Kingsway Financial Services (KFS) 10-Q 7 Aug 17 2017 Q2 Quarterly report Financial data

Document and Entity Information

Document and Entity Information Document - shares	6 Months Ended
	Jun. 30, 2017	Aug. 07, 2017
Document Information [Line Items]
Entity Registrant Name	KINGSWAY FINANCIAL SERVICES INC.
Entity Central Index Key	1,072,627
Current Fiscal Year End Date	--12-31
Entity Filer Category	Accelerated Filer
Document Type	10-Q
Document Period End Date	Jun. 30, 2017
Document Fiscal Year Focus	2,017
Document Fiscal Period Focus	Q2
Amendment Flag	false
Entity Common Stock, Shares Outstanding		23,410,855

Consolidated Balance Sheet

Consolidated Balance Sheet - USD ($) $ in Thousands	Jun. 30, 2017	Dec. 31, 2016
Investments [Abstract]
Fixed maturities, at fair value (amortized cost of $57,172 and $62,136, respectively)	$ 56,965	$ 61,764
Equity investments, at fair value (cost of $16,699 and $19,099, respectively)	19,441	23,230
Limited liability investments	25,533	22,974
Limited liability investment, at fair value	8,220	10,700
Other investments, at cost which approximates fair value	7,550	7,975
Short-term investments, at cost which approximates fair value	151	401
Total investments	117,860	127,044
Cash and cash equivalents	33,776	36,475
Investment in investee	5,355	3,116
Accrued investment income	893	790
Premiums receivable, net of allowance for doubtful accounts of $115 and $115, respectively	30,113	31,564
Service fee receivable, net of allowance for doubtful accounts of $276 and $274, respectively	1,408	1,320
Other receivables, net of allowance for doubtful accounts of $806 and $806, respectively	6,765	4,692
Reinsurance recoverable	569	784
Deferred acquisition costs, net	13,709	13,609
Property and equipment, net of accumulated depreciation of $12,894 and $10,603, respectively	114,809	116,961
Goodwill	71,061	71,061
Intangible assets, net of accumulated amortization of $7,761 and $7,181, respectively	88,187	89,017
Other assets	4,539	4,588
Total Assets	489,044	501,021
Unpaid loss and loss adjustment [Abstract]
Property and casualty	45,874	53,795
Vehicle service agreements	2,794	2,915
Total unpaid loss and loss adjustment expenses	48,668	56,710
Unearned premiums	40,770	40,176
Reinsurance payable	87	100
Note payable	188,328	190,074
Subordinated debt, at fair value	48,210	43,619
Deferred income tax liability	49,726	48,720
Deferred service fees	37,883	35,822
Income taxes payable	2,352	2,051
Accrued expenses and other liabilities	19,912	20,487
Total Liabilities	435,936	437,759
Class A preferred stock, no par value; unlimited number authorized; 262,876 and 262,876 issued and outstanding at June 30, 2017 and December 31, 2016, respectively; redemption amount of $6,572	6,444	6,427
Shareholders' Equity [Abstract]
Additional paid-in capital	354,422	353,882
Accumulated deficit	(307,328)	(297,668)
Accumulated other comprehensive loss	(1,467)	(208)
Shareholders' equity attributable to common shareholders	45,627	56,006
Noncontrolling interests in consolidated subsidiaries	1,037	829
Total Shareholders' Equity	46,664	56,835
Total Liabilities, Class A preferred stock and Shareholders' Equity	$ 489,044	$ 501,021

Consolidated Balance Sheet Bala

Consolidated Balance Sheet Balance Sheet Parenthetical - USD ($) $ in Thousands	Jun. 30, 2017	Dec. 31, 2016
Balance Sheet Parenthetical [Abstract]
Fixed maturities, cost	$ 57,172	$ 62,136
Equity investments, cost	16,699	19,099
Premiums receivable, allowance for doubtful accounts	115	165
Other receivables, allowance for doubtful accounts	806	806
Service fee receivable, allowance for doubtful accounts	276	276
Property and equipment, accumulated depreciation	12,894	10,603
Intangible assets accumulated amortization	7,761	7,181
Class A preferred stock, no par value; unlimited number authorized; 262,876 and 262,876 issued and outstanding at June 30, 2017 and December 31, 2016, respectively; redemption amount of $6,572	$ 6,572	$ 6,572
Common stock, shares outstanding	21,458,190	21,458,190

Consolidated Statement of Opera

Consolidated Statement of Operations - USD ($) shares in Thousands, $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Revenues [Abstract]
Net premiums earned	$ 33,518	$ 31,813	$ 66,440	$ 61,240
Service fee and commission income	6,873	5,394	13,435	10,716
Rental income	3,341	0	6,682	0
Net investment (loss) income	(2,366)	1,072	(1,663)	1,000
Net realized gains (losses)	734	67	1,132	(104)
Other income	2,815	2,791	5,630	5,165
Total revenues	44,915	41,137	91,656	78,017
Operating Expenses [Abstract]
Loss and loss adjustment expenses	27,468	24,838	53,878	48,335
Commissions and premium taxes	6,475	6,103	12,753	11,701
Cost of services sold	1,291	770	2,595	1,543
General and administrative expenses	11,380	10,826	22,652	20,377
Leased real estate segment interest expense	1,569	0	3,143	0
Amortization of intangible assets	289	307	580	602
Contingent consideration benefit	(212)	(657)	(212)	(657)
Impairment of intangible assets	0	0	250	0
Total operating expenses	48,260	42,187	95,639	81,901
Operating loss	(3,345)	(1,050)	(3,983)	(3,884)
Other (revenues) expenses, net: [Abstract]
Interest expense not allocated to segments	1,216	1,108	2,375	2,201
Foreign exchange losses, net	0	(9)	(4)	(10)
Loss (gain) on change in fair value of debt	2,702	(1,068)	4,591	(3,596)
Equity in net loss (income) of investees	145	874	(2,240)	943
Total other expenses (revenues), net	4,063	923	4,730	(442)
Loss from continuing operations before income tax expense	(7,408)	(1,973)	(8,713)	(3,442)
Income tax expense	1,251	26	1,430	52
Loss from continuing operations	(8,659)	(1,999)	(10,143)	(3,494)
Gain on disposal of discontinued operations, net of taxes	1,017	1,124	1,017	1,124
Net loss	(7,642)	(875)	(9,126)	(2,370)
Less: net income (loss) attributable to noncontrolling interests in consolidated subsidiaries	100	(361)	205	(400)
Less: dividends on preferred stock	123	82	244	164
Net loss attributable to common shareholders	$ (7,865)	$ (596)	$ (9,575)	$ (2,134)
Loss per share - continuing operations [Abstract]
Basic:	$ (0.41)	$ (0.09)	$ (0.49)	$ (0.16)
Diluted:	(0.41)	(0.09)	(0.49)	(0.16)
Income (Loss) from Discontinued Operations and Disposal of Discontinued Operations, Net of Tax, Per Basic and Diluted Share [Abstract]
Basic:	0.05	0.06	0.05	0.06
Diluted:	0.05	0.06	0.05	0.06
Earnings Per Share, Basic and Diluted [Abstract]
Basic:	(0.37)	(0.03)	(0.45)	(0.11)
Diluted:	$ (0.37)	$ (0.03)	$ (0.45)	$ (0.11)
Weighted Average Number of Shares Outstanding, Diluted [Abstract]
Basic:	21,458	19,818	21,458	19,764
Diluted:	21,458	19,818	21,458	19,764

Consolidated Statements of Comp

Consolidated Statements of Comprehensive Loss - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Net loss	$ (7,642)	$ (875)	$ (9,126)	$ (2,370)
Unrealized gains (losses) on fixed maturities and equity investments: [Abstract]
Unrealized (losses) gains arising during the period	(1,064)	430	(1,227)	705
Reclassification adjustment for amounts included in net loss	478	(73)	(29)	(505)
Other comprehensive (loss) income	(586)	357	(1,256)	200
Comprehensive loss	(8,228)	(518)	(10,382)	(2,170)
Less: comprehensive income (loss) attributable to noncontrolling interests in consolidated subsidiaries	102	(360)	208	(399)
Comprehensive loss attributable to common shareholders	$ (8,330)	$ (158)	$ (10,590)	$ (1,771)

Consolidated Statement of Cash

Consolidated Statement of Cash Flows - USD ($) $ in Thousands	6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016
Net Cash Provided by (Used in) Operating Activities [Abstract]
Net loss	$ (9,126)	$ (2,370)
Adjustments to Reconcile Net Income (Loss) to Cash Provided by (Used in) Operating Activities [Abstract]
Gain on disposal of discontinued operations, net of taxes	1,017	1,124
Equity in net (income) loss of investee	(2,240)	943
Equity in net loss (income) of limited liability investments	(281)	310
Loss on change in fair value of investments	(2,433)	(246)
Depreciation and amortization expense	2,793	697
Contingent consideration benefit	(212)	(657)
Stock-based compensation expense, net of forfeitures	600	500
Net realized (gains) losses	(1,132)	104
Loss (gain) on change in fair value of debt	(4,591)	3,596
Deferred income taxes	1,005	44
Intangible asset impairment	250	0
Amortization of fixed maturities premiums and discounts	(112)	(133)
Amortization of note payable premium	(483)	0
Increase (Decrease) in Other Operating Assets and Liabilities, Net [Abstract]
Premiums and service fee receivable, net	(1,363)	4,864
Other receivables, net	2,073	(682)
Reinsurance recoverable	215	463
Deferred acquisition costs, net	100	1,681
Income taxes recoverable	0	5
Unpaid loss and loss adjustment expenses	(8,042)	(3,276)
Unearned premiums	594	5,888
Reinsurance payable	(13)	139
Deferred service fees	2,061	1,680
Other, net	(161)	1,358
Net cash used in operating activities	(8,313)	(5,032)
Net Cash Provided by (Used in) Investing Activities [Abstract]
Proceeds from sales and maturities of fixed maturities	9,863	13,349
Proceeds from sales of equity investments	5,879	3,721
Purchases of fixed maturities	4,981	19,781
Purchases of equity investments	2,644	1,541
Net acquisitions of limited liability investments	2,870	1,017
Net proceeds from (purchases of) other investments	425
Net proceeds from (purchases of) other investments		(1,357)
Net proceeds from (purchases of) short-term investments	(250)	533
Net proceeds from sale of discontinued operations	1,017	1,124
Net purchases of property and equipment	(61)	(622)
Net cash provided by (used in) investing activities	6,878	(6,657)
Net Cash Provided by (Used in) Financing Activities, Continuing Operations [Abstract]
Repurchase of common stock for cancellation	0	(125)
Principal payments on note payable	1,264	0
Net cash used in financing activities	(1,264)	(125)
Net decrease in cash and cash equivalents	(2,699)	(11,814)
Cash and cash equivalents at beginning of period	36,475	51,701
Cash and cash equivalents at end of period	$ 33,776	$ 39,887

Business

Business	6 Months Ended
	Jun. 30, 2017
Business [Abstract]
Nature of Operations [Text Block]	BUSINESS Kingsway Financial Services Inc. (the "Company" or "Kingsway") was incorporated under the Business Corporations Act (Ontario) on September 19, 1989. Kingsway is a Canadian holding company with operating subsidiaries located in the United States. The Company operates as a merchant bank with a focus on long-term value-creation. The Company owns or controls subsidiaries primarily in the insurance, extended warranty, asset management and real estate industries and pursues non-control investments and other opportunities acting as an advisor, an investor and a financier.

Basis of Presentation (Notes)

Basis of Presentation (Notes)	6 Months Ended
	Jun. 30, 2017
Basis of Presentation [Abstract]
Basis of Presentation and Significant Accounting Policies [Text Block]	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 (" 2016 Annual Report") for the year ended December 31, 2016 . The unaudited consolidated interim financial statements include the accounts of the Company and its subsidiaries. All material intercompany transactions and balances have been eliminated in consolidation. The preparation of consolidated financial statements in conformity 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 investment, at fair value; valuation of deferred income taxes; valuation and impairment assessment of intangible assets; goodwill recoverability; deferred acquisition costs; fair value assumptions for performance shares; fair value assumptions for subordinated debt obligations; and contingent consideration. The fair values of the Company's investments in fixed maturities and equity investments, limited liability investment, at fair value, performance shares, subordinated debt and contingent consideration are estimated using a fair value hierarchy to categorize the inputs it uses in valuation techniques. The fair value of the Company's investment in investee is based on quoted market prices. Fair values for other investments approximate their unpaid principal balance. The carrying amounts reported in the consolidated balance sheets approximate fair values for 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.

Summary of Significant Accounti

Summary of Significant Accounting Polocies	6 Months Ended
	Jun. 30, 2017
Summary of significant accounting policies [Abstract]
Significant Accounting Policies [Text Block]	SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES There have been no material changes to our significant accounting policies as reported in our 2016 Annual Report.

Recently Issued Accounting Stan

Recently Issued Accounting Standards	6 Months Ended
	Jun. 30, 2017
Recently Issued Accounting Standards [Abstract]
New Accounting Pronouncements, Policy [Policy Text Block]	RECENTLY ISSUED ACCOUNTING STANDARDS (a) Adoption of New Accounting Standards: In March 2016, the FASB issued ASU 2016-09, Compensation - Stock Compensation (Topic 718): Improvements to Employee Share-Based Payment Accounting ("ASU 2016-09"). ASU 2016-09 was issued to simplify the accounting for share-based payment awards. The guidance requires, prospectively, all tax effects related to share-based payments be made through the statement of operations at the time of settlement as opposed to excess tax benefits being recognized in additional paid-in-capital under the current guidance. ASU 2016-09 also removes the requirement to delay recognition of a tax benefit until it reduces current taxes payable. This change is required to be applied on a modified retrospective basis, with a cumulative-effect adjustment to opening accumulated deficit. Additionally, all tax related cash flows resulting from share-based payments are to be reported as operating activities on the statement of cash flows, a change from the current requirement to present tax benefits as an inflow from financing activities and an outflow from operating activities. ASU 2016-09 is effective for annual and interim reporting periods beginning after December 15, 2016. Early adoption is permitted with any adjustments reflected as of the beginning of the fiscal year of adoption. Effective January 1, 2017, the Company adopted ASU 2016-09. The adoption of the standard did not affect the Company's consolidated financial statements. (b) Accounting Standards Not Yet Adopted: In May 2014, the FASB issued ASU 2014-09, Revenue from Contracts with Customers ("ASU 2014-09"), which outlines a single comprehensive model for entities to use in accounting for revenue arising from contracts with customers. The core principle of ASU 2014-09 is that an entity recognizes revenue to depict the transfer of promised goods or services to customers in an amount that reflects the consideration to which the entity expects to be entitled in exchange for those goods or services. In August 2015, the FASB issued ASU 2015-14, Revenue from Contracts with Customers (Topic 606): Deferral of the Effective Date ("ASU 2015-14"). This amendment defers the effective date of the previously issued ASU 2014-09 until the interim and annual reporting periods beginning after December 15, 2017. Earlier application is permitted for interim and annual reporting periods beginning after December 15, 2016. In addition, the FASB has issued four related ASU's on principal versus agent guidance (ASU 2016-08), identifying performance obligations and the licensing implementation guidance (ASU 2016-10), a revision of certain SEC Staff Observer comments (ASU 2016-11) and implementation guidance (ASU 2016-12). Insurance contracts are not within the scope of ASU 2014-09; therefore, this standard would not apply to the Company's Insurance Underwriting segment. The Company is currently evaluating the potential effect of the adoption of ASU 2014-09 on its consolidated financial statements, but, at this time, the Company does not believe the adoption of ASU 2014-09 will have a material effect on its consolidated financial statements. In January 2016, the FASB issued ASU 2016-01, Financial Instruments-Overall (Subtopic 825-10): Recognition and Measurement of Financial Assets and Financial Liabilities ("ASU 2016-01"). The amendments in ASU 2016-01 address certain aspects of recognition, measurement, presentation, and disclosure of financial instruments. Most significantly, ASU 2016-01 requires equity investments (except those accounted for under the equity method of accounting or those that result in consolidation of an investee) to be measured at fair value with changes in fair value recognized in net income (loss). For public business entities, the amendments in ASU 2016-01 are effective for fiscal years beginning after December 15, 2017, including interim periods within those fiscal years, and will be applied using a cumulative-effect adjustment to accumulated deficit as of the beginning of the fiscal year of adoption. The Company currently records its equity investments at fair value with net unrealized gains or losses reported in accumulated other comprehensive loss. Adoption of ASU 2016-01 will require the changes in fair value on equity investments with readily determinable fair values to be recorded in net income (loss). Subsequent to adoption, ASU 2016-01 could have a significant effect on the Company's results of operations and earnings (loss) per share as changes in fair value will be presented in net income (loss) rather than other comprehensive income (loss). In February 2016, the FASB issued ASU 2016-02, Leases ("ASU 2016-02"). ASU 2016-02 was issued to improve the financial reporting of leasing transactions. Under current guidance for lessees, leases are only included on the balance sheet if certain criteria, classifying the agreement as a capital lease, are met. This update will require the recognition of a right-of-use asset and a corresponding lease liability, discounted to the present value, for all leases that extend beyond 12 months. For operating leases, the asset and liability will be expensed over the lease term on a straight-line basis, with all cash flows included in the operating section of the statement of cash flows. For finance leases, interest on the lease liability will be recognized separately from the amortization of the right-of-use asset in the statement of comprehensive income and the repayment of the principal portion of the lease liability will be classified as a financing activity while the interest component will be included in the operating section of the statement of cash flows. ASU 2016-02 is effective for annual and interim reporting periods beginning after December 15, 2018. Early adoption is permitted. Upon adoption, leases will be recognized and measured at the beginning of the earliest period presented using a modified retrospective approach. The Company does not believe the adoption of ASU 2016-02 will have a material effect on its consolidated financial statements. In August 2016, the FASB issued ASU 2016-15, Classification of Certain Cash Receipts and Cash Payments ("ASU 2016-15"). The objective of ASU 2016-15 is to reduce diversity in the classification of cash receipts and payments for specific cash flow issues, including debt prepayment or debt extinguishment costs, contingent consideration payments made after a business combination and proceeds from the settlement of insurance claims. ASU 2016-15 is effective for fiscal years beginning after December 31, 2017, and interim periods within those fiscal years. Early adoption of ASU 2016-15 is permitted. The Company does not believe the adoption of ASU 2016-15 will have a material effect on its consolidated financial statements. In January 2017, the FASB issued 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. ASU 2017-04 is effective for annual and interim reporting periods beginning after December 15, 2019. Early adoption is permitted. The Company does not believe the adoption of ASU 2017-04 will have a material effect on its consolidated financial statements.

