lease payments 3,895 Imputed interest 503 Total lease liabilities $ 3,392 The weighted-average remaining lease term for our operating leases was 5.46 years as of March 31, 2020 . The weighted average discount rate of our operating leases was 5.32% as of March 31, 2020 . Cash paid for amounts included in the measurement of lease liabilities was $0.2 million and $0.3 million for the three months ended March 31, 2020 and 2019 , respectively. Lessor Leases The Company owns a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property") that is subject to a long-term triple net lease agreement with an unrelated third-party. The lease provides for future rent escalations and renewal options. The initial lease term ends in May 2034. The lessee bears the cost of maintenance and property taxes. Rental income from operating leases is recognized on a straight-line basis, based on contractual lease terms with fixed and determinable increases over the non-cancellable term of the related lease when collectability is reasonably assured. Rental income includes a de minimus amount of amortization of below market lease liabilities for the March 31, 2020 and March 31, 2019 . The estimated aggregate future amortization of below market lease liabilities is $0.1 million for 2020, $0.1 million for 2021, $0.1 million for 2022, $0.1 million for 2023 and $0.1 million for 2024. Realization of the residual values of the assets under lease is dependent on the future ability to market the assets under prevailing market conditions. The lease is classified as an operating lease and the underlying leased assets are included in Property and Equipment (Note 10 , " Property and Equipment "). Lease income related to operating leases for the three months ended March 31, 2020 and March 31, 2019 was $3.3 million and $3.3 million , respectively. The following table provides the net book value of operating lease property included in property and equipment in the consolidated balance sheets at March 31, 2020 and December 31, 2019 : (in thousands) March 31, 2020 December 31, 2019 Land $ 21,120 $21,120 Site improvements 91,308 91,308 Buildings 580 580 Gross property and equipment leased 113,008 113,008 Accumulation depreciation (15,382 ) (14,345 ) Net property and equipment leased $ 97,626 $ 98,663 As of March 31, 2020 , future undiscounted cash flows to be received in each of the next five years and thereafter, on non-cancelable operating leases are as follows: (in thousands) 2020 $ 8,913 2021 12,099 2022 12,371 2023 12,649 2024 12,934 Thereafter 136,963
LEASES	LEASES The Company adopted ASU 2016-02 on January 1, 2019 using the modified retrospective adoption method. The adoption resulted in an increase of the ROU assets of approximately $2.7 million and lease liabilities of $2.9 million . The difference of $0.2 million relates to straight-line rent accruals and lease incentive liabilities that were reclassified to ROU assets for operating leases. Lessee Leases Operating lease costs and variable lease costs included in selling and administrative costs for the three months ended March 31, 2020 were $0.2 million and de minimis, respectively. The annual maturities of lease liabilities as of March 31, 2020 were as follows: (in thousands) Lease Commitments 2020 $ 549 2021 802 2022 824 2023 624 2024 550 2025 and thereafter 546 Total undiscounted lease payments 3,895 Imputed interest 503 Total lease liabilities $ 3,392 The weighted-average remaining lease term for our operating leases was 5.46 years as of March 31, 2020 . The weighted average discount rate of our operating leases was 5.32% as of March 31, 2020 . Cash paid for amounts included in the measurement of lease liabilities was $0.2 million and $0.3 million for the three months ended March 31, 2020 and 2019 , respectively. Lessor Leases The Company owns a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property") that is subject to a long-term triple net lease agreement with an unrelated third-party. The lease provides for future rent escalations and renewal options. The initial lease term ends in May 2034. The lessee bears the cost of maintenance and property taxes. Rental income from operating leases is recognized on a straight-line basis, based on contractual lease terms with fixed and determinable increases over the non-cancellable term of the related lease when collectability is reasonably assured. Rental income includes a de minimus amount of amortization of below market lease liabilities for the March 31, 2020 and March 31, 2019 . The estimated aggregate future amortization of below market lease liabilities is $0.1 million for 2020, $0.1 million for 2021, $0.1 million for 2022, $0.1 million for 2023 and $0.1 million for 2024. Realization of the residual values of the assets under lease is dependent on the future ability to market the assets under prevailing market conditions. The lease is classified as an operating lease and the underlying leased assets are included in Property and Equipment (Note 10 , " Property and Equipment "). Lease income related to operating leases for the three months ended March 31, 2020 and March 31, 2019 was $3.3 million and $3.3 million , respectively. The following table provides the net book value of operating lease property included in property and equipment in the consolidated balance sheets at March 31, 2020 and December 31, 2019 : (in thousands) March 31, 2020 December 31, 2019 Land $ 21,120 $21,120 Site improvements 91,308 91,308 Buildings 580 580 Gross property and equipment leased 113,008 113,008 Accumulation depreciation (15,382 ) (14,345 ) Net property and equipment leased $ 97,626 $ 98,663 As of March 31, 2020 , future undiscounted cash flows to be received in each of the next five years and thereafter, on non-cancelable operating leases are as follows: (in thousands) 2020 $ 8,913 2021 12,099 2022 12,371 2023 12,649 2024 12,934 Thereafter 136,963

REVENUE FROM CONTRACTS WITH CUS

REVENUE FROM CONTRACTS WITH CUSTOMERS	3 Months Ended
	Mar. 31, 2020
Revenue from Contract with Customer [Abstract]
REVENUE FROM CONTRACTS WITH CUSTOMERS	REVENUE FROM CONTRACTS WITH CUSTOMERS Revenue from contracts with customers relates to Extended Warranty segment service fee and commission income. Service fee and commission income represents vehicle service agreement fees, GAP commissions, maintenance support service fees, warranty product commissions, homebuilder warranty service fees and homebuilder warranty commissions based on terms of various agreements with credit unions, consumers, businesses and homebuilders. Customers either pay in full at the inception of a warranty contract or commission product sale, or on terms subject to the Company’s customary credit reviews. The following table disaggregates revenues from contracts with customers by revenue type: (in thousands) Three months ended March 31, 2020 2019 Vehicle service agreement fees - IWS and Geminus $ 7,707 $ 5,366 GAP commissions - IWS and Geminus 269 265 Maintenance support service fees - Trinity 554 1,968 Warranty product commissions - Trinity 861 582 Homebuilder warranty service fees - PWSC 1,437 1,423 Homebuilder warranty commissions - PWSC 358 211 Service fee and commission income $ 11,186 $ 9,815 IWS' vehicle service agreement fees include the fees collected to cover the costs of future automobile mechanical breakdown claims and the associated administration of those claims. Vehicle service agreement contract fees are earned over the duration of the vehicle service agreement contracts as the single performance obligation is satisfied. IWS' GAP commissions include fees collected from the sale of GAP contracts. IWS acts as an agent on behalf of the third-party insurance company that underwrites and guaranties these GAP contracts. IWS does not assume any insurance risk from the sale of GAP contracts. IWS receives a single commission fee as its transaction price at the time it sells a GAP contract to a customer. Each GAP contract contains two separate performance obligations - sale of a GAP contract and GAP claims administration. The first performance obligation is related to the sale of a GAP contract and is satisfied upon closing the sale. The second performance obligation is related to the administration of claims during the GAP contract period, generally four years . Standalone selling prices are not directly observable in the GAP contract for each of the separate performance obligations. As a result, IWS has applied the expected cost plus a margin approach to develop models to estimate the standalone selling price for each of its performance obligations in order to allocate the transaction price to the two separate performance obligations identified. For the model related to the sale of a GAP contract performance obligation, IWS makes judgments about which of its actual costs are associated with selling activities. For the model related to the GAP claims administration performance obligation, IWS makes judgments about which of its actual costs are associated with claim-handling activities, which are performed over the life of the GAP contract period. The relative percentage of expected costs plus a margin associated with the sale of a GAP contract performance obligation is applied to the transaction price to determine the estimated standalone selling price of the sale of a GAP contract performance obligation, which IWS recognizes as earned at the time of the GAP contract sale. The relative percentage of expected costs plus a margin associated with the GAP claims administration performance obligation is applied to the transaction price to determine the estimated standalone selling price of the GAP claims administration performance obligation, which IWS recognizes as earned as services are performed over the GAP contract period. For the GAP claims administration performance obligation, IWS applies an input method of measurement, based on the expected costs of providing services, to determine the transfer of its services over the GAP contract period. IWS uses historical data regarding the number of claims it receives and activities performed, in addition to the number of GAP contracts sold, to estimate the number of claims to be received by year until coverage expires, which allows IWS to develop a revenue recognition pattern that it believes provides a faithful depiction of the transfer of services over time for the GAP claims administration performance obligation. Trinity's maintenance support service fees include the service fees collected to administer equipment breakdown and maintenance support services and are earned as services are rendered. Trinity’s warranty product commissions include the commissions from the sale of warranty contracts for certain new and used heating, ventilation, air conditioning ("HVAC"), standby generator, commercial LED lighting and refrigeration equipment. Trinity acts as an agent on behalf of the third-party insurance companies that underwrite and guaranty these warranty contracts. Trinity does not guaranty the performance underlying the warranty contracts it sells. Warranty product commissions are earned at the time of the warranty product sales. PWSC’s homebuilder warranty service fees include fees collected from the sale of warranties issued by new homebuilders. PWSC receives a single warranty service fee as its transaction price at the time it enters into a written contract with each of its builder customers. Each contract contains two separate performance obligations - warranty administrative services and other warranty services. Warranty administrative services include enrolling each home sold by the builder into the program and the warranty administrative system and delivering the warranty product. Other warranty services include answering builder or homeowner questions regarding the home warranty and dispute resolution services over the warranty term. Standalone selling prices are not directly observable in the contract for each of the separate performance obligations. As a result, PWSC has applied the expected cost plus a margin approach to develop models to estimate the standalone selling price for each of its performance obligations in order to allocate the transaction price to the two separate performance obligations identified. For the model related to the warranty administrative services performance obligation, PWSC makes judgments about which of its actual costs are associated with enrolling each home sold by the builder into the program and the warranty administrative system and delivering the warranty product. For the model related to the other warranty services performance obligation, PWSC makes judgments about which of its actual costs are associated with activities, such as answering builder or homeowner questions regarding the home warranty and dispute resolution services, which are performed over the life of the warranty coverage period. The relative percentage of expected costs plus a margin associated with the warranty administrative services performance obligation is applied to the transaction price to determine the estimated standalone selling price of the warranty administrative services performance obligation, which PWSC recognizes as earned at the time the home is enrolled and the warranty product is delivered. The relative percentage of expected costs plus a margin associated with the other warranty services performance obligation is applied to the transaction price to determine the estimated standalone selling price of the other warranty services performance obligation, which PWSC recognizes as earned as services are performed over the warranty coverage period. For the other warranty services performance obligation, PWSC applies an input method of measurement, based on the expected costs of providing services, to determine the transfer of its services over the warranty coverage period. PWSC uses historical data regarding the number of calls it receives and activities performed, in addition to the number of homes enrolled, to estimate the number of complaints and dispute resolution requests to be received by year until coverage expires, which allows PWSC to develop a revenue recognition pattern that it believes provides a faithful depiction of the transfer of services over time for the other warranty services performance obligation. PWSC’s homebuilder warranty commissions include commissions from the sale of warranty contracts for those builders who have requested and receive insurance backing of their warranty obligations. PWSC acts as an agent on behalf of the third-party insurance company that underwrites and guaranties these warranty contracts. Homebuilder warranty commissions are earned on the certification date, which is typically the date of the closing of the sale of the home to the buyer. The Company also earns fees to manage remediation or repair services related to claims on insurance-backed warranty obligations, which are earned when the claims are closed. Geminus' vehicle service agreement fees include the fees collected to cover the costs of future automobile mechanical breakdown claims and the associated administration of those claims. Vehicle service agreement contract fees are earned over the duration of the vehicle service agreement contracts as the single performance obligation is satisfied. Receivables from contracts with customers are reported as service fee receivable, net in the consolidated balance sheets and at March 31, 2020 and December 31, 2019 were $3.3 million and $3.4 million , respectively. The Company records deferred service fees resulting from contracts with customers when payment is received in advance of satisfying the performance obligations. The Company expects to recognize within one year as service fee and commission income approximately 43.7% of the deferred service fees as of March 31, 2020 . Approximately $5.5 million of service fee and commission income recognized during the three months ended March 31, 2020 was included in deferred service fees as of December 31, 2019 .

INCOME TAXES

INCOME TAXES	3 Months Ended
	Mar. 31, 2020
Income Tax Disclosure [Abstract]
INCOME TAXES	INCOME TAXES Income tax expense (benefit) for the three months ended March 31, 2020 and March 31, 2019 varies from the amount that would result by applying the applicable U.S. federal corporate income tax rate of 21% to (loss) income before income tax expense (benefit). The following table summarizes the differences: (in thousands) Three months ended March 31, 2020 2019 Income tax (benefit) expense at United States statutory income tax rate $ (47 ) $ 520 Valuation allowance 241 (1,331 ) Non-deductible compensation (43 ) 66 9 Investment income (128 ) (23 ) State income tax 38 26 Change in unrecognized tax benefits (1) 68 70 Indefinite life intangibles 54 33 Other (13 ) (17 ) Income tax expense (benefit) $ 170 $ (713 ) (1) Includes interest and penalty expense related to unrecognized tax benefits. The Company maintains a valuation allowance for its gross deferred tax assets at March 31, 2020 and December 31, 2019 . The Company's operations have generated substantial operating losses in prior years. These losses can be available to reduce income taxes that might otherwise be incurred on future taxable income; however, it is uncertain whether the Company will generate the taxable income necessary to utilize these losses or other reversing temporary differences. This uncertainty has caused management to place a full valuation allowance on its March 31, 2020 and December 31, 2019 net deferred tax asset, excluding the deferred income tax asset and liability amounts set forth in the paragraph below. In the quarter ended March 31, 2019, the Company released into income $0.8 million of its valuation allowance, as a result of its acquisition of Geminus, due to net deferred income tax liabilities that are expected to reverse during the period in which the Company will have deferred income tax assets available. The Company carries net deferred income tax liabilities of $29.1 million and $29.0 million at March 31, 2020 and December 31, 2019 , respectively. At March 31, 2020 , $8.0 million relates to deferred income tax liabilities scheduled to reverse in periods after the expiration of the Company's consolidated U.S. net operating loss carryforwards, $21.8 million relates to deferred income tax liabilities associated with land and indefinite lived intangible assets and $0.7 million relates to deferred income tax assets associated with state income taxes. At December 31, 2019 , $8.0 million relates to deferred income tax liabilities scheduled to reverse in periods after the expiration of the Company's consolidated U.S. net operating loss carryforwards, $21.7 million relates to deferred income tax liabilities associated with land and indefinite lived intangible assets, $0.6 million relates to deferred income tax assets associated with state income taxes and $0.1 million relates to deferred income tax assets associated with alternative minimum tax credits. As of March 31, 2020 and December 31, 2019 , the Company carried a liability for unrecognized tax benefits of $1.4 million which is included in income taxes payable in the consolidated balance sheets. The Company classifies interest and penalty accruals, if any, related to unrecognized tax benefits as income tax expense. The Company recorded income tax expense of $0.1 million related to interest and penalty accruals for each of the three months ended March 31, 2020 and March 31, 2019 . At March 31, 2020 and December 31, 2019 , the Company carried an accrual for the payment of interest and penalties of $1.4 million and $1.3 million , respectively, included in income taxes payable in the consolidated balance sheets.

(LOSS) EARNINGS PER SHARE

(LOSS) EARNINGS PER SHARE	3 Months Ended
	Mar. 31, 2020
Earnings Per Share [Abstract]
(LOSS) EARNINGS PER SHARE	LOSS) EARNINGS PER SHARE The following table sets forth the reconciliation of numerators and denominators for the basic and diluted (loss) earnings per share computation for the three months ended March 31, 2020 and March 31, 2019 : (in thousands, except per share data) Three months ended March 31, 2020 2019 Numerator: Net (loss) income $ (393 ) $ 3,189 Less: net income attributable to noncontrolling interests (721 ) (211 ) Less: dividends on preferred stock (377 ) (246 ) Net (loss) income attributable to common shareholders $ (1,491 ) $ 2,732 Denominator: Weighted average basic shares Weighted average common shares outstanding 22,069 21,841 Weighted average diluted shares Weighted average common shares outstanding 22,069 21,841 Effect of potentially dilutive securities Stock options — — Unvested restricted stock awards — — Warrants — — Convertible preferred stock — — Total weighted average diluted shares 22,069 21,841 Basic (loss) earnings per share $ (0.07 ) $ 0.13 Diluted (loss) earnings per share $ (0.07 ) $ 0.13 Basic loss per share is calculated using weighted-average common shares outstanding. Diluted loss per share is calculated using weighted-average diluted shares. Weighted-average diluted shares is calculated by adding the effect of potentially dilutive securities to weighted-average common shares outstanding. Potentially dilutive securities consist of stock options, unvested restricted stock awards, warrants and convertible preferred stock. Because the Company is reporting a net loss for the three months ended March 31, 2020 , all potentially dilutive securities outstanding were excluded from the calculation of diluted loss per share since their inclusion would have been anti-dilutive. The following weighted-average potentially dilutive securities are not included in the diluted (loss) earnings per share calculations above because they would have had an antidilutive effect on the (loss) earnings per share from continuing operations: Three months ended March 31, 2020 2019 Stock options 40,000 40,000 Unvested restricted stock awards 500,000 976,950 Warrants 4,423,765 4,673,765 Convertible preferred stock 1,142,975 1,392,975 Total 6,106,740 7,083,690

