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Segment Information (Financial Data by Segment) (Details) - USD ($)
$ in Thousands
 3 Months Ended 9 Months Ended
Sep. 30, 2023
Sep. 30, 2022
Sep. 30, 2023
Sep. 30, 2022
Segment Reporting Information [Line Items]        
Net premiums earned $ 242,420 $ 258,355 $ 730,068 $ 771,337
Net investment income 32,754 24,745 94,714 67,132
Equity in earnings (loss) of unconsolidated subsidiaries (61) (6,852) 5,450 5,948
Net investment gains (losses) (4,202) (8,262) (1,344) (45,652)
Other income (expense) 3,336 5,097 6,864 13,215
Net losses and loss adjustment expenses (208,891) (198,073) (605,245) (585,166)
Underwriting, policy acquisition and operating expenses (74,014) (80,679) (218,779) (227,926)
SPC U.S. federal income taxes expense 175 (433) (1,351) (1,424)
SPC dividend (expense) income 2,518 (183) (3,171) (1,697)
Interest expense (5,514) (5,513) (16,478) (14,872)
Income tax benefit (expense) 4,655 2,673 3,901 6,232
Segment results (6,824) (9,125) (5,371) (12,873)
Goodwill impairment 44,110 0 44,110 0
Contingent consideration adjustment     (5,500) 0
Net income (loss) (49,434) (9,125) (44,981) (14,344)
Depreciation and amortization, net of accretion 6,454 9,637 20,085 30,046
Income tax expense (benefit) (4,655) (2,673) (3,901) (6,623)
NORCAL Group        
Segment Reporting Information [Line Items]        
Transaction-related costs       (1,900)
Income tax expense (benefit)       400
Specialty P&C        
Segment Reporting Information [Line Items]        
Net premiums earned 195,772 198,481 562,206 593,534
Workers' Compensation Insurance        
Segment Reporting Information [Line Items]        
Net premiums earned 39,885 42,063 121,706 124,456
Segregated Portfolio Cell Reinsurance        
Segment Reporting Information [Line Items]        
Net premiums earned 6,763 17,811 46,156 53,347
Operating segments | Specialty P&C        
Segment Reporting Information [Line Items]        
Net premiums earned 195,772 198,481 562,206 593,534
Net investment income 0 0 0 0
Equity in earnings (loss) of unconsolidated subsidiaries 0 0 0 0
Net investment gains (losses) 0 0 0 0
Other income (expense) 1,089 1,000 3,106 4,185
Net losses and loss adjustment expenses (162,677) (158,518) (476,187) (469,690)
Underwriting, policy acquisition and operating expenses (49,395) (53,166) (140,949) (148,339)
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 (15,211) (12,203) (51,824) (20,310)
Goodwill impairment 0   0  
Depreciation and amortization, net of accretion 2,728 2,290 7,927 7,830
Operating segments | Workers' Compensation Insurance        
Segment Reporting Information [Line Items]        
Net premiums earned 39,885 42,063 121,706 124,456
Net investment income 0 0 0 0
Equity in earnings (loss) of unconsolidated subsidiaries 0 0 0 0
Net investment gains (losses) 0 0 0 0
Other income (expense) 333 554 1,565 1,753
Net losses and loss adjustment expenses (41,208) (28,148) (101,813) (83,306)
Underwriting, policy acquisition and operating expenses (13,542) (14,146) (40,923) (40,816)
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 (14,532) 323 (19,465) 2,087
Goodwill impairment 0   0  
Depreciation and amortization, net of accretion 851 872 2,573 2,620
Operating segments | Segregated Portfolio Cell Reinsurance        
Segment Reporting Information [Line Items]        
Net premiums earned 6,763 17,811 46,156 53,347
Net investment income 601 294 1,625 617
Equity in earnings (loss) of unconsolidated subsidiaries 0 0 0 0
Net investment gains (losses) (525) (732) 1,830 (4,225)
Other income (expense) 2 1 3 2
Net losses and loss adjustment expenses (5,006) (11,407) (27,245) (32,170)
Underwriting, policy acquisition and operating expenses (3,668) (5,599) (15,241) (15,203)
SPC U.S. federal income taxes expense 175 (433) (1,351) (1,424)
SPC dividend (expense) income 2,518 (183) (3,171) (1,697)
Interest expense 0 0 0 0
Income tax benefit (expense) 0 0 0 0
Segment results 860 (248) 2,606 (753)
Goodwill impairment 0   0  
Depreciation and amortization, net of accretion 300 294 (187) 1,009
Operating segments | Corporate        
Segment Reporting Information [Line Items]        
Net premiums earned 0 0 0 0
Net investment income 32,153 24,451 93,089 66,515
Equity in earnings (loss) of unconsolidated subsidiaries (61) (6,852) 5,450 5,948
Net investment gains (losses) (3,677) (7,530) (3,174) (41,427)
Other income (expense) 2,847 4,695 5,347 10,386
Net losses and loss adjustment expenses 0 0 0 0
Underwriting, policy acquisition and operating expenses (8,344) (8,921) (24,823) (26,679)
SPC U.S. federal income taxes expense 0 0 0 0
SPC dividend (expense) income 0 0 0 0
Interest expense (5,514) (5,513) (16,478) (14,872)
Income tax benefit (expense) 4,655 2,673 3,901 6,232
Segment results 22,059 3,003 63,312 6,103
Goodwill impairment 0   0  
Depreciation and amortization, net of accretion 2,575 6,181 9,772 18,587
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 investment gains (losses) 0 0 0 0
Other income (expense) (935) (1,153) (3,157) (3,111)
Net losses and loss adjustment expenses 0 0 0 0
Underwriting, policy acquisition and operating expenses 935 1,153 3,157 3,111
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
Goodwill impairment 0   0  
Depreciation and amortization, net of accretion 0 $ 0 0 0
Segment reconciling items        
Segment Reporting Information [Line Items]        
Goodwill impairment (44,110)   (44,110)  
Contingent consideration adjustment $ 1,500   $ 4,500  
Transaction-related costs       $ (1,471)