Acquisitions, Deconsolidation a

Acquisitions, Deconsolidation and Discontinued Operations (Notes)	6 Months Ended
	Jun. 30, 2017
Acquisition, Deconsolidation and Discontinued Operations [Abstract]
Disposal Groups, Including Discontinued Operations, Disclosure [Text Block]	ACQUISITIONS, DECONSOLIDATION AND DISCONTINUED OPERATIONS (a) Acquisitions CMC Industries, Inc.: On July 14, 2016, the Company completed the acquisition of 81.0% of CMC Industries, Inc. ("CMC") for cash consideration of $1.5 million . As further discussed in Note 17 , " Segmented Information ," CMC is included in the Leased Real Estate segment. CMC owns, through an indirect wholly owned subsidiary (the "Property Owner"), a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property"). The Real Property is leased to a third party pursuant to a long-term triple net lease. Effective beginning the first quarter of 2017, the Company executed a lease amendment between CMC and its tenant under which the tenant will pay an aggregate $25.0 million of additional rental income through May 2034, the remaining term of the lease. The Real Property is also subject to 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 (including the Property Owner), and the Mortgage is not, nor will it be, guaranteed by Kingsway or its affiliates. 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. During the fourth quarter of 2016, the Company completed its fair value analysis on the assets acquired and liabilities assumed. Goodwill of $61.0 million was recognized. The goodwill is not deductible for tax purposes. Separately identifiable intangible assets of $74.8 million were recognized resulting from the valuations of in-place lease and a tenant relationship. Refer to Note 9 , " Intangible Assets ," for further disclosure of the intangible assets related to this acquisition. 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 . Refer to Note 11 , " Debt ," for further discussion of the Mortgage. The Company also recognized a below market lease liability of $0.9 million , which is included in accrued expenses and other liabilities. The below market lease liability resulted from the terms of the acquired operating lease contract being unfavorable relative to market terms of comparable leases on the date of acquisition. The below market lease liability is amortized on a straight-line basis over the remaining term of the lease, as determined at the acquisition date. Amortization of below market lease liabilities is included in rental income in the consolidated statements of operations. Argo Management Group LLC: Effective April 21, 2016, the Company issued 160,000 shares of its common stock to acquire Argo Management Group LLC ("Argo"). The Argo purchase price of $0.7 million was determined using the closing price of Kingsway common stock on the date the 160,000 shares were issued. Argo’s primary business is to act as the Managing Member of Argo Holdings Fund I, LLC, an investment fund organized for purposes of making control-oriented equity investments in established lower middle market companies based in North America, with a focus on search fund investments. 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. During the second quarter of 2016, the Company completed its fair value analysis on the assets acquired and liabilities assumed. Separately identifiable intangible assets of $0.7 million were recognized resulting from the valuations of contract-based management fee and promote fee revenues. Refer to Note 9 , " Intangible Assets ," for further disclosure of the intangible assets related to this acquisition. (b) Deconsolidation 1347 Investors LLC: At June 30, 2016, the Company owned 61.0% of the outstanding units of 1347 Investors LLC ("1347 Investors"). Because the Company owned more than 50% of the outstanding units, 1347 Investors was included in the unaudited consolidated interim financial statements of the Company. 1347 Investors had an investment in the common stock and private units of 1347 Capital Corp., which was reflected in investment in investee in the consolidated balance sheets. 1347 Capital Corp., which completed an initial public offering on July 21, 2014 and had 24 months from the date of the initial public offering to complete a successful business combination, was formed for the purpose of entering into a merger, share exchange, asset acquisition or other similar business combination with one or more businesses or entities. On March 23, 2016, 1347 Capital Corp. announced the signing of a definitive agreement with Limbach Holdings LLC ("Limbach"), in which 1347 Capital Corp. would merge with Limbach. On July 21, 2016, Limbach announced the closing of the previously announced merger, and 1347 Capital Corp. was renamed Limbach Holdings, Inc. As a result of this transaction, the Company's ownership percentage in 1347 Investors was reduced to 26.7% at the transaction date. Subsequent to the transaction date, the Company is accounting for its remaining noncontrolling investment in 1347 Investors at fair value. (c) Discontinued Operations On April 1, 2015, the Company closed on the sale of its subsidiary, Assigned Risk Solutions Ltd. ("ARS") for $47.0 million in cash. During the second quarter of 2015, the Company received additional post-closing cash consideration of $2.0 million . The terms of the sale also provide for potential receipt by the Company of future earnout payments equal to 1.25% of ARS' written premium and fee income during the earnout periods. The earnout payments are payable in three annual installments beginning in April 2016 through April 2018. During the second quarters of 2017 and 2016 , the Company received cash consideration, before expenses, of $1.3 million and $1.4 million , respectively, representing the first two annual installment earnout payments. Net of expenses, the Company recorded an additional gain on disposal of ARS of $1.0 million and $1.1 million for the three and six months ended June 30, 2017 and 2016 , respectively. As a result of the sale, ARS, previously disclosed as part of the Extended Warranty (formerly Insurance Services) segment, has been classified as a discontinued operation. The earnings of ARS are disclosed as discontinued operations in the unaudited consolidated statements of operations for all periods presented. Summary financial information included in income from discontinued operations, net of taxes for the three and six months ended June 30, 2017 and June 30, 2016 is presented below: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Gain on disposal of discontinued operations before income tax benefit $ 1,017 $ 1,124 $ 1,017 $ 1,124 Income tax benefit — — — — Gain on disposal of discontinued operations, net of taxes $ 1,017 $ 1,124 $ 1,017 $ 1,124

Investments

Investments	6 Months Ended
	Jun. 30, 2017
Investments [Abstract]
Summary of Investments, Other than Investments in Related Parties [Text Block]	INVESTMENTS The amortized cost, gross unrealized gains and losses, and estimated fair value of the Company's investments in fixed maturities and equity investments at June 30, 2017 and December 31, 2016 are summarized in the tables shown below: (in thousands) June 30, 2017 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 27,033 $ 24 $ 153 $ 26,904 States, municipalities and political subdivisions 3,722 9 37 3,694 Mortgage-backed 8,419 14 80 8,353 Asset-backed securities and collateralized mortgage obligations 2,197 4 6 2,195 Corporate 15,801 98 80 15,819 Total fixed maturities 57,172 149 356 56,965 Equity investments: Common stock 15,222 2,996 602 17,616 Warrants - publicly traded 517 199 78 638 Warrants - not publicly traded 960 227 — 1,187 Total equity investments 16,699 3,422 680 19,441 Total fixed maturities and equity investments $ 73,871 $ 3,571 $ 1,036 $ 76,406 (in thousands) December 31, 2016 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 28,312 $ 22 $ 186 $ 28,148 States, municipalities and political subdivisions 3,131 1 44 3,088 Mortgage-backed 8,610 12 116 8,506 Asset-backed securities and collateralized mortgage obligations 3,468 4 5 3,467 Corporate 18,615 94 154 18,555 Total fixed maturities 62,136 133 505 61,764 Equity investments: Common stock 17,701 4,156 431 21,426 Warrants - publicly traded 438 279 53 664 Warrants - not publicly traded 960 180 — 1,140 Total equity investments 19,099 4,615 484 23,230 Total fixed maturities and equity investments $ 81,235 $ 4,748 $ 989 $ 84,994 Net unrealized gains and losses in the tables above are reported as other comprehensive (loss) income with the exception of net unrealized gains of $0.2 million , at June 30, 2017 , and $0.2 million , at December 31, 2016 , related to warrants - not publicly traded, which are reported in the consolidated statements of operations. The table below summarizes the Company's fixed maturities at June 30, 2017 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) June 30, 2017 Amortized Cost Estimated Fair Value Due in one year or less $ 7,518 $ 7,504 Due after one year through five years 40,198 40,077 Due after five years through ten years 3,107 3,082 Due after ten years 6,349 6,302 Total $ 57,172 $ 56,965 The following tables highlight the aggregate unrealized loss position, by security type, of fixed maturities and equity investments in unrealized loss positions as of June 30, 2017 and December 31, 2016 . The tables segregate the holdings based on the period of time the investments have been continuously held in unrealized loss positions. (in thousands) June 30, 2017 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 $ 23,371 $ 153 $ — $ — $ 23,371 $ 153 States, municipalities and political subdivisions 2,330 37 — — 2,330 37 Mortgage-backed 7,090 79 136 1 7,226 80 Asset-backed securities and collateralized mortgage obligations 1,092 3 299 3 1,391 6 Corporate 6,870 80 — — 6,870 80 Total fixed maturities 40,753 352 435 4 41,188 356 Equity investments: Common stock 1,317 146 666 456 1,983 602 Warrants 258 31 1 47 259 78 Total equity investments 1,575 177 667 503 2,242 680 Total $ 42,328 $ 529 $ 1,102 $ 507 $ 43,430 $ 1,036 (in thousands) December 31, 2016 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 $ 18,509 $ 186 $ — $ — $ 18,509 $ 186 States, municipalities and political subdivisions 2,594 44 — — 2,594 44 Mortgage-backed 7,709 116 58 — 7,767 116 Asset-backed securities and collateralized mortgage obligations 1,830 5 44 — 1,874 5 Corporate 10,956 154 — — 10,956 154 Total fixed maturities 41,598 505 102 — 41,700 505 Equity investments: Common stock 900 293 868 138 1,768 431 Warrants 31 20 — 33 31 53 Total equity investments 931 313 868 171 1,799 484 Total $ 42,529 $ 818 $ 970 $ 171 $ 43,499 $ 989 Fixed maturities and equity investments contain approximately 168 and 173 individual investments that were in unrealized loss positions as of June 30, 2017 and December 31, 2016 , 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 the 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, there were no write-downs for other-than-temporary impairments related to investments recorded for the three and six months ended June 30, 2017 and June 30, 2016 . 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, limited partnerships and a general partnership that primarily invest in income-producing real estate or real estate related investments. 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 June 30, 2017 and December 31, 2016 , the carrying value of limited liability investments totaled $25.5 million and $23.0 million , respectively. At June 30, 2017 , the Company has unfunded commitments totaling $1.2 million to fund limited liability investments. 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 (loss) income. Limited liability investment, at fair value represents the Company's investment in 1347 Investors. In connection with the deconsolidation of 1347 Investors during the third quarter of 2016, the Company retained a minority investment in 1347 Investors. The Company made an irrevocable election to account for this investment at fair value. As of June 30, 2017 and December 31, 2016 , the carrying value of the Company's limited liability investment, at fair value was $8.2 million and $10.7 million , respectively. At June 30, 2017 , there was no unfunded commitment related to the limited liability investment, at fair value. Other investments include mortgage and collateral loans and are reported at their unpaid principal balance. As of June 30, 2017 and December 31, 2016 , the carrying value of other investments totaled $7.6 million and $8.0 million , respectively. The Company had previously entered into two separate performance share grant agreements with 1347 Property Insurance Holdings, Inc. ("PIH"), whereby the Company will be entitled to receive up to an aggregate of 475,000 shares of PIH common stock upon achievement of certain milestones for PIH’s stock price. Pursuant to the performance share grant agreements, if at any time the last sales price of PIH’s common stock equals or exceeds: (i) $10.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 100,000 shares of PIH common stock; (ii) $12.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 100,000 shares of common stock earned pursuant to clause (i) herein); (iii) $15.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 225,000 shares of common stock earned pursuant to clauses (i) and (ii) herein); and (iv) $18.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 350,000 shares of common stock earned pursuant to clauses (i), (ii) and (iii) herein). To the extent shares of PIH common stock are granted to the Company under either of the performance share grant agreements, they will be recorded at the time the shares are granted and will have a valuation equal to the last sales price of PIH common stock on the day prior to such grant. No shares were received by the Company under either of the performance share grant agreements as of June 30, 2017 . Refer to Note 18 , " Fair Value of Financial Instruments ," for further details regarding the performance shares. Gross realized gains and losses on fixed maturities and equity investments for the three and six months ended June 30, 2017 and June 30, 2016 are comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Gross realized gains $ 735 $ 214 $ 1,159 $ 248 Gross realized losses (1 ) (147 ) (27 ) (352 ) Net realized gains (losses) $ 734 $ 67 $ 1,132 $ (104 ) Net investment (loss) income for the three and six months ended June 30, 2017 and June 30, 2016 is comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Investment (loss) income: Interest from fixed maturities $ 228 $ 242 $ 434 $ 460 Dividends 127 126 269 392 (Loss) income from limited liability investments (581 ) 511 (281 ) 310 Loss on change in fair value of limited liability investment, at fair value (2,113 ) — (2,480 ) — (Loss) gain on change in fair value of warrants - not publicly traded (198 ) 141 47 (246 ) Other 205 100 415 139 Gross investment (loss) income (2,332 ) 1,120 (1,596 ) 1,055 Investment expenses (34 ) (48 ) (67 ) (55 ) Net investment (loss) income $ (2,366 ) $ 1,072 $ (1,663 ) $ 1,000 Fixed maturities and short-term investments with an estimated fair value of $12.8 million and $13.1 million were on deposit with state and provincial regulatory authorities at June 30, 2017 and December 31, 2016 , respectively. From time to time, the Company pledges investments to third parties as deposits or to collateralize liabilities incurred under its policies of insurance. The amount of such pledged investments was $16.9 million and $16.4 million at June 30, 2017 and December 31, 2016 , respectively.

Investment in Investees (Notes)

Investment in Investees (Notes)	6 Months Ended
	Jun. 30, 2017
Schedule of Equity Method Investments [Line Items]
Equity Method Investments and Joint Ventures Disclosure [Text Block]	INVESTMENT IN INVESTEE Investment in investee includes the Company's investment in the common stock of Itasca Capital Ltd. ("ICL") and is accounted for under the equity method. Prior to the second quarter of 2016, the Company's investment in ICL was included in equity investments in the consolidated balance sheets. During the second quarter of 2016, the Company's ownership percentage in ICL was increased to 31.2% . As a result of this change in ownership, the Company determined its investment in the common stock of ICL qualified for the equity method of accounting and, thus, is included in investment in investee in the consolidated balance sheets at June 30, 2017 and December 31, 2016 . The Company's investment in ICL is recorded on a three-month lag basis. The carrying value, estimated fair value and approximate equity percentage for the Company's investment in ICL at June 30, 2017 and December 31, 2016 were as follows: (in thousands, except for percentages) June 30, 2017 December 31, 2016 Equity Percentage Estimated Fair Value Carrying Value Equity Percentage Estimated Fair Value Carrying Value ICL 31.2 % $ 4,192 $ 5,355 31.2 % $ 4,251 $ 3,116 The estimated fair value of the Company's investment in ICL at June 30, 2017 in the table above is calculated based on the published closing price of ICL at March 31, 2017 to be consistent with the three-month lag in reporting its carrying value under the equity method. The estimated fair value of the Company's investment in ICL based on the published closing price of ICL at June 30, 2017 is $3.7 million . Equity in net loss of investee of $0.1 million and equity in net income of investee of $2.2 million for the three and six months ended June 30, 2017 , respectively, relates to the Company's investment in ICL. The Company previously had an investment in the common stock and private units of 1347 Capital Corp., which was included in investment in investee in the consolidated balance sheet at June 30, 2016 . Equity in net loss of investees of $0.9 million and $0.9 million for the three and six months ended June 30, 2016 , respectively, relates to the Company's investment in 1347 Capital Corp.

Deferred Acquisition Costs

Deferred Acquisition Costs	6 Months Ended
	Jun. 30, 2017
Deferred Acquisition Costs [Abstract]
Deferred Policy Acquisition Costs [Text Block]	DEFERRED ACQUISITION COSTS Policy acquisition costs consist primarily of commissions, premium taxes, and underwriting and agency expenses, net of ceding commission income, incurred related to successful efforts to acquire new or renewal insurance contracts and vehicle service agreements. Acquisition costs deferred on both property and casualty insurance products and vehicle service agreements are amortized over the period in which the related revenues are earned. The components of deferred acquisition costs and the related amortization expense for the three and six months ended June 30, 2017 and June 30, 2016 are comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Beginning balance, net $ 14,113 $ 13,440 $ 13,609 $ 12,143 Additions 7,011 7,180 14,698 14,769 Amortization (7,415 ) (6,796 ) (14,598 ) (13,088 ) Balance at June 30, net $ 13,709 $ 13,824 $ 13,709 $ 13,824

Intangible Assets

Intangible Assets	6 Months Ended
	Jun. 30, 2017
Intangible Assets [Abstract]
Intangible Assets Disclosure [Text Block]	9 INTANGIBLE ASSETS Intangible assets at June 30, 2017 and December 31, 2016 are comprised as follows: (in thousands) June 30, 2017 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 2,275 $ 2,643 Vehicle service agreements in-force 3,680 3,597 83 Customer relationships 3,611 1,748 1,863 In-place lease 1,125 60 1,065 Contract-based revenues 731 81 650 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Insurance licenses 7,553 — 7,553 Trade name 663 — 663 Total $ 95,948 $ 7,761 $ 88,187 (in thousands) December 31, 2016 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 2,029 $ 2,889 Vehicle service agreements in-force 3,680 3,554 126 Customer relationships 3,611 1,521 2,090 In-place lease 1,125 29 1,096 Contract-based revenues 731 48 683 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Insurance licenses 7,803 — 7,803 Trade name 663 — 663 Total $ 96,198 $ 7,181 $ 89,017 As further discussed in Note 5 , " Acquisitions, Deconsolidation and Discontinued Operations ," during 2016, the Company recorded $74.8 million of separately identifiable intangible assets related to in-place lease and tenant relationship, as part of the acquisition of CMC. The in-place lease intangible asset of $1.1 million is being amortized on a straight-line basis over its estimated useful life of approximately 18 years, which is based on the term of the existing operating lease. The tenant relationship intangible asset of $73.7 million relates to a single long-term tenant relationship. The Company has determined there are no legal, regulatory, contractual, competitive, economic or other factors limiting the useful life of the tenant relationship; therefore, the tenant relationship intangible asset is deemed to have an indefinite useful life and is not amortized. As further discussed in Note 5 , " Acquisitions, Deconsolidation and Discontinued Operations ," during the second quarter of 2016, the Company recorded $0.7 million of separately identifiable intangible assets for contract-based management fee and promote fee revenues as part of the acquisition of Argo. The contract-based management fee revenue intangible asset is being amortized over nine years. The contract-based promote fee revenue intangible asset is being amortized over a three-year period beginning in 2022. The amortization periods for the contract-based revenues intangible assets are based on the patterns in which the economic benefits of the intangible assets are expected to be consumed. 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 seven to fifteen years. Amortization of intangible assets was $0.3 million and $0.3 million for the three months ended June 30, 2017 and June 30, 2016 , respectively ( $0.6 million and $0.6 million for the six months ended June 30, 2017 and June 30, 2016 , respectively). The tenant relationship, insurance licenses and trade name intangible assets have indefinite useful lives and are not amortized. During the six months ended June 30, 2017 , the Company recorded an impairment charge of $0.3 million related to its insurance licenses indefinite lived intangible asset. The impairment recorded was the result of Mendota Insurance Company ("Mendota") and Mendakota Insurance Company ("Mendakota") surrendering their insurance licenses in the state of New Mexico during the first quarter of 2017.

