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Fair Value Measurements - Summary of Assets Fair Value on a Recurring Basis (Details) - USD ($)
$ in Thousands
Jun. 30, 2020
Dec. 31, 2019
Jun. 30, 2019
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale $ 1,747,404 $ 1,433,626  
Equity securities:      
Total equity securities 78,045 80,735  
Bank loan participations 127,698    
Fixed maturity securities      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 1,747,404 1,433,626  
State and municipal      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 269,922 167,101  
Residential mortgage-backed      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 291,188 264,146  
Corporate      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 754,442 632,221  
Commercial mortgage and asset-backed      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 311,181 252,457  
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 118,680 115,667  
Redeemable preferred stock      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 1,991 2,034  
Recurring basis      
Equity securities:      
Bank loan participations 127,698    
Short-term investments 96,265 156,925  
Recurring basis | Fixed maturity securities      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 1,747,404 1,433,626  
Recurring basis | State and municipal      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 269,922 167,101  
Recurring basis | Residential mortgage-backed      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 291,188 264,146  
Recurring basis | Corporate      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 754,442 632,221  
Recurring basis | Commercial mortgage and asset-backed      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 311,181 252,457  
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 118,680 115,667  
Recurring basis | Redeemable preferred stock      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 1,991 2,034  
Recurring basis | Equity securities      
Equity securities:      
Total equity securities 78,045 80,735  
Recurring basis | Preferred stock      
Equity securities:      
Total equity securities 62,880 62,747  
Recurring basis | Common stock      
Equity securities:      
Total equity securities 15,165 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 118,235 115,173  
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 118,235 115,173  
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 9,536 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 9,536 14,669  
Recurring basis | Significant Other Observable Inputs Level 2      
Equity securities:      
Bank loan participations 127,394    
Short-term investments 96,265 156,925  
Recurring basis | Significant Other Observable Inputs Level 2 | Fixed maturity securities      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 1,629,169 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 269,922 167,101  
Recurring basis | Significant Other Observable Inputs Level 2 | Residential mortgage-backed      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 291,188 264,146  
Recurring basis | Significant Other Observable Inputs Level 2 | Corporate      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 754,442 632,221  
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 311,181 252,457  
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 445 494  
Recurring basis | Significant Other Observable Inputs Level 2 | Redeemable preferred stock      
Fixed maturity securities, available-for-sale:      
Total fixed maturity securities, available-for-sale 1,991 2,034  
Recurring basis | Significant Other Observable Inputs Level 2 | Equity securities      
Equity securities:      
Total equity securities 68,501 66,023  
Recurring basis | Significant Other Observable Inputs Level 2 | Preferred stock      
Equity securities:      
Total equity securities 62,880 62,747  
Recurring basis | Significant Other Observable Inputs Level 2 | Common stock      
Equity securities:      
Total equity securities 5,621 3,276  
Recurring basis | Significant Unobservable Inputs Level 3      
Equity securities:      
Total equity securities 312    
Bank loan participations 304    
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 8 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 $ 8 $ 43 $ 3,100