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Fair Value Measurements - Summary of Assets Fair Value on a Recurring Basis (Details) - USD ($)
$ in Thousands
Mar. 31, 2020
Dec. 31, 2019
Mar. 31, 2019
Dec. 31, 2018
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale $ 1,570,605 $ 1,433,626    
Equity securities:        
Total equity securities 71,394 80,735    
Bank loan participations 202,888      
Fixed maturity securities        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 1,570,605 1,433,626    
State and municipal        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 181,375 167,101    
Residential mortgage-backed        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 307,439 264,146    
Corporate        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 685,021 632,221    
Commercial mortgage and asset-backed        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 268,979 252,457    
U.S. Treasury securities and obligations guaranteed by the U.S. government        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 126,023 115,667    
Redeemable preferred stock        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 1,768 2,034    
Recurring basis        
Equity securities:        
Bank loan participations 202,888      
Short-term investments 71,058 156,925    
Recurring basis | Fixed maturity securities        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 1,570,605 1,433,626    
Recurring basis | State and municipal        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 181,375 167,101    
Recurring basis | Residential mortgage-backed        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 307,439 264,146    
Recurring basis | Corporate        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 685,021 632,221    
Recurring basis | Commercial mortgage and asset-backed        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 268,979 252,457    
Recurring basis | U.S. Treasury securities and obligations guaranteed by the U.S. government        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 126,023 115,667    
Recurring basis | Redeemable preferred stock        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 1,768 2,034    
Recurring basis | Equity securities        
Equity securities:        
Total equity securities 71,394 80,735    
Recurring basis | Preferred stock        
Equity securities:        
Total equity securities 60,861 62,747    
Recurring basis | Common stock        
Equity securities:        
Total equity securities 10,533 17,988    
Recurring basis | Quoted Prices in Active Markets for Identical Assets Level 1        
Equity securities:        
Bank loan participations 0      
Short-term investments 0 0    
Recurring basis | Quoted Prices in Active Markets for Identical Assets Level 1 | Fixed maturity securities        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 125,580 115,173    
Recurring basis | Quoted Prices in Active Markets for Identical Assets Level 1 | State and municipal        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Quoted Prices in Active Markets for Identical Assets Level 1 | Residential mortgage-backed        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Quoted Prices in Active Markets for Identical Assets Level 1 | Corporate        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Quoted Prices in Active Markets for Identical Assets Level 1 | Commercial mortgage and asset-backed        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Quoted Prices in Active Markets for Identical Assets Level 1 | U.S. Treasury securities and obligations guaranteed by the U.S. government        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 125,580 115,173    
Recurring basis | Quoted Prices in Active Markets for Identical Assets Level 1 | Redeemable preferred stock        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Quoted Prices in Active Markets for Identical Assets Level 1 | Equity securities        
Equity securities:        
Total equity securities 7,980 14,669    
Recurring basis | Quoted Prices in Active Markets for Identical Assets Level 1 | Preferred stock        
Equity securities:        
Total equity securities 0 0    
Recurring basis | Quoted Prices in Active Markets for Identical Assets Level 1 | Common stock        
Equity securities:        
Total equity securities 7,980 14,669    
Recurring basis | Significant Other Observable Inputs Level 2        
Equity securities:        
Bank loan participations 201,860      
Short-term investments 71,058 156,925    
Recurring basis | Significant Other Observable Inputs Level 2 | Fixed maturity securities        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 1,445,025 1,318,453    
Recurring basis | Significant Other Observable Inputs Level 2 | State and municipal        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 181,375 167,101    
Recurring basis | Significant Other Observable Inputs Level 2 | Residential mortgage-backed        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 307,439 264,146    
Recurring basis | Significant Other Observable Inputs Level 2 | Corporate        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 685,021 632,221    
Recurring basis | Significant Other Observable Inputs Level 2 | Commercial mortgage and asset-backed        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 268,979 252,457    
Recurring basis | Significant Other Observable Inputs Level 2 | U.S. Treasury securities and obligations guaranteed by the U.S. government        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 443 494    
Recurring basis | Significant Other Observable Inputs Level 2 | Redeemable preferred stock        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 1,768 2,034    
Recurring basis | Significant Other Observable Inputs Level 2 | Equity securities        
Equity securities:        
Total equity securities 63,410 66,023    
Recurring basis | Significant Other Observable Inputs Level 2 | Preferred stock        
Equity securities:        
Total equity securities 60,861 62,747    
Recurring basis | Significant Other Observable Inputs Level 2 | Common stock        
Equity securities:        
Total equity securities 2,549 3,276    
Recurring basis | Significant Unobservable Inputs Level 3        
Equity securities:        
Total equity securities 1,000   $ 177 $ 214
Bank loan participations 1,028      
Short-term investments 0 0    
Recurring basis | Significant Unobservable Inputs Level 3 | Fixed maturity securities        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Significant Unobservable Inputs Level 3 | State and municipal        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Significant Unobservable Inputs Level 3 | Residential mortgage-backed        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Significant Unobservable Inputs Level 3 | Corporate        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Significant Unobservable Inputs Level 3 | Commercial mortgage and asset-backed        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Significant Unobservable Inputs Level 3 | U.S. Treasury securities and obligations guaranteed by the U.S. government        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Significant Unobservable Inputs Level 3 | Redeemable preferred stock        
Fixed maturity securities, available-for-sale:        
Total fixed maturity securities, available-for-sale 0 0    
Recurring basis | Significant Unobservable Inputs Level 3 | Equity securities        
Equity securities:        
Total equity securities 4 43    
Recurring basis | Significant Unobservable Inputs Level 3 | Preferred stock        
Equity securities:        
Total equity securities 0 0    
Recurring basis | Significant Unobservable Inputs Level 3 | Common stock        
Equity securities:        
Total equity securities $ 4 $ 43