STOCK-BASED COMPENSATION

STOCK-BASED COMPENSATION	3 Months Ended
	Mar. 31, 2020
Share-based Payment Arrangement [Abstract]
STOCK-BASED COMPENSATION	STOCK-BASED COMPENSATION (a) Stock Options The following table summarizes the stock option activity during the three months ended March 31, 2020 : Number of Options Outstanding Weighted-Average Exercise Price Weighted-Average Remaining Contractual Term (in Years) Aggregate Intrinsic Value (in Thousands) Outstanding at December 31, 2019 40,000 $ 4.67 0.3 $ — Granted — — Expired — — Outstanding at March 31, 2020 40,000 $ 4.67 0.1 $ — Exercisable at March 31, 2020 40,000 $ 4.67 0.1 $ — The aggregate intrinsic value of stock options outstanding and exercisable is the difference between the March 31, 2020 market price for the Company's common shares and the exercise price of the options, multiplied by the number of options where the fair value exceeds the exercise price. The Company uses the Black-Scholes option pricing model to estimate the fair value of each option on the date of grant. No options were granted during the three months ended March 31, 2020 . (b) Restricted Stock Awards Under the 2013 Equity Incentive Plan (the "2013 Plan"), the Company made grants of restricted common stock awards to certain officers of the Company on March 28, 2014 (the "2014 Restricted Stock Awards"). The 2014 Restricted Stock Awards shall become fully vested and the restriction period shall lapse as of March 28, 2024 subject to the officers' continued employment through the vesting date. The 2014 Restricted Stock Awards are amortized on a straight-line basis over the ten -year requisite service period. The grant-date fair value of the 2014 Restricted Stock Awards was determined using the closing price of Kingsway common stock on the date of grant. Total unamortized compensation expense related to unvested 2014 Restricted Stock Awards at March 31, 2020 was zero . On September 5, 2018, the Company executed an Amended and Restated Restricted Stock Award Agreement ("Amended RSA Agreement") with its former Chief Executive Officer. Pursuant to the terms of the Amended RSA Agreement, the Company granted to the former Chief Executive Officer a modified award of 350,000 shares of restricted common stock (the "2018 Modified Restricted Stock Award"). The Company deemed the 2018 Modified Restricted Stock Award to be taxable to the former Chief Executive Officer on the modification date. As a result, the Company cancelled 102,550 of the 350,000 shares of the 2018 Modified Restricted Stock Award to satisfy the tax withholding obligation. The remaining 247,450 shares of the 2018 Modified Restricted Stock Award shall become fully vested after the satisfaction of certain performance conditions, as defined in the Amended RSA Agreement. Pursuant to the Amended RSA Agreement, the 2018 Modified Restricted Stock Award is to vest upon (i) the completion of the sale by 1347 Investors of its entire interest in the shares of Limbach common stock and (ii) the subsequent completion of the liquidation of 1347 Investors and the distribution of its assets to its members. Pursuant to a Distribution and Redemption Agreement, dated as of September 30, 2019, by and among 1347 Investors and its members, the Company received distributions of cash proceeds of $0.6 million , 594,750 shares of Limbach common stock and 400,000 warrants, exercisable at $15 and expiring July 20, 2023, on Limbach common shares, which the Company deemed as having satisfied the performance obligations described in the Amended RSA Agreement. On October 31, 2019, the Company executed an agreement to acquire the remaining 247,450 shares of the 2018 Modified Restricted Stock Award as partial consideration in exchange for selling its remaining investment in the common stock of ICL. See Note 22 , " Related Parties ," for further discussion. During the fourth quarter of 2019, the Company recorded $0.6 million of compensation expense equal to the fair value of the remaining 247,450 fully vested shares of the 2018 Modified Restricted Stock Award. The grant-date fair value of the 2018 Modified Restricted Stock Award was determined using the closing price of Kingsway common stock on the modification date. On January 31, 2019, the Company executed an Employee Separation Agreement and Release ("2019 Separation Agreement") with a former officer. The 2019 Separation Agreement modified the vesting terms related to 115,500 shares of the original 2014 Restricted Stock Awards ("2014 Modified Restricted Stock Award"), such that they became fully vested on January 31, 2019. The Company deemed the 2014 Modified Restricted Stock Award to be taxable to the former officer on the vesting date. Pursuant to the terms of the 2013 Plan and the 2019 Separation Agreement, the former officer was entitled to satisfy the tax withholding obligation by authorizing the Company to withhold restricted common shares, which would otherwise be deliverable, having an aggregate fair market value, determined as of the tax date, equal to the tax withholding obligation. The former officer chose to satisfy the tax withholding obligation in this manner. As a result, the Company cancelled 36,269 of the 115,500 shares of the 2014 Modified Restricted Stock Award and recognized payroll tax expense of $0.1 million during the first quarter of 2019. The Company also recorded during the first quarter of 2019 $0.1 million of compensation expense equal to the fair value of the remaining 79,231 fully vested shares of the 2014 Modified Restricted Stock Award. The grant-date fair value of the 2014 Modified Restricted Stock Award was determined using the closing price of Kingsway common stock on the grant date. On February 28, 2020, the Company executed an Employment Separation Agreement and Release ("2020 Separation Agreement") with a former officer. Under the terms of the 2020 Separation Agreement, the former officer forfeited 93,713 shares of the 2014 Restricted Stock Awards. The Company’s accounting policy is to account for forfeitures when they occur. As a result, the Company reversed during the first quarter of 2020 $0.2 million of compensation expense previously recognized from March 28, 2014 through February 28, 2020. The former officer's remaining 135,787 shares of the original 2014 Restricted Stock Awards ("2020 Restricted Stock Award") became partially vested on February 28, 2020. The Company deemed the 2020 Restricted Stock Award to be taxable to the former officer on the vesting date. Pursuant to the terms of the 2013 Plan, the former officer was entitled to satisfy the tax withholding obligation by authorizing the Company to withhold restricted common shares, which would otherwise be deliverable, having an aggregate fair market value, determined as of the tax date, equal to the tax withholding obligation. The former officer chose to satisfy the tax withholding obligation in this manner. As a result, the Company cancelled 41,677 of the 135,787 shares of the 2020 Restricted Stock Award and recognized payroll tax expense of $0.1 million during the first quarter of 2020. Total unamortized compensation expense related to the unvested 2020 Restricted Stock Award at March 31, 2020 was zero . On September 5, 2018, the Company granted 500,000 restricted common stock awards to an officer (the "2018 Restricted Stock Award"). The 2018 Restricted Stock Award shall become fully vested and the restriction period shall lapse as of March 28, 2024 subject to the officer's continued employment through the vesting date. The 2018 Restricted Stock Award is amortized on a straight-line basis over the requisite service period. The grant-date fair value of the 2018 Restricted Stock Award was determined using the closing price of Kingsway common stock on the date of grant. Total unamortized compensation expense related to unvested 2018 Restricted Stock Award at March 31, 2020 was $1.5 million . The following table summarizes the activity related to unvested 2014 Restricted Stock Awards, 2020 Restricted Stock Award and 2018 Restricted Stock Award (collectively "Restricted Stock Awards") for the three months ended March 31, 2020 : Number of Restricted Stock Awards Weighted-Average Grant Date Fair Value (per Share) Unvested at December 31, 2019 729,500 $ 5.23 Vested (94,110 ) 4.14 Cancelled for Tax Withholding (41,677 ) 4.14 Forfeited (93,713 ) 4.14 Unvested at March 31, 2020 500,000 $ 5.73 The unvested balance at March 31, 2020 in the table above is comprised of 500,000 shares of the 2018 Restricted Stock Award. (c) Restricted Stock Awards of PWSC PWSC granted 1,000 restricted common stock awards ("PWSC Restricted Stock Award") to an officer of PWSC pursuant to an agreement dated September 7, 2018. The PWSC Restricted Stock Award contains both a service and a performance condition that affects vesting. The service condition vests according to a graded vesting schedule and shall become fully vested on February 20, 2022 subject to the officer's continued employment through the applicable vesting dates. The service condition component of the PWSC Restricted Stock Award is amortized on a straight-line basis over the requisite service period. The performance condition vests on February 20, 2022 and is based on the internal rate of return of PWSC. Accruals of compensation expense for the performance condition component of the PWSC Restricted Stock Award is estimated based on the probable outcome of the performance condition. At March 31, 2020 , the Company determined that the performance condition component is not probable of being achieved. As a result, no compensation expense has been recorded related to the performance condition component through March 31, 2020 . The grant-date fair value of the PWSC Restricted Stock Award was estimated using a valuation model. At March 31, 2020 , there were 750 unvested shares of the PWSC Restricted Stock Award with a weighted-average grant date fair value of $824.47 per share. Total unamortized compensation expense related to unvested PWSC Restricted Stock Award at March 31, 2020 was $0.6 million . Total stock-based compensation, inclusive of Stock Options, Restricted Stock Awards and Restricted Stock Awards of PWSC described above, net of forfeitures, was a benefit of less than $0.1 million and an expense of $0.2 million for the three months ended March 31, 2020 and March 31, 2019 , respectively.

ACCUMULATED OTHER COMPREHENSIVE

ACCUMULATED OTHER COMPREHENSIVE INCOME	3 Months Ended
	Mar. 31, 2020
Equity [Abstract]
ACCUMULATED OTHER COMPREHENSIVE INCOME	ACCUMULATED OTHER COMPREHENSIVE INCOME The tables below detail the changes in the balances of each component of accumulated other comprehensive income, net of tax, for the three months ended March 31, 2020 and March 31, 2019 as relates to shareholders' equity attributable to common shareholders on the consolidated balance sheets. However, the unaudited consolidated statements of comprehensive income present the components of other comprehensive income (loss), net of tax, only for the three months ended March 31, 2020 and March 31, 2019 and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries. (in thousands) Three months ended March 31, 2020 Unrealized Gains on Available-for-Sale Investments Foreign Currency Translation Adjustments Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk Total Accumulated Other Comprehensive Income Balance at January 1, 2020 $ 59 $ (3,286 ) $ 38,574 $ 35,347 Other comprehensive income arising during the period 47 — 11,623 11,670 Amounts reclassified from accumulated other comprehensive income 61 — — 61 Net current-period other comprehensive income 108 — 11,623 11,731 Balance at March 31, 2020 $ 167 $ (3,286 ) $ 50,197 $ 47,078 (in thousands) Three months ended March 31, 2019 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk Equity in Other Comprehensive Loss of Limited Liability Investment Total Accumulated Other Comprehensive Income Balance at January 1, 2019 $ (160 ) $ (3,286 ) $ 44,259 $ (45 ) $ 40,768 Other comprehensive income (loss) arising during the period 105 — (945 ) — (840 ) Amounts reclassified from accumulated other comprehensive income (6 ) — — — (6 ) Net current-period other comprehensive income income 99 — (945 ) — (846 ) Balance at March 31, 2019 $ (61 ) $ (3,286 ) $ 43,314 $ (45 ) $ 39,922 Components of accumulated other comprehensive income were reclassified to the following lines of the unaudited consolidated statements of operations for the three months ended March 31, 2020 and March 31, 2019 : (in thousands) Three months ended March 31, 2020 2019 Reclassification of accumulated other comprehensive income from unrealized gains (losses) on available-for-sale investments to: Net realized gains $ (61 ) $ 6 Other-than-temporary impairment loss — — (Loss) income before income tax expense (benefit) (61 ) 6 Income tax expense (benefit) — — Net (loss) income $ (61 ) $ 6

SEGMENTED INFORMATION

SEGMENTED INFORMATION	3 Months Ended
	Mar. 31, 2020
Segment Reporting [Abstract]
SEGMENTED INFORMATION	SEGMENTED INFORMATION The Company conducts its business through the following two reportable segments: Extended Warranty and Leased Real Estate. Extended Warranty Segment Extended Warranty includes the following subsidiaries of the Company: IWS, Trinity, PWSC and Geminus (collectively, "Extended Warranty"). IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by credit unions in 27 states and the District of Columbia to their members. Trinity sells HVAC, standby generator, commercial LED lighting and refrigeration warranty products and provides equipment breakdown and maintenance support services to companies across the United States. As a seller of warranty products, Trinity markets and administers product warranty contracts for certain new and used products in the HVAC, standby generator, commercial LED lighting and refrigeration industries throughout the United States. Trinity acts as an agent on behalf of the third-party insurance companies that underwrite and guaranty these warranty contracts. Trinity does not guaranty the performance underlying the warranty contracts it sells. As a provider of equipment breakdown and maintenance support services, Trinity acts as a single point of contact to its clients for both certain equipment breakdowns and scheduled maintenance of equipment. Trinity will provide such repair and breakdown services by contracting with certain HVAC providers. PWSC sells new home warranty products and provides administration services to home builders and homeowners across the United States. PWSC distributes its products and services through an in house sales team and through insurance brokers and insurance carriers throughout all states except Alaska and Louisiana. Geminus primarily sells vehicle service agreements to used car buyers across the United States, through its subsidiaries, Penn and Prime. Penn and Prime distribute these products in 32 and 40 states, respectively, via independent used car dealerships and franchised car dealerships. Leased Real Estate Segment Leased Real Estate includes the Company's subsidiary, CMC, which was acquired on July 14, 2016. CMC owns the Real Property that is leased to a third party pursuant to a long-term triple net lease. The Real Property is also subject to the Mortgage. When assessing and measuring the operational and financial performance of the Leased Real Estate segment, interest expense related to the Mortgage is included in Leased Real Estate's segment operating income. Revenues and Operating Income by Reportable Segment Results for the Company's reportable segments are based on the Company's internal financial reporting systems and are consistent with those followed in the preparation of the unaudited consolidated interim financial statements. The following tables provide financial data used by management. Segment assets are not allocated for management use and, therefore, are not included in the segment disclosures below. Revenues by reportable segment reconciled to consolidated revenues for the three months ended March 31, 2020 and March 31, 2019 were: (in thousands) Three months ended March 31, 2020 2019 Revenues: Extended Warranty: Service fee and commission income $ 11,186 $ 9,815 Other income 74 75 Total Extended Warranty 11,260 9,890 Leased Real Estate: Rental income 3,341 3,341 Other income 68 70 Total Leased Real Estate 3,409 3,411 Total revenues $ 14,669 $ 13,301 The operating income by reportable segment in the following table is before income taxes and includes revenues and direct segment costs. Total segment operating income reconciled to the consolidated net (loss) income for the three months ended March 31, 2020 and March 31, 2019 were: (in thousands) Three months ended March 31, 2020 2019 Segment operating income: Extended Warranty $ 850 $ 567 Leased Real Estate 597 452 Total segment operating income 1,447 1,019 Net investment income 719 699 Net realized gains 208 315 (Loss) gain on change in fair value of equity investments (597 ) 78 Gain on change in fair value of limited liability investments, at fair value 1,899 4,265 Net change in unrealized (loss) gain on private company investments (670 ) 19 Other-than-temporary impairment loss (117 ) (75 ) Interest expense not allocated to segments (2,153 ) (2,102 ) Other income and expenses not allocated to segments, net (3,030 ) (1,764 ) Amortization of intangible assets (574 ) (521 ) Gain on change in fair value of debt 2,645 576 Equity in net loss of investee — (33 ) (Loss) income before income tax expense (benefit) (223 ) 2,476 Income tax expense (benefit) 170 (713 ) Net (loss) income $ (393 ) $ 3,189