Unpaid Loss and Loss Adjustment

Unpaid Loss and Loss Adjustment Expenses	6 Months Ended
	Jun. 30, 2017
Unpaid loss and loss adjustment [Abstract]
Liability for Future Policy Benefits and Unpaid Claims Disclosure [Text Block]	10 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. (a) Property and Casualty The results of this comparison and the changes in the provision for property and casualty unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of June 30, 2017 and June 30, 2016 were as follows: (in thousands) June 30, 2017 June 30, 2016 Balance at beginning of period, gross $ 53,795 $ 55,471 Less reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 681 1,207 Balance at beginning of period, net 53,114 54,264 Incurred related to: Current year 50,324 45,614 Prior years 996 67 Paid related to: Current year (23,094 ) (22,060 ) Prior years (35,975 ) (26,535 ) Balance at end of period, net 45,365 51,350 Plus reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 509 845 Balance at end of period, gross $ 45,874 $ 52,195 The Company reported unfavorable development on property and casualty unpaid loss and loss adjustment expenses of $1.0 million and $0.1 million for the six months ended June 30, 2017 and June 30, 2016 , respectively. The unfavorable development for the six months ended June 30, 2017 was primarily related to an increase in property and casualty loss and loss adjustment expenses at Mendota. The unfavorable development reported for the six months ended June 30, 2016 was primarily related to property and casualty loss and loss adjustment expenses at Mendota, partially offset by a decrease in property and casualty unpaid loss and loss adjustment expenses at Amigo. (b) Vehicle Service Agreements The results of the comparison and the changes in the provision for vehicle service agreement unpaid loss and loss adjustment expenses as of June 30, 2017 and June 30, 2016 were as follows: (in thousands) June 30, 2017 June 30, 2016 Balance at beginning of period $ 2,915 $ 2,975 Incurred related to: Current year 2,558 2,654 Prior years — — Paid related to: Current year (2,616 ) (2,502 ) Prior years (63 ) (152 ) Balance at end of period $ 2,794 $ 2,975

Debt

Debt	6 Months Ended
	Jun. 30, 2017
Debt Instruments [Abstract]
Debt Disclosure [Text Block]	11 DEBT Debt consists of the following instruments at June 30, 2017 and December 31, 2016 : (in thousands) June 30, 2017 December 31, 2016 Principal Carrying Value Fair Value Principal Carrying Value Fair Value Note payable $ 177,518 $ 188,328 $ 186,341 $ 178,781 $ 190,074 $ 190,074 Subordinated debt 90,500 48,210 48,210 90,500 43,619 43,619 Total $ 268,018 $ 236,538 $ 234,551 $ 269,281 $ 233,693 $ 233,693 As further discussed in Note 5 , " Acquisitions, Deconsolidation and Discontinued Operations ," as part of the acquisition of CMC, the Mortgage, which is recorded as note payable in the consolidated balance sheets, 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. The subordinated debt is carried in the consolidated balance sheets at fair value. See Note 18 , " Fair Value of Financial Instruments ," for further discussion of the subordinated debt. Subordinated debt 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 1/8/2004 annual interest rate equal to LIBOR, plus 4.00% payable quarterly 1/8/2034

Finance Lease Obligation Liabil

Finance Lease Obligation Liability (Notes)	6 Months Ended
	Jun. 30, 2017
Asset Retirement Obligation [Abstract]
Schedule of Asset Retirement Obligations [Table Text Block]	FINANCE LEASE OBLIGATION LIABILITY On October 2, 2014, the Company completed a sale and leaseback transaction involving building and land located in Miami, Florida, which was previously recorded as asset held for sale. The transaction did not qualify for sales recognition and was accounted for as a financing due to the Company's continuing involvement with the property as a result of nonrecourse financing provided to the buyer in the form of prepaid rent. A finance lease obligation liability equal to the selling price of the property was established at the date of the transaction. During the lease term, the Company will record interest expense on the finance lease obligation at its incremental borrowing rate and will increase the finance lease obligation liability by the same amount. During the second quarter of 2017, the Company was informed of the landlord's intent to terminate the lease agreement effective October 10, 2017. The Company has the option to vacate the property and effectively terminate the lease earlier than October 10, 2017. Upon termination of the lease, the Company will no longer have continuing involvement with the property and will, then, recognize the sale of the property as well as a related gain of approximately $0.7 million . The gain will result primarily from removing the carrying values of the land, building and finance lease obligation liability from the consolidated balance sheets and from the return of part of the original prepaid rent. At June 30, 2017 and December 31, 2016 , finance lease obligation liability of $5.1 million and $5.1 million , respectively, is included in accrued expenses and other liabilities in the consolidated balance sheets. At June 30, 2017 and December 31, 2016 , the carrying value of the land and building of $4.7 million and $4.8 million , respectively, is included in property and equipment in the consolidated balance sheets.

Income Taxes

Income Taxes	6 Months Ended
	Jun. 30, 2017
Income Tax Disclosure [Abstract]
Income Tax Disclosure [Text Block]	INCOME TAXES Income tax expense for the three and six months ended June 30, 2017 and June 30, 2016 varies from the amount that would result by applying the applicable United States corporate income tax rate of 34% to loss before income tax expense. The following table summarizes the differences: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Income tax benefit at United States statutory income tax rate $ (2,519 ) $ (671 ) $ (2,962 ) $ (1,170 ) Valuation allowance 2,401 251 2,945 640 Indefinite life intangibles 1,058 22 1,005 44 Change in unrecognized tax benefits (1) 160 — 372 — Non-deductible compensation 101 381 200 449 Foreign operations subject to different tax rates 45 38 (94 ) 74 Other 5 5 (36 ) 15 Income tax expense $ 1,251 $ 26 $ 1,430 $ 52 (1) Includes interest and penalty expense related to unrecognized tax benefits. The Company maintains a valuation allowance for its gross deferred tax assets at June 30, 2017 and December 31, 2016 . 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 June 30, 2017 and December 31, 2016 net deferred tax asset, excluding the deferred income tax liability amounts set forth in the paragraph below. The Company carries a deferred income tax liability of $49.7 million and $48.7 million at June 30, 2017 and December 31, 2016 , respectively. At June 30, 2017 , $13.4 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 and $36.3 million relates to land and indefinite lived intangible assets. At December 31, 2016, $13.4 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 and $35.3 million relates to land and indefinite lived intangible assets. The Company considered a tax planning strategy in arriving at its June 30, 2017 and December 31, 2016 deferred income tax liability. As of June 30, 2017 and December 31, 2016 , the Company carried a liability for unrecognized tax benefits of $1.3 million and $1.3 million , respectively, 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 $0.2 million and zero related to interest and penalty accruals for the three months ended June 30, 2017 and June 30, 2016 , respectively ( $0.4 million and zero for the six months ended June 30, 2017 and June 30, 2016 , respectively). At June 30, 2017 and December 31, 2016 , the Company carried an accrual for the payment of interest and penalties of $0.8 million and $0.4 million , respectively, included in income taxes payable in the consolidated balance sheets.

Loss per Share

Loss per Share	6 Months Ended
	Jun. 30, 2017
Net Loss per Share [Abstract]
Earnings Per Share [Text Block]	LOSS FROM CONTINUING OPERATIONS PER SHARE The following table sets forth the reconciliation of numerators and denominators for the basic and diluted loss from continuing operations per share computation for the three and six months ended June 30, 2017 and June 30, 2016 : (in thousands, except per share data) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Numerator: Loss from continuing operations $ (8,659 ) $ (1,999 ) $ (10,143 ) $ (3,494 ) (Less) plus: net (income) loss attributable to noncontrolling interests (100 ) 361 (205 ) 400 Less: dividends on preferred stock (123 ) (82 ) (244 ) (164 ) Loss from continuing operations attributable to common shareholders $ (8,882 ) $ (1,720 ) $ (10,592 ) $ (3,258 ) Denominator: Weighted-average common shares outstanding 21,458 19,818 21,458 19,764 Effect of potentially dilutive securities — — — — Weighted-average diluted shares 21,458 19,818 21,458 19,764 Basic loss from continuing operations per share $ (0.41 ) $ (0.09 ) $ (0.49 ) $ (0.16 ) Diluted loss from continuing operations per share $ (0.41 ) $ (0.09 ) $ (0.49 ) $ (0.16 ) Basic loss from continuing operations per share is calculated using weighted-average common shares outstanding. Diluted loss from continuing operations 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, unvested restricted stock units, warrants and convertible preferred stock. Because the Company is reporting a loss from continuing operations for the three and six months ended June 30, 2017 and June 30, 2016 , all potentially dilutive securities outstanding were excluded from the calculation of diluted loss from continuing operations per share since their inclusion would have been anti-dilutive.

Stock-Based Compensation

Stock-Based Compensation	6 Months Ended
	Jun. 30, 2017
Stock-Based Compensation [Abstract]
Disclosure of Compensation Related Costs, Share-based Payments [Text Block]	STOCK-BASED COMPENSATION (a) Stock Options The following table summarizes the stock option activity during the six months ended June 30, 2017 : Number of Options Outstanding Weighted-Average Exercise Price Weighted-Average Remaining Contractual Term (in Years) Aggregate Intrinsic Value (in Thousands) Outstanding at December 31, 2016 651,875 $ 4.51 1.4 $ 1,134 Granted — — Expired — — Outstanding at June 30, 2017 651,875 $ 4.51 0.9 $ 1,004 Exercisable at June 30, 2017 651,875 $ 4.51 0.9 $ 1,004 The aggregate intrinsic value of stock options outstanding and exercisable is the difference between the June 30, 2017 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 six months ended June 30, 2017 . (b) Restricted Stock Awards Under the 2013 Equity Incentive Plan, the Company made grants of restricted common stock awards ("Restricted Stock Awards") to certain officers of the Company on March 28, 2014. The 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 Restricted Stock Awards are amortized on a straight-line basis over the ten-year requisite service period. Total unamortized compensation expense related to unvested Restricted Stock Awards at June 30, 2017 was $5.5 million . The grant-date fair value of the Restricted Stock Awards was determined using the closing price of Kingsway common stock on the date of grant. The following table summarizes the activity related to unvested Restricted Stock Awards for the six months ended June 30, 2017 : Number of Restricted Stock Awards Weighted-Average Grant Date Fair Value (per Share) Unvested at December 31, 2016 1,952,665 $ 4.14 Granted — — Forfeited — — Unvested at June 30, 2017 1,952,665 $ 4.14 (c) Restricted Stock Units The Company granted restricted common stock units ("Restricted Stock Units") to an officer of the Company pursuant to a Restricted Stock Unit Agreement dated August 24, 2016. Each Restricted Stock Unit represents a right to receive one common share on the vesting date. The Restricted Stock Units 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 Restricted Stock Units are amortized on a straight-line basis over the requisite service period. Total unamortized compensation expense related to unvested Restricted Stock Units at June 30, 2017 was $2.5 million . The grant-date fair value of the Restricted Stock Units was determined using the closing price of Kingsway common stock on the date of grant. The following table summarizes the activity related to unvested Restricted Stock Units for the six months ended June 30, 2017 : Number of Restricted Stock Units Weighted-Average Grant Date Fair Value (per Share) Unvested at December 31, 2016 500,000 $ 5.73 Granted — — Vested — — Forfeited — — Unvested at June 30, 2017 500,000 $ 5.73 Total stock-based compensation expense, net of forfeitures, was $0.3 million and $0.3 million for the three months ended June 30, 2017 and June 30, 2016 , respectively ( $0.6 million and $0.5 million for the six months ended June 30, 2017 and June 30, 2016 , respectively).

Accumulated Other Comprehensive

Accumulated Other Comprehensive Income	6 Months Ended
	Jun. 30, 2017
Accumulated Other Comprehensive Income [Abstract]
Comprehensive Income (Loss) Note [Text Block]	16 ACCUMULATED OTHER COMPREHENSIVE LOSS The tables below detail the changes in the balances of each component of accumulated other comprehensive loss, net of tax, for the three and six months ended June 30, 2017 and June 30, 2016 as relates to shareholders' equity attributable to common shareholders on the consolidated balance sheets. On the other hand, the unaudited consolidated statements of comprehensive loss present the components of other comprehensive (loss) income, net of tax, only for the three and six months ended June 30, 2017 and June 30, 2016 and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries. (in thousands) Three months ended June 30, 2017 Unrealized Gains (Losses) on Fixed Maturities and Equity Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at April 1, 2017 $ 2,901 $ (3,780 ) $ (879 ) Other comprehensive loss arising during the period (1,066 ) — (1,066 ) Amounts reclassified from accumulated other comprehensive loss 478 — 478 Net current-period other comprehensive loss (588 ) — (588 ) Balance at June 30, 2017 $ 2,313 $ (3,780 ) $ (1,467 ) (in thousands) Three months ended June 30, 2016 Unrealized Gains (Losses) on Fixed Maturities and Equity Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at April 1, 2016 $ 1,137 $ (3,780 ) $ (2,643 ) Other comprehensive income arising during the period 430 — 430 Amounts reclassified from accumulated other comprehensive loss (73 ) — (73 ) Net current-period other comprehensive income 357 — 357 Balance at June 30, 2016 $ 1,494 $ (3,780 ) $ (2,286 ) (in thousands) Six months ended June 30, 2017 Unrealized Gains (Losses) on Fixed Maturities and Equity Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at January 1, 2017 $ 3,572 $ (3,780 ) $ (208 ) Other comprehensive loss arising during the period (1,230 ) — (1,230 ) Amounts reclassified from accumulated other comprehensive loss (29 ) — (29 ) Net current-period other comprehensive loss (1,259 ) — (1,259 ) Balance at June 30, 2017 $ 2,313 $ (3,780 ) $ (1,467 ) (in thousands) Six months ended June 30, 2016 Unrealized Gains (Losses) on Fixed Maturities and Equity Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at January 1, 2016 $ 1,294 $ (3,780 ) $ (2,486 ) Other comprehensive income arising during the period 705 — 705 Amounts reclassified from accumulated other comprehensive loss (505 ) — (505 ) Net current-period other comprehensive loss 200 — 200 Balance at June 30, 2016 $ 1,494 $ (3,780 ) $ (2,286 ) Components of accumulated other comprehensive loss were reclassified to the following lines of the unaudited consolidated statements of operations for the three and six months ended June 30, 2017 and June 30, 2016 : (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Reclassification of accumulated other comprehensive loss from unrealized gains (losses) on fixed maturities and equity investments to: Net realized (losses) gains $ (478 ) $ 73 $ 29 $ 505 Other-than-temporary impairment loss — — — — Loss before income tax expense (478 ) 73 29 505 Income tax expense — — — — Net (loss) gain $ (478 ) $ 73 29 505

