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Segment Information (Financial Data by Segment) (Details) - USD ($)
$ in Thousands
 3 Months Ended 9 Months Ended 12 Months Ended
May 05, 2021
Sep. 30, 2021
Sep. 30, 2020
Sep. 30, 2021
Sep. 30, 2020
Dec. 31, 2020
Segment Reporting Information [Line Items]            
Net premiums earned   $ 272,248 $ 194,559 $ 698,598 $ 605,708  
Net investment income   19,278 16,924 51,713 55,877  
Equity in earnings (loss) of unconsolidated subsidiaries   15,244 4,853 33,959 (22,065)  
Net realized gains (losses)   530 8,838 20,212 150  
Other income (loss) (expense)   2,400 1,723 6,862 5,668  
Net losses and loss adjustment expenses   (223,393) (145,581) (555,030) (521,412)  
Underwriting, policy acquisition and operating expenses   (64,485) (59,433) (176,915) (180,178)  
SPC U.S. federal income taxes expense   (431) (871) (1,291) (1,573)  
SPC dividend (expense) income   (1,320) (3,854) (5,926) (7,988)  
Interest expense   (5,814) (3,881) (14,203) (11,725)  
Income tax benefit (expense)   (219) (2,141) (1,369) 48,621  
Segment results   14,038 11,136 56,610 (28,917)  
Gain on bargain purchase   0 0 74,408 0  
Goodwill impairment   0 161,115 0 161,115 $ 161,115
Net income (loss)   12,200 (149,979) 111,984 (190,032)  
Depreciation and amortization, net of accretion   10,246 6,345 26,566 16,168  
Income tax expense (benefit)   (270) 2,141 (3,132) (48,621)  
NORCAL Group            
Segment Reporting Information [Line Items]            
Gain on bargain purchase $ 74,408          
Transaction-related costs   (2,300) (500) (23,500) (1,600)  
Income tax expense (benefit)   (500)   (4,500)    
Specialty P&C            
Segment Reporting Information [Line Items]            
Net premiums earned   203,716 117,849 487,963 365,305  
Workers' Compensation Insurance            
Segment Reporting Information [Line Items]            
Net premiums earned   42,235 42,516 122,872 129,437  
Segregated Portfolio Cell Reinsurance            
Segment Reporting Information [Line Items]            
Net premiums earned   15,344 16,052 47,500 49,780  
Lloyd's Syndicates            
Segment Reporting Information [Line Items]            
Net premiums earned   10,953 18,142 40,263 61,186  
Operating segments | Specialty P&C            
Segment Reporting Information [Line Items]            
Net premiums earned   203,716 117,849 487,963 365,305  
Net investment income   0 0 0 0  
Equity in earnings (loss) of unconsolidated subsidiaries   0 0 0 0  
Net realized gains (losses)   0 0 0 0  
Other income (loss) (expense)   860 726 2,800 3,515  
Net losses and loss adjustment expenses   (176,490) (102,951) (417,890) (373,442)  
Underwriting, policy acquisition and operating expenses   (36,147) (28,074) (91,369) (82,894)  
SPC U.S. federal income taxes expense   0 0 0 0  
SPC dividend (expense) income   0 0 0 0  
Interest expense   0 0 0 0  
Income tax benefit (expense)   0 0 0 0  
Segment results   (8,061) (12,450) (18,496) (87,516)  
Depreciation and amortization, net of accretion   1,956 2,669 7,261 5,930  
Operating segments | Workers' Compensation Insurance            
Segment Reporting Information [Line Items]            
Net premiums earned   42,235 42,516 122,872 129,437  
Net investment income   0 0 0 0  
Equity in earnings (loss) of unconsolidated subsidiaries   0 0 0 0  
Net realized gains (losses)   0 0 0 0  
Other income (loss) (expense)   437 441 1,730 1,717  
Net losses and loss adjustment expenses   (31,364) (26,455) (85,323) (84,648)  
Underwriting, policy acquisition and operating expenses   (13,521) (14,983) (38,519) (42,604)  
SPC U.S. federal income taxes expense   0 0 0 0  
SPC dividend (expense) income   0 0 0 0  