FAIR VALUE OF FINANCIAL INSTRUM

FAIR VALUE OF FINANCIAL INSTRUMENTS	3 Months Ended
	Mar. 31, 2020
Fair Value Disclosures [Abstract]
FAIR VALUE OF FINANCIAL INSTRUMENTS	FAIR VALUE OF FINANCIAL INSTRUMENTS Fair value is the price that would be received upon sale of an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date. Fair value is best evidenced by quoted bid or ask price, as appropriate, in an active market. Where bid or ask prices are not available, such as in an illiquid or inactive market, the closing price of the most recent transaction of that instrument subject to appropriate adjustments as required is used. Where quoted market prices are not available, the quoted prices of similar financial instruments or valuation models with observable market-based inputs are used to estimate the fair value. These valuation models may use multiple observable market inputs, including observable interest rates, foreign exchange rates, index levels, credit spreads, equity prices, counterparty credit quality, corresponding market volatility levels and option volatilities. Minimal management judgment is required for fair values calculated using quoted market prices or observable market inputs for models. Greater subjectivity is required when making valuation adjustments for financial instruments in inactive markets or when using models where observable parameters do not exist. Also, the calculation of estimated fair value is based on market conditions at a specific point in time and may not be reflective of future fair values. For the Company's financial instruments carried at cost or amortized cost, the book value is not adjusted to reflect increases or decreases in fair value due to market fluctuations, including those due to interest rate changes, as it is the Company's intention to hold them until there is a recovery of fair value, which may be to maturity. The Company employs a fair value hierarchy to categorize the inputs it uses in valuation techniques to measure the fair value. The following fair value hierarchy is used in selecting inputs, with the highest priority given to Level 1: • Level 1 – Quoted prices for identical instruments in active markets. • Level 2 – Quoted prices for similar instruments in active markets; quoted prices for identical or similar instruments in markets that are not active; and model-derived valuations in which all significant inputs are observable in active markets. • Level 3 – Valuations derived from valuation techniques in which one or more significant inputs are not observable. The Company classifies its investments in fixed maturities as available-for-sale and reports these investments at fair value. The Company's equity investments, limited liability investments, at fair value, real estate investments, subordinated debt and warrant liability are measured and reported at fair value. Fixed maturities - Fair values of fixed maturities for which no active market exists are derived from quoted market prices of similar instruments or other third party evidence. All classes of the Company’s fixed maturities, primarily consisting of investments in US. Treasury bills and government bonds; obligations of states, municipalities and political subdivisions; mortgage-backed securities; and corporate securities, are classified as Level 2. Level 2 is applied to valuations based upon quoted prices for similar assets in active markets; quoted prices for identical or similar assets in markets that are inactive; or valuations based on models where the significant inputs are observable or can be corroborated by observable market data. The Company engages a third-party vendor who utilizes third-party pricing sources and primarily employs a market approach to determine the fair values of our fixed maturities. The market approach includes primarily obtaining prices from independent third-party pricing services as well as, to a lesser extent, quotes from broker-dealers. Our third-party vendor also monitors market indicators, as well as industry and economic events, to ensure pricing is appropriate. All classes of our fixed maturities are valued using this technique. The Company has obtained an understanding of our third-party vendor’s valuation methodologies and inputs. Fair values obtained from our third-party vendor are not adjusted by the Company. The following is a description of the significant inputs, by asset class, used by the third-party pricing services to determine the fair values of our fixed maturities included in Level 2: • U.S. government, government agencies and authorities are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets and maturity. • States, municipalities and political subdivisions are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, new issuances and credit spreads. • Mortgage-backed securities are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, expected prepayments, expected credit default rates, delinquencies and issue specific information including, but not limited to, collateral type, seniority and vintage. • Corporate securities are generally priced using the market approach using pricing vendors. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, issuer rating, benchmark yields, maturity and credit spreads. Equity investments - Fair values of equity investments, including warrants, reflect quoted market values based on latest bid prices, where active markets exist, or models based on significant market observable inputs, where no active markets exist. Limited liability investments, at fair value - Limited liability investments, at fair value include the underlying investments of Net Lease and Argo Holdings. Net Lease owns investments in limited liability companies that hold investment properties. Argo Holdings makes investments in limited liability companies and limited partnerships that hold investments in search funds and private operating companies. • The fair value of Net Lease's investments in limited liability companies is based upon the net asset values of the underlying investments companies as a practical expedient to estimate fair value. The Company applies the net asset value practical expedient to Net Lease's limited liability investments on an investment-by-investment basis unless it is probable that the Company will sell a portion of an investment at an amount different from the net asset value of the investment. Investments that are measured at fair value using the net asset value practical expedient are not required to be classified using the fair value hierarchy. • The fair value of Argo Holdings' limited liability investments that hold investments in search funds is based on the initial investment in the search funds. The fair value of Argo Holdings' limited liability investments that hold investments in private operating companies is valued using a market approach including valuation multiples applied to corresponding performance metrics, such as earnings before interest, tax, depreciation and amortization; revenue; or net earnings. The selected valuation multiples were estimated using multiples provided by the investees and review of those multiples in light of investor updates, performance reports, financial statements and other relevant information. These investments are categorized in Level 3 of the fair value hierarchy. Real estate investments - The fair value of real estate investments involves a combination of the market and income valuation techniques. Under this approach, a market-based capitalization rate is derived from comparable transactions, adjusted for any unique characteristics of each asset, and applied to the asset under consideration. The cap rates used during underwriting and subsequent valuation incorporate the consideration of risks of vacancy and collection loss, administrative costs of owning net leased assets and possible capital expenditures that could be determined a landlord expense. These investments are categorized in Level 3 of the fair value hierarchy. Subordinated debt - The fair value of the subordinated debt is calculated using a model based on significant market observable inputs and inputs developed by a third party. These inputs include credit spread assumptions developed by a third party and market observable swap rates. The subordinated debt is categorized in Level 2 of the fair value hierarchy. Warrant liability - As described in Note 13 , " Debt ," the Company issued the KWH Warrants on March 1, 2019. The KWH Warrants are measured and reported at fair value and are included in accrued expenses and other liabilities in the consolidated balance sheets. The fair value of the warrant liability is estimated using an internal model without relevant observable market inputs. The significant inputs used in the model include an enterprise value multiple applied to earnings before interest, tax, depreciation and amortization. The implied enterprise value is reduced by the remaining debt associated with the KWH Loan to determine an implied equity value. The liability classified warrants are categorized in Level 3 of the fair value hierarchy. Assets and Liabilities Measured at Fair Value on a Recurring Basis The balances of the Company's financial assets and liabilities measured at fair value on a recurring basis by level within the fair value hierarchy as of March 31, 2020 and December 31, 2019 are as follows. Certain investments in limited liability companies that are measured at fair value using the net asset value practical expedient are not required to be classified using the fair value hierarchy, but are presented in the following tables to permit reconciliation of the fair value hierarchy to the amounts presented in the consolidated balance sheets: (in thousands) March 31, 2020 Fair Value Measurements at the End of the Reporting Period Using Total Quoted Prices in Active Markets for Identical Assets (Level 1) Significant Other Observable Inputs (Level 2) Significant Unobservable Inputs (Level 3) Measured at Net Asset Value Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 5,629 $ — $ 5,629 $ — $ — States, municipalities and political subdivisions 603 — 603 — — Mortgage-backed 4,054 — 4,054 — — Corporate 4,961 — 4,961 — — Total fixed maturities 15,247 — 15,247 — — Equity investments: Common stock 1,817 1,817 — — — Warrants 8 3 5 — — Total equity investments 1,825 1,820 5 — — Limited liability investments, at fair value 30,986 — — 4,413 26,573 Real estate investments 10,662 — — 10,662 — Other investments 841 — 841 — — Short-term investments 156 — 156 — — Total assets $ 59,717 $ 1,820 $ 16,249 $ 15,075 $ 26,573 Liabilities: Subordinated debt $ 40,387 $ — $ 40,387 $ — $ — Warrant liability 216 — — 216 — Total liabilities $ 40,603 $ — $ 40,387 $ 216 $ — (in thousands) December 31, 2019 Fair Value Measurements at the End of the Reporting Period Using Total Quoted Prices in Active Markets for Identical Assets (Level 1) Significant Other Observable Inputs (Level 2) Significant Unobservable Inputs (Level 3) Measured at Net Asset Value Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 13,316 $ — $ 13,316 $ — $ — States municipalities and political subdivisions 600 — 600 — — Mortgage-backed 2,939 — 2,939 — — Corporate 5,340 — 5,340 — — Total fixed maturities 22,195 — 22,195 — — Equity investments: Common stock 2,406 2,406 — — — Warrants 15 5 10 — — Total equity investments 2,421 2,411 10 — — Limited liability investments, at fair value 29,078 — — 4,392 24,686 Real estate investments 10,662 — — 10,662 — Other investments 1,009 — 1,009 — — Short-term investments 155 — 155 — — Total assets $ 65,520 $ 2,411 $ 23,369 $ 15,054 $ 24,686 Liabilities: Subordinated debt $ 54,655 $ — $ 54,655 $ — $ — Warranty liability 249 — — 249 — Total liabilities $ 54,904 $ — $ 54,655 $ 249 $ — The following table provides a reconciliation of the fair value of recurring Level 3 fair value measurements for the three months ended March 31, 2020 and March 31, 2019 : (in thousands) Three months ended March 31, 2020 2019 Assets: Limited liability investments, at fair value: Beginning balance $ 4,392 $ 4,124 Purchases — 75 Distributions received (77 ) (324 ) Realized gains included in net (loss) income 86 69 Change in fair value of limited liability investments, at fair value included in net (loss) income 12 116 Ending balance $ 4,413 $ 4,060 Unrealized gains on limited liability investments, at fair value held at end of period: Included in net (loss) income $ 12 $ 116 Included in other comprehensive income (loss) $ — $ — Real estate investments: Beginning balance $ 10,662 $ 10,662 Change in fair value of real estate investments included in net (loss) income — — Ending balance $ 10,662 $ 10,662 Unrealized gains recognized on real estate investments held at end of period: Included in net (loss) income — — Included in other comprehensive income (loss) — — Ending balance - assets $ 15,075 $ 14,722 Liabilities: Warrant liability: Beginning balance $ 249 $ — Issuance of warrants — 361 Change in fair value of warrant liability included in net (loss) income (33 ) (44 ) Ending balance - liabilities $ 216 $ 317 Unrealized gains recognized on warrant liability held at end of period: Included in net (loss) income $ (33 ) $ (44 ) Included in other comprehensive income (loss) $ — $ — The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's investments that are categorized as Level 3 at March 31, 2020 : Categories Fair Value Valuation Techniques Unobservable Inputs Input Value(s) Limited liability investments, at fair value $ 4,413 Market approach Valuation multiples 3.1x-7.0x Real estate investments $ 10,662 Market and income approach Cap rates 7.5 % Warrant liability $ 216 Market approach Valuation multiple 6.0x The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's investments that are categorized as Level 3 at December 31, 2019 : Categories Fair Value Valuation Techniques Unobservable Inputs Input Value(s) Limited liability investments, at fair value $ 4,392 Market approach Valuation multiples 3.1x-7.0x Real estate investments $ 10,662 Market and income approach Cap rates 7.5 % Warrant liability $ 249 Market approach Valuation multiple 6.0x Investments Measured Using the Net Asset Value per Share Practical Expedient The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at March 31, 2020 : Category Fair Value (in thousands) Unfunded Commitments Redemption Frequency Redemption Notice Period Limited liability investments, at fair value $ 26,573 n/a n/a n/a The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at December 31, 2019 : Category Fair Value (in thousands) Unfunded Commitments Redemption Frequency Redemption Notice Period Limited liability investments, at fair value $ 24,686 n/a n/a n/a Assets and Liabilities Measured at Fair Value on a Nonrecurring Basis Certain assets and liabilities are measured at fair value on a nonrecurring basis, including assets that are adjusted for observable price changes or written down to fair value as a result of an impairment. For the three months ended March 31, 2020 , the Company recorded adjustments to increase the fair value of an certain investments in private companies for observable price changes of zero and less than $0.1 million , respectively, which are included in net change in unrealized (loss) gain on private company investments in the consolidated statements of operations. The Company recorded impairments related to investments in private companies of $0.7 million and zero for the three months ended March 31, 2020 and March 31, 2019 , respectively, which are included in net change in unrealized (loss) gain on private company investments in the consolidated statements of operations. The impairment recorded for the three months ended March 31, 2020 is a result of the impact of COVID-19 on the investment's underlying business. To determine the fair value of investments in these private companies, the Company considered rounds of financing and third-party transactions, discounted cash flow analyses and market-based information, including comparable transactions, trading multiples and changes in market outlook, among other factors. The Company has classified the fair value measurements of these investments in private companies as Level 3 because they involve significant unobservable inputs.

RELATED PARTIES

RELATED PARTIES	3 Months Ended
	Mar. 31, 2020
Related Party Transactions [Abstract]
RELATED PARTIES	RELATED PARTIES Related party transactions, including services provided to or received by the Company's subsidiaries, are measured in part by the amount of consideration paid or received as established and agreed by the parties. Except where disclosed elsewhere in these unaudited consolidated interim financial statements, the following is a summary of related party relationships and transactions. (a) Argo Management Group, LLC The Company acquired Argo Management Group, LLC ("Argo Management") in April 2016. Argo Management's primary business is to act as Managing Member of Argo Holdings. At March 31, 2020 and December 31, 2019 , each of the Company, John T. Fitzgerald ("Fitzgerald"), the Company's Chief Executive Officer and President, and certain of Fitzgerald’s immediate family members owns equity interests in Argo Holdings, all of which interests were acquired prior to the Company’s acquisition of Argo Management. Subject to certain limitations, Argo Holdings' governing documents require all individuals and entities owning an equity interest in Argo Holdings to fund upon request his/her/its pro rata share of any funding requirements of Argo Holdings up to an aggregate maximum amount equal to his/her/its total capital commitment (each request for funds being referred to as a "Capital Call"). During 2020 and 2019 , the Company funded approximately zero and $0.6 million , respectively, in response to Capital Calls. During 2019 , Fitzgerald and Fitzgerald’s immediate family members funded their respective Capital Calls. Argo Holdings used the proceeds of the Capital Calls to make investments, cover general operating expenses and pay the management fee owed to Argo Management. Argo Holdings made no Capital Calls during the three months ended March 31, 2020 . (b) Itasca Capital Ltd. The Company formerly held an investment in the common stock of ICL, a publicly traded Canadian corporation, that was recorded as investment in investee in the consolidated balance sheets. During the fourth quarter of 2019, the Company sold its remaining investment in the common stock of ICL. The Company owned zero common shares of ICL at March 31, 2020 and December 31, 2019 . Fitzgerald has served as a member of the ICL Board of Directors since June 9, 2016. Fitzgerald joined the Company as an Executive Vice President in April 2016 following the Company’s acquisition of Argo. Fitzgerald has served as the Company’s Chief Executive Officer since September 5, 2018 and has served on the Company’s Board of Directors since April 21, 2016. On October 9, 2019, the Company executed an agreement to sell 1,974,113 shares of ICL common stock, at a price of C$0.35 per share, to a third party for cash proceeds totaling C$0.7 million . On October 31, 2019, the Company executed an agreement to sell 3,011,447 shares of ICL common stock, at a price of C$0.35 per share, to Larry G. Swets, Jr. ("Swets") for consideration totaling C$1.1 million , comprised of cash proceeds of C$0.2 million and 247,450 shares of the Company’s common stock. Both transactions closed during the fourth quarter of 2019. The 247,450 shares of the Company’s common stock were awarded to Swets pursuant to the Amended RSA Agreement executed on September 5, 2018 related to Swets’ departure from the Company. Refer to Note 18 , " Stock-Based Compensation ," for further information. Pursuant to the Amended RSA Agreement, Swets retained 350,000 shares of restricted Company common stock that were to vest upon (i) the completion of the sale by 1347 Investors of its entire interest in the shares of Limbach common stock and (ii) the subsequent completion of the liquidation of 1347 Investors and the distribution of its assets to its members. Pursuant to a Distribution and Redemption Agreement, dated as of September 30, 2019, by and among 1347 Investors and its members, the Company received distributions of cash proceeds of $0.6 million , 594,750 shares of Limbach common stock and 400,000 warrants, exercisable at $15 and expiring July 20, 2023, on Limbach common shares, which the Company deemed as having satisfied the performance obligations described in the Amended RSA Agreement. Also, pursuant to the Amended RSA Agreement, Swets exercised his right to authorize the Company to withhold 102,550 shares of restricted Company common stock, which would otherwise have been delivered or available for vesting, in order to satisfy all federal, state, local or other taxes required to be withheld or paid in connection with such award, leaving Swets with 247,450 shares of the Company’s common stock. Swets served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. (c) Insurance Income Strategies Ltd. Insurance Income Strategies Ltd. ("IIS") is a Bermuda corporation, formed in October 2017, organized to offer collateralized reinsurance in the property catastrophe market through its wholly owned operating subsidiary IIS Re Ltd. The Company held 100% of the outstanding common stock of IIS at March 31, 2020 and December 31, 2019 . The Company did not invest any capital against the common shares and has not invested any capital in IIS via any other security of IIS. The Company also does not have any commitment to provide capital to IIS. Effective August 10, 2018, simultaneous with IIS issuing preferred stock to a third-party investor, the Company and IIS entered into a management service agreement, which describes the Company’s duties and rights to remuneration. The management service agreement describes the Company’s duties to include (a) identification and due diligence of potential transaction counterparties for consideration by IIS management; (b) advice on capital structure and corporate development opportunities; (c) support for compliance with the rules and regulations of the SEC; and (d) other periodic and special requests deemed within the scope of the management service agreement. The management service agreement provides for a fee 0.9% of the assets of IIS and 9% of the annual net profits. Pursuant to other agreements executed August 10, 2018 simultaneous with IIS issuing preferred stock to a third-party investor, the Company (a) is obligated to share with the IIS third-party investor 50% of any future fees generated under the management service agreement and (b) waives its right to receive any fees until such time that the IIS third-party investor is either redeemed or exchanged into publicly traded equity shares of IIS, in either case for consideration not less than the IIS third-party investor’s original $15.0 million investment. As of March 31, 2020 , neither of these scenarios had occurred, so the Company is not entitled to any fees under the management service agreement and has not recorded any such fees. (d) Limited liability investments The Company’s investments include investments in limited liability companies in which an officer of the Company is named as a Manager or is authorized to act on behalf of the Manager under the respective operating agreement. 1347 Energy Holdings LLC: 1347 Energy Holdings LLC ("Energy") was formed on April 20, 2016 for the purpose of making investments in hydrocarbon assets as described in the operating agreement. At March 31, 2020 and December 31, 2019 , the Company owned zero of the membership interests. Fitzgerald owned zero of the membership interests at March 31, 2020 and December 31, 2019 , respectively. Energy was managed through a Board of Managers comprised of five managers, one of whom, Fitzgerald, was appointed by 1347 Capital LLC, a former wholly owned subsidiary of the Company. With respect to any matter before the Board of Managers, the act of a majority of the managers constituting a quorum constituted the act of the Board. During 2018, Energy entered into a purchase and sale agreement dated, February 12, 2018, for the sale of Energy to an unrelated third party, pursuant to which the Company’s $1.8 million collateralized loan to Energy and a $0.7 million surety deposit were repaid in full and the Company’s equity investment, previously written down to zero under the equity method of accounting, was purchased. The transaction closed in a series of installments during the fourth quarter of 2018 and the first quarter of 2019. 1347 Investors LLC: 1347 Investors was formed on April 15, 2014 for the purpose of investing in and holding securities of 1347 Capital Corp., which subsequently merged with Limbach, a publicly traded company. The Company owned zero of the membership units at March 31, 2020 and December 31, 2019 . The Company's investment in 1347 Investors prior to liquidation in the fourth quarter of 2019 was accounted for at fair value and reported as limited liability investments, at fair value in the consolidated balance sheets, with any changes in fair value to be reported in gain on change in fair value of limited liability investment, at fair value in the consolidated statements of operations. The fair value of this investment is calculated based on a model that distributes the net equity of 1347 Investors to all classes of membership interests. The model uses quoted market prices and significant market observable inputs. The most significant input to the model is the observed stock price of Limbach common stock. ICL owned 100.0% of the membership units at March 31, 2020 and December 31, 2019 and Fitzgerald has served as a member of the ICL Board of Directors since June 9, 2016. Pursuant to a Distribution and Redemption Agreement, dated as of September 30, 2019, by and among 1347 Investors and its members, the Company received distributions on November 19, 2019 of cash proceeds of $0.6 million , 594,750 shares of Limbach common stock and 400,000 warrants, exercisable at $15 and expiring July 20, 2023, on Limbach common shares. As a result of this distribution, the Company no longer owns membership units in 1347 Investors. (e) Atlas Financial Holdings, Inc. In November 2010, the Company issued promissory notes (the "Notes") to five employees (each a "Debtor" and collectively the "Debtors") for a total of $1.1 million , each Note bearing an interest rate of 3% (not compounding). The Debtors used the proceeds to purchase shares of common stock in Atlas Financial Holdings, Inc. ("Atlas"). Atlas was created via a triangular merger and spun-off from the Company in December 2010, at which time the Debtors became employees of Atlas and were no longer employees of the Company. The Notes required annual payments of interest on the anniversary date of the Notes, with the principal and any unpaid interest due in full on or before January 1, 2017, in the case of one of the Debtors, and November 1, 2017, in the case of the other four Debtors. Each Debtor was required to pledge to the Company the shares purchased utilizing the Notes proceeds, and such pledge was to be released once the note was paid in full. The current market value of the pledged shares is $0.1 million . The Notes have been amended three times since their issuance, generally to extend payments of principal while also requiring progress payments that were not part of the original Notes. No principal has been waived, and interest continues to accrue on unpaid principal. The remaining principal amount outstanding on the Notes was $0.5 million as of March 31, 2020 . During the three months ended March 31, 2020 , the Company recorded a write-down of $0.1 million for other-than-temporary impairment related to the Notes for one of the Debtors. The remaining Debtors are current with the amended terms of the Notes. The Company has concluded there are no indications the remaining Debtors were experiencing financial difficulties at the time of the amendments, and the Company expects to collect all remaining amounts due. (f) Other related party transactions On February 28, 2020, the Company entered into a Consulting Agreement (the "Consulting Agreement") with William A. Hickey, Jr. ("Hickey"), its former Chief Financial Officer, pursuant to which Hickey will provide consulting and transition support through at least April 30, 2020, subject to renewal thereafter by agreement of the parties. In accordance with the Consulting Agreement, Hickey will receive a consulting fee of $0.1 million for the months of March and April 2020 and an hourly consulting fee of $165 for time worked in subsequent months.

