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Reserve for Losses and Loss Adjustment Expenses - Incurred Losses and Loss Adjustment Expenses (Details) - USD ($)
$ in Thousands
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2015
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Dec. 31, 2010
Casualty Reinsurance                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance $ 1,145,314                  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 863,436                  
All outstanding losses and loss adjustment expenses prior to 2010, net of reinsurance 1,798                  
Total outstanding losses and loss adjustment expenses, net of reinsurance 283,676                  
Casualty Reinsurance | Accident year 2010                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 63,357 $ 62,605 $ 61,619 $ 60,978 $ 60,949 $ 61,344 $ 62,714 $ 61,068 $ 60,476 $ 64,413
Cumulative paid losses and loss adjustment expenses, net of reinsurance 59,634 58,707 57,013 54,659 52,761 49,263 44,921 38,430 31,500 21,918
Casualty Reinsurance | Accident year 2011                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 105,333 103,196 101,276 99,282 98,993 97,812 97,366 103,123 114,908  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 99,511 97,715 94,627 90,287 87,267 78,164 68,616 61,922 48,688  
Casualty Reinsurance | Accident year 2012                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 146,045 143,305 139,978 136,813 135,594 131,281 132,388 148,251    
Cumulative paid losses and loss adjustment expenses, net of reinsurance 137,430 133,606 128,567 121,026 113,943 97,215 81,859 73,124    
Casualty Reinsurance | Accident year 2013                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 146,760 143,124 137,801 134,446 131,352 130,361 133,230      
Cumulative paid losses and loss adjustment expenses, net of reinsurance 134,644 127,732 119,256 108,396 93,902 75,094 59,756      
Casualty Reinsurance | Accident year 2014                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 126,160 121,200 116,981 114,636 115,927 118,881        
Cumulative paid losses and loss adjustment expenses, net of reinsurance 110,374 101,366 89,899 76,302 58,601 41,421        
Casualty Reinsurance | Accident year 2015                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 114,517 109,117 108,699 108,870 119,157          
Cumulative paid losses and loss adjustment expenses, net of reinsurance 90,661 80,208 68,002 53,986 40,021          
Casualty Reinsurance | Accident year 2016                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 108,222 103,544 105,533 112,759            
Cumulative paid losses and loss adjustment expenses, net of reinsurance 78,145 65,409 50,905 36,268            
Casualty Reinsurance | Accident year 2017                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 129,800 128,472 134,628              
Cumulative paid losses and loss adjustment expenses, net of reinsurance 90,117 72,891 47,739              
Casualty Reinsurance | Accident year 2018                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 119,098 121,529                
Cumulative paid losses and loss adjustment expenses, net of reinsurance 50,274 30,903                
Casualty Reinsurance | Accident year 2019                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 86,022                  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 12,646                  
Commercial Auto | Excess and Surplus Lines                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 968,285                  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 535,232                  
Total outstanding losses and loss adjustment expenses, net of reinsurance 433,053                  
Commercial Auto | Excess and Surplus Lines | Accident year 2013                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 1,277 1,277 1,301 1,351 1,451 1,300 1,255      
Cumulative paid losses and loss adjustment expenses, net of reinsurance 1,275 1,275 1,275 1,291 1,285 1,182 60      
Commercial Auto | Excess and Surplus Lines | Accident year 2014                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 18,303 19,779 18,953 17,233 14,071 20,487        
Cumulative paid losses and loss adjustment expenses, net of reinsurance 17,745 18,678 16,359 12,679 8,645 6,166        
Commercial Auto | Excess and Surplus Lines | Accident year 2015                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 36,636 36,139 35,149 33,113 30,109          
Cumulative paid losses and loss adjustment expenses, net of reinsurance 34,819 31,592 24,282 15,234 8,356          
Commercial Auto | Excess and Surplus Lines | Accident year 2016                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 147,122 126,791 109,286 74,340            
Cumulative paid losses and loss adjustment expenses, net of reinsurance 125,108 89,381 54,054 18,295            
Commercial Auto | Excess and Surplus Lines | Accident year 2017                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 272,421 208,743 207,355              
Cumulative paid losses and loss