Segmented Information

Segmented Information	6 Months Ended
	Jun. 30, 2017
Segmented Information [Abstract]
Segment Reporting Disclosure [Text Block]	SEGMENTED INFORMATION The Company conducts its business through the following three reportable segments: Insurance Underwriting, Extended Warranty (formerly Insurance Services) and Leased Real Estate. Insurance Underwriting Segment Insurance Underwriting includes the following subsidiaries of the Company: Mendota, Mendakota, Mendakota Casualty Company ("MCC"), Kingsway Amigo Insurance Company ("Amigo") and Kingsway Reinsurance Corporation (collectively, "Insurance Underwriting"). Insurance Underwriting principally offers personal automobile insurance to drivers who do not meet the criteria for coverage by standard automobile insurers. Insurance Underwriting has policyholders in 12 states; however, new business is accepted in only eight states. The Company previously placed Amigo and MCC into voluntary run-off in 2012 and 2011, respectively. Each of Amigo and MCC entered into a comprehensive run-off plan that was approved by its respective state of domicile. Kingsway continues to manage Amigo and MCC in a manner consistent with the run-off plans. During the first quarter of 2015, MCC sent a letter of intent to the Illinois Department of Insurance to resume writing private passenger automobile policies in the state of Illinois. MCC began writing these policies on April 1, 2015. Extended Warranty Segment Extended Warranty includes the following subsidiaries of the Company: IWS Acquisition Corporation ("IWS") and Trinity Warranty Solutions LLC ("Trinity") (collectively, "Extended Warranty"). Prior to the second quarter of 2017, Extended Warranty was referred to as Insurance Services. IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by credit unions in 24 states to their members. Trinity is a provider of warranty products and maintenance support to consumers and businesses in the heating, ventilation, air conditioning, standby generator, commercial LED lighting and refrigeration industries. Trinity distributes its warranty products through original equipment manufacturers, HVAC distributors and commercial and residential contractors. Trinity distributes its maintenance support directly through corporate owners of retail spaces throughout the United States. 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, which 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 (Loss) 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 and six months ended June 30, 2017 and June 30, 2016 were: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Revenues: Insurance Underwriting: Net premiums earned $ 33,518 $ 31,813 $ 66,440 $ 61,240 Other income 2,560 2,665 5,033 4,938 Total Insurance Underwriting 36,078 34,478 71,473 66,178 Extended Warranty: Service fee and commission income 6,873 5,394 13,435 10,716 Other income 51 62 136 116 Total Extended Warranty 6,924 5,456 13,571 10,832 Leased Real Estate: Rental income 3,341 — 6,682 — Other income 160 — 372 — Total Leased Real Estate 3,501 — 7,054 — Total segment revenues 46,503 39,934 92,098 77,010 Net premiums earned not allocated to segments — — — — Net investment (loss) income (2,366 ) 1,072 (1,663 ) 1,000 Net realized gains (losses) 734 67 1,132 (104 ) Other income not allocated to segments 44 64 89 111 Total revenues $ 44,915 $ 41,137 $ 91,656 $ 78,017 The operating income (loss) by reportable segment in the following table is before income taxes and includes revenues and direct segment costs. Total segment operating income (loss) reconciled to the consolidated net loss for the three and six months ended June 30, 2017 and June 30, 2016 was: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Segment operating income (loss): Insurance Underwriting $ (417 ) $ 181 $ (1,159 ) $ (58 ) Extended Warranty 685 (780 ) 1,271 (936 ) Leased Real Estate 872 — 1,790 — Total segment operating income (loss) 1,140 (599 ) 1,902 (994 ) Net investment (loss) income (2,366 ) 1,072 (1,663 ) 1,000 Net realized gains (losses) 734 67 1,132 (104 ) Amortization of intangible assets (289 ) (307 ) (580 ) (602 ) Contingent consideration benefit 212 657 212 657 Impairment of intangible assets — — (250 ) — Interest expense not allocated to segments (1,216 ) (1,108 ) (2,375 ) (2,201 ) Other income and expenses not allocated to segments, net (2,776 ) (1,940 ) (4,736 ) (3,841 ) Foreign exchange losses, net — (9 ) (4 ) (10 ) (Loss) gain on change in fair value of debt (2,702 ) 1,068 (4,591 ) 3,596 Equity in net (loss) income of investee (145 ) (874 ) 2,240 (943 ) Loss from continuing operations before income tax expense (7,408 ) (1,973 ) (8,713 ) (3,442 ) Income tax expense 1,251 26 1,430 52 Net loss from continuing operations $ (8,659 ) $ (1,999 ) $ (10,143 ) $ (3,494 ) Insurance Underwriting net premiums earned by line of business for the three and six months ended June 30, 2017 and June 30, 2016 were: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Insurance Underwriting: Private passenger auto liability $ 22,933 $ 21,656 $ 45,309 $ 41,731 Auto physical damage 10,585 10,157 21,131 19,509 Total net premiums earned $ 33,518 $ 31,813 $ 66,440 $ 61,240

Fair Value of Financial Instrum

Fair Value of Financial Instruments	6 Months Ended
	Jun. 30, 2017
Fair Value of Financial Instruments [Abstract]
Fair Value of Financial Instruments, Policy [Policy Text Block]	FAIR VALUE OF FINANCIAL INSTRUMENTS Fair value amounts represent estimates of the consideration that would currently be agreed upon between knowledgeable, willing parties who are under no compulsion to act. 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 classifies its investments in fixed maturities and equity investments as available-for-sale and reports these investments at fair value. The Company's limited liability investment, at fair value, performance shares, subordinated debt and contingent consideration liabilities are measured and reported at fair value. Fixed maturities and equity investments - 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. 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 investment, at fair value - The fair value of the limited liability investment, at fair value 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. Performance shares - The performance shares, for which no active market exists, are required to be valued at fair value as determined in good faith by the Company. Such determination of fair value would require the Company to develop a model based upon relevant observable market inputs as well as significant unobservable inputs, including developing a sufficiently reliable estimate for an appropriate discount to reflect the illiquidity and unique structure of the security. The Company determined its model for the performance shares was not sufficiently reliable. As a result, the Company has assigned a fair value of zero to the performance shares. Refer to Note 6 , " Investments ," for further details regarding the performance shares. 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. Contingent consideration - The consideration for certain of the Company's acquisitions included future payments to the former owners that are contingent upon the achievement of certain targets over future reporting periods. Liabilities for contingent consideration 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 contingent consideration liabilities is estimated using internal models without relevant observable market inputs. Estimated payments are discounted using present value techniques to arrive at estimated fair value. Contingent consideration liabilities are revalued each reporting period. Changes in the fair value of contingent consideration liabilities can result from changes to one or multiple inputs, including adjustments to the discount rates or changes in the assumed achievement or timing of any targets. Any changes in fair value are reported in the unaudited consolidated statements of operations as contingent consideration benefit. During the second quarter of 2017, the Company settled its remaining contingent consideration liability; therefore, no contingent consideration liability remains on the consolidated balance sheets as of June 30, 2017 . The Company employs a fair value hierarchy to categorize the inputs it uses in valuation techniques to measure the fair value. The extent of use of quoted market prices (Level 1), valuation models using observable market information (Level 2) and internal models without observable market information (Level 3) in the valuation of the Company's financial assets and liabilities measured at fair value on a recurring basis as of June 30, 2017 and December 31, 2016 was as follows: (in thousands) June 30, 2017 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) Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 26,904 $ — $ 26,904 $ — States, municipalities and political subdivisions 3,694 — 3,694 — Mortgage-backed 8,353 — 8,353 — Asset-backed securities and collateralized mortgage obligations 2,195 — 2,195 — Corporate 15,819 — 15,819 — Total fixed maturities 56,965 — 56,965 — Equity investments: Common stock 17,616 17,616 — — Warrants 1,825 638 1,187 — Total equity investments 19,441 18,254 1,187 — Limited liability investment, at fair value 8,220 — 8,220 — Other investments 7,550 — 7,550 — Short-term investments 151 — 151 — Total assets $ 92,327 $ 18,254 $ 74,073 $ — Liabilities: Subordinated debt $ 48,210 $ — $ 48,210 $ — Total liabilities $ 48,210 $ — $ 48,210 $ — (in thousands) December 31, 2016 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) Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 28,148 $ — $ 28,148 $ — States municipalities and political subdivisions 3,088 — 3,088 — Mortgage-backed 8,506 — 8,506 — Asset-backed securities and collateralized mortgage obligations 3,467 — 3,467 — Corporate 18,555 — 18,555 — Total fixed maturities 61,764 — 61,764 — Equity investments: Common stock 21,426 21,426 — — Warrants 1,804 664 1,140 — Total equity investments 23,230 22,090 1,140 — Limited liability investment, at fair value 10,700 — 10,700 — Other investments 7,975 — 7,975 — Short-term investments 401 — 401 — Total assets $ 104,070 $ 22,090 $ 81,980 $ — Liabilities: Subordinated debt $ 43,619 $ — $ 43,619 $ — Contingent consideration 325 — — 325 Total liabilities $ 43,944 $ — $ 43,619 $ 325 The following table provides a reconciliation of the fair value of recurring Level 3 fair value measurements for the three and six months ended June 30, 2017 and June 30, 2016 : (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Contingent consideration: Beginning balance $ 325 $ 1,982 $ 325 $ 1,982 Settlement of contingent consideration liabilities (113 ) (1,000 ) (113 ) (1,000 ) Change in fair value of contingent consideration included in net loss (212 ) (657 ) (212 ) (657 ) Ending balance $ — $ 325 $ — $ 325

Related Party Transactions

Related Party Transactions	6 Months Ended
	Jun. 30, 2017
Related Party Transactions [Abstract]
Related Party Transactions Disclosure [Text Block]	RELATED PARTY TRANSACTIONS 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. Management believes consideration paid for such services in each case approximates fair value. Except where disclosed elsewhere in these unaudited consolidated interim financial statements, the following is a summary of related party transactions. On April 20, 2016, John T. Fitzgerald, the Managing Member of Argo, joined the Company as an Executive Vice President. As part of the agreement to purchase Argo, Mr. Fitzgerald received 160,000 common shares of the Company. On April 21, 2016, the Board of Directors appointed Mr. Fitzgerald as a new director. Pursuant to a Restricted Stock Unit Agreement dated August 24, 2016, the Company granted 500,000 restricted stock units to Mr. Fitzgerald. On December 14, 2016, the Company sold 100,000 shares of PIH common stock to Ballantyne Strong, Inc. ("Ballantyne") at a price of $7.57 per share. Kyle Cerminara is the Chief Executive Officer of Ballantyne and Fundamental Global Investors ("FGI"). FGI is a greater than 5% shareholder of the Company.

Commitment and Contingencies

Commitment and Contingencies	6 Months Ended
	Jun. 30, 2017
Commitments and Contingencies [Abstract]
Commitments and Contingencies Disclosure [Text Block]	COMMITMENTS AND CONTINGENCIES (a) Legal proceedings: In connection with its operations in the ordinary course of business, the Company and its subsidiaries are named as defendants in various actions for damages and costs allegedly sustained by the plaintiffs. While it is not possible to estimate the loss, or range of loss, if any, that may be incurred in connection with any of the various proceedings at this time, it is possible an individual action may result in a loss having a material adverse effect on the Company's financial condition or results of operations. (b) Guarantee: The Company provided an indemnity and hold harmless agreement to a third party for certain customs bonds reinsured by Lincoln General Insurance Company ("Lincoln General") during a period of the time Lincoln General was a subsidiary of the Company. This agreement may require the Company to compensate the third party if Lincoln General is unable to fulfill its obligations relating to the customs bonds. The Company's potential exposure under this agreement is not determinable, and no liability has been recorded in the unaudited consolidated interim financial statements at June 30, 2017 . The third party filed a lawsuit on May 11, 2016 seeking damages of $0.2 million from the Company. The third party’s claim has subsequently been amended to seek damages of $0.9 million from the Company. With respect to this particular lawsuit, the Company does not believe the likelihood of an unfavorable outcome is probable. As a result, no liability has been accrued in the unaudited consolidated interim financial statements at June 30, 2017 with respect to this particular lawsuit. No assurances can be given, however, the Company will not be required to perform under this agreement in a manner that has a material adverse effect on the Company's business, results of operations and financial condition. (c) Commitment: The Company has entered into subscription agreements to commit up to $2.5 million of capital to allow for participation in limited liability investments. At June 30, 2017 , the unfunded commitment was $1.2 million .

Acquisitions, Deconsolidation27

Acquisitions, Deconsolidation and Discontinued Operations Discontinued Operations (Tables)	6 Months Ended
	Jun. 30, 2017
Discontinued Operations and Disposal Groups [Abstract]
Disposal Groups, Including Discontinued Operations [Table Text Block]	(in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Gain on disposal of discontinued operations before income tax benefit $ 1,017 $ 1,124 $ 1,017 $ 1,124 Income tax benefit — — — — Gain on disposal of discontinued operations, net of taxes $ 1,017 $ 1,124 $ 1,017 $ 1,124

Investments (Tables)

Investments (Tables)	6 Months Ended
	Jun. 30, 2017
Investments [Abstract]
Schedule of Unrealized Loss on Investments [Table Text Block]	(in thousands) June 30, 2017 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 27,033 $ 24 $ 153 $ 26,904 States, municipalities and political subdivisions 3,722 9 37 3,694 Mortgage-backed 8,419 14 80 8,353 Asset-backed securities and collateralized mortgage obligations 2,197 4 6 2,195 Corporate 15,801 98 80 15,819 Total fixed maturities 57,172 149 356 56,965 Equity investments: Common stock 15,222 2,996 602 17,616 Warrants - publicly traded 517 199 78 638 Warrants - not publicly traded 960 227 — 1,187 Total equity investments 16,699 3,422 680 19,441 Total fixed maturities and equity investments $ 73,871 $ 3,571 $ 1,036 $ 76,406 (in thousands) December 31, 2016 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 28,312 $ 22 $ 186 $ 28,148 States, municipalities and political subdivisions 3,131 1 44 3,088 Mortgage-backed 8,610 12 116 8,506 Asset-backed securities and collateralized mortgage obligations 3,468 4 5 3,467 Corporate 18,615 94 154 18,555 Total fixed maturities 62,136 133 505 61,764 Equity investments: Common stock 17,701 4,156 431 21,426 Warrants - publicly traded 438 279 53 664 Warrants - not publicly traded 960 180 — 1,140 Total equity investments 19,099 4,615 484 23,230 Total fixed maturities and equity investments $ 81,235 $ 4,748 $ 989 $ 84,994
Investments Classified by Contractual Maturity Date [Table Text Block]	(in thousands) June 30, 2017 Amortized Cost Estimated Fair Value Due in one year or less $ 7,518 $ 7,504 Due after one year through five years 40,198 40,077 Due after five years through ten years 3,107 3,082 Due after ten years 6,349 6,302 Total $ 57,172 $ 56,965
Available-for-sale Securities, Continuous Unrealized Loss Position, Fair Value [Table Text Block]	(in thousands) June 30, 2017 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 $ 23,371 $ 153 $ — $ — $ 23,371 $ 153 States, municipalities and political subdivisions 2,330 37 — — 2,330 37 Mortgage-backed 7,090 79 136 1 7,226 80 Asset-backed securities and collateralized mortgage obligations 1,092 3 299 3 1,391 6 Corporate 6,870 80 — — 6,870 80 Total fixed maturities 40,753 352 435 4 41,188 356 Equity investments: Common stock 1,317 146 666 456 1,983 602 Warrants 258 31 1 47 259 78 Total equity investments 1,575 177 667 503 2,242 680 Total $ 42,328 $ 529 $ 1,102 $ 507 $ 43,430 $ 1,036 (in thousands) December 31, 2016 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 $ 18,509 $ 186 $ — $ — $ 18,509 $ 186 States, municipalities and political subdivisions 2,594 44 — — 2,594 44 Mortgage-backed 7,709 116 58 — 7,767 116 Asset-backed securities and collateralized mortgage obligations 1,830 5 44 — 1,874 5 Corporate 10,956 154 — — 10,956 154 Total fixed maturities 41,598 505 102 — 41,700 505 Equity investments: Common stock 900 293 868 138 1,768 431 Warrants 31 20 — 33 31 53 Total equity investments 931 313 868 171 1,799 484 Total $ 42,529 $ 818 $ 970 $ 171 $ 43,499 $ 989
Schedule of Realized Gain (Loss) [Table Text Block]	(in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Gross realized gains $ 735 $ 214 $ 1,159 $ 248 Gross realized losses (1 ) (147 ) (27 ) (352 ) Net realized gains (losses) $ 734 $ 67 $ 1,132 $ (104 )
Investment Income [Table Text Block]	(in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Investment (loss) income: Interest from fixed maturities $ 228 $ 242 $ 434 $ 460 Dividends 127 126 269 392 (Loss) income from limited liability investments (581 ) 511 (281 ) 310 Loss on change in fair value of limited liability investment, at fair value (2,113 ) — (2,480 ) — (Loss) gain on change in fair value of warrants - not publicly traded (198 ) 141 47 (246 ) Other 205 100 415 139 Gross investment (loss) income (2,332 ) 1,120 (1,596 ) 1,055 Investment expenses (34 ) (48 ) (67 ) (55 ) Net investment (loss) income $ (2,366 ) $ 1,072 $ (1,663 ) $ 1,000

Investments Amortized cost, gro

Investments Amortized cost, gross unrealized gains and losses, and estimated fair value (Tables)	6 Months Ended
	Jun. 30, 2017
Schedule of Available-for-sale Securities [Line Items]
Schedule of Unrealized Loss on Investments [Table Text Block]	(in thousands) June 30, 2017 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 27,033 $ 24 $ 153 $ 26,904 States, municipalities and political subdivisions 3,722 9 37 3,694 Mortgage-backed 8,419 14 80 8,353 Asset-backed securities and collateralized mortgage obligations 2,197 4 6 2,195 Corporate 15,801 98 80 15,819 Total fixed maturities 57,172 149 356 56,965 Equity investments: Common stock 15,222 2,996 602 17,616 Warrants - publicly traded 517 199 78 638 Warrants - not publicly traded 960 227 — 1,187 Total equity investments 16,699 3,422 680 19,441 Total fixed maturities and equity investments $ 73,871 $ 3,571 $ 1,036 $ 76,406 (in thousands) December 31, 2016 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 28,312 $ 22 $ 186 $ 28,148 States, municipalities and political subdivisions 3,131 1 44 3,088 Mortgage-backed 8,610 12 116 8,506 Asset-backed securities and collateralized mortgage obligations 3,468 4 5 3,467 Corporate 18,615 94 154 18,555 Total fixed maturities 62,136 133 505 61,764 Equity investments: Common stock 17,701 4,156 431 21,426 Warrants - publicly traded 438 279 53 664 Warrants - not publicly traded 960 180 — 1,140 Total equity investments 19,099 4,615 484 23,230 Total fixed maturities and equity investments $ 81,235 $ 4,748 $ 989 $ 84,994

Investments Fixed maturities by

Investments Fixed maturities by contractual periods (Tables)	6 Months Ended
	Jun. 30, 2017
Schedule of Held-to-maturity Securities [Line Items]
Investments Classified by Contractual Maturity Date [Table Text Block]	(in thousands) June 30, 2017 Amortized Cost Estimated Fair Value Due in one year or less $ 7,518 $ 7,504 Due after one year through five years 40,198 40,077 Due after five years through ten years 3,107 3,082 Due after ten years 6,349 6,302 Total $ 57,172 $ 56,965
Schedule of Realized Gain (Loss) [Table Text Block]	(in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Gross realized gains $ 735 $ 214 $ 1,159 $ 248 Gross realized losses (1 ) (147 ) (27 ) (352 ) Net realized gains (losses) $ 734 $ 67 $ 1,132 $ (104 )