COMMITMENTS AND CONTINGENCIES

COMMITMENTS AND CONTINGENCIES	3 Months Ended
	Mar. 31, 2020
Commitments and Contingencies Disclosure [Abstract]
COMMITMENTS AND CONTINGENCIES	COMMITMENTS AND CONTINGENCIES (a) Legal proceedings: In April 2018, TRT LeaseCo, LLC ("TRT LeaseCo"), an indirect subsidiary of Kingsway, was named as a defendant in a lawsuit filed in the United States District Court for the Southern District of New York relating to CMC and its subsidiaries. Kingsway indirectly owns 81% of CMC. TRT LeaseCo (an indirect wholly owned subsidiary of CMC) entered into a Management Services Agreement (the "MSA") with DGI-BNSF Corp. ("DGI") (an affiliate of the entity that owns the remaining 19% of CMC) in July 2016 pursuant to which, among other things, DGI agreed to provide services to TRT LeaseCo in exchange for the fees specified in the MSA. The complaint filed by DGI alleges that DGI is owed certain fees under the MSA that have not been paid. If the case is decided against TRT LeaseCo, CMC and its subsidiaries (including TRT LeaseCo) would be unable to fulfill certain payment obligations to Kingsway under the transaction documents such that Kingsway may no longer be able to realize a material portion of the economic benefits originally anticipated to result from the CMC transaction, which could have a material adverse effect on Kingsway’s financial position, results of operations and cash flows. Kingsway disagrees with DGI’s allegations and is vigorously defending these claims; however, there can be no assurance that Kingsway will ultimately prevail. The Company’s potential exposure under these agreements is not reasonably determinable, and no liability has been recorded in the unaudited consolidated interim financial statements at March 31, 2020 . No assurances can be given, however, that the Company will not be required to perform under these agreements in a manner that would have a material adverse effect on the Company’s financial position, results of operations and cash flow. In May 2016, Aegis Security Insurance Company ("Aegis") filed a complaint for breach of contract and declaratory relief against the Company in the Eastern District of Pennsylvania alleging, among other things, that the Company breached a contractual obligation to indemnify Aegis for certain customs bond losses incurred by Aegis under the indemnity and hold harmless agreements provided by the Company to Aegis for certain customs bonds reinsured by Lincoln General Insurance Company ("Lincoln General") during the period of time that Lincoln General was a subsidiary of the Company. Lincoln General was placed into liquidation in November 2015 and Aegis subsequently invoked its rights to indemnity under the indemnity and hold harmless agreements. Effective January 20, 2020, Aegis and the Company entered into a Settlement Agreement with respect to such litigation pursuant to which the Company agreed to pay Aegis a one-time settlement amount of $0.9 million , which the Company reported in its consolidated statement of operations for the three months ended March 31, 2020 , and to reimburse Aegis for 60% of future losses that Aegis may sustain in connection with such customs bonds, up to a maximum reimbursement amount of $4.8 million . The Company’s potential exposure under these agreements was not reasonably determinable at March 31, 2020 , and no liability has been recorded in the unaudited consolidated interim financial statements at March 31, 2020 . (b) Guarantee: As further discussed in Note 5 , " Acquisition and Discontinued Operations ," as part of the transaction to sell Mendota, the Company will indemnify the buyer for loss and loss adjustment expenses with respect to open claims in excess of Mendota's carried unpaid loss and loss adjustment expenses at June 30, 2018 related to the open claims. The Company's potential exposure under these agreements was not reasonably determinable at March 31, 2020 , and no liability has been recorded in the unaudited consolidated interim financial statements at March 31, 2020 . (c) Commitments: The Company has entered into subscription agreements to commit up to $2.6 million of capital to allow for participation in limited liability investments. At March 31, 2020 , the unfunded commitment was zero .

SUBSEQUENT EVENTS

SUBSEQUENT EVENTS	3 Months Ended
	Mar. 31, 2020
Subsequent Events [Abstract]
SUBSEQUENT EVENT	SUBSEQUENT EVENTS (a) COVID-19 In March 2020, the outbreak of COVID-19 caused by a novel strain of the coronavirus was recognized as a pandemic by the World Health Organization, and the outbreak has become increasingly widespread in the United States, including in the markets in which we operate. The COVID-19 outbreak has had a notable impact on general economic conditions, including but not limited to the temporary closures of many businesses; "shelter in place" and other governmental regulations; and reduced consumer spending due to both job losses and other effects attributable to COVID-19. The near-term impacts of COVID-19 are primarily with respect to the Company’s Extended Warranty segment. As consumer spending has been impacted, including a decline in the purchase of new and used vehicles, and many businesses through which the Company distributes its products remain closed, the Company has seen cash flows being affected by a reduction in new warranty sales for vehicle service agreements. With respect to homeowner warranties, the Company has seen a reduction in new enrollments in its home warranty programs associated with the impact of COVID-19 on new home sales in the United States. There remain many unknowns and the Company continues to monitor the expected trends and related demand for its services and has and will continue to adjust its operations accordingly. The Company could experience other potential impacts as a result of COVID-19, including, but not limited to, potential impairment charges to the carrying amounts of goodwill, indefinite-lived intangibles and long-lived assets, as well as the loss in value of investments. Actual results may differ materially from the Company’s current estimates as the scope of COVID-19 evolves or if the duration of business disruptions is longer than initially anticipated. (b) Paycheck Protection Program In April 2020, certain subsidiaries of the Company received loan proceeds under the Paycheck Protection Program ("PPP"), totaling $2.9 million with a stated annual interest rate of 1.00%. The PPP, established as part of the CARES Act, provides for loans to qualifying businesses for amounts up to 2.5 times of the average monthly payroll costs (as defined for purposes of the PPP) of the qualifying business. The loans and accrued interest are forgivable as long as the borrower uses the loan proceeds for eligible purposes, including payroll, costs, rent and utilities, during the twenty-four week period following the borrower’s receipt of the loan and maintains its payroll levels and employee headcount. The amount of loan forgiveness will be reduced if the borrower reduces its employee headcount below its average employee headcount during a benchmark period or significantly reduces salaries for certain employees during the covered period. The Company intends to use the entire loan amount for qualifying expenses, but there is no guarantee that the loans will be forgiven.

RECENTLY ISSUED ACCOUNTING ST_2

RECENTLY ISSUED ACCOUNTING STANDARDS RECENTLY ISSUED ACCOUNTING STANDARDS (Policies)	3 Months Ended	12 Months Ended
	Mar. 31, 2020	Dec. 31, 2019
Accounting Policies [Abstract]
Accounting Standards	Adoption of New Accounting Standards: Effective January 1, 2020, the Company adopted ASU 2017-04, Intangibles - Goodwill and Other (Topic 350): Simplifying the Test for Goodwill Impairment ("ASU 2017-04"). ASU 2017-04 was issued to simplify the subsequent measurement of goodwill. This update changes the impairment test by requiring an entity to compare the fair value of a reporting unit with its carrying amount as opposed to comparing the carrying amount of goodwill with its implied fair value. The adoption of ASU 2017-04 did not have an impact on the Company's consolidated financial statements. Effective January 1, 2020, the Company adopted ASU 2018-17, Consolidation (Topic 810): Targeted Improvements to Related Party Guidance for Variable Interest Entities ("ASU 2018-17"). Among other things, ASU 2018-17 changes how all entities that apply the variable interest entity ("VIE") guidance evaluate decision making fees. Under ASU 2018-17, when an entity determines whether a decision-making fee is a variable interest, it considers indirect interests held through related parties under common control on a proportionate basis rather than in their entirety. The new approach is consistent with how indirect interests held by related parties under common control are evaluated when determining whether a reporting entity is the primary beneficiary of a VIE. The adoption of ASU 2018-17 did not have an impact on the Company's consolidated financial statements. Effective January 1, 2020, the Company adopted ASU 2018-13, Fair Value Measurements (Topic 820): Disclosure Framework - Changes to the Disclosure Requirements for Fair Value Measurement ("ASU 2018-13"). ASU 2018-13 modifies the disclosure requirements for assets and liabilities measured at fair value. The requirements to disclose the amount of and reasons for transfers between Level 1 and Level 2 of the fair value hierarchy, the policy for timing of transfers between levels and the valuation processes for Level 3 fair value measurements have all been removed. However, the changes in unrealized gains and losses included in other comprehensive income for recurring Level 3 fair value measurements held at the end of the reporting period must be disclosed along with the range and weighted average of significant unobservable inputs used to develop Level 3 fair value measurements (or other quantitative information if it is more reasonable). Finally, for investments measured at net asset value, the requirements have been modified so that the timing of liquidation and the date when restrictions from redemption might lapse are only disclosed if the investee has communicated the timing to the entity or announced the timing publicly. As the amendments are only disclosure related, the effect of adoption did not have a material impact on the Company's consolidated financial statements. (b) Accounting Standards Not Yet Adopted: In June 2016, the Financial Accounting Standards Board ("FASB") issued ASU 2016-13, Financial Instruments-Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments ("ASU 2016-13"). ASU 2016-13 replaces the current incurred loss model used to measure impairment losses with an expected loss model for trade, reinsurance, and other receivables as well as financial instruments measured at amortized cost. ASU 2016-13 will require a financial asset measured at amortized cost, including reinsurance balances recoverable, to be presented at the net amount expected to be collected by means of an allowance for credit losses that runs through net loss. Credit losses relating to available-for-sale debt securities will also be recorded through an allowance for credit losses. However, the amendments would limit the amount of the allowance to the amount by which fair value is below amortized cost. The measurement of credit losses on available-for-sale investments is similar under current GAAP, but the update requires the use of the allowance account through which amounts can be reversed, rather than through irreversible write-downs. On November 15, 2019, the FASB issued ASU 2019-10, which (1) provides a framework to stagger effective dates for future major accounting standards and (2) amends the effective dates for certain major new accounting standards to give implementation relief to certain types of entities. Specifically, per ASU 2019-10 the Company would adopt ASU 2016-13 beginning January 1, 2023, as the Company is considered to be a smaller reporting company. The Company is currently evaluating ASU 2016-13 to determine the potential impact that adopting this standard will have on its consolidated financial statements.	The Company adopted ASU 2016-02 on January 1, 2019 using the modified retrospective adoption method. The adoption resulted in an increase of the ROU assets of approximately $2.7 million and lease liabilities of $2.9 million . The difference of $0.2 million relates to straight-line rent accruals and lease incentive liabilities that were reclassified to ROU assets for operating leases.

ACQUISITION AND DISCONTINUED _2

ACQUISITION AND DISCONTINUED OPERATIONS (Tables)	3 Months Ended
	Mar. 31, 2020
Business Combinations [Abstract]
Schedule of Estimated Fair Values of Assets Acquired and Liabilities Assumed	The following table summarizes the estimated fair values of the assets acquired and liabilities assumed at the date of acquisition: (in thousands) March 1, 2019 Investments $ 4,405 Cash and cash equivalents 755 Restricted cash 2,650 Accrued investment income 32 Service fee receivable 513 Other receivables 12 Property and equipment, net 79 Goodwill 7,445 Intangible assets not subject to amortization - trade names 1,974 Intangible asset subject to amortization - customer relationships 3,732 Other assets 620 Total assets $ 22,217 Accrued expenses and other liabilities $ 2,018 Income taxes payable 1 Deferred service fees 10,564 Net deferred income tax liabilities 1,263 Total liabilities $ 13,846 Purchase price $ 8,371

INVESTMENTS (Tables)

INVESTMENTS (Tables)	3 Months Ended
	Mar. 31, 2020
Investments [Abstract]
Schedule of Unrealized Loss on Investments	The amortized cost, gross unrealized gains and losses, and estimated fair value of the Company's available-for-sale investments at March 31, 2020 and December 31, 2019 are summarized in the tables shown below: (in thousands) March 31, 2020 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 5,503 $ 126 $ — $ 5,629 States, municipalities and political subdivisions 600 3 — 603 Mortgage-backed 4,009 48 3 4,054 Corporate 4,953 22 14 4,961 Total fixed maturities $ 15,065 $ 199 $ 17 $ 15,247 (in thousands) December 31, 2019 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 13,246 $ 74 $ 4 $ 13,316 States, municipalities and political subdivisions 601 — 1 600 Mortgage-backed 2,951 2 14 2,939 Corporate 5,338 8 6 5,340 Total fixed maturities $ 22,136 $ 84 $ 25 $ 22,195
Investments Classified by Contractual Maturity Date	The table below summarizes the Company's fixed maturities at March 31, 2020 by contractual maturity periods. Actual results may differ as issuers may have the right to call or prepay obligations, with or without penalties, prior to the contractual maturity of these obligations. (in thousands) March 31, 2020 Amortized Cost Estimated Fair Value Due in one year or less $ 4,166 $ 4,183 Due after one year through five years 9,530 9,676 Due after five years through ten years 538 549 Due after ten years 831 839 Total $ 15,065 $ 15,247
Available-for-sale Securities, Continuous Unrealized Loss Position, Fair Value	The following tables highlight the aggregate unrealized loss position, by security type, of available-for-sale investments in unrealized loss positions as of March 31, 2020 and December 31, 2019 . The tables segregate the holdings based on the period of time the investments have been continuously held in unrealized loss positions. (in thousands) March 31, 2020 Less than 12 Months Greater than 12 Months Total Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Fixed maturities: States, municipalities and political subdivisions $ 100 $ — $ — $ — $ 100 $ — Mortgage-backed 354 3 149 — 503 3 Corporate 1,176 12 199 2 1,375 14 Total fixed maturities $ 1,630 $ 15 $ 348 $ 2 $ 1,978 $ 17 (in thousands) December 31, 2019 Less than 12 Months Greater than 12 Months Total Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Fixed maturities: U.S. government, government agencies and authorities $ 305 $ — $ 1,002 $ 4 $ 1,307 $ 4 States, municipalities and political subdivisions — — 453 1 453 1 Mortgage-backed 1,063 1 1,271 13 2,334 14 Corporate 2,495 4 526 2 3,021 6 Total fixed maturities $ 3,863 $ 5 $ 3,252 $ 20 $ 7,115 $ 25
Investment Income	Net investment income for the three months ended March 31, 2020 and March 31, 2019 is comprised as follows: (in thousands) Three months ended March 31, 2020 2019 Investment income: Interest from fixed maturities $ 102 $ 73 Dividends 45 58 Income (loss) from limited liability investments 23 (18 ) Income from limited liability investments, at fair value 234 235 Income from real estate investments 200 200 Other 127 178 Gross investment income 731 726 Investment expenses (12 ) (27 ) Net investment income $ 719 $ 699
Schedule of Realized Gain (Loss)	Gross realized gains and losses on available-for-sale investments, limited liability investments, limited liability investments, at fair value and investments in private companies for the three months ended March 31, 2020 and March 31, 2019 are comprised as follows: (in thousands) Three months ended March 31, 2020 2019 Gross realized gains $ 208 $ 315 Gross realized losses — — Net realized gains gains $ 208 $ 315
Schedule of Gain on Change in Fair Value of Equity Investments	(Loss) gain on change in fair value of equity investments for the three months ended March 31, 2020 and March 31, 2019 is comprised as follows: (in thousands) Three months ended March 31, 2020 2019 Net losses recognized on equity investments sold during the period $ — $ — Change in unrealized (losses) gains on equity investments held at end of the period (597 ) 78 (Loss) gain on change in fair value of equity investments $ (597 ) $ 78

DEFERRED ACQUISITION COSTS (Tab

DEFERRED ACQUISITION COSTS (Tables)	12 Months Ended
	Dec. 31, 2019
Deferred Policy Acquisition Costs Disclosures [Abstract]
Components of Deferred Acquisition Costs and Amortization Expense	The components of deferred acquisition costs and the related amortization expense for the three months ended March 31, 2020 and March 31, 2019 are comprised as follows: (in thousands) Three months ended March 31, 2020 2019 Beginning balance, net $ 8,604 $ 6,904 Additions 1,096 1,201 Amortization (956 ) (885 ) Balance at March 31, net $ 8,744 $ 7,220

INTANGIBLE ASSETS (Tables)

INTANGIBLE ASSETS (Tables)	3 Months Ended
	Mar. 31, 2020
Goodwill and Intangible Assets Disclosure [Abstract]
Schedule of Intangible Assets	Intangible assets at March 31, 2020 and December 31, 2019 are comprised as follows: (in thousands) March 31, 2020 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 3,628 $ 1,290 Vehicle service agreements in-force 3,680 3,680 — Customer relationships 12,646 6,044 6,602 In-place lease 1,125 234 891 Non-compete 266 130 136 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Trade names 3,264 — 3,264 Total $ 99,566 $ 13,716 $ 85,850 (in thousands) December 31, 2019 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 3,505 $ 1,413 Vehicle service agreements in-force 3,680 3,680 — Customer relationships 12,646 5,622 7,024 In-place lease 1,125 218 907 Non-compete 266 117 149 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Trade names 3,264 — 3,264 Total $ 99,566 $ 13,142 $ 86,424

PROPERTY AND EQUIPMENT (Tables)

PROPERTY AND EQUIPMENT (Tables)	3 Months Ended
	Mar. 31, 2020
Property, Plant and Equipment [Abstract]
Property and Equipment	Property and equipment at March 31, 2020 and December 31, 2019 are comprised as follows: (in thousands) March 31, 2020 Total Property and Equipment Cost Accumulated Depreciation Carrying Value Land $ 21,120 $ — $ 21,120 Site improvements 91,308 15,328 75,980 Buildings 580 54 526 Leasehold improvements 159 111 48 Furniture and equipment 1,127 1,019 108 Computer hardware 5,313 5,084 229 Total $ 119,607 $ 21,596 $ 98,011 (in thousands) December 31, 2019 Total Property and Equipment Cost Accumulated Depreciation Carrying Value Land $ 21,120 $ — $ 21,120 Site improvements 91,308 14,295 77,013 Buildings 580 50 530 Leasehold improvements 156 109 47 Furniture and equipment 1,121 1,010 111 Computer hardware 5,282 5,039 243 Total $ 119,567 $ 20,503 $ 99,064