Interest expense   0 0 0 0  
Income tax benefit (expense)   0 0 0 0  
Segment results   (2,213) 1,519 760 3,902  
Depreciation and amortization, net of accretion   903 923 2,709 2,771  
Operating segments | Segregated Portfolio Cell Reinsurance            
Segment Reporting Information [Line Items]            
Net premiums earned   15,344 16,052 47,500 49,780  
Net investment income   193 273 620 832  
Equity in earnings (loss) of unconsolidated subsidiaries   0 0 0 0  
Net realized gains (losses)   204 1,495 2,772 894  
Other income (loss) (expense)   0 12 2 203  
Net losses and loss adjustment expenses   (8,693) (6,858) (26,560) (23,890)  
Underwriting, policy acquisition and operating expenses   (4,758) (5,036) (15,078) (15,474)  
SPC U.S. federal income taxes expense   (431) (871) (1,291) (1,573)  
SPC dividend (expense) income   (1,320) (3,854) (5,926) (7,988)  
Interest expense   0 0 0 0  
Income tax benefit (expense)   0 0 0 0  
Segment results   539 1,213 2,039 2,784  
Depreciation and amortization, net of accretion   397 210 1,074 371  
Operating segments | Lloyd's Syndicates            
Segment Reporting Information [Line Items]            
Net premiums earned   10,953 18,142 40,263 61,186  
Net investment income   431 951 1,677 3,236  
Equity in earnings (loss) of unconsolidated subsidiaries   0 0 0 0  
Net realized gains (losses)   35 489 9 1,100  
Other income (loss) (expense)   283 411 864 219  
Net losses and loss adjustment expenses   (6,846) (9,317) (25,257) (39,432)  
Underwriting, policy acquisition and operating expenses   (3,909) (6,938) (15,219) (23,373)  
SPC U.S. federal income taxes expense   0 0 0 0  
SPC dividend (expense) income   0 0 0 0  
Interest expense   0 0 0 0  
Income tax benefit (expense)   0 0 0 29  
Segment results   947 3,738 2,337 2,965  
Depreciation and amortization, net of accretion   17 3 49 26  
Operating segments | Corporate            
Segment Reporting Information [Line Items]            
Net premiums earned   0 0 0 0  
Net investment income   18,654 15,700 49,416 51,809  
Equity in earnings (loss) of unconsolidated subsidiaries   15,244 4,853 33,959 (22,065)  
Net realized gains (losses)   291 6,854 17,431 (1,844)  
Other income (loss) (expense)   1,542 775 3,786 1,813  
Net losses and loss adjustment expenses   0 0 0 0  
Underwriting, policy acquisition and operating expenses   (6,872) (5,044) (19,050) (17,632)  
SPC U.S. federal income taxes expense   0 0 0 0  
SPC dividend (expense) income   0 0 0 0  
Interest expense   (5,814) (3,881) (14,203) (11,725)  
Income tax benefit (expense)   (219) (2,141) (1,369) 48,592  
Segment results   22,826 17,116 69,970 48,948  
Depreciation and amortization, net of accretion   6,973 2,540 15,473 7,070  
Inter-segment Eliminations            
Segment Reporting Information [Line Items]            
Net premiums earned   0 0 0 0  
Net investment income   0 0 0 0  
Equity in earnings (loss) of unconsolidated subsidiaries   0 0 0 0  
Net realized gains (losses)   0 0 0 0  
Other income (loss) (expense)   (722) (642) (2,320) (1,799)  
Net losses and loss adjustment expenses   0 0 0 0  
Underwriting, policy acquisition and operating expenses   722 642 2,320 1,799  
SPC U.S. federal income taxes expense   0 0 0 0  
SPC dividend (expense) income   0 0 0 0  
Interest expense   0 0 0 0  
Income tax benefit (expense)   0 0 0 0  
Segment results   0 0 0 0  
Depreciation and amortization, net of accretion   0 0 0 0  
Segment reconciling items            
Segment Reporting Information [Line Items]            
Gain on bargain purchase       74,408    
Transaction-related costs   $ (1,838)   $ (19,034)    
Goodwill impairment     $ 161,115   $ 161,115