Investments Continuous Unrealiz

Investments Continuous Unrealized Loss Position (Tables)	6 Months Ended
	Jun. 30, 2017
Schedule of Available-for-sale Securities [Line Items]
Available-for-sale Securities, Continuous Unrealized Loss Position, Fair Value [Table Text Block]	(in thousands) June 30, 2017 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 $ 23,371 $ 153 $ — $ — $ 23,371 $ 153 States, municipalities and political subdivisions 2,330 37 — — 2,330 37 Mortgage-backed 7,090 79 136 1 7,226 80 Asset-backed securities and collateralized mortgage obligations 1,092 3 299 3 1,391 6 Corporate 6,870 80 — — 6,870 80 Total fixed maturities 40,753 352 435 4 41,188 356 Equity investments: Common stock 1,317 146 666 456 1,983 602 Warrants 258 31 1 47 259 78 Total equity investments 1,575 177 667 503 2,242 680 Total $ 42,328 $ 529 $ 1,102 $ 507 $ 43,430 $ 1,036 (in thousands) December 31, 2016 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 $ 18,509 $ 186 $ — $ — $ 18,509 $ 186 States, municipalities and political subdivisions 2,594 44 — — 2,594 44 Mortgage-backed 7,709 116 58 — 7,767 116 Asset-backed securities and collateralized mortgage obligations 1,830 5 44 — 1,874 5 Corporate 10,956 154 — — 10,956 154 Total fixed maturities 41,598 505 102 — 41,700 505 Equity investments: Common stock 900 293 868 138 1,768 431 Warrants 31 20 — 33 31 53 Total equity investments 931 313 868 171 1,799 484 Total $ 42,529 $ 818 $ 970 $ 171 $ 43,499 $ 989

Investments Gross realized gain

Investments Gross realized gains and losses (Tables)	6 Months Ended
	Jun. 30, 2017
Gain (Loss) on Investments [Line Items]
Schedule of Realized Gain (Loss) [Table Text Block]	(in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Gross realized gains $ 735 $ 214 $ 1,159 $ 248 Gross realized losses (1 ) (147 ) (27 ) (352 ) Net realized gains (losses) $ 734 $ 67 $ 1,132 $ (104 )

Investments Investments income

Investments Investments income (Tables)	6 Months Ended
	Jun. 30, 2017
Net Investment Income [Line Items]
Investment Income [Table Text Block]	(in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Investment (loss) income: Interest from fixed maturities $ 228 $ 242 $ 434 $ 460 Dividends 127 126 269 392 (Loss) income from limited liability investments (581 ) 511 (281 ) 310 Loss on change in fair value of limited liability investment, at fair value (2,113 ) — (2,480 ) — (Loss) gain on change in fair value of warrants - not publicly traded (198 ) 141 47 (246 ) Other 205 100 415 139 Gross investment (loss) income (2,332 ) 1,120 (1,596 ) 1,055 Investment expenses (34 ) (48 ) (67 ) (55 ) Net investment (loss) income $ (2,366 ) $ 1,072 $ (1,663 ) $ 1,000

Investment in Investees (Tables

Investment in Investees (Tables)	6 Months Ended
	Jun. 30, 2017
Investment in Investee [Abstract]
Equity Method Investments [Table Text Block]	The carrying value, estimated fair value and approximate equity percentage for the Company's investment in ICL at June 30, 2017 and December 31, 2016 were as follows: (in thousands, except for percentages) June 30, 2017 December 31, 2016 Equity Percentage Estimated Fair Value Carrying Value Equity Percentage Estimated Fair Value Carrying Value ICL 31.2 % $ 4,192 $ 5,355 31.2 % $ 4,251 $ 3,116

Deferred Acquisition Costs (Tab

Deferred Acquisition Costs (Tables)	6 Months Ended
	Jun. 30, 2017
Deferred Acquisition Costs [Line Items]
Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Table Text Block]	The components of deferred acquisition costs and the related amortization expense for the three and six months ended June 30, 2017 and June 30, 2016 are comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Beginning balance, net $ 14,113 $ 13,440 $ 13,609 $ 12,143 Additions 7,011 7,180 14,698 14,769 Amortization (7,415 ) (6,796 ) (14,598 ) (13,088 ) Balance at June 30, net $ 13,709 $ 13,824 $ 13,709 $ 13,824

Intangible Assets (Tables)

Intangible Assets (Tables)	6 Months Ended
	Jun. 30, 2017
Finite-Lived Intangible Assets [Line Items]
Schedule of Finite-Lived Intangible Assets [Table Text Block]	Intangible assets at June 30, 2017 and December 31, 2016 are comprised as follows: (in thousands) June 30, 2017 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 2,275 $ 2,643 Vehicle service agreements in-force 3,680 3,597 83 Customer relationships 3,611 1,748 1,863 In-place lease 1,125 60 1,065 Contract-based revenues 731 81 650 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Insurance licenses 7,553 — 7,553 Trade name 663 — 663 Total $ 95,948 $ 7,761 $ 88,187 (in thousands) December 31, 2016 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 2,029 $ 2,889 Vehicle service agreements in-force 3,680 3,554 126 Customer relationships 3,611 1,521 2,090 In-place lease 1,125 29 1,096 Contract-based revenues 731 48 683 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Insurance licenses 7,803 — 7,803 Trade name 663 — 663 Total $ 96,198 $ 7,181 $ 89,017

Unpaid Loss and Loss Adjustme37

Unpaid Loss and Loss Adjustment Expenses (Tables)	6 Months Ended
	Jun. 30, 2017
Liability for Future Policy Benefit, by Product Segment [Line Items]
Liability for Future Policy Benefits and Unpaid Claims Disclosure [Text Block]	10 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. (a) Property and Casualty The results of this comparison and the changes in the provision for property and casualty unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of June 30, 2017 and June 30, 2016 were as follows: (in thousands) June 30, 2017 June 30, 2016 Balance at beginning of period, gross $ 53,795 $ 55,471 Less reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 681 1,207 Balance at beginning of period, net 53,114 54,264 Incurred related to: Current year 50,324 45,614 Prior years 996 67 Paid related to: Current year (23,094 ) (22,060 ) Prior years (35,975 ) (26,535 ) Balance at end of period, net 45,365 51,350 Plus reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 509 845 Balance at end of period, gross $ 45,874 $ 52,195 The Company reported unfavorable development on property and casualty unpaid loss and loss adjustment expenses of $1.0 million and $0.1 million for the six months ended June 30, 2017 and June 30, 2016 , respectively. The unfavorable development for the six months ended June 30, 2017 was primarily related to an increase in property and casualty loss and loss adjustment expenses at Mendota. The unfavorable development reported for the six months ended June 30, 2016 was primarily related to property and casualty loss and loss adjustment expenses at Mendota, partially offset by a decrease in property and casualty unpaid loss and loss adjustment expenses at Amigo. (b) Vehicle Service Agreements The results of the comparison and the changes in the provision for vehicle service agreement unpaid loss and loss adjustment expenses as of June 30, 2017 and June 30, 2016 were as follows: (in thousands) June 30, 2017 June 30, 2016 Balance at beginning of period $ 2,915 $ 2,975 Incurred related to: Current year 2,558 2,654 Prior years — — Paid related to: Current year (2,616 ) (2,502 ) Prior years (63 ) (152 ) Balance at end of period $ 2,794 $ 2,975

Unpaid Loss and Loss Adjustme38

Unpaid Loss and Loss Adjustment Expenses Insurance Product Line (Tables)	6 Months Ended
	Jun. 30, 2017
Liability for Claims and Claims Adjustment Expense [Line Items]
Liability for Future Policy Benefits and Unpaid Claims Disclosure [Text Block]	10 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. (a) Property and Casualty The results of this comparison and the changes in the provision for property and casualty unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of June 30, 2017 and June 30, 2016 were as follows: (in thousands) June 30, 2017 June 30, 2016 Balance at beginning of period, gross $ 53,795 $ 55,471 Less reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 681 1,207 Balance at beginning of period, net 53,114 54,264 Incurred related to: Current year 50,324 45,614 Prior years 996 67 Paid related to: Current year (23,094 ) (22,060 ) Prior years (35,975 ) (26,535 ) Balance at end of period, net 45,365 51,350 Plus reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 509 845 Balance at end of period, gross $ 45,874 $ 52,195 The Company reported unfavorable development on property and casualty unpaid loss and loss adjustment expenses of $1.0 million and $0.1 million for the six months ended June 30, 2017 and June 30, 2016 , respectively. The unfavorable development for the six months ended June 30, 2017 was primarily related to an increase in property and casualty loss and loss adjustment expenses at Mendota. The unfavorable development reported for the six months ended June 30, 2016 was primarily related to property and casualty loss and loss adjustment expenses at Mendota, partially offset by a decrease in property and casualty unpaid loss and loss adjustment expenses at Amigo. (b) Vehicle Service Agreements The results of the comparison and the changes in the provision for vehicle service agreement unpaid loss and loss adjustment expenses as of June 30, 2017 and June 30, 2016 were as follows: (in thousands) June 30, 2017 June 30, 2016 Balance at beginning of period $ 2,915 $ 2,975 Incurred related to: Current year 2,558 2,654 Prior years — — Paid related to: Current year (2,616 ) (2,502 ) Prior years (63 ) (152 ) Balance at end of period $ 2,794 $ 2,975
Property, Liability and Casualty Insurance Product Line [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Liability for Future Policy Benefits and Unpaid Claims Disclosure [Text Block]	The results of this comparison and the changes in the provision for property and casualty unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of June 30, 2017 and June 30, 2016 were as follows: (in thousands) June 30, 2017 June 30, 2016 Balance at beginning of period, gross $ 53,795 $ 55,471 Less reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 681 1,207 Balance at beginning of period, net 53,114 54,264 Incurred related to: Current year 50,324 45,614 Prior years 996 67 Paid related to: Current year (23,094 ) (22,060 ) Prior years (35,975 ) (26,535 ) Balance at end of period, net 45,365 51,350 Plus reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 509 845 Balance at end of period, gross $ 45,874 $ 52,195

Unpaid Loss and Loss Adjustme39

Unpaid Loss and Loss Adjustment Expenses Vehicle Service Agreements (Tables)	6 Months Ended
	Jun. 30, 2017
Other Insurance Product Line [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Schedule of Liability for Unpaid Claims and Claims Adjustment Expense [Table Text Block]	The results of the comparison and the changes in the provision for vehicle service agreement unpaid loss and loss adjustment expenses as of June 30, 2017 and June 30, 2016 were as follows: (in thousands) June 30, 2017 June 30, 2016 Balance at beginning of period $ 2,915 $ 2,975 Incurred related to: Current year 2,558 2,654 Prior years — — Paid related to: Current year (2,616 ) (2,502 ) Prior years (63 ) (152 ) Balance at end of period $ 2,794 $ 2,975

Debt (Tables)

Debt (Tables)	6 Months Ended
	Jun. 30, 2017
Debt Instrument [Line Items]
Schedule of Carrying Values and Estimated Fair Values of Debt Instruments [Table Text Block]	Debt consists of the following instruments at June 30, 2017 and December 31, 2016 : (in thousands) June 30, 2017 December 31, 2016 Principal Carrying Value Fair Value Principal Carrying Value Fair Value Note payable $ 177,518 $ 188,328 $ 186,341 $ 178,781 $ 190,074 $ 190,074 Subordinated debt 90,500 48,210 48,210 90,500 43,619 43,619 Total $ 268,018 $ 236,538 $ 234,551 $ 269,281 $ 233,693 $ 233,693
Schedule of Subordinated Borrowing [Table Text Block]	Subordinated debt 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 1/8/2004 annual interest rate equal to LIBOR, plus 4.00% payable quarterly 1/8/2034

Income Taxes Income Taxes (tabl

Income Taxes Income Taxes (table) (Tables)	6 Months Ended
	Jun. 30, 2017
Income Tax (table) [Abstract]
Income Tax (Benefit) Expense [Table Text Block]	The following table summarizes the differences: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Income tax benefit at United States statutory income tax rate $ (2,519 ) $ (671 ) $ (2,962 ) $ (1,170 ) Valuation allowance 2,401 251 2,945 640 Indefinite life intangibles 1,058 22 1,005 44 Change in unrecognized tax benefits (1) 160 — 372 — Non-deductible compensation 101 381 200 449 Foreign operations subject to different tax rates 45 38 (94 ) 74 Other 5 5 (36 ) 15 Income tax expense $ 1,251 $ 26 $ 1,430 $ 52 (1) Includes interest and penalty expense related to unrecognized tax benefits.

Loss per Share Net Loss per Sha

Loss per Share Net Loss per Share (Tables)	6 Months Ended
	Jun. 30, 2017
Earnings Per Share, Basic, by Common Class, Including Two Class Method [Line Items]
Schedule of Earnings Per Share, Basic and Diluted [Table Text Block]	The following table sets forth the reconciliation of numerators and denominators for the basic and diluted loss from continuing operations per share computation for the three and six months ended June 30, 2017 and June 30, 2016 : (in thousands, except per share data) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Numerator: Loss from continuing operations $ (8,659 ) $ (1,999 ) $ (10,143 ) $ (3,494 ) (Less) plus: net (income) loss attributable to noncontrolling interests (100 ) 361 (205 ) 400 Less: dividends on preferred stock (123 ) (82 ) (244 ) (164 ) Loss from continuing operations attributable to common shareholders $ (8,882 ) $ (1,720 ) $ (10,592 ) $ (3,258 ) Denominator: Weighted-average common shares outstanding 21,458 19,818 21,458 19,764 Effect of potentially dilutive securities — — — — Weighted-average diluted shares 21,458 19,818 21,458 19,764 Basic loss from continuing operations per share $ (0.41 ) $ (0.09 ) $ (0.49 ) $ (0.16 ) Diluted loss from continuing operations per share $ (0.41 ) $ (0.09 ) $ (0.49 ) $ (0.16 )

Stock-Based Compensation (Table

Stock-Based Compensation (Tables)	6 Months Ended
	Jun. 30, 2017
Stock-Based Compensation [Abstract]
Share-based Compensation, Stock Options, Activity [Table Text Block]	The following table summarizes the stock option activity during the six months ended June 30, 2017 : Number of Options Outstanding Weighted-Average Exercise Price Weighted-Average Remaining Contractual Term (in Years) Aggregate Intrinsic Value (in Thousands) Outstanding at December 31, 2016 651,875 $ 4.51 1.4 $ 1,134 Granted — — Expired — — Outstanding at June 30, 2017 651,875 $ 4.51 0.9 $ 1,004 Exercisable at June 30, 2017 651,875 $ 4.51 0.9 $ 1,004
Schedule of Share-based Payment Award, Stock Options, Valuation Assumptions [Table Text Block]	No options were granted during the six months ended June 30, 2017 .
Schedule of Share-based Compensation, Restricted Stock and Restricted Stock Units Activity [Table Text Block]	The grant-date fair value of the Restricted Stock Awards was determined using the closing price of Kingsway common stock on the date of grant. The following table summarizes the activity related to unvested Restricted Stock Awards for the six months ended June 30, 2017 : Number of Restricted Stock Awards Weighted-Average Grant Date Fair Value (per Share) Unvested at December 31, 2016 1,952,665 $ 4.14 Granted — — Forfeited — — Unvested at June 30, 2017 1,952,665 $ 4.14
Schedule of Share-based Compensation, Restricted Stock Units Award Activity [Table Text Block]	The following table summarizes the activity related to unvested Restricted Stock Units for the six months ended June 30, 2017 : Number of Restricted Stock Units Weighted-Average Grant Date Fair Value (per Share) Unvested at December 31, 2016 500,000 $ 5.73 Granted — — Vested — — Forfeited — — Unvested at June 30, 2017 500,000 $ 5.73

Accumulated Other Comprehensi44

Accumulated Other Comprehensive Income (Tables)	6 Months Ended
	Jun. 30, 2017
Accumulated Other Comprehensive Income [Abstract]
Schedule of Accumulated Other Comprehensive Income (Loss) [Table Text Block]	On the other hand, the unaudited consolidated statements of comprehensive loss present the components of other comprehensive (loss) income, net of tax, only for the three and six months ended June 30, 2017 and June 30, 2016 and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries. (in thousands) Three months ended June 30, 2017 Unrealized Gains (Losses) on Fixed Maturities and Equity Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at April 1, 2017 $ 2,901 $ (3,780 ) $ (879 ) Other comprehensive loss arising during the period (1,066 ) — (1,066 ) Amounts reclassified from accumulated other comprehensive loss 478 — 478 Net current-period other comprehensive loss (588 ) — (588 ) Balance at June 30, 2017 $ 2,313 $ (3,780 ) $ (1,467 ) (in thousands) Three months ended June 30, 2016 Unrealized Gains (Losses) on Fixed Maturities and Equity Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at April 1, 2016 $ 1,137 $ (3,780 ) $ (2,643 ) Other comprehensive income arising during the period 430 — 430 Amounts reclassified from accumulated other comprehensive loss (73 ) — (73 ) Net current-period other comprehensive income 357 — 357 Balance at June 30, 2016 $ 1,494 $ (3,780 ) $ (2,286 )
Reclassification out of Accumulated Other Comprehensive Income [Table Text Block]	(in thousands) Three months ended June 30, 2017 Unrealized Gains (Losses) on Fixed Maturities and Equity Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at April 1, 2017 $ 2,901 $ (3,780 ) $ (879 ) Other comprehensive loss arising during the period (1,066 ) — (1,066 ) Amounts reclassified from accumulated other comprehensive loss 478 — 478 Net current-period other comprehensive loss (588 ) — (588 ) Balance at June 30, 2017 $ 2,313 $ (3,780 ) $ (1,467 ) (in thousands) Three months ended June 30, 2016 Unrealized Gains (Losses) on Fixed Maturities and Equity Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at April 1, 2016 $ 1,137 $ (3,780 ) $ (2,643 ) Other comprehensive income arising during the period 430 — 430 Amounts reclassified from accumulated other comprehensive loss (73 ) — (73 ) Net current-period other comprehensive income 357 — 357 Balance at June 30, 2016 $ 1,494 $ (3,780 ) $ (2,286 ) (in thousands) Six months ended June 30, 2017 Unrealized Gains (Losses) on Fixed Maturities and Equity Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at January 1, 2017 $ 3,572 $ (3,780 ) $ (208 ) Other comprehensive loss arising during the period (1,230 ) — (1,230 ) Amounts reclassified from accumulated other comprehensive loss (29 ) — (29 ) Net current-period other comprehensive loss (1,259 ) — (1,259 ) Balance at June 30, 2017 $ 2,313 $ (3,780 ) $ (1,467 ) (in thousands) Six months ended June 30, 2016 Unrealized Gains (Losses) on Fixed Maturities and Equity Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at January 1, 2016 $ 1,294 $ (3,780 ) $ (2,486 ) Other comprehensive income arising during the period 705 — 705 Amounts reclassified from accumulated other comprehensive loss (505 ) — (505 ) Net current-period other comprehensive loss 200 — 200 Balance at June 30, 2016 $ 1,494 $ (3,780 ) $ (2,286 ) Components of accumulated other comprehensive loss were reclassified to the following lines of the unaudited consolidated statements of operations for the three and six months ended June 30, 2017 and June 30, 2016 : (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Reclassification of accumulated other comprehensive loss from unrealized gains (losses) on fixed maturities and equity investments to: Net realized (losses) gains $ (478 ) $ 73 $ 29 $ 505 Other-than-temporary impairment loss — — — — Loss before income tax expense (478 ) 73 29 505 Income tax expense — — — — Net (loss) gain $ (478 ) $ 73 29 505