VEHICLE SERVICE AGREEMENT LIA_2

VEHICLE SERVICE AGREEMENT LIABILITY (Tables)	12 Months Ended
	Dec. 31, 2019
Guarantees and Product Warranties [Abstract]
Schedule of Product Warranty Liability	A reconciliation of the changes in the vehicle service agreement liability, including deferred service fees related to vehicle service agreements, as of March 31, 2020 and March 31, 2019 were as follows: (in thousands) March 31, 2020 March 31, 2019 Balance at January 1, net $ 51,723 $ 43,734 Vehicle service agreement liability acquired during the year related to the purchase of Geminus — 10,792 Gross service fees for vehicle service agreements sold 4,666 6,055 Recognition of service fees on vehicle service agreements (5,701 ) (5,367 ) Liability for claims authorized on vehicle service agreements 2,380 1,887 Payments of claims authorized on vehicle service agreements (1,475 ) (970 ) Re-estimation of deferred service fees (121 ) (148 ) Balance at March 31, net $ 51,472 $ 55,983
Components of Vehicle Service Agreement Liability	The vehicle service agreement liability is presented as components of deferred services fees and accrued expenses and other liabilities in the consolidated balance sheets as follows: (in thousands) March 31, December 31, 2020 2019 Deferred service fees $ 50,946 $ 51,226 Accrued expenses and other liabilities 526 497 Balance at end of period, net $ 51,472 $ 51,723

UNPAID LOSS AND LOSS ADJUSTME_2

UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES (Tables)	12 Months Ended
	Dec. 31, 2019
Insurance [Abstract]
Schedule of Liability for Unpaid Claims and Claims Adjustment Expense	The results of this comparison and the changes in the provision for unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of March 31, 2020 and March 31, 2019 were as follows: (in thousands) March 31, 2020 March 31, 2019 Balance at beginning of period, gross $ 1,774 $ 2,073 Less reinsurance recoverable related to unpaid loss and loss adjustment expenses — — Balance at beginning of period, net 1,774 2,073 Incurred related to: Current year — — Prior years 13 107 Paid related to: Current year — — Prior years (96 ) (741 ) Balance at end of period, net 1,691 1,439 Plus reinsurance recoverable related to unpaid loss and loss adjustment expenses — — Balance at end of period, gross $ 1,691 $ 1,439

DEBT (Tables)

DEBT (Tables)	3 Months Ended	12 Months Ended
	Mar. 31, 2020	Dec. 31, 2019
Debt Disclosure [Abstract]
Schedule of Carrying Values and Estimated Fair Values of Debt Instruments		Debt consists of the following instruments at March 31, 2020 and December 31, 2019 : (in thousands) March 31, 2020 December 31, 2019 Principal Carrying Value Fair Value Principal Carrying Value Fair Value Bank loans: PWSC Loan $ — $ — $ — $ 437 $ 437 $ 435 KWH Loan 9,500 8,727 10,966 9,625 8,803 11,820 Total bank loans 9,500 8,727 10,966 10,062 9,240 12,255 Notes payable: Mortgage 168,938 177,192 182,941 169,818 178,297 182,265 Flower Note 7,226 7,226 7,890 7,337 7,337 8,071 Net Lease Note 9,000 9,000 8,785 9,000 9,000 9,396 Total notes payable 185,164 193,418 199,616 186,155 194,634 199,732 Subordinated debt 90,500 40,387 40,387 90,500 54,655 54,655 Total $ 285,164 $ 242,532 $ 250,969 $ 286,717 $ 258,529 $ 266,642
Schedule of Subordinated Debt	Subordinated debt mentioned above consists of the following trust preferred debt instruments: Issuer Principal (in thousands) Issue date Interest Redemption date Kingsway CT Statutory Trust I $ 15,000 12/4/2002 annual interest rate equal to LIBOR, plus 4.00% payable quarterly 12/4/2032 Kingsway CT Statutory Trust II $ 17,500 5/15/2003 annual interest rate equal to LIBOR, plus 4.10% payable quarterly 5/15/2033 Kingsway CT Statutory Trust III $ 20,000 10/29/2003 annual interest rate equal to LIBOR, plus 3.95% payable quarterly 10/29/2033 Kingsway DE Statutory Trust III $ 15,000 5/22/2003 annual interest rate equal to LIBOR, plus 4.20% payable quarterly 5/22/2033 Kingsway DE Statutory Trust IV $ 10,000 9/30/2003 annual interest rate equal to LIBOR, plus 3.85% payable quarterly 9/30/2033 Kingsway DE Statutory Trust VI $ 13,000 12/16/2003 annual interest rate equal to LIBOR, plus 4.00% payable quarterly 1/8/2034

LEASES (Tables)

LEASES (Tables)	3 Months Ended
	Mar. 31, 2020
Leases [Abstract]
Annual Maturities of Lease Liabilities	The annual maturities of lease liabilities as of March 31, 2020 were as follows: (in thousands) Lease Commitments 2020 $ 549 2021 802 2022 824 2023 624 2024 550 2025 and thereafter 546 Total undiscounted lease payments 3,895 Imputed interest 503 Total lease liabilities $ 3,392
Schedule of Net Book Value of Operating Lease Property	The following table provides the net book value of operating lease property included in property and equipment in the consolidated balance sheets at March 31, 2020 and December 31, 2019 : (in thousands) March 31, 2020 December 31, 2019 Land $ 21,120 $21,120 Site improvements 91,308 91,308 Buildings 580 580 Gross property and equipment leased 113,008 113,008 Accumulation depreciation (15,382 ) (14,345 ) Net property and equipment leased $ 97,626 $ 98,663
Future Undiscounted Cash Flows to be Received	As of March 31, 2020 , future undiscounted cash flows to be received in each of the next five years and thereafter, on non-cancelable operating leases are as follows: (in thousands) 2020 $ 8,913 2021 12,099 2022 12,371 2023 12,649 2024 12,934 Thereafter 136,963

REVENUE FROM CONTRACTS WITH C_2

REVENUE FROM CONTRACTS WITH CUSTOMERS (Tables)	3 Months Ended
	Mar. 31, 2020
Revenue from Contract with Customer [Abstract]
Disaggregation of Revenue	The following table disaggregates revenues from contracts with customers by revenue type: (in thousands) Three months ended March 31, 2020 2019 Vehicle service agreement fees - IWS and Geminus $ 7,707 $ 5,366 GAP commissions - IWS and Geminus 269 265 Maintenance support service fees - Trinity 554 1,968 Warranty product commissions - Trinity 861 582 Homebuilder warranty service fees - PWSC 1,437 1,423 Homebuilder warranty commissions - PWSC 358 211 Service fee and commission income $ 11,186 $ 9,815

Income Taxes (table) (Tables)

Income Taxes (table) (Tables)	3 Months Ended
	Mar. 31, 2020
Income Tax Disclosure [Abstract]
Income Tax (Benefit) Expense	The following table summarizes the differences: (in thousands) Three months ended March 31, 2020 2019 Income tax (benefit) expense at United States statutory income tax rate $ (47 ) $ 520 Valuation allowance 241 (1,331 ) Non-deductible compensation (43 ) 66 9 Investment income (128 ) (23 ) State income tax 38 26 Change in unrecognized tax benefits (1) 68 70 Indefinite life intangibles 54 33 Other (13 ) (17 ) Income tax expense (benefit) $ 170 $ (713 ) (1) Includes interest and penalty expense related to unrecognized tax benefits.

(LOSS) EARNINGS PER SHARE (Tabl

(LOSS) EARNINGS PER SHARE (Tables)	3 Months Ended
	Mar. 31, 2020
Earnings Per Share [Abstract]
Schedule of Earnings Per Share	The following table sets forth the reconciliation of numerators and denominators for the basic and diluted (loss) earnings per share computation for the three months ended March 31, 2020 and March 31, 2019 : (in thousands, except per share data) Three months ended March 31, 2020 2019 Numerator: Net (loss) income $ (393 ) $ 3,189 Less: net income attributable to noncontrolling interests (721 ) (211 ) Less: dividends on preferred stock (377 ) (246 ) Net (loss) income attributable to common shareholders $ (1,491 ) $ 2,732 Denominator: Weighted average basic shares Weighted average common shares outstanding 22,069 21,841 Weighted average diluted shares Weighted average common shares outstanding 22,069 21,841 Effect of potentially dilutive securities Stock options — — Unvested restricted stock awards — — Warrants — — Convertible preferred stock — — Total weighted average diluted shares 22,069 21,841 Basic (loss) earnings per share $ (0.07 ) $ 0.13 Diluted (loss) earnings per share $ (0.07 ) $ 0.13
Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share	The following weighted-average potentially dilutive securities are not included in the diluted (loss) earnings per share calculations above because they would have had an antidilutive effect on the (loss) earnings per share from continuing operations: Three months ended March 31, 2020 2019 Stock options 40,000 40,000 Unvested restricted stock awards 500,000 976,950 Warrants 4,423,765 4,673,765 Convertible preferred stock 1,142,975 1,392,975 Total 6,106,740 7,083,690

Stock-Based Compensation (Table

Stock-Based Compensation (Tables)	3 Months Ended
	Mar. 31, 2020
Share-based Payment Arrangement [Abstract]
Schedule of Stock Option Activity	The following table summarizes the stock option activity during the three months ended March 31, 2020 : Number of Options Outstanding Weighted-Average Exercise Price Weighted-Average Remaining Contractual Term (in Years) Aggregate Intrinsic Value (in Thousands) Outstanding at December 31, 2019 40,000 $ 4.67 0.3 $ — Granted — — Expired — — Outstanding at March 31, 2020 40,000 $ 4.67 0.1 $ — Exercisable at March 31, 2020 40,000 $ 4.67 0.1 $ —
Schedule of Unvested Restricted Stock Award Activity	The following table summarizes the activity related to unvested 2014 Restricted Stock Awards, 2020 Restricted Stock Award and 2018 Restricted Stock Award (collectively "Restricted Stock Awards") for the three months ended March 31, 2020 : Number of Restricted Stock Awards Weighted-Average Grant Date Fair Value (per Share) Unvested at December 31, 2019 729,500 $ 5.23 Vested (94,110 ) 4.14 Cancelled for Tax Withholding (41,677 ) 4.14 Forfeited (93,713 ) 4.14 Unvested at March 31, 2020 500,000 $ 5.73

Accumulated Other Comprehensi_2

Accumulated Other Comprehensive Income (Tables)	3 Months Ended
	Mar. 31, 2020
Equity [Abstract]
Schedule of Accumulated Other Comprehensive Income (Loss)	, the unaudited consolidated statements of comprehensive income present the components of other comprehensive income (loss), net of tax, only for the three months ended March 31, 2020 and March 31, 2019 and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries. (in thousands) Three months ended March 31, 2020 Unrealized Gains on Available-for-Sale Investments Foreign Currency Translation Adjustments Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk Total Accumulated Other Comprehensive Income Balance at January 1, 2020 $ 59 $ (3,286 ) $ 38,574 $ 35,347 Other comprehensive income arising during the period 47 — 11,623 11,670 Amounts reclassified from accumulated other comprehensive income 61 — — 61 Net current-period other comprehensive income 108 — 11,623 11,731 Balance at March 31, 2020 $ 167 $ (3,286 ) $ 50,197 $ 47,078 (in thousands) Three months ended March 31, 2019 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk Equity in Other Comprehensive Loss of Limited Liability Investment Total Accumulated Other Comprehensive Income Balance at January 1, 2019 $ (160 ) $ (3,286 ) $ 44,259 $ (45 ) $ 40,768 Other comprehensive income (loss) arising during the period 105 — (945 ) — (840 ) Amounts reclassified from accumulated other comprehensive income (6 ) — — — (6 ) Net current-period other comprehensive income income 99 — (945 ) — (846 ) Balance at March 31, 2019 $ (61 ) $ (3,286 ) $ 43,314 $ (45 ) $ 39,922
Reclassification out of Accumulated Other Comprehensive Income	Components of accumulated other comprehensive income were reclassified to the following lines of the unaudited consolidated statements of operations for the three months ended March 31, 2020 and March 31, 2019 : (in thousands) Three months ended March 31, 2020 2019 Reclassification of accumulated other comprehensive income from unrealized gains (losses) on available-for-sale investments to: Net realized gains $ (61 ) $ 6 Other-than-temporary impairment loss — — (Loss) income before income tax expense (benefit) (61 ) 6 Income tax expense (benefit) — — Net (loss) income $ (61 ) $ 6

Segmented Information (Tables)

Segmented Information (Tables)	3 Months Ended
	Mar. 31, 2020
Segment Reporting [Abstract]
Reconciliation of Revenue from Segments to Consolidated	Revenues by reportable segment reconciled to consolidated revenues for the three months ended March 31, 2020 and March 31, 2019 were: (in thousands) Three months ended March 31, 2020 2019 Revenues: Extended Warranty: Service fee and commission income $ 11,186 $ 9,815 Other income 74 75 Total Extended Warranty 11,260 9,890 Leased Real Estate: Rental income 3,341 3,341 Other income 68 70 Total Leased Real Estate 3,409 3,411 Total revenues $ 14,669 $ 13,301
Reconciliation of Operating Profit (Loss) from Segments to Consolidated	Total segment operating income reconciled to the consolidated net (loss) income for the three months ended March 31, 2020 and March 31, 2019 were: (in thousands) Three months ended March 31, 2020 2019 Segment operating income: Extended Warranty $ 850 $ 567 Leased Real Estate 597 452 Total segment operating income 1,447 1,019 Net investment income 719 699 Net realized gains 208 315 (Loss) gain on change in fair value of equity investments (597 ) 78 Gain on change in fair value of limited liability investments, at fair value 1,899 4,265 Net change in unrealized (loss) gain on private company investments (670 ) 19 Other-than-temporary impairment loss (117 ) (75 ) Interest expense not allocated to segments (2,153 ) (2,102 ) Other income and expenses not allocated to segments, net (3,030 ) (1,764 ) Amortization of intangible assets (574 ) (521 ) Gain on change in fair value of debt 2,645 576 Equity in net loss of investee — (33 ) (Loss) income before income tax expense (benefit) (223 ) 2,476 Income tax expense (benefit) 170 (713 ) Net (loss) income $ (393 ) $ 3,189

Fair Value of Financial Instr_2

Fair Value of Financial Instruments (Tables)	3 Months Ended
	Mar. 31, 2020
Fair Value Disclosures [Abstract]
Schedule of Financial Assets and Liabilities Measured at Fair Value on Recurring Basis	Certain investments in limited liability companies that are measured at fair value using the net asset value practical expedient are not required to be classified using the fair value hierarchy, but are presented in the following tables to permit reconciliation of the fair value hierarchy to the amounts presented in the consolidated balance sheets: (in thousands) March 31, 2020 Fair Value Measurements at the End of the Reporting Period Using Total Quoted Prices in Active Markets for Identical Assets (Level 1) Significant Other Observable Inputs (Level 2) Significant Unobservable Inputs (Level 3) Measured at Net Asset Value Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 5,629 $ — $ 5,629 $ — $ — States, municipalities and political subdivisions 603 — 603 — — Mortgage-backed 4,054 — 4,054 — — Corporate 4,961 — 4,961 — — Total fixed maturities 15,247 — 15,247 — — Equity investments: Common stock 1,817 1,817 — — — Warrants 8 3 5 — — Total equity investments 1,825 1,820 5 — — Limited liability investments, at fair value 30,986 — — 4,413 26,573 Real estate investments 10,662 — — 10,662 — Other investments 841 — 841 — — Short-term investments 156 — 156 — — Total assets $ 59,717 $ 1,820 $ 16,249 $ 15,075 $ 26,573 Liabilities: Subordinated debt $ 40,387 $ — $ 40,387 $ — $ — Warrant liability 216 — — 216 — Total liabilities $ 40,603 $ — $ 40,387 $ 216 $ — (in thousands) December 31, 2019 Fair Value Measurements at the End of the Reporting Period Using Total Quoted Prices in Active Markets for Identical Assets (Level 1) Significant Other Observable Inputs (Level 2) Significant Unobservable Inputs (Level 3) Measured at Net Asset Value Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 13,316 $ — $ 13,316 $ — $ — States municipalities and political subdivisions 600 — 600 — — Mortgage-backed 2,939 — 2,939 — — Corporate 5,340 — 5,340 — — Total fixed maturities 22,195 — 22,195 — — Equity investments: Common stock 2,406 2,406 — — — Warrants 15 5 10 — — Total equity investments 2,421 2,411 10 — — Limited liability investments, at fair value 29,078 — — 4,392 24,686 Real estate investments 10,662 — — 10,662 — Other investments 1,009 — 1,009 — — Short-term investments 155 — 155 — — Total assets $ 65,520 $ 2,411 $ 23,369 $ 15,054 $ 24,686 Liabilities: Subordinated debt $ 54,655 $ — $ 54,655 $ — $ — Warranty liability 249 — — 249 — Total liabilities $ 54,904 $ — $ 54,655 $ 249 $ —
Schedule of Reconciliation of Fair Value of Recurring Level 3 Measurements	The following table provides a reconciliation of the fair value of recurring Level 3 fair value measurements for the three months ended March 31, 2020 and March 31, 2019 : (in thousands) Three months ended March 31, 2020 2019 Assets: Limited liability investments, at fair value: Beginning balance $ 4,392 $ 4,124 Purchases — 75 Distributions received (77 ) (324 ) Realized gains included in net (loss) income 86 69 Change in fair value of limited liability investments, at fair value included in net (loss) income 12 116 Ending balance $ 4,413 $ 4,060 Unrealized gains on limited liability investments, at fair value held at end of period: Included in net (loss) income $ 12 $ 116 Included in other comprehensive income (loss) $ — $ — Real estate investments: Beginning balance $ 10,662 $ 10,662 Change in fair value of real estate investments included in net (loss) income — — Ending balance $ 10,662 $ 10,662 Unrealized gains recognized on real estate investments held at end of period: Included in net (loss) income — — Included in other comprehensive income (loss) — — Ending balance - assets $ 15,075 $ 14,722 Liabilities: Warrant liability: Beginning balance $ 249 $ — Issuance of warrants — 361 Change in fair value of warrant liability included in net (loss) income (33 ) (44 ) Ending balance - liabilities $ 216 $ 317 Unrealized gains recognized on warrant liability held at end of period: Included in net (loss) income $ (33 ) $ (44 ) Included in other comprehensive income (loss) $ — $ —
Schedule of Fair Value Valuation Techniques Used to Measure Investments	The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's investments that are categorized as Level 3 at March 31, 2020 : Categories Fair Value Valuation Techniques Unobservable Inputs Input Value(s) Limited liability investments, at fair value $ 4,413 Market approach Valuation multiples 3.1x-7.0x Real estate investments $ 10,662 Market and income approach Cap rates 7.5 % Warrant liability $ 216 Market approach Valuation multiple 6.0x The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's investments that are categorized as Level 3 at December 31, 2019 : Categories Fair Value Valuation Techniques Unobservable Inputs Input Value(s) Limited liability investments, at fair value $ 4,392 Market approach Valuation multiples 3.1x-7.0x Real estate investments $ 10,662 Market and income approach Cap rates 7.5 % Warrant liability $ 249 Market approach Valuation multiple 6.0x
Schedule of Investments at Fair Value Using Net Asset Value Per Share as Practical Expedient	The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at March 31, 2020 : Category Fair Value (in thousands) Unfunded Commitments Redemption Frequency Redemption Notice Period Limited liability investments, at fair value $ 26,573 n/a n/a n/a The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at December 31, 2019 : Category Fair Value (in thousands) Unfunded Commitments Redemption Frequency Redemption Notice Period Limited liability investments, at fair value $ 24,686 n/a n/a n/a