Segmented Information (Tables)

Segmented Information (Tables)	6 Months Ended
	Jun. 30, 2017
Segmented Information [Abstract]
Segment Reporting Disclosure [Text Block]	SEGMENTED INFORMATION The Company conducts its business through the following three reportable segments: Insurance Underwriting, Extended Warranty (formerly Insurance Services) and Leased Real Estate. Insurance Underwriting Segment Insurance Underwriting includes the following subsidiaries of the Company: Mendota, Mendakota, Mendakota Casualty Company ("MCC"), Kingsway Amigo Insurance Company ("Amigo") and Kingsway Reinsurance Corporation (collectively, "Insurance Underwriting"). Insurance Underwriting principally offers personal automobile insurance to drivers who do not meet the criteria for coverage by standard automobile insurers. Insurance Underwriting has policyholders in 12 states; however, new business is accepted in only eight states. The Company previously placed Amigo and MCC into voluntary run-off in 2012 and 2011, respectively. Each of Amigo and MCC entered into a comprehensive run-off plan that was approved by its respective state of domicile. Kingsway continues to manage Amigo and MCC in a manner consistent with the run-off plans. During the first quarter of 2015, MCC sent a letter of intent to the Illinois Department of Insurance to resume writing private passenger automobile policies in the state of Illinois. MCC began writing these policies on April 1, 2015. Extended Warranty Segment Extended Warranty includes the following subsidiaries of the Company: IWS Acquisition Corporation ("IWS") and Trinity Warranty Solutions LLC ("Trinity") (collectively, "Extended Warranty"). Prior to the second quarter of 2017, Extended Warranty was referred to as Insurance Services. IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by credit unions in 24 states to their members. Trinity is a provider of warranty products and maintenance support to consumers and businesses in the heating, ventilation, air conditioning, standby generator, commercial LED lighting and refrigeration industries. Trinity distributes its warranty products through original equipment manufacturers, HVAC distributors and commercial and residential contractors. Trinity distributes its maintenance support directly through corporate owners of retail spaces throughout the United States. 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, which 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 (Loss) 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 and six months ended June 30, 2017 and June 30, 2016 were: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Revenues: Insurance Underwriting: Net premiums earned $ 33,518 $ 31,813 $ 66,440 $ 61,240 Other income 2,560 2,665 5,033 4,938 Total Insurance Underwriting 36,078 34,478 71,473 66,178 Extended Warranty: Service fee and commission income 6,873 5,394 13,435 10,716 Other income 51 62 136 116 Total Extended Warranty 6,924 5,456 13,571 10,832 Leased Real Estate: Rental income 3,341 — 6,682 — Other income 160 — 372 — Total Leased Real Estate 3,501 — 7,054 — Total segment revenues 46,503 39,934 92,098 77,010 Net premiums earned not allocated to segments — — — — Net investment (loss) income (2,366 ) 1,072 (1,663 ) 1,000 Net realized gains (losses) 734 67 1,132 (104 ) Other income not allocated to segments 44 64 89 111 Total revenues $ 44,915 $ 41,137 $ 91,656 $ 78,017 The operating income (loss) by reportable segment in the following table is before income taxes and includes revenues and direct segment costs. Total segment operating income (loss) reconciled to the consolidated net loss for the three and six months ended June 30, 2017 and June 30, 2016 was: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Segment operating income (loss): Insurance Underwriting $ (417 ) $ 181 $ (1,159 ) $ (58 ) Extended Warranty 685 (780 ) 1,271 (936 ) Leased Real Estate 872 — 1,790 — Total segment operating income (loss) 1,140 (599 ) 1,902 (994 ) Net investment (loss) income (2,366 ) 1,072 (1,663 ) 1,000 Net realized gains (losses) 734 67 1,132 (104 ) Amortization of intangible assets (289 ) (307 ) (580 ) (602 ) Contingent consideration benefit 212 657 212 657 Impairment of intangible assets — — (250 ) — Interest expense not allocated to segments (1,216 ) (1,108 ) (2,375 ) (2,201 ) Other income and expenses not allocated to segments, net (2,776 ) (1,940 ) (4,736 ) (3,841 ) Foreign exchange losses, net — (9 ) (4 ) (10 ) (Loss) gain on change in fair value of debt (2,702 ) 1,068 (4,591 ) 3,596 Equity in net (loss) income of investee (145 ) (874 ) 2,240 (943 ) Loss from continuing operations before income tax expense (7,408 ) (1,973 ) (8,713 ) (3,442 ) Income tax expense 1,251 26 1,430 52 Net loss from continuing operations $ (8,659 ) $ (1,999 ) $ (10,143 ) $ (3,494 ) Insurance Underwriting net premiums earned by line of business for the three and six months ended June 30, 2017 and June 30, 2016 were: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Insurance Underwriting: Private passenger auto liability $ 22,933 $ 21,656 $ 45,309 $ 41,731 Auto physical damage 10,585 10,157 21,131 19,509 Total net premiums earned $ 33,518 $ 31,813 $ 66,440 $ 61,240
Reconciliation of Revenue from Segments to Consolidated [Table Text Block]	Revenues by reportable segment reconciled to consolidated revenues for the three and six months ended June 30, 2017 and June 30, 2016 were: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Revenues: Insurance Underwriting: Net premiums earned $ 33,518 $ 31,813 $ 66,440 $ 61,240 Other income 2,560 2,665 5,033 4,938 Total Insurance Underwriting 36,078 34,478 71,473 66,178 Extended Warranty: Service fee and commission income 6,873 5,394 13,435 10,716 Other income 51 62 136 116 Total Extended Warranty 6,924 5,456 13,571 10,832 Leased Real Estate: Rental income 3,341 — 6,682 — Other income 160 — 372 — Total Leased Real Estate 3,501 — 7,054 — Total segment revenues 46,503 39,934 92,098 77,010 Net premiums earned not allocated to segments — — — — Net investment (loss) income (2,366 ) 1,072 (1,663 ) 1,000 Net realized gains (losses) 734 67 1,132 (104 ) Other income not allocated to segments 44 64 89 111 Total revenues $ 44,915 $ 41,137 $ 91,656 $ 78,017
Reconciliation of Operating Profit (Loss) from Segments to Consolidated [Table Text Block]	egment operating income (loss) reconciled to the consolidated net loss for the three and six months ended June 30, 2017 and June 30, 2016 was: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Segment operating income (loss): Insurance Underwriting $ (417 ) $ 181 $ (1,159 ) $ (58 ) Extended Warranty 685 (780 ) 1,271 (936 ) Leased Real Estate 872 — 1,790 — Total segment operating income (loss) 1,140 (599 ) 1,902 (994 ) Net investment (loss) income (2,366 ) 1,072 (1,663 ) 1,000 Net realized gains (losses) 734 67 1,132 (104 ) Amortization of intangible assets (289 ) (307 ) (580 ) (602 ) Contingent consideration benefit 212 657 212 657 Impairment of intangible assets — — (250 ) — Interest expense not allocated to segments (1,216 ) (1,108 ) (2,375 ) (2,201 ) Other income and expenses not allocated to segments, net (2,776 ) (1,940 ) (4,736 ) (3,841 ) Foreign exchange losses, net — (9 ) (4 ) (10 ) (Loss) gain on change in fair value of debt (2,702 ) 1,068 (4,591 ) 3,596 Equity in net (loss) income of investee (145 ) (874 ) 2,240 (943 ) Loss from continuing operations before income tax expense (7,408 ) (1,973 ) (8,713 ) (3,442 ) Income tax expense 1,251 26 1,430 52 Net loss from continuing operations $ (8,659 ) $ (1,999 ) $ (10,143 ) $ (3,494 )
Revenue from External Customers by Geographic Areas [Table Text Block]	et premiums earned by line of business for the three and six months ended June 30, 2017 and June 30, 2016 were: (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Insurance Underwriting: Private passenger auto liability $ 22,933 $ 21,656 $ 45,309 $ 41,731 Auto physical damage 10,585 10,157 21,131 19,509 Total net premiums earned $ 33,518 $ 31,813 $ 66,440 $ 61,240

Fair Value of Financial Instr46

Fair Value of Financial Instruments (Tables)	6 Months Ended
	Jun. 30, 2017
Fair Value of Financial Instruments [Abstract]
Fair Value Inputs, Assets, Quantitative Information [Table Text Block]	The Company employs a fair value hierarchy to categorize the inputs it uses in valuation techniques to measure the fair value. The extent of use of quoted market prices (Level 1), valuation models using observable market information (Level 2) and internal models without observable market information (Level 3) in the valuation of the Company's financial assets and liabilities measured at fair value on a recurring basis as of June 30, 2017 and December 31, 2016 was as follows: (in thousands) June 30, 2017 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) Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 26,904 $ — $ 26,904 $ — States, municipalities and political subdivisions 3,694 — 3,694 — Mortgage-backed 8,353 — 8,353 — Asset-backed securities and collateralized mortgage obligations 2,195 — 2,195 — Corporate 15,819 — 15,819 — Total fixed maturities 56,965 — 56,965 — Equity investments: Common stock 17,616 17,616 — — Warrants 1,825 638 1,187 — Total equity investments 19,441 18,254 1,187 — Limited liability investment, at fair value 8,220 — 8,220 — Other investments 7,550 — 7,550 — Short-term investments 151 — 151 — Total assets $ 92,327 $ 18,254 $ 74,073 $ — Liabilities: Subordinated debt $ 48,210 $ — $ 48,210 $ — Total liabilities $ 48,210 $ — $ 48,210 $ — (in thousands) December 31, 2016 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) Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 28,148 $ — $ 28,148 $ — States municipalities and political subdivisions 3,088 — 3,088 — Mortgage-backed 8,506 — 8,506 — Asset-backed securities and collateralized mortgage obligations 3,467 — 3,467 — Corporate 18,555 — 18,555 — Total fixed maturities 61,764 — 61,764 — Equity investments: Common stock 21,426 21,426 — — Warrants 1,804 664 1,140 — Total equity investments 23,230 22,090 1,140 — Limited liability investment, at fair value 10,700 — 10,700 — Other investments 7,975 — 7,975 — Short-term investments 401 — 401 — Total assets $ 104,070 $ 22,090 $ 81,980 $ — Liabilities: Subordinated debt $ 43,619 $ — $ 43,619 $ — Contingent consideration 325 — — 325 Total liabilities $ 43,944 $ — $ 43,619 $ 325
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Table Text Block]	The following table provides a reconciliation of the fair value of recurring Level 3 fair value measurements for the three and six months ended June 30, 2017 and June 30, 2016 : (in thousands) Three months ended June 30, Six months ended June 30, 2017 2016 2017 2016 Contingent consideration: Beginning balance $ 325 $ 1,982 $ 325 $ 1,982 Settlement of contingent consideration liabilities (113 ) (1,000 ) (113 ) (1,000 ) Change in fair value of contingent consideration included in net loss (212 ) (657 ) (212 ) (657 ) Ending balance $ — $ 325 $ — $ 325

Acquisitions, Deconsolidation47

Acquisitions, Deconsolidation and Discontinued Operations Acquisition of CMC Industries, Inc. (Details) a in Thousands, $ in Thousands	3 Months Ended
	Mar. 31, 2017USD ($)	Sep. 30, 2016USD ($)	Jun. 30, 2016	Jun. 30, 2017USD ($)	Dec. 31, 2016USD ($)	Jul. 14, 2016USD ($)a
Business Acquisition [Line Items]
Subsidiary or Equity Method Investee, Cumulative Percentage Ownership after All Transactions		26.70%	61.00%
Business Combination, Consideration Transferred, Equity Interests Issued and Issuable		$ 1,500
Land Subject to Ground Leases | a						0
Deferred Revenue, Additions	$ 25,000
Goodwill				$ 71,061	$ 71,061	$ 60,983
Other Intangible Assets, Net						74,800
Long-term Debt, Fair Value				$ 186,341	$ 190,074
Debt Instrument, Face Amount						180,000
Debt Instrument, Unamortized Premium						11,700
Off-market Lease, Unfavorable						900
Series of Individually Immaterial Business Acquisitions [Member]
Business Acquisition [Line Items]
Subsidiary or Equity Method Investee, Cumulative Percentage Ownership after All Transactions		81.00%
Long-term Debt [Member]
Business Acquisition [Line Items]
Long-term Debt, Fair Value						$ 191,700

Acquisitions, Deconsolidation48

Acquisitions, Deconsolidation and Discontinued Operations Acquisition of Argo Management Group LLC (Details) - USD ($) shares in Thousands, $ in Thousands	3 Months Ended
	Jun. 30, 2016	Jun. 30, 2017	Dec. 31, 2016	Apr. 20, 2016
Business Acquisition [Line Items]
Business Combination, Step Acquisition, Equity Interest in Acquiree, Fair Value	$ 744
Intangible assets, net of accumulated amortization of $7,761 and $7,181, respectively		$ 88,187	$ 89,017	$ 731
Executive Vice President [Member]
Business Acquisition [Line Items]
Common Stock, Shares, Issued				160

Acquisitions, Deconsolidation49

Acquisitions, Deconsolidation and Discontinued Operations Deconsolidation (Details)	3 Months Ended
	Sep. 30, 2016	Jun. 30, 2016
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Subsidiary or Equity Method Investee, Cumulative Percentage Ownership after All Transactions	26.70%	61.00%

Acquisitions, Deconsolidation50

Acquisitions, Deconsolidation and Discontinued Operations Discontinued Operations of Assigned Risk Solutions Ltd. (Details) - USD ($) $ in Thousands	Apr. 01, 2015	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2015	Jun. 30, 2017	Jun. 30, 2016
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Disposal Group, Including Discontinued Operation, Consideration		$ 1,300	$ 1,400		$ 1,300	$ 1,400
Premiums, Percentage Assumed to Net					1.30%
Proceeds from Divestiture of Interest in Consolidated Subsidiaries	$ 47,000			$ 2,000
Disposal Group, Not Discontinued Operation, Gain (Loss) on Disposal		1,017	1,124		$ 1,017	1,124
Discontinued Operation, Tax Effect of Gain (Loss) from Disposal of Discontinued Operation		0	0		0	0
Gain on disposal of discontinued operations, net of taxes		$ 1,017	$ 1,124		$ 1,017	$ 1,124

Investments (Details)

Investments (Details) $ / shares in Units, number in Thousands, $ in Thousands	Jun. 30, 2017USD ($)	Dec. 31, 2016USD ($)	Jun. 30, 2014$ / sharesshares
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities and equity investments unrealized loss positions	168	173
Limited liability investments	$ 25,533	$ 22,974
Limited liability investments	8,220	10,700
Fair Value, Investments, Entities that Calculate Net Asset Value Per Share, Unfunded Commitments	1,200
Other investments, at cost which approximates fair value	7,550	7,975
Available-for-sale Securities Pledged as Collateral	12,760	13,073
Pledged Assets Separately Reported, Nonsecuritized Investments Pledged as Collateral, at Fair Value	16,900	16,400
Minimum [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares			100,000,000
Share Price | $ / shares			$ 10
Maximum [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares			125,000
Share Price | $ / shares			$ 18
Fair Value, Inputs, Level 2 [Member]
Schedule of Available-for-sale Securities [Line Items]
Limited liability investments		10,700
Fair Value, Inputs, Level 2 [Member] | Warrant [Member]
Schedule of Available-for-sale Securities [Line Items]
Available-for-sale Equity Securities, Accumulated Gross Unrealized Gain, before Tax	$ 227	$ 180
Performance Share Grant Agreement [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares			475,000
Clause 2 [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares			125,000
Share Price | $ / shares			$ 12
Clause 3 [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares			125,000
Share Price | $ / shares			$ 15
Clause 1, 2 and 3 [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares			350,000
Clause 1 and 2 [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares			225,000

Investments Amortized cost, g52

Investments Amortized cost, gross unrealized gains and losses, and estimated fair value (Details) - USD ($) $ in Thousands	Jun. 30, 2017	Mar. 31, 2017	Dec. 31, 2016
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities, cost	$ 57,172		$ 62,136
Gross Unrealized Gain, Fixed Maturities	149		133
Gross Unrealized Loss, Fixed Maturities	356		505
Total Fixed Maturities	56,965		61,764
Equity investments, cost	16,699		19,099
Total Equity Investments	19,441		23,230
Amortized Cost	73,871		81,235
Gross Unrealized Gain	3,571		4,748
Gross Unrealized Loss	1,036		989
Estimated Fair Value, Fixed Maturities and Equity Investments	76,406		84,994
US Government Agencies Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities, cost	27,033		28,312
Gross Unrealized Gain, Fixed Maturities	24		22
Gross Unrealized Loss, Fixed Maturities	153		186
Total Fixed Maturities	26,904		28,148
Gross Unrealized Loss		$ 153	186
US States and Political Subdivisions Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities, cost	3,722		3,131
Gross Unrealized Gain, Fixed Maturities	9		1
Gross Unrealized Loss, Fixed Maturities	37		44
Total Fixed Maturities	3,694		3,088
Gross Unrealized Loss		37	44
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities, cost	8,419		8,610
Gross Unrealized Gain, Fixed Maturities	14		12
Gross Unrealized Loss, Fixed Maturities	80		116
Total Fixed Maturities	8,353		8,506
Gross Unrealized Loss		80	116
Asset-backed Securities, Securitized Loans and Receivables [Member]
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities, cost	2,197		3,468
Gross Unrealized Gain, Fixed Maturities	4		4
Gross Unrealized Loss, Fixed Maturities	6		5
Total Fixed Maturities	2,195		3,467
Corporate Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities, cost	15,801		18,615
Gross Unrealized Gain, Fixed Maturities	98		94
Gross Unrealized Loss, Fixed Maturities	80		154
Total Fixed Maturities	15,819		18,555
Gross Unrealized Loss		80	154
Common Stock [Member]
Schedule of Available-for-sale Securities [Line Items]
Equity investments, cost	15,222		17,701
Total Equity Investments	17,616		21,426
Unrealized Gain, Equity Investments	2,996		4,156
Gross Unrealized Loss, Equity Investments	602		431
Gross Unrealized Loss		602	431
Warrant [Member]
Schedule of Available-for-sale Securities [Line Items]
Gross Unrealized Loss		78	53
Equity Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Equity investments, cost	16,699		19,099
Total Equity Investments	19,441		23,230
Unrealized Gain, Equity Investments	3,422		4,615
Gross Unrealized Loss, Equity Investments	680		484
Gross Unrealized Loss		$ 680	484
Fair Value, Inputs, Level 1 [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	0		0
Total Equity Investments	18,254		22,090
Fair Value, Inputs, Level 1 [Member] | US States and Political Subdivisions Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	0		0
Fair Value, Inputs, Level 1 [Member] | Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	0		0
Fair Value, Inputs, Level 1 [Member] | Asset-backed Securities, Securitized Loans and Receivables [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities			0
Fair Value, Inputs, Level 1 [Member] | Corporate Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	0		0
Fair Value, Inputs, Level 1 [Member] | Warrant [Member]
Schedule of Available-for-sale Securities [Line Items]
Equity investments, cost	517		438
Total Equity Investments	638		664
Unrealized Gain, Equity Investments	199		279
Gross Unrealized Loss, Equity Investments	78		53
Fair Value, Inputs, Level 2 [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	56,965		61,764
Total Equity Investments	1,187		1,140
Fair Value, Inputs, Level 2 [Member] | US Government Agencies Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities			28,148
Estimated Fair Value, Fixed Maturities and Equity Investments	26,904
Fair Value, Inputs, Level 2 [Member] | US States and Political Subdivisions Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities			3,088
Estimated Fair Value, Fixed Maturities and Equity Investments	3,694
Fair Value, Inputs, Level 2 [Member] | Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities			8,506
Estimated Fair Value, Fixed Maturities and Equity Investments	8,353
Fair Value, Inputs, Level 2 [Member] | Asset-backed Securities, Securitized Loans and Receivables [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities			3,467
Estimated Fair Value, Fixed Maturities and Equity Investments	2,195
Fair Value, Inputs, Level 2 [Member] | Corporate Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities			18,555
Estimated Fair Value, Fixed Maturities and Equity Investments	15,819
Fair Value, Inputs, Level 2 [Member] | Warrant [Member]
Schedule of Available-for-sale Securities [Line Items]
Equity investments, cost	960		960
Total Equity Investments	1,187		1,140
Unrealized Gain, Equity Investments	227		180
Gross Unrealized Loss, Equity Investments	$ 0		$ 0

Investments Fixed Maturities 53

Investments Fixed Maturities by Contractual Maturity Periods (Details) - USD ($) $ in Thousands	Jun. 30, 2017	Dec. 31, 2016
Schedule of Held-to-maturity Securities [Line Items]
Due In One Year or Less, Amortized Cost	$ 7,518
Due In One Year or Less, Fair Value	7,504
Due After One Year Through Five Years, Amortized Cost	40,198
Due After One Year Through Five Years, Fair Value	40,077
Due After Five Year Through Ten Years, Amortized Cost	3,107
Due After Five Year Through Ten Years, Fair Value	3,082
Due After Ten Years, Amortized Cost	6,349
Due After Ten Years, Fair Value	6,302
Fixed maturities, cost	57,172	$ 62,136
Estimated Fair Value, Fixed Maturities	$ 56,965	$ 61,764

Investments Unrealized Loss Pos

Investments Unrealized Loss Position (Details) - USD ($) $ in Thousands	Jun. 30, 2017	Mar. 31, 2017	Dec. 31, 2016
Gain (Loss) on Investments [Line Items]
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	$ 1,036		$ 989
US Government Agencies Debt Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	23,371		18,509
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	153		186
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	0		0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	0		0
Continuous Unrealized Loss Position, Fair Value	23,371		18,509
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		$ 153	186
US States and Political Subdivisions Debt Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	2,330		2,594
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	37		44
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	0		0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	0		0
Continuous Unrealized Loss Position, Fair Value	2,330		2,594
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		37	44
Fixed Maturities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	40,753		41,598
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	352		505
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	4		0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	435		102
Continuous Unrealized Loss Position, Fair Value	41,188		41,700
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		356	505
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	7,090		7,709
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	79		116
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	1		0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	136		58
Continuous Unrealized Loss Position, Fair Value	7,226		7,767
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		80	116
Asset-backed Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	1,092		1,830
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	3		5
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	3		0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	299		44
Continuous Unrealized Loss Position, Fair Value	1,391		1,874
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		6	5
Corporate Debt Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	6,870		10,956
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	80		154
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	0		0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	0		0
Continuous Unrealized Loss Position, Fair Value	6,870		10,956
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		80	154
Equity Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	1,317		900
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	146		293
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	456		138
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	666		868
Continuous Unrealized Loss Position, Fair Value	1,983		1,768
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		602	431
Warrant [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	258		31
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	31		20
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	47		33
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	1		0
Continuous Unrealized Loss Position, Fair Value	259		31
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		78	53
Equity Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	1,575		931
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	177		313
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	503		171
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	667		868
Continuous Unrealized Loss Position, Fair Value	2,242		1,799
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		680	484
Available-for-sale Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	42,328		42,529
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	529		818
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	507		171
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	1,102		970
Continuous Unrealized Loss Position, Fair Value	$ 43,430		43,499
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		$ 1,036	$ 989

Investments Continuous Unreal55

Investments Continuous Unrealized Loss Position (Details) - USD ($) $ in Thousands	Jun. 30, 2017	Mar. 31, 2017	Dec. 31, 2016
Schedule of Available-for-sale Securities [Line Items]
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	$ 1,036		$ 989
US Government Agencies Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	23,371		18,509
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	0		0
Continuous Unrealized Loss Position, Fair Value	23,371		18,509
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		$ 153	186
US States and Political Subdivisions Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	2,330		2,594
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	0		0
Continuous Unrealized Loss Position, Fair Value	2,330		2,594
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		37	44
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	7,090		7,709
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	1		0
Continuous Unrealized Loss Position, Fair Value	7,226		7,767
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		80	116
Asset-backed Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	1,092		1,830
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	3		0
Continuous Unrealized Loss Position, Fair Value	1,391		1,874
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		6	5
Corporate Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	6,870		10,956
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	0		0
Continuous Unrealized Loss Position, Fair Value	6,870		10,956
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		80	154
Fixed Maturities [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	40,753		41,598
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	4		0
Continuous Unrealized Loss Position, Fair Value	41,188		41,700
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		356	505
Common Stock [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	1,317		900
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	456		138
Continuous Unrealized Loss Position, Fair Value	1,983		1,768
Available-for-sale Equity Securities, Accumulated Gross Unrealized Loss, before Tax	602		431
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		602	431
Warrant [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	258		31
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	47		33
Continuous Unrealized Loss Position, Fair Value	259		31
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		78	53
Available-for-sale Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	42,328		42,529
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	507		171
Continuous Unrealized Loss Position, Fair Value	$ 43,430		43,499
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		$ 1,036	$ 989

Investments Gross Realized Ga56

Investments Gross Realized Gains and Losses on Fixed Maturities (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Gain (Loss) on Investments [Line Items]
Gross realized gains	$ 735	$ 214	$ 1,159	$ 248
Gross realized losses	(1)	(147)	(27)	(352)
Net realized gains (losses)	$ 734	$ 67	$ 1,132	$ (104)

Investments Net Investment Inco

Investments Net Investment Income (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Net Investment Income [Line Items]
Interest from fixed maturities	$ 228	$ 242	$ 434	$ 460
Dividends	127	126	269	392
(Loss) income from limited liability investments	581	(511)	281	(310)
Loss on change in fair value of limited liability investment, at fair value	(2,113)	0	(2,480)	0
Other	205	100	415	139
Gross investment (loss) income	(2,332)	(1,120)	(1,596)	(1,055)
Investment expenses	(34)	(48)	(67)	(55)
Net investment (loss) income	(2,366)	1,072	(1,663)	1,000
Warrant [Member]
Net Investment Income [Line Items]
(Loss) gain on change in fair value of warrants - not publicly traded	$ (198)	$ 141	$ 47	$ (246)

Investment in Investees (Detail

Investment in Investees (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016	Mar. 31, 2017	Dec. 31, 2016	Sep. 30, 2016
Schedule of Equity Method Investments [Line Items]
Carrying Value	$ 5,355		$ 5,355			$ 3,116
Equity in net loss of investees	(145)	$ (874)	2,240	$ (943)
Corporate Segment [Member]
Schedule of Equity Method Investments [Line Items]
Equity Percentage					31.20%		31.20%
Carrying Value	$ 3,671		$ 3,671		$ 4,192		$ 4,251
Carrying Value					$ 5,355		$ 3,116

Deferred Acquisition Costs (Det

Deferred Acquisition Costs (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016	Mar. 31, 2017	Dec. 31, 2016	Mar. 31, 2016	Dec. 31, 2015	Dec. 31, 2014
Deferred Acquisition Costs [Line Items]
Beginning balance, net	$ (13,709)	$ (13,824)	$ (13,709)	$ (13,824)	$ (14,113)	$ (13,609)	$ (13,440)	$ (13,609)	$ (12,143)
Additions	7,011	7,180	14,698	14,769
Amortization	7,415	6,796	14,598	13,088
Balance at June 30, net	$ 13,709	$ 13,824	$ 13,709	$ 13,824

Intangible Assets (Details)

Intangible Assets (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016	Dec. 31, 2016	Jul. 14, 2016	Apr. 20, 2016
Finite-Lived Intangible Assets [Line Items]
Other Intangible Assets, Net						$ 74,800
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Finite-Lived Intangibles						1,125
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Indefinite-Lived Intangible Assets						$ 73,667
Intangible assets, net of accumulated amortization of $7,761 and $7,181, respectively	$ 88,187		$ 88,187		$ 89,017		$ 731
Finite-Lived Intangible Assets, Gross	95,948		95,948		96,198
Amortization of Intangible Assets	289	$ 307	580	$ 602
Gain (Loss) on Sale of Assets and Asset Impairment Charges	0	0	$ 250	0
Noncompete Agreements [Member]
Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Asset, Useful Life			18 years
Finite-Lived Intangible Assets, Gross	$ 1,125		$ 1,125		1,125
Contract-Based Intangible Assets [Member]
Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Asset, Useful Life			9 years
Finite-Lived Intangible Assets, Gross		$ 731		$ 731	$ 731
Minimum [Member]
Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Asset, Useful Life			7 years
Maximum [Member]
Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Asset, Useful Life			15 years

Intangible Assets Intangible As

Intangible Assets Intangible Assets (Tables) (Details) - USD ($) $ in Thousands	Jun. 30, 2017	Dec. 31, 2016	Jun. 30, 2016	Apr. 20, 2016
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross	$ 95,948	$ 96,198
Finite-Lived Intangible Assets, Accumulated Amortization	7,761	7,181
Intangible Assets, Net (Excluding Goodwill)	88,187	89,017		$ 731
Database Rights [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross	4,918	4,918
Finite-Lived Intangible Assets, Accumulated Amortization	2,275	2,029
Finite-Lived Intangible Assets, Net	2,643	2,889
Service Agreements [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross	3,680	3,680
Finite-Lived Intangible Assets, Accumulated Amortization	3,597	3,554
Finite-Lived Intangible Assets, Net	83	126
Customer Relationships [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross	3,611	3,611
Finite-Lived Intangible Assets, Accumulated Amortization	1,748	1,521
Finite-Lived Intangible Assets, Net	1,863	2,090
Noncompete Agreements [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross	1,125	1,125
Finite-Lived Intangible Assets, Accumulated Amortization	60	29
Finite-Lived Intangible Assets, Net	1,065	1,096
Contract-Based Intangible Assets [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross		731	$ 731
Finite-Lived Intangible Assets, Accumulated Amortization	81	48
Finite-Lived Intangible Assets, Net		683
Other Intangible Assets [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Net	650
Insurance Contracts Acquired in Business Combination [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross		73,667
Finite-Lived Intangible Assets, Accumulated Amortization	0	0
Indefinite-Lived Intangible Assets (Excluding Goodwill)	73,667
Indefinite-Lived License Agreements	73,667	73,667
Contractual Rights [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Accumulated Amortization	0	0
Indefinite-Lived Intangible Assets (Excluding Goodwill)	7,553	7,803
Indefinite-Lived Contractual Rights	7,553	7,803
Trademarks and Trade Names [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Accumulated Amortization	0	0
Indefinite-Lived Intangible Assets (Excluding Goodwill)	663	663
Indefinite-Lived License Agreements	$ 663	$ 663

Unpaid Loss and Loss Adjustme62

Unpaid Loss and Loss Adjustment Expenses Property and Casualty (tables) (Details) - USD ($) $ in Thousands	6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Dec. 31, 2016	Dec. 31, 2015
Liability for Claims and Claims Adjustment Expense [Line Items]
Property and casualty	$ 45,874	$ 52,195	$ 53,795
Balance at end of period, gross	45,874	52,195
Property, Liability and Casualty Insurance Product Line [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Property and casualty			53,795	$ 55,471
Less reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses	509	845
Balance at beginning of period, net	45,365	51,350
Current year	50,324	45,614
Prior years	996	67
Current year	23,094	22,060
Prior years	35,975	26,535
Balance at end of period, net	45,365	51,350	53,114	54,264
Plus reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses	$ 509	$ 845	$ 681	$ 1,207

Unpaid Loss and Loss Adjustme63

Unpaid Loss and Loss Adjustment Expenses Vehicle Service Agreements (Details) - USD ($) $ in Thousands	6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Dec. 31, 2016	Dec. 31, 2015
Liability for Claims and Claims Adjustment Expense [Line Items]
Vehicle service agreements	$ 2,794	$ 2,975	$ 2,915
Other Insurance Product Line [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Current year	2,558	2,654
Prior years	0	0
Current year	2,616	2,502
Prior years	$ (63)	$ (152)
Vehicle service agreements			$ 2,915	$ 2,975

Debt Carrying Value of Debt Ins

Debt Carrying Value of Debt Instruments (Tables) (Details) - USD ($) $ in Thousands	Jun. 30, 2017	Dec. 31, 2016	Jul. 14, 2016
Debt Instrument [Line Items]
Debt Instrument, Principal Value	$ 268,018	$ 269,281
Notes Payable	188,328	190,074
Debt Instrument, Unamortized Discount (Premium), Net	236,538	233,693
Total liabilities	234,551	233,693
Long-term Debt, Fair Value	186,341	190,074
Subordinated debt, at fair value	48,210	43,619
Long-term Debt [Member]
Debt Instrument [Line Items]
Debt Instrument, Principal Value	177,518	178,781
Total liabilities	48,210	43,944
Long-term Debt, Fair Value			$ 191,700
Subordinated Debt [Member]
Debt Instrument [Line Items]
Debt Instrument, Principal Value	90,500	90,500
Debt Instrument, Unamortized Discount (Premium), Net	$ 48,210	$ 43,619

Debt Subordinated Borrowing (Ta

Debt Subordinated Borrowing (Table) (Details) - USD ($)	6 Months Ended
	Jun. 30, 2017	Jul. 14, 2016
Debt Instrument [Line Items]
Debt Instrument, Face Amount		$ 180,000,000
Annual Interest Rate		4.07%
Connecticut Statutory Trust I [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 15,000
Issue date of trust	Dec. 4, 2002
Redemption date	Dec. 4, 2032
Annual Interest Rate	0.00%
Connecticut Statutory Trust II [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 17,500
Issue date of trust	May 15, 2003
Redemption date	May 15, 2033
Annual Interest Rate	0.00%
Connecticut Statutory Trust III [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 20,000
Issue date of trust	Oct. 29, 2003
Redemption date	Oct. 29, 2033
Annual Interest Rate	0.00%
Delaware Statutory Trust III [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 15,000
Issue date of trust	May 22, 2003
Redemption date	May 22, 2033
Annual Interest Rate	0.00%
Delaware Statutory Trust IV [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 10,000
Issue date of trust	Sep. 30, 2003
Redemption date	Sep. 30, 2033
Annual Interest Rate	0.00%
Delaware Statutory Trust VI [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 13,000
Issue date of trust	Jan. 8, 2004
Redemption date	Jan. 8, 2034
Annual Interest Rate	0.00%

Debt Debt (Details)

Debt Debt (Details) - USD ($) $ in Thousands	Jun. 30, 2017	Dec. 31, 2016	Jul. 14, 2016
Debt Instrument [Line Items]
Long-term Debt, Fair Value	$ 186,341	$ 190,074
Debt Instrument, Face Amount			$ 180,000
Debt Instrument, Unamortized Premium			$ 11,700
Debt Instrument, Interest Rate, Stated Percentage			4.07%
Long-term Debt [Member]
Debt Instrument [Line Items]
Long-term Debt, Fair Value			$ 191,700