SUMMARY OF SIGNIFICANT ACCOUN_2

SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES (Details) $ in Thousands	Mar. 31, 2021USD ($)	Mar. 31, 2020USD ($)subsidiary_trustshares	Dec. 16, 2003subsidiary_trust	Apr. 01, 2021USD ($)	Jun. 30, 2020shares	Dec. 31, 2019USD ($)shares
Temporary Equity [Line Items]
Interest payment deferral period		5 years
Number of subsidiary trusts | subsidiary_trust		6	6
Cash		$ 4,000				$ 2,300
Cash and cash equivalents		$ 14,036				$ 13,478
Preferred stock issued (in shares) | shares		182,876				222,876
Preferred stock outstanding (in shares) | shares		182,876				222,876
Redemption amount		$ 6,400				$ 7,696
Interest expense on trust preferred securities		$ 10,400
Subsequent Event
Temporary Equity [Line Items]
Redemption amount				$ 6,700
Interest expense on trust preferred securities	$ 14,900
Forecast
Temporary Equity [Line Items]
Preferred stock issued (in shares) | shares					182,876

RECENTLY ISSUED ACCOUNTING ST_3

RECENTLY ISSUED ACCOUNTING STANDARDS RECENTLY ISSUED ACCOUNTING STANDARDS (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019	Jan. 01, 2019
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Right-of-use asset	$ 3,178	$ 3,327
Lease liability	3,392	3,529
Other Liabilities	$ 27,266	$ 26,993
ASU 2016-02
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Right-of-use asset			$ 2,700
Lease liability			2,900
Other Liabilities			$ 200

ACQUISITION AND DISCONTINUED _3

ACQUISITION AND DISCONTINUED OPERATIONS - Narrative (Details) - USD ($) $ in Thousands	Mar. 01, 2019	Mar. 31, 2020	Dec. 31, 2019	Mar. 31, 2019
Business Acquisition [Line Items]
Goodwill		$ 82,104	$ 82,104
Geminus
Business Acquisition [Line Items]
Percentage of acquisition	100.00%
Purchase price	$ 8,371
Cash payments to acquire businesses	7,700
Liabilities incurred	700
Goodwill	7,445
Intangible assets acquired	$ 5,700			$ 5,700
Revenue of acquiree since acquisition date		900
Earnings or loss of acquiree since acquisition date		$ 600

ACQUISITION AND DISCONTINUED _4

ACQUISITION AND DISCONTINUED OPERATIONS - Schedule of Estimated Fair Values of Assets Acquired and Liabilities Assumed (Details) - USD ($) $ in Thousands	Mar. 01, 2019	Mar. 31, 2020	Dec. 31, 2019	Mar. 31, 2019
Business Acquisition [Line Items]
Goodwill		$ 82,104	$ 82,104
Accrued expenses and other liabilities		$ 27,266	$ 26,993
Geminus
Business Acquisition [Line Items]
Investments	$ 4,405
Cash and cash equivalents	755
Restricted cash	2,650
Accrued investment income	32
Service fee receivable	513
Other receivables	12
Property and equipment, net	79
Goodwill	7,445
Other assets	620
Total assets	22,217
Accrued expenses and other liabilities	2,018
Income taxes payable	1
Accrued expenses and other liabilities	10,564
Net deferred income tax liabilities	1,263
Total liabilities	13,846
Purchase price	8,371
Geminus | Customer relationships
Business Acquisition [Line Items]
Intangible asset subject to amortization - customer relationships	3,732			$ 3,700
Geminus | Trade names
Business Acquisition [Line Items]
Intangible assets not subject to amortization - trade names	$ 1,974			$ 2,000

ACQUISITION AND DISCONTINUED _5

ACQUISITION AND DISCONTINUED OPERATIONS - Discontinued Operations (Details) - Mendota $ in Millions	3 Months Ended		12 Months Ended
	Mar. 31, 2020USD ($)	Mar. 31, 2019USD ($)claim	Dec. 31, 2019USD ($)	Oct. 18, 2018USD ($)
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Gain (loss) on disposal of discontinued operations, net of taxes			$ 1.5
Final aggregate purchase price				$ 28.6
Escrow deposit	$ 5			$ 5
Maximum obligation	2.5
Number of claims settled | claim		1
Indemnification claim settled		$ 0.5
Estimated net loss	1.6		$ 1.6
Released escrow deposit	$ 3.4

INVESTMENTS - Amortized Cost, G

INVESTMENTS - Amortized Cost, Gross Unrealized Gains and Losses, and Estimated Fair Value (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 15,065	$ 22,136
Gross Unrealized Gains	199	84
Gross Unrealized Losses	17	25
Estimated Fair Value	15,247	22,195
U.S. government, government agencies and authorities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	5,503	13,246
Gross Unrealized Gains	126	74
Gross Unrealized Losses	0	4
Estimated Fair Value	5,629	13,316
States, municipalities and political subdivisions
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	600	601
Gross Unrealized Gains	3	0
Gross Unrealized Losses	0	1
Estimated Fair Value	603	600
Mortgage-backed
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	4,009	2,951
Gross Unrealized Gains	48	2
Gross Unrealized Losses	3	14
Estimated Fair Value	4,054	2,939
Corporate
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	4,953	5,338
Gross Unrealized Gains	22	8
Gross Unrealized Losses	14	6
Estimated Fair Value	$ 4,961	$ 5,340

INVESTMENTS - Fixed Maturities

INVESTMENTS - Fixed Maturities by Contractual Maturity Periods (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019
Amortized Cost
Due in one year or less	$ 4,166
Due after one year through five years	9,530
Due after five years through ten years	538
Due after ten years	831
Amortized Cost	15,065	$ 22,136
Estimated Fair Value
Due in one year or less	4,183
Due after one year through five years	9,676
Due after five years through ten years	549
Due after ten years	839
Estimated Fair Value, Fixed Maturities	$ 15,247	$ 22,195

INVESTMENTS - Unrealized Loss P

INVESTMENTS - Unrealized Loss Position (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019
Fixed Maturities
Estimated Fair Value
Less than 12 Months	$ 1,630	$ 3,863
Greater than 12 Months	348	3,252
Total	1,978	7,115
Unrealized Loss
Less than 12 Months	15	5
Greater than 12 Months	2	20
Total	17	25
U.S. government, government agencies and authorities
Estimated Fair Value
Less than 12 Months		305
Greater than 12 Months		1,002
Total		1,307
Unrealized Loss
Less than 12 Months		0
Greater than 12 Months		4
Total		4
States, municipalities and political subdivisions
Estimated Fair Value
Less than 12 Months	100	0
Greater than 12 Months	0	453
Total	100	453
Unrealized Loss
Less than 12 Months	0	0
Greater than 12 Months	0	1
Total	0	1
Mortgage-backed
Estimated Fair Value
Less than 12 Months	354	1,063
Greater than 12 Months	149	1,271
Total	503	2,334
Unrealized Loss
Less than 12 Months	3	1
Greater than 12 Months	0	13
Total	3	14
Corporate
Estimated Fair Value
Less than 12 Months	1,176	2,495
Greater than 12 Months	199	526
Total	1,375	3,021
Unrealized Loss
Less than 12 Months	12	4
Greater than 12 Months	2	2
Total	$ 14	$ 6

INVESTMENTS - Additional Inform

INVESTMENTS - Additional Information (Details)	3 Months Ended
	Mar. 31, 2020USD ($)security	Mar. 31, 2019USD ($)	Dec. 31, 2019USD ($)security
Debt Securities, Available-for-sale [Line Items]
Securities in unrealized loss positions | security	14		48
Other-than-temporary impairment loss	$ 117,000	$ 75,000
Limited liability investments	3,776,000		$ 3,841,000
Gain on change in fair value of limited liability investments, at fair value	1,899,000	4,265,000
Limited liability investments, at fair value	30,986,000		29,078,000
Investment impairment losses	0
Unfunded commitments	0
Investments in private companies, at adjusted cost	1,364,000		2,035,000
Other-than-temporary impairment loss	117,000	75,000
Net change in unrealized (loss) gain on private company investments	(670,000)	19,000
Real estate investments	10,662,000		10,662,000
Other investments	841,000		1,009,000
Restricted cash	17,891,000		12,183,000
Variable Interest Entity, Primary Beneficiary
Debt Securities, Available-for-sale [Line Items]
Unfunded commitments			0
State and Provincial Regulatory Authorities
Debt Securities, Available-for-sale [Line Items]
Restricted cash equivalents	200,000
Restricted cash	2,000,000		1,900,000
Mendota
Debt Securities, Available-for-sale [Line Items]
Escrow deposit	0		1,100,000
IWS
Debt Securities, Available-for-sale [Line Items]
Restricted cash	15,300,000		$ 8,600,000
Third Parties
Debt Securities, Available-for-sale [Line Items]
Restricted cash	600,000
Private Company Investments
Debt Securities, Available-for-sale [Line Items]
Other-than-temporary impairment loss	700,000	0
Net change in unrealized (loss) gain on private company investments	0	100,000
Other Investments
Debt Securities, Available-for-sale [Line Items]
Other-than-temporary impairment loss		0
Limited LIability Investments [Member]
Debt Securities, Available-for-sale [Line Items]
Other-than-temporary impairment loss		$ (100,000)
Investment impairment losses	0
1347 Investors LLC
Debt Securities, Available-for-sale [Line Items]
Gain on change in fair value of limited liability investments, at fair value	$ (600,000)

INVESTMENTS - Net Investment In

INVESTMENTS - Net Investment Income (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Investment income:
Interest from fixed maturities	$ 102	$ 73
Dividends	45	58
Income (loss) from limited liability investments	23	(18)
Income from limited liability investments, at fair value	234	235
Income from real estate investments	200	200
Other	127	178
Gross investment income	731	726
Investment expenses	(12)	(27)
Net investment income	$ 719	$ 699

INVESTMENTS - Gross Realized Ga

INVESTMENTS - Gross Realized Gains and Losses on Fixed Maturities (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Investments [Abstract]
Gross realized gains	$ 208	$ 315
Gross realized losses	0	0
Net realized gains gains	$ 208	$ 315

INVESTMENTS - Gain in change fa

INVESTMENTS - Gain in change fair value of equity investments (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Investments [Abstract]
Net losses recognized on equity investments sold during the period	$ 0	$ 0
Change in unrealized (losses) gains on equity investments held at end of the period	(597)	78
(Loss) gain on change in fair value of equity investments	$ (597)	$ 78

INVESTMENT IN INVESTEE (Details

INVESTMENT IN INVESTEE (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Schedule of Equity Method Investments [Line Items]
Equity in net loss of investees	$ 0	$ (33)
Itasca Capital Ltd
Schedule of Equity Method Investments [Line Items]
Equity in net loss of investees		$ 100

DEFERRED ACQUISITION COSTS (Det

DEFERRED ACQUISITION COSTS (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019	Dec. 31, 2019	Dec. 31, 2018
Deferred Acquisition Costs
Beginning balance, net	$ 8,744	$ 7,220	$ 8,604	$ 6,904
Additions	1,096	1,201
Amortization	(956)	(885)
Balance at March 31, net	$ 8,744	$ 7,220

INTANGIBLE ASSETS Schedule of I

INTANGIBLE ASSETS Schedule of Intangible Assets (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019
Gross Carrying Value
Total	$ 99,566	$ 99,566
Accumulated Amortization
Intangible assets accumulated amortization	13,716	13,142
Net Carrying Value
Total	85,850	86,424
Tenant relationship
Gross Carrying Value
Intangible assets not subject to amortization	73,667	73,667
Net Carrying Value
Intangible assets not subject to amortization	73,667	73,667
Trade names
Gross Carrying Value
Intangible assets not subject to amortization	3,264	3,264
Net Carrying Value
Intangible assets not subject to amortization	3,264	3,264
Database
Gross Carrying Value
Intangible assets subject to amortization	4,918	4,918
Accumulated Amortization
Intangible assets accumulated amortization	3,628	3,505
Net Carrying Value
Intangible assets subject to amortization	1,290	1,413
Vehicle service agreements in-force
Gross Carrying Value
Intangible assets subject to amortization	3,680	3,680
Accumulated Amortization
Intangible assets accumulated amortization	3,680	3,680
Net Carrying Value
Intangible assets subject to amortization	0	0
Customer relationships
Gross Carrying Value
Intangible assets subject to amortization	12,646	12,646
Accumulated Amortization
Intangible assets accumulated amortization	6,044	5,622
Net Carrying Value
Intangible assets subject to amortization	6,602	7,024
In-place lease
Gross Carrying Value
Intangible assets subject to amortization	1,125	1,125
Accumulated Amortization
Intangible assets accumulated amortization	234	218
Net Carrying Value
Intangible assets subject to amortization	891	907
Non-compete
Gross Carrying Value
Intangible assets subject to amortization	266	266
Accumulated Amortization
Intangible assets accumulated amortization	130	117
Net Carrying Value
Intangible assets subject to amortization	$ 136	$ 149

INTANGIBLE ASSETS (Details)

INTANGIBLE ASSETS (Details) - USD ($)	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019	Mar. 01, 2019
Finite-Lived Intangible Assets [Line Items]
Amortization of intangible assets	$ 574,000	$ 521,000
Impairment charges	$ 0	$ 0
Minimum
Finite-Lived Intangible Assets [Line Items]
Intangible asset useful life	5 years
Maximum
Finite-Lived Intangible Assets [Line Items]
Intangible asset useful life	18 years
Customer relationships
Finite-Lived Intangible Assets [Line Items]
Intangible asset useful life		10 years
Geminus
Finite-Lived Intangible Assets [Line Items]
Intangible assets acquired		$ 5,700,000	$ 5,700,000
Geminus | Trade names
Finite-Lived Intangible Assets [Line Items]
Intangible asset acquired		2,000,000	1,974,000
Geminus | Customer relationships
Finite-Lived Intangible Assets [Line Items]
Recognized identifiable assets acquired and liabilities assumed		$ 3,700,000	$ 3,732,000

PROPERTY AND EQUIPMENT - Fixed

PROPERTY AND EQUIPMENT - Fixed Assets Roll forward (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019
Total Property and Equipment
Cost	$ 119,607	$ 119,567
Accumulated Depreciation	21,596	20,503
Carrying Value	98,011	99,064
Land
Total Property and Equipment
Cost	21,120	21,120
Accumulated Depreciation	0	0
Carrying Value	21,120	21,120
Site improvements
Total Property and Equipment
Cost	91,308	91,308
Accumulated Depreciation	15,328	14,295
Carrying Value	75,980	77,013
Buildings
Total Property and Equipment
Cost	580	580
Accumulated Depreciation	54	50
Carrying Value	526	530
Leasehold improvements
Total Property and Equipment
Cost	159	156
Accumulated Depreciation	111	109
Carrying Value	48	47
Furniture and equipment
Total Property and Equipment
Cost	1,127	1,121
Accumulated Depreciation	1,019	1,010
Carrying Value	108	111
Computer hardware
Total Property and Equipment
Cost	5,313	5,282
Accumulated Depreciation	5,084	5,039
Carrying Value	$ 229	$ 243

VEHICLE SERVICE AGREEMENT LIA_3

VEHICLE SERVICE AGREEMENT LIABILITY - Narrative (Details)	Mar. 31, 2020
Minimum
Product Warranty Liability [Line Items]
Vehicle service agreement fee, percentage of refund on original amount	9.00%
Maximum
Product Warranty Liability [Line Items]
Vehicle service agreement fee, percentage of refund on original amount	13.00%

VEHICLE SERVICE AGREEMENT LIA_4

VEHICLE SERVICE AGREEMENT LIABILITY - Reconciliation of the changes in the vehicle service agreement (Details) - USD ($) $ in Thousands	3 Months Ended		12 Months Ended
	Mar. 31, 2020	Mar. 31, 2019	Dec. 31, 2019
Movement in Standard Product Warranty Accrual [Roll Forward]
Recognition of service fees on vehicle service agreements			$ (5,500)
Vehicle service agreement fees
Movement in Standard Product Warranty Accrual [Roll Forward]
Balance at January 1, net	$ 51,723	$ 43,734	43,734
Vehicle service agreement liability acquired during the year related to the purchase of Geminus	0	10,792
Gross service fees for vehicle service agreements sold	4,666	6,055
Recognition of service fees on vehicle service agreements	(5,701)	(5,367)
Liability for claims authorized on vehicle service agreements	2,380	1,887
Payments of claims authorized on vehicle service agreements	(1,475)	(970)
Re-estimation of deferred service fees	(121)	(148)
Balance at March 31, net	$ 51,472	$ 55,983	$ 51,723

VEHICLE SERVICE AGREEMENT LIA_5

VEHICLE SERVICE AGREEMENT LIABILITY - Components of deferred services fees and accrued expenses (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019	Mar. 31, 2019	Dec. 31, 2018
Product Warranty Liability [Line Items]
Deferred service fees	$ 56,219	$ 56,252
Accrued expenses and other liabilities	27,266	26,993
Vehicle service agreement fees
Product Warranty Liability [Line Items]
Deferred service fees	50,946	51,226
Accrued expenses and other liabilities	526	497
Balance at end of period, net	$ 51,472	$ 51,723	$ 55,983	$ 43,734

UNPAID LOSS AND LOSS ADJUSTME_3

UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES - Property and Casualty (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019	Dec. 31, 2019	Dec. 31, 2018
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Balance at beginning of period, gross	$ 1,774
Paid related to:
Balance at end of period, gross	1,691	$ 1,439
Property, Liability and Casualty Insurance Product Line
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Balance at beginning of period, gross	1,774	2,073
Less reinsurance recoverable related to unpaid loss and loss adjustment expenses	0	0
Balance at beginning of period, net	1,691	1,439
Incurred related to:
Current year	0	0
Prior Year Claims and Claims Adjustment Expense	13
Paid related to:
Current year	0	0
Prior years	96	741
Balance at end of period, net	1,691	1,439	$ 1,774	$ 2,073
Plus reinsurance recoverable related to unpaid loss and loss adjustment expenses	0	0	$ 0	$ 0
Unpaid Loss And Loss Adjustment Expense	$ 100	$ 107

DEBT - Carrying Value of Debt I

DEBT - Carrying Value of Debt Instruments (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019	Jul. 31, 2016
Debt Instrument [Line Items]
Principal	$ 285,164	$ 286,717
Carrying Value	242,532	258,529
Fair Value	250,969	266,642
Bank loans
Debt Instrument [Line Items]
Principal	9,500	10,062
Carrying Value	8,727	9,240
Fair Value	10,966	12,255
Bank loans | PWSC Loan
Debt Instrument [Line Items]
Principal	0	437
Carrying Value	0	437
Fair Value	0	435
Bank loans | KWH Loan
Debt Instrument [Line Items]
Principal	9,500	9,625
Carrying Value	8,727	8,803
Fair Value	10,966	11,820
Notes payable
Debt Instrument [Line Items]
Principal	185,164	186,155
Carrying Value	193,418	194,634
Fair Value	199,616	199,732
Notes payable | Flower Note
Debt Instrument [Line Items]
Principal	7,226	7,337
Carrying Value	7,226	7,337
Fair Value	7,890	8,071
Notes payable | Net Lease Note
Debt Instrument [Line Items]
Principal	9,000	9,000
Carrying Value	9,000	9,000
Fair Value	8,785	9,396
Mortgage
Debt Instrument [Line Items]
Principal	168,938	169,818
Carrying Value	177,192	178,297
Fair Value	182,941	182,265	$ 191,700
Subordinated debt
Debt Instrument [Line Items]
Principal	90,500	90,500
Carrying Value	40,387	54,655
Fair Value	$ 40,387	$ 54,655

DEBT - Additional Details (Deta

DEBT - Additional Details (Details)		Mar. 01, 2019USD ($)	Mar. 31, 2020USD ($)subsidiary_trust	Mar. 31, 2019USD ($)	Dec. 16, 2003USD ($)subsidiary_trust	Dec. 31, 2019USD ($)	Oct. 12, 2017USD ($)	Jul. 31, 2016USD ($)	Oct. 15, 2015USD ($)	Jan. 05, 2015USD ($)
Debt Instrument [Line Items]
Number of subsidiary trusts | subsidiary_trust			6		6
Membership interest		1.25%
Long-term debt, fair value			$ 250,969,000			$ 266,642,000
Carrying value			242,532,000			258,529,000
Gain (loss) included in earnings			(14,300,000)
Gain on change in fair value of debt			2,645,000	$ 576,000
Change in fair value of debt attributable to instrument-specific credit risk	[1]		11,623,000	$ (945,000)
Interest expense on trust preferred securities			10,400,000
Bank loans
Debt Instrument [Line Items]
Long-term debt, fair value			10,966,000			12,255,000
Carrying value			8,727,000			9,240,000
Notes payable
Debt Instrument [Line Items]
Long-term debt, fair value			199,616,000			199,732,000
Carrying value			193,418,000			194,634,000
Mortgage
Debt Instrument [Line Items]
Debt face amount								$ 180,000,000
Interest rate								4.07%
Long-term debt, fair value			182,941,000			182,265,000		$ 191,700,000
Unamortized premium								$ 11,700,000
Carrying value			177,192,000			178,297,000
PWSC Loan | Bank loans
Debt Instrument [Line Items]
Debt face amount							$ 5,000,000
Interest rate							5.00%
Long-term debt, fair value			0			435,000
Carrying value			0			437,000
KWH Loan | Bank loans
Debt Instrument [Line Items]
Debt face amount		$ 10,000,000
Proceeds from issuance of debt		400,000
Unamortized discount (premium), net		$ 1,000,000
Long-term debt, fair value			10,966,000			11,820,000
Carrying value			8,727,000			8,803,000
KWH Loan | LIBOR | Bank loans
Debt Instrument [Line Items]
Annual interest rate		9.25%
Flower Note | Notes payable
Debt Instrument [Line Items]
Debt face amount										$ 9,200,000
Interest rate										4.81%
Long-term debt, fair value			7,890,000			8,071,000
Carrying value			7,226,000			7,337,000
Net Lease Note | Notes payable
Debt Instrument [Line Items]
Debt face amount									$ 9,000,000
Interest rate									10.25%
Long-term debt, fair value			8,785,000			9,396,000
Carrying value			$ 9,000,000			$ 9,000,000
30-Year Capital Securities
Debt Instrument [Line Items]
Debt face amount					$ 90,500,000
Minimum | LIBOR
Debt Instrument [Line Items]
Annual interest rate					3.85%
Minimum | KWH Loan | LIBOR | Bank loans
Debt Instrument [Line Items]
Annual interest rate		2.00%
Maximum | LIBOR
Debt Instrument [Line Items]
Annual interest rate					4.20%
[1]	Net of income tax expense (benefit) of $0 and $0 for the three months ended March 31, 2020 and March 31, 2019, respectively.

DEBT - Subordinated Borrowing (

DEBT - Subordinated Borrowing (Details) $ in Thousands	3 Months Ended
	Mar. 31, 2020USD ($)
Kingsway CT Statutory Trust I
Debt Instrument [Line Items]
Principal	$ 15,000
Kingsway CT Statutory Trust I | LIBOR
Debt Instrument [Line Items]
Annual interest rate	4.00%
Kingsway CT Statutory Trust II
Debt Instrument [Line Items]
Principal	$ 17,500
Kingsway CT Statutory Trust II | LIBOR
Debt Instrument [Line Items]
Annual interest rate	4.10%
Kingsway CT Statutory Trust III
Debt Instrument [Line Items]
Principal	$ 20,000
Kingsway CT Statutory Trust III | LIBOR
Debt Instrument [Line Items]
Annual interest rate	3.95%
Kingsway DE Statutory Trust III
Debt Instrument [Line Items]
Principal	$ 15,000
Kingsway DE Statutory Trust III | LIBOR
Debt Instrument [Line Items]
Annual interest rate	4.20%
Kingsway DE Statutory Trust IV
Debt Instrument [Line Items]
Principal	$ 10,000
Kingsway DE Statutory Trust IV | LIBOR
Debt Instrument [Line Items]
Annual interest rate	3.85%
Kingsway DE Statutory Trust VI
Debt Instrument [Line Items]
Principal	$ 13,000
Kingsway DE Statutory Trust VI | LIBOR
Debt Instrument [Line Items]
Annual interest rate	4.00%

LEASES - Adoption of ASU 2016-0

LEASES - Adoption of ASU 2016-02 (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019	Jan. 01, 2019
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Right-of-use asset	$ 3,178	$ 3,327
Lease liabilities	3,392	3,529
Accrued expenses and other liabilities	$ 27,266	$ 26,993
ASU 2016-02
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Right-of-use asset			$ 2,700
Lease liabilities			2,900
Accrued expenses and other liabilities			$ 200

LEASES - Narrative (Details)

LEASES - Narrative (Details)	3 Months Ended
	Mar. 31, 2020USD ($)a	Mar. 31, 2019USD ($)
Leases [Abstract]
Operating lease cost	$ 200,000
Variable lease cost	$ 0
Weighted average remaining lease term	5 years 5 months 16 days
Weighted average discount rate	5.32%
Cash paid for amounts included in measurement of lease liabilities	$ 200,000	$ 300,000
Land subject to ground leases (acres) | a	192
Below market lease, amortization 2019	$ 100,000
Below market lease, amortization 2020	100,000
Below market lease, amortization 2021	100,000
Below market lease, amortization 2022	100,000
Below market Lease, amortization 2023	100,000
Lease income	$ 3,341,000	$ 3,341,000

LEASES - Annual Maturities of L

LEASES - Annual Maturities of Lease Liabilities (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019
Leases [Abstract]
2019	$ 549
2020	802
2021	824
2022	624
2023	550
2025 and thereafter	546
Total undiscounted lease payments	3,895
Imputed interest	503
Total lease liabilities	$ 3,392	$ 3,529

LEASES - Net Book Value of Oper

LEASES - Net Book Value of Operating Lease Property Included in Property and Equipment (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019
Operating Leased Assets [Line Items]
Gross property and equipment leased	$ 113,008	$ 113,008
Accumulation depreciation	(15,382)	(14,345)
Net property and equipment leased	97,626	98,663
Land
Operating Leased Assets [Line Items]
Gross property and equipment leased	21,120	21,120
Site improvements
Operating Leased Assets [Line Items]
Gross property and equipment leased	91,308	91,308
Buildings
Operating Leased Assets [Line Items]
Gross property and equipment leased	$ 580	$ 580

LEASES - Future Undiscounted Ca

LEASES - Future Undiscounted Cash Flows to be Received (Details) $ in Thousands	Mar. 31, 2020USD ($)
Leases [Abstract]
2019	$ 8,913
2020	12,099
2021	12,371
2022	12,649
2023	12,934
Thereafter	$ 136,963

REVENUE FROM CONTRACTS WITH C_3

REVENUE FROM CONTRACTS WITH CUSTOMERS Disaggregation of revenues from contracts with customer by revenue type (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Disaggregation of Revenue [Line Items]
Service fee and commission income	$ 11,186	$ 9,815
Extended Warranty | IWS | Vehicle service agreement fees
Disaggregation of Revenue [Line Items]
Service fee and commission income	7,707	5,366
Extended Warranty | IWS | GAP commissions
Disaggregation of Revenue [Line Items]
Service fee and commission income	269	265
Extended Warranty | Trinity | Maintenance support service fees
Disaggregation of Revenue [Line Items]
Service fee and commission income	554	1,968
Extended Warranty | Trinity | Warranty product commissions
Disaggregation of Revenue [Line Items]
Service fee and commission income	861	582
Extended Warranty | PWSC | Homebuilder warranty service fees
Disaggregation of Revenue [Line Items]
Service fee and commission income	1,437	1,423
Extended Warranty | PWSC | Homebuilder warranty commissions
Disaggregation of Revenue [Line Items]
Service fee and commission income	$ 358	$ 211

REVENUE FROM CONTRACTS WITH C_4

REVENUE FROM CONTRACTS WITH CUSTOMERS Narrative (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2019	Mar. 31, 2020
Revenue from Contract with Customer [Abstract]
Contract period	4 years
Service fee receivable, net	$ 3,400	$ 3,262
Service fee and commission income recognized during the period	$ 5,500

REVENUE FROM CONTRACTS WITH C_5

REVENUE FROM CONTRACTS WITH CUSTOMERS Performance Obligations (Details) - Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction, Start Date [Axis]: 2019-10-01	Mar. 31, 2020
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction [Line Items]
Remaining performance obligation, expected timing of satisfaction, period	1 year
Performance obligation satisfied	43.70%

INCOME TAXES Shcedule of Income

INCOME TAXES Shcedule of Income Tax Expense (Benefit) (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Income Tax Disclosure [Abstract]
Income tax (benefit) expense at United States statutory income tax rate	$ (47)	$ 520
Valuation allowance	241	(1,331)
Non-deductible compensation	(43)	9
Investment income	(128)	(23)
State income tax	38	26
Change in unrecognized tax benefits	68	70
Indefinite life intangibles	54	33
Other	(13)	(17)
Income tax expense (benefit)	$ 170	$ (713)

INCOME TAXES Narrative (Details

INCOME TAXES Narrative (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019	Dec. 31, 2019
Income Tax Disclosure [Abstract]
Deferred tax asset, increase (decrease), amount		$ 800
Net deferred income tax liabilities	$ 29,146		$ 29,015
Operating loss carryforwards, subject to expiration	8,000		8,000
Goodwill and intangible assets	21,800
Tax deferred income	700		600
Deferred tax liabilities, other			21,700
Regulatory assets and liabilities			100
Unrecognized tax benefits	1,400		1,400
Penalties and interest expense	100
Penalties and interest accrued	$ 1,400		$ 1,300

(LOSS) EARNINGS PER SHARE (Deta

(LOSS) EARNINGS PER SHARE (Details) - USD ($) $ / shares in Units, shares in Thousands, $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Numerator:
Net (loss) income	$ (393)	$ 3,189
Less: net income attributable to noncontrolling interests	(721)	(211)
Plus (less): dividends on preferred stock	(377)	(246)
Net (loss) income attributable to common shareholders	$ (1,491)	$ 2,732
Denominator:
Weighted average common shares outstanding (in shares)	22,069	21,841
Incremental common shares attributable to dilutive effect of call options and warrants (in shares)	0	0
Unvested restricted stock awards (in shares)	0	0
Convertible preferred stock (in shares)	0	0
Total weighted average diluted shares (in shares)	22,069	21,841
Basic (loss) earnings per share (in dollars per share)	$ (0.07)	$ 0.13
Diluted (loss) earnings per share (in dollars per share)	$ (0.07)	$ 0.13
Stock options
Denominator:
Incremental common shares attributable to dilutive effect of call options and warrants (in shares)	0	0

(LOSS) EARNINGS PER SHARE - Wei

(LOSS) EARNINGS PER SHARE - Weighted-average Potentially Dilutive Securities (Details) - shares shares in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities excluded from computation of earnings per share, amount (in shares)	6,106,740	7,083,690
Stock options
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities excluded from computation of earnings per share, amount (in shares)	40,000	40,000
Unvested restricted stock awards
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities excluded from computation of earnings per share, amount (in shares)	500,000	976,950
Warrants
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities excluded from computation of earnings per share, amount (in shares)	4,423,765	4,673,765
Convertible preferred stock
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities excluded from computation of earnings per share, amount (in shares)	1,142,975	1,392,975

Stock-Based Compensation - Stoc

Stock-Based Compensation - Stock Option Activity (Details) - USD ($)	3 Months Ended	12 Months Ended
	Mar. 31, 2020	Dec. 31, 2019
Number of Options Outstanding
Outstanding, beginning of period (in shares)	40,000
Granted (in shares)	0
Expired (in shares)	0
Outstanding, end of period (in shares)	40,000	40,000
Exercisable (in shares)	40,000
Weighted-Average Exercise Price
Outstanding, beginning of period (in dollars per share)	$ 4.67
Granted (in dollars per share)	0
Expired (in dollars per share)	0
Outstanding, end of period (in dollars per share)	4.67	$ 4.67
Exercisable (in dollars per share)	$ 4.67
Weighted-Average Remaining Contractual Term (in Years)
Outstanding	1 month 18 days	3 months 18 days
Exercisable at March 31, 2019	1 month 18 days
Aggregate Intrinsic Value (in Thousands)
Outstanding	$ 0	$ 0
Exercisable at March 31, 2019	$ 0

Stock-Based Compensation - Addi

Stock-Based Compensation - Additional Information (Details) - USD ($)	Feb. 28, 2020	Nov. 19, 2019	Sep. 30, 2019	Jan. 31, 2019	Sep. 07, 2018	Sep. 05, 2018	Mar. 31, 2020	Mar. 31, 2019	Sep. 30, 2019	Dec. 31, 2019	Oct. 31, 2019
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)							0
Consideration received, cash		$ 600,000	$ 600,000
Consideration received (in shares)		594,750	594,750
Consideration received, warrants (in shares)		400,000	400,000
Warrant exercise price (in dollars per share)		$ 15	$ 15
Stock-based compensation (benefit) expense, net of forfeitures							$ 38,000	$ (242,000)
Payroll tax expense							83,000	89,000
Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock-based compensation (benefit) expense, net of forfeitures							$ (200,000)
Restricted Stock
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares unvested (in shares)							500,000			729,500
Vesting of restricted stock awards, net of share settlements for tax withholdings (in shares)							94,110		79,231
Weighted-average grant date fair value (in dollars per share)							$ 5.73			$ 5.23
Restricted Stock | 2014 Restricted Stock Awards
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award requisite service period							10 years
Unamortized compensation expense							$ 0
Restricted Stock | 2014 Restricted Stock Awards | Former Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares withheld for tax obligation (in shares)	41,677			36,269
Vesting of restricted stock awards, net of share settlements for tax withholdings (in shares)	93,713			115,500
Payroll tax expense							$ 100,000	100,000
Restricted Stock | 2018 Restricted Stock Awards
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares unvested (in shares)							500,000
Restricted Stock | 2018 Restricted Stock Awards | Former Chief Executive Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unamortized compensation expense										$ 600,000
Shares granted (in shares)						350,000
Shares withheld for tax obligation (in shares)						102,550
Shares unvested (in shares)						247,450					247,450
Restricted Stock | Modified Restricted Stock Award
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unamortized compensation expense							$ 0.6
Compensation expense (reversal of expense)								100,000
Restricted Stock | PWSC Restricted Stock Award | Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unamortized compensation expense							$ 600,000
Shares granted (in shares)					1,000
Shares unvested (in shares)							750
Compensation expense (reversal of expense)							$ 100,000	$ 200,000		$ 0
Weighted-average grant date fair value (in dollars per share)							$ 824.47
Restricted Stock Units (RSUs) | 2018 Restricted Stock Awards | Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unamortized compensation expense							$ 1,500,000
Shares granted (in shares)						500,000
Partially Vested | Restricted Stock | 2014 Restricted Stock Awards | Former Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Vesting of restricted stock awards, net of share settlements for tax withholdings (in shares)	135,787

Stock-Based Compensation - Rest

Stock-Based Compensation - Restricted Stock Awards (Details) - Restricted Stock - $ / shares	3 Months Ended	9 Months Ended
	Mar. 31, 2020	Sep. 30, 2019
Number of Restricted Stock Awards
Unvested, beginning of period (in shares)	729,500
Vested (in shares)	(94,110)	(79,231)
Cancelled for Tax Withholding (in shares)	(41,677)
Forfeited (in shares)	(93,713)
Unvested, end of period (in shares)	500,000
Weighted-Average Grant Date Fair Value (per Share)
Unvested, beginning of period (in dollars per share)	$ 5.23
Vested (in dollars per share)	4.14
Cancelled for Tax Withholding (in dollars per share)	4.14
Forfeited (in dollars per share)	4.14
Unvested, end of period (in dollars per share)	$ 5.73

Accumulated Other Comprehensi_3

Accumulated Other Comprehensive Income - AOCI Rollforward with Reclassification (Details) - USD ($) $ in Thousands		3 Months Ended
		Mar. 31, 2020	Mar. 31, 2019
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period		$ 13,954	$ 24,258
Other comprehensive income (loss)	[1]	11,739	(840)
Balance, end of period		26,223	26,603
Total Accumulated Other Comprehensive Income
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period		35,347	40,768
Other comprehensive income (loss) arising during the period		11,670	(840)
Amounts reclassified from accumulated other comprehensive income		61	(6)
Other comprehensive income (loss)		11,731	(846)
Balance, end of period		47,078	39,922
Unrealized Gains (Losses) on Available-for-Sale Investments
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period		59	(160)
Other comprehensive income (loss) arising during the period		47	105
Amounts reclassified from accumulated other comprehensive income		61	(6)
Other comprehensive income (loss)		108	99
Balance, end of period		167	(61)
Foreign Currency Translation Adjustments
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period		(3,286)	(3,286)
Other comprehensive income (loss) arising during the period		0	0
Amounts reclassified from accumulated other comprehensive income		0	0
Other comprehensive income (loss)		0	0
Balance, end of period		(3,286)	(3,286)
Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period		38,574	44,259
Other comprehensive income (loss) arising during the period		11,623	(945)
Amounts reclassified from accumulated other comprehensive income		0	0
Other comprehensive income (loss)		11,623	(945)
Balance, end of period		$ 50,197	43,314
Equity in Other Comprehensive Loss of Limited Liability Investment
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period			(45)
Other comprehensive income (loss) arising during the period			0
Amounts reclassified from accumulated other comprehensive income			0
Other comprehensive income (loss)			0
Balance, end of period			$ (45)
[1]	Net of income tax expense (benefit) of $0 and $0 for the three months ended March 31, 2020 and March 31, 2019, respectively.