Finance Lease Obligation Liab67

Finance Lease Obligation Liability (Details) - USD ($) $ in Thousands	Jun. 30, 2017	Dec. 31, 2016
Sale Leaseback Transaction [Line Items]
Sale Leaseback Transaction, Deferred Gain, Net	$ 700
Land and Building [Member]
Sale Leaseback Transaction [Line Items]
Sale Leaseback Transaction, Net Book Value	5,140	$ 5,060
Net Assets	$ 4,700	$ 4,800

Income Taxes Income Taxes Table

Income Taxes Income Taxes Table (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Income Tax Contingency [Line Items]
Income tax benefit at United States statutory income tax rate	$ (2,519)	$ (671)	$ (2,962)	$ (1,170)
Valuation allowance	2,401	251	2,945	640
Indefinite life intangibles	1,058	22	1,005	(44)
Change in unrecognized tax benefits(1)	160	0	372	0
Non-deductible compensation	101	381	200	449
Foreign operations subject to different tax rates	45	38	(94)	74
Other	5	5	(36)	15
Income tax expense	$ 1,251	$ 26	$ 1,430	$ 52

Income Taxes (Details)

Income Taxes (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016	Mar. 31, 2017	Dec. 31, 2016
Income Tax Disclosure [Abstract]
Deferred income tax liability	$ 49,726		$ 49,726			$ 48,720
Deferred Tax Assets, Operating Loss Carryforwards, Subject to Expiration	13,400		13,400			13,400
Deferred Tax Liabilities, Goodwill and Intangible Assets					$ 36,300
Unrecognized Tax Benefits	1,300		1,300			1,300
Income Tax Examination, Penalties and Interest Expense	200	$ 0	400	$ 0
Income Tax Examination, Penalties and Interest Accrued	$ 800		$ 800			$ 400

Loss per Share Net Loss Per S70

Loss per Share Net Loss Per Share (Tables) (Details) - USD ($) $ / shares in Units, shares in Thousands, $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Earnings Per Share, Basic, by Common Class, Including Two Class Method [Line Items]
Net loss	$ (8,659)	$ (1,999)	$ (10,143)	$ (3,494)
Less: net income (loss) attributable to noncontrolling interests in consolidated subsidiaries	100	(361)	205	(400)
Less: dividends on preferred stock	123	82	244	164
Loss from continuing operations attributable to common shareholders	$ (8,882)	$ (1,720)	$ (10,592)	$ (3,258)
Weighted-average common shares outstanding	21,458	19,818	21,458	19,764
Diluted:	21,458	19,818	21,458	19,764
Basic:	$ (0.41)	$ (0.09)	$ (0.49)	$ (0.16)
Diluted:	$ (0.41)	$ (0.09)	$ (0.49)	$ (0.16)

Stock-Based Compensation (Detai

Stock-Based Compensation (Details) - USD ($) $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock-based compensation expense, net of forfeitures	$ 0.3	$ 0.3	$ 0.6	$ 0.5
Allocated Share-based Compensation Expense			2.5
Restricted Stock [Member]
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Deferred Compensation Equity	$ 5.5		$ 5.5

Stock-Based Compensation Stock

Stock-Based Compensation Stock Option Activity (Table) (Details)	6 Months Ended
	Jun. 30, 2017USD ($)$ / sharesshares	Dec. 31, 2016USD ($)$ / sharesshares
Class of Stock [Line Items]
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range, Number of Outstanding Options | shares	651,875	651,875
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range, Outstanding Options, Weighted Average Exercise Price | $ / shares	$ 4.51	$ 4.51
Remaining Contractual Life (Years)	1
Share-based Compensation Arrangement by Share-based Payment Award, Options, Vested and Expected to Vest, Outstanding, Aggregate Intrinsic Value | $	$ 1,004,000
Share-based Compensation Arrangement by Share-based Payment Award, Options, Grants in Period, Gross | shares	0
Share-based Compensation Arrangements by Share-based Payment Award, Options, Grants in Period, Weighted Average Exercise Price | $ / shares	$ 0
Share-based Compensation Arrangement by Share-based Payment Award, Options, Expirations in Period | shares	0
Share-based Compensation Arrangement by Share-based Payment Award, Options, Outstanding, Weighted Average Exercise Price | $ / shares	$ 4.51
Share-based Compensation Arrangement by Share-based Payment Award, Options, Outstanding, Number | shares	651,875
Options Expired [Member]
Class of Stock [Line Items]
Share-based Compensation Arrangements by Share-based Payment Award, Options, Expirations in Period, Weighted Average Exercise Price | $ / shares	$ 0
Options Outstanding [Member]
Class of Stock [Line Items]
Remaining Contractual Life (Years)	1	1
Share-based Compensation Arrangement by Share-based Payment Award, Options, Vested and Expected to Vest, Outstanding, Aggregate Intrinsic Value | $	$ 1,004,000	$ 1,134

Stock-Based Compensation Restri

Stock-Based Compensation Restricted Stock Awards (Tables) (Details) - $ / shares	6 Months Ended
	Jun. 30, 2017	Dec. 31, 2016
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range [Line Items]
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Number	500,000	500,000
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range, Exercisable Options, Weighted Average Exercise Price	$ 0	$ 5.73
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value	$ 5.73
Restricted Stock [Member]
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range [Line Items]
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Number	1,952,665	1,952,665
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range, Exercisable Options, Weighted Average Exercise Price		$ 4.14
Stock Issued During Period, Shares, Restricted Stock Award, Forfeited	0
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value	$ 4.14
Share-based Compensation Arrangement by Share-based Payment Award, Options, Nonvested Options Forfeited, Weighted Average Grant Date Fair Value	$ 0

Stock-Based Compensation Rest74

Stock-Based Compensation Restricted Stock Units (Details) - $ / shares	6 Months Ended
	Jun. 30, 2017	Dec. 31, 2016
Restricted Stock Units [Abstract]
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Grants in Period	0
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range, Exercisable Options, Weighted Average Exercise Price	$ 0	$ 5.73
Unvested at September 30, 2016	500,000	500,000
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value	$ 5.73

Accumulated Other Comprehensi75

Accumulated Other Comprehensive Income AOCI (Table) (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016	Mar. 31, 2017	Dec. 31, 2016	Mar. 31, 2016	Dec. 31, 2015
Accumulated Other Comprehensive Income (Loss) [Line Items]
Accumulated Other Comprehensive Income (Loss), Net of Tax	$ (1,467)		$ (1,467)			$ (208)
Other Comprehensive Income (Loss), Net of Tax	(586)	$ 357	(1,256)	$ 200
Accumulated Net Investment Gain (Loss) Including Portion Attributable to Noncontrolling Interest [Member]
Accumulated Other Comprehensive Income (Loss) [Line Items]
Accumulated Other Comprehensive Income (Loss), Net of Tax	2,313	1,494	2,313	1,494	$ 2,901	3,572	$ 1,137	$ 1,294
Other Comprehensive Income (Loss), before Reclassifications, Net of Tax	(1,066)	430	(1,230)	705
Reclassification from Accumulated Other Comprehensive Income, Current Period, Net of Tax	(478)	(73)	(29)	(505)
Other Comprehensive Income (Loss), Reclassification Adjustment from AOCI for Sale of Securities, before Tax	(588)	357	(1,259)	200
Accumulated Foreign Currency Adjustment Including Portion Attributable to Noncontrolling Interest [Member]
Accumulated Other Comprehensive Income (Loss) [Line Items]
Accumulated Other Comprehensive Income (Loss), Net of Tax	(3,780)	(3,780)	(3,780)	(3,780)	(3,780)	(3,780)	(3,780)
Other Comprehensive Income (Loss), before Reclassifications, Net of Tax	0	0	0
Reclassification from Accumulated Other Comprehensive Income, Current Period, Net of Tax	0	0	0
Other Comprehensive Income (Loss), Net of Tax	0	0	0	0
Comprehensive Income [Member]
Accumulated Other Comprehensive Income (Loss) [Line Items]
Accumulated Other Comprehensive Income (Loss), Net of Tax	(1,467)	(2,286)	(1,467)	(2,286)	$ (879)	$ (208)	$ (2,643)	$ (2,486)
Other Comprehensive Income (Loss), before Reclassifications, Net of Tax	(1,066)	430	(1,230)	705
Reclassification from Accumulated Other Comprehensive Income, Current Period, Net of Tax	(478)	(73)	(29)	(505)
Other Comprehensive Income (Loss), Net of Tax	$ (588)	$ 357	$ (1,259)	$ 200

Accumulated Other Comprehensi76

Accumulated Other Comprehensive Income Reclassification of AOCI (table) (Details) - Reclassification out of Accumulated Other Comprehensive Income [Member] - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Net realized gains (losses)	$ 478	$ (73)	$ (29)	$ (505)
Other-than-temporary impairment loss	0	0	0	0
Loss before income tax expense	478	(73)	(29)	505
Income tax expense	0	0	0	0
Net loss	$ 478	$ (73)	$ (29)	$ (505)

Segmented Information (Details)

Segmented Information (Details)	Jun. 30, 2017USD ($)
Segment Reporting Information [Line Items]
Number of States in which New Business is Accepted	8
Other Segments [Member]
Segment Reporting Information [Line Items]
Number of States in which Entity Operates	12
Reportable Subsegments [Member]
Segment Reporting Information [Line Items]
Number of States in which Entity Operates	0

Segmented Information Revenues

Segmented Information Revenues (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Segment Reporting Information [Line Items]
Net premiums earned	$ 33,518	$ 31,813	$ 66,440	$ 61,240
Other income	2,815	2,791	5,630	5,165
Service fee and commission income	6,873	5,394	13,435	10,716
Rental income	3,341	0	6,682	0
Total segment revenues	44,915	41,137	91,656	78,017
Net investment (loss) income	(2,366)	1,072	(1,663)	1,000
Net realized gains (losses)	734	67	1,132	(104)
Other income not allocated to segments	44	64	89	111
Reportable Subsegments [Member]
Segment Reporting Information [Line Items]
Other income	51	62	136	116
Service fee and commission income	6,873	5,394	13,435	10,716
Total segment revenues	6,924	5,456	13,571	10,832
Other Segments [Member]
Segment Reporting Information [Line Items]
Net premiums earned	33,518	31,813	66,440	61,240
Other income	2,560	2,665	5,033	4,938
Total segment revenues	36,078	34,478	71,473	66,178
Reportable Legal Entities [Member]
Segment Reporting Information [Line Items]
Other income	160	0	372	0
Rental income	3,341	0	6,682	0
Total segment revenues	3,501	0	7,054	0
Operating Segments [Member]
Segment Reporting Information [Line Items]
Total segment revenues	46,503	39,934	92,098	77,010
Corporate, Non-Segment [Member]
Segment Reporting Information [Line Items]
Net premiums earned	$ 0	$ 0	$ 0	$ 0

Segmented Information Segment (

Segmented Information Segment (loss) income (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Segment Reporting Information [Line Items]
Gain (Loss) on Sale of Assets and Asset Impairment Charges	$ 0	$ 0	$ (250)	$ 0
Total segment operating income (loss)	1,140	(599)	1,902	(994)
Net investment (loss) income	(2,366)	1,072	(1,663)	1,000
Net realized gains (losses)	734	67	1,132	(104)
Amortization of intangible assets	289	307	580	602
Accretion Expense	212	657	212	657
Interest expense not allocated to segments	1,216	1,108	2,375	2,201
Other income and expenses not allocated to segments, net	(2,776)	(1,940)	(4,736)	(3,841)
Foreign exchange losses, net	0	(9)	(4)	(10)
(Loss) gain on change in fair value of debt	(2,702)	1,068	(4,591)	3,596
Equity in net (loss) income of investee	(145)	(874)	2,240	(943)
Loss from continuing operations before income tax expense	(7,408)	(1,973)	(8,713)	(3,442)
Income tax expense	1,251	26	1,430	52
Net loss	(8,659)	(1,999)	(10,143)	(3,494)
Reportable Subsegments [Member]
Segment Reporting Information [Line Items]
Total segment operating income (loss)	685	(780)	1,271	(936)
Other Segments [Member]
Segment Reporting Information [Line Items]
Total segment operating income (loss)	(417)	181	(1,159)	(58)
Operating Segments [Member]
Segment Reporting Information [Line Items]
Total segment operating income (loss)	$ 872	$ 0	$ 1,790	$ 0

Segmented Information Net Earne

Segmented Information Net Earned by Line of Business (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Segment Reporting Information [Line Items]
Net premiums earned	$ 33,518	$ 31,813	$ 66,440	$ 61,240
Private passenger auto liability [Member]
Segment Reporting Information [Line Items]
Net premiums earned	22,933	21,656	45,309	41,731
Auto physical damage [Member]
Segment Reporting Information [Line Items]
Net premiums earned	10,585	10,157	21,131	19,509
Other Segments [Member]
Segment Reporting Information [Line Items]
Net premiums earned	$ 33,518	$ 31,813	$ 66,440	$ 61,240

Fair Value of Financial Instr81

Fair Value of Financial Instruments (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Contingent consideration benefit	$ (212)	$ (657)	$ (212)	$ (657)

Fair Value of Financial Instr82

Fair Value of Financial Instruments Fair Value Inputs (Table) (Details) - USD ($) $ in Thousands	Jun. 30, 2017	Dec. 31, 2016
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	$ 56,965	$ 61,764
Available-for-sale Securities	76,406	84,994
Common stock	17,616
Total equity investments	19,441	23,230
Limited liability investment, at fair value	8,220	10,700
Other investments, at cost which approximates fair value	7,550	7,975
Short-term investments, at cost which approximates fair value	151	401
Total assets	117,860	127,044
Subordinated debt, at fair value	48,210	43,619
Contingent consideration		325
Total liabilities	234,551	233,693
Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Warrants	638	664
Total equity investments	18,254	22,090
Other investments, at cost which approximates fair value	0	0
Short-term investments, at cost which approximates fair value		0
Total assets	18,254	22,090
Subordinated debt, at fair value	0	0
Total liabilities	0	0
Fair Value, Inputs, Level 3 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Other investments, at cost which approximates fair value	0	0
Short-term investments, at cost which approximates fair value		0
Total assets	0	0
Subordinated debt, at fair value		0
Contingent consideration		325
Total liabilities	0	325
Fair Value, Inputs, Level 2 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	56,965	61,764
Warrants	1,187	1,140
Total equity investments	1,187	1,140
Limited liability investment, at fair value		10,700
Total assets	74,073	81,980
Total liabilities	48,210	43,619
Asset-backed Securities, Securitized Loans and Receivables [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	2,195	3,467
Asset-backed Securities, Securitized Loans and Receivables [Member] | Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities		0
Asset-backed Securities, Securitized Loans and Receivables [Member] | Fair Value, Inputs, Level 3 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Asset-backed Securities, Securitized Loans and Receivables [Member] | Fair Value, Inputs, Level 2 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities		3,467
Available-for-sale Securities	2,195
Asset-backed Securities [Member] | Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0
US States and Political Subdivisions Debt Securities [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	3,694	3,088
US States and Political Subdivisions Debt Securities [Member] | Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
US States and Political Subdivisions Debt Securities [Member] | Fair Value, Inputs, Level 3 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
US States and Political Subdivisions Debt Securities [Member] | Fair Value, Inputs, Level 2 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities		3,088
Available-for-sale Securities	3,694
US Government Agencies Debt Securities [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	26,904	28,148
US Government Agencies Debt Securities [Member] | Fair Value, Inputs, Level 2 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities		28,148
Available-for-sale Securities	26,904
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	8,353	8,506
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member] | Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member] | Fair Value, Inputs, Level 3 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member] | Fair Value, Inputs, Level 2 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities		8,506
Available-for-sale Securities	8,353
Corporate Debt Securities [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	15,819	18,555
Corporate Debt Securities [Member] | Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Corporate Debt Securities [Member] | Fair Value, Inputs, Level 3 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Corporate Debt Securities [Member] | Fair Value, Inputs, Level 2 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities		18,555
Available-for-sale Securities	15,819
Equity Securities [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total equity investments	19,441	23,230
Equity Securities [Member] | Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Common stock	17,616	21,426
Long-term Debt [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total liabilities	48,210	43,944
Common Stock [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total equity investments		21,426
Equity Securities [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Warrants	1,825	1,804
Other Security Investments [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total assets	$ 92,327	$ 104,070

Fair Value of Financial Instr83

Fair Value of Financial Instruments Contingent Consideration (Tables) (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016	Jun. 30, 2017	Jun. 30, 2016	Mar. 31, 2017	Dec. 31, 2016	Mar. 31, 2016	Dec. 31, 2015
Site Contingency [Line Items]
Proceeds from (Payments for) Other Financing Activities	$ 100	$ 1,000	$ 100	$ 1,000
Change in fair value of contingent consideration included in net loss	(212)	(657)	(212)	(657)
Fair Value, Inputs, Level 3 [Member]
Site Contingency [Line Items]
Beginning balance	0	325	0	325
Ending balance	$ 0	$ 325	$ 0	$ 325	$ 325	$ 1,982	$ 325	$ 1,982

Related Party Transactions (Det

Related Party Transactions (Details) - $ / shares	3 Months Ended
	Dec. 31, 2016	Sep. 30, 2016	Apr. 20, 2016
Executive Vice President [Member]
Related Party Transaction [Line Items]
Common Stock, Shares, Issued			160,000
Stockholders' Equity, Other Shares		500,000
Management [Member]
Related Party Transaction [Line Items]
Sale of Stock, Number of Shares Issued in Transaction	100,000
Share Price	$ 7.57
Related Party Transaction, Rate	5.00%

Commitment and Contingencies (D

Commitment and Contingencies (Details) - USD ($) $ in Millions	6 Months Ended
	Jun. 30, 2017	Jun. 30, 2016
Commitments and Contingencies [Abstract]
Loss Contingency, Estimate of Possible Loss	$ 0.9	$ 0.2
Long-term Purchase Commitment, Amount	2.5
Fair Value, Investments, Entities that Calculate Net Asset Value Per Share, Unfunded Commitments	$ 1.2