Accumulated Other Comprehensi_4

Accumulated Other Comprehensive Income - Reclassification out of AOCI (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Net realized gains	$ 208	$ 315
Other-than-temporary impairment loss	(117)	(75)
(Loss) income before income tax expense (benefit)	(223)	2,476
Income tax expense (benefit)	170	(713)
Net (loss) income	(393)	3,189
Unrealized Gains (Losses) on Available-for-Sale Investments | Reclassification out of Accumulated Other Comprehensive Income
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Net realized gains	(61)	6
Other-than-temporary impairment loss	0	0
(Loss) income before income tax expense (benefit)	(61)	6
Income tax expense (benefit)	0	0
Net (loss) income	$ (61)	$ 6

Segmented Information - Additio

Segmented Information - Additional Information (Details)	12 Months Ended
	Dec. 31, 2019segment	Mar. 31, 2020astate
Segment Reporting Information [Line Items]
Number of reportable segments | segment	2
Number of states in which entity operates		27
Land subject to ground leases (acres) | a		192
Penn
Segment Reporting Information [Line Items]
Number of states in which entity operates		32
Prime
Segment Reporting Information [Line Items]
Number of states in which entity operates		40

Segmented Information - Revenue

Segmented Information - Revenue by Reportable Segment (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Segment Reporting Information [Line Items]
Service fee and commission income	$ 11,186	$ 9,815
Other income	142	145
Rental income	3,341	3,341
Total revenues	14,669	13,301
Extended Warranty | Operating Segments
Segment Reporting Information [Line Items]
Service fee and commission income	11,186	9,815
Other income	74	75
Total revenues	11,260	9,890
Leased Real Estate | Operating Segments
Segment Reporting Information [Line Items]
Other income	68	70
Rental income	3,341
Rental income		3,341
Total revenues	$ 3,409	$ 3,411

Segmented Information - Segment

Segmented Information - Segment (loss) income (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Segment Reporting Information [Line Items]
Total segment operating income	$ (1,622)	$ (899)
Net investment income	719	699
Net realized gains	208	315
(Loss) gain on change in fair value of equity investments	(597)	78
Gain on change in fair value of limited liability investments, at fair value	1,899	4,265
Net change in unrealized (loss) gain on private company investments	(670)	19
Other-than-temporary impairment loss	(117)	(75)
Interest expense not allocated to segments	(2,153)	(2,102)
Other income and expenses not allocated to segments, net	(3,030)	(1,764)
Amortization of intangible assets	(574)	(521)
Gain on change in fair value of debt	2,645	576
Equity in net loss of investee	0	(33)
(Loss) income before income tax expense (benefit)	(223)	2,476
Income tax expense (benefit)	170	(713)
Income from continuing operations	(393)	3,189
Operating Segments
Segment Reporting Information [Line Items]
Total segment operating income	1,447	1,019
Extended Warranty | Operating Segments
Segment Reporting Information [Line Items]
Total segment operating income	850	567
Leased Real Estate | Operating Segments
Segment Reporting Information [Line Items]
Total segment operating income	$ 597	$ 452

Fair Value of Financial Instr_3

Fair Value of Financial Instruments - Financial Assets and Liabilities Measured at Fair Value on Recurring Basis (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019	Mar. 31, 2019	Dec. 31, 2018
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	$ 15,247	$ 22,195
Total equity investments	1,825	2,421
Limited liability investments, at fair value	30,986	29,078
Real estate investments	10,662	10,662
Other investments	841	1,009
Short-term investments	156	155
Total assets	59,717	65,520
Subordinated debt, at fair value	40,387	54,655
Warrant liability	216	249
Total liabilities	40,603	54,904
U.S. government, government agencies and authorities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	5,629	13,316
States, municipalities and political subdivisions
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	603	600
Mortgage-backed
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	4,054	2,939
Corporate
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	4,961	5,340
Common Stock
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total equity investments	1,817	2,406
Warrants
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total equity investments	8	15
Quoted Prices in Active Markets for Identical Assets (Level 1)
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Total equity investments	1,820	2,411
Limited liability investments, at fair value	0	0
Real estate investments	0	0
Other investments	0	0
Short-term investments	0	0
Total assets	1,820	2,411
Subordinated debt, at fair value	0	0
Warrant liability	0	0
Total liabilities	0	0
Quoted Prices in Active Markets for Identical Assets (Level 1) | U.S. government, government agencies and authorities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Quoted Prices in Active Markets for Identical Assets (Level 1) | States, municipalities and political subdivisions
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Quoted Prices in Active Markets for Identical Assets (Level 1) | Mortgage-backed
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Quoted Prices in Active Markets for Identical Assets (Level 1) | Corporate
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Quoted Prices in Active Markets for Identical Assets (Level 1) | Common Stock
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total equity investments	1,817	2,406
Quoted Prices in Active Markets for Identical Assets (Level 1) | Warrants
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total equity investments	3	5
Significant Other Observable Inputs (Level 2)
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	15,247	22,195
Total equity investments	5	10
Limited liability investments, at fair value	0	0
Real estate investments	0	0
Other investments	841	1,009
Short-term investments	156	155
Total assets	16,249	23,369
Subordinated debt, at fair value	40,387	54,655
Warrant liability	0	0
Total liabilities	40,387	54,655
Significant Other Observable Inputs (Level 2) | U.S. government, government agencies and authorities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	5,629	13,316
Significant Other Observable Inputs (Level 2) | States, municipalities and political subdivisions
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	603	600
Significant Other Observable Inputs (Level 2) | Mortgage-backed
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	4,054	2,939
Significant Other Observable Inputs (Level 2) | Corporate
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	4,961	5,340
Significant Other Observable Inputs (Level 2) | Common Stock
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total equity investments	0	0
Significant Other Observable Inputs (Level 2) | Warrants
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total equity investments	5	10
Significant Unobservable Inputs (Level 3)
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Total equity investments	0	0
Limited liability investments, at fair value	4,413	4,392	$ 4,060	$ 4,124
Real estate investments	10,662	10,662	10,662	10,662
Other investments	0	0
Short-term investments	0	0
Total assets	15,075	15,054	14,722
Subordinated debt, at fair value	0	0
Warrant liability	216	249	$ 317	$ 0
Total liabilities	216	249
Significant Unobservable Inputs (Level 3) | U.S. government, government agencies and authorities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Significant Unobservable Inputs (Level 3) | States, municipalities and political subdivisions
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Significant Unobservable Inputs (Level 3) | Mortgage-backed
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Significant Unobservable Inputs (Level 3) | Corporate
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Significant Unobservable Inputs (Level 3) | Common Stock
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total equity investments	0	0
Significant Unobservable Inputs (Level 3) | Warrants
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total equity investments	0	0
Measured at Net Asset Value
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Total equity investments	0	0
Limited liability investments, at fair value	26,573	24,686
Real estate investments	0	0
Other investments	0	0
Short-term investments	0	0
Total assets	26,573	24,686
Subordinated debt, at fair value	0	0
Warrant liability	0	0
Total liabilities	0	0
Measured at Net Asset Value | U.S. government, government agencies and authorities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Measured at Net Asset Value | States, municipalities and political subdivisions
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Measured at Net Asset Value | Mortgage-backed
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Measured at Net Asset Value | Corporate
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total fixed maturities	0	0
Measured at Net Asset Value | Common Stock
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total equity investments	0	0
Measured at Net Asset Value | Warrants
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Total equity investments	$ 0	$ 0

Fair Value of Financial Instr_4

Fair Value of Financial Instruments - Reconciliation of Fair Value of Recurring Level 3 Measurements (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019	Dec. 31, 2019
Limited liability investments, at fair value:
Beginning balance	$ 29,078
Purchases	(60)	$ (249)
Net realized gains	208	315
Ending balance	30,986
Real estate investments:
Beginning balance	10,662
Ending balance	10,662
Total assets	59,717		$ 65,520
Warrant liability:
Beginning balance	249
Ending balance - liabilities	216
Included in other comprehensive income (loss)	0	0
Significant Unobservable Inputs (Level 3)
Limited liability investments, at fair value:
Beginning balance	4,392	4,124
Purchases	0	75
Distributions received	(77)	(324)
Net realized gains	86	69
Change in fair value of limited liability investments, at fair value included in net (loss) income	12	116
Ending balance	4,413	4,060
Included in other comprehensive income (loss)	12	116
Fair Value, Asset (Liability), Recurring Basis, Still Held, Unrealized Gain (Loss), OCI	0	0
Real estate investments:
Beginning balance	10,662	10,662
Change in fair value of real estate investments included in net (loss) income	0	0
Ending balance	10,662	10,662
Unrealized gains recognized on real estate investments held at end of period:	0	0
Total assets	15,075	14,722	$ 15,054
Warrant liability:
Beginning balance	249	0
Issuance of warrants	0	361
Change in fair value of warrant liability included in net (loss) income	(33)	(44)
Ending balance - liabilities	216	317
Included in net (loss) income	$ (33)	$ (44)

Fair Value of Financial Instr_5

Fair Value of Financial Instruments - Valuation Techniques Used to Measure Investments (Details) $ in Thousands	Mar. 31, 2020USD ($)	Dec. 31, 2019USD ($)	Mar. 31, 2019USD ($)	Dec. 31, 2018USD ($)
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, at fair value	$ 30,986	$ 29,078
Real estate investments	10,662	10,662
Warrant liability	216	249
Significant Unobservable Inputs (Level 3)
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, at fair value	4,413	4,392	$ 4,060	$ 4,124
Real estate investments	10,662	10,662	10,662	10,662
Warrant liability	$ 216	$ 249	$ 317	$ 0
Significant Unobservable Inputs (Level 3) | Cap rates
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Real estate investments, measurement input	0.075	0.075
Significant Unobservable Inputs (Level 3) | Minimum | Valuation multiples
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, measurement input	3.1	3.1
Warrant liability, measurement input	6	6
Significant Unobservable Inputs (Level 3) | Maximum | Valuation multiples
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, measurement input	7	7

Fair Value of Financial Instr_6

Fair Value of Financial Instruments - Investments at Fair Value Using Net Asset Value Per Share As Practical Expedient (Details) - USD ($) $ in Thousands	Mar. 31, 2020	Dec. 31, 2019
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, at fair value	$ 30,986	$ 29,078
Measured at Net Asset Value
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, at fair value	$ 26,573	$ 24,686

Fair Value of Financial Instr_7

Fair Value of Financial Instruments - Assets and Liabilities Measured at Fair Value on a Nonrecurring Basis (Details) - USD ($)	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Net change in unrealized (loss) gain on private company investments	$ (670,000)	$ 19,000
Other-than-temporary impairment loss	(117,000)	(75,000)
Private Company Investments
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Net change in unrealized (loss) gain on private company investments	0	100,000
Other-than-temporary impairment loss	$ (700,000)	$ 0

Fair Value of Financial Instr_8

Fair Value of Financial Instruments - Valuation Techniques and Significant Unobservable Inputs (Details) $ in Thousands	3 Months Ended
	Mar. 31, 2020USD ($)	Mar. 31, 2019USD ($)
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Net change in unrealized (loss) gain on private company investments	$ (670)	$ 19
Minimum | Relief from royalty | Significant Unobservable Inputs (Level 3) | Royalty rate
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Input Value(s)	0.0025
Maximum | Relief from royalty | Significant Unobservable Inputs (Level 3) | Royalty rate
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Input Value(s)	0.020
Private Company Investments
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Net change in unrealized (loss) gain on private company investments	$ 0	$ 100

Related Parties - Argo Manageme

Related Parties - Argo Management Group, LLC (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019
Management
Related Party Transaction [Line Items]
Funding received	$ 0	$ 600

Related Parties - Itasca Capita

Related Parties - Itasca Capital Ltd. (Details) $ / shares in Units, $ / shares in Units, $ in Millions, $ in Millions	Nov. 19, 2019USD ($)$ / sharesshares	Oct. 31, 2019CAD ($)$ / sharesshares	Oct. 09, 2019CAD ($)$ / sharesshares	Sep. 30, 2019USD ($)$ / sharesshares	Sep. 05, 2018shares	Mar. 31, 2020shares	Dec. 31, 2019shares
Related Party Transaction [Line Items]
Consideration received, cash | $	$ 0.6			$ 0.6
Consideration received (in shares)	594,750			594,750
Consideration received, warrants (in shares)	400,000			400,000
Warrant exercise price (in dollars per share) | $ / shares	$ 15			$ 15
Corporate Segment
Related Party Transaction [Line Items]
Equity method investment, ownership percentage						0.00%	0.00%
Restricted Stock
Related Party Transaction [Line Items]
Shares unvested (in shares)						500,000	729,500
2018 Restricted Stock Awards | Restricted Stock
Related Party Transaction [Line Items]
Shares unvested (in shares)						500,000
Former Chief Executive Officer | 2018 Restricted Stock Awards | Restricted Stock
Related Party Transaction [Line Items]
Shares granted (in shares)					350,000
Shares withheld for tax obligation (in shares)					102,550
Shares unvested (in shares)		247,450			247,450
ICL | ICL | Affiliated Entity
Related Party Transaction [Line Items]
Number of shares to be sold (in shares)		3,011,447	1,974,113
Share price (in dollars per share) | $ / shares		$ 0.35	$ 0.35
ICL | ICL | Affiliated Entity | Execution of Share Agreement With Related Party
Related Party Transaction [Line Items]
Amount of related party transaction | $		$ 1.1	$ 0.7
Number of shares (in shares)		247,450
ICL | ICL | Affiliated Entity | Execution of Share Agreement With Related Party, Portion Received in Cash
Related Party Transaction [Line Items]
Amount of related party transaction | $		$ 0.2

Related Parties - 1347 Energy H

Related Parties - 1347 Energy Holdings LLC (Details) - USD ($) $ in Millions	Feb. 12, 2018	Mar. 31, 2020	Dec. 31, 2019
Principal Owner
Related Party Transaction [Line Items]
Equity method investment, ownership percentage		0.00%	0.00%
Chief Executive Officer
Related Party Transaction [Line Items]
Equity method investment, ownership percentage		0.00%	0.00%
1347 Energy Holdings LLC | Affiliated Entity
Related Party Transaction [Line Items]
Collateralized agreements	$ 1.8
Proceeds from surety bonds	$ 0.7

Related Parties - 1347 Investor

Related Parties - 1347 Investors LLC (Details) - USD ($) $ / shares in Units, $ in Millions	Nov. 19, 2019	Sep. 30, 2019	Mar. 31, 2020	Dec. 31, 2019
Related Party Transaction [Line Items]
Consideration received, cash	$ 0.6	$ 0.6
Consideration received (in shares)	594,750	594,750
Consideration received, warrants (in shares)	400,000	400,000
Warrant exercise price (in dollars per share)	$ 15	$ 15
Limited Liability Company
Related Party Transaction [Line Items]
Equity method investment, ownership percentage			0.00%	0.00%
Equity Method Investee
Related Party Transaction [Line Items]
Equity method investment, ownership percentage			100.00%	100.00%

Related Parties - Atlas Financi

Related Parties - Atlas Financial Holdings, Inc. (Details) - USD ($) $ in Thousands	Nov. 30, 2010	Mar. 31, 2020	Mar. 31, 2019
Related Party Transactions [Abstract]
Notes receivable, related parties	$ 1,100	$ 500
Receivable interest rate	3.00%
Market value of pledged shares	$ 100
Other-than-temporary impairment loss		$ 117	$ 75

Related Parties - Other Related

Related Parties - Other Related Party Transactions (Details) - Forecast - Chief Financial Officer - USD ($)	2 Months Ended	8 Months Ended
	Apr. 30, 2020	Dec. 31, 2020
Related Party Transaction [Line Items]
Consulting agreement, fee	$ 100,000
Consulting agreement, hourly fee		$ 165

Related Parties - Insurance Inc

Related Parties - Insurance Income Strategies Ltd. (Details) - USD ($) $ in Millions	Dec. 31, 2019	Aug. 10, 2018
Equity Method Investee
Related Party Transaction [Line Items]
Percentage of assets		0.90%
Percentage of net profits		9.00%
Percentage of future fees		50.00%
Preferred stock issued		$ 15
IIS Re Ltd
Related Party Transaction [Line Items]
Ownership percentage by parent	100.00%

Commitment and Contingencies (D

Commitment and Contingencies (Details) - USD ($)	Jan. 20, 2020	Mar. 31, 2020	Dec. 31, 2019
Loss Contingencies [Line Items]
Subscription agreement amount		$ 2,600,000
Unfunded commitments		$ 0
Aegis | Breach of contract
Loss Contingencies [Line Items]
Maximum litigation reimbursement amount	$ 900,000
Percentage of future losses reimbursable		60.00%
Estimate of possible loss		$ 4,800,000
Settlement amount		$ 0
CMC | Subsidiaries
Loss Contingencies [Line Items]
Indirect ownership percentage owned by parent			81.00%
CMC | Subsidiaries | DGI
Loss Contingencies [Line Items]
Remaining ownership percentage owned by noncontrolling interest			19.00%

SUBSEQUENT EVENTS Subsequent Ev

SUBSEQUENT EVENTS Subsequent Events (Details) $ in Millions	Apr. 30, 2020USD ($)
Bank loans | PPP loan | Subsequent Event
Subsequent Event [Line Items]
Debt face amount	$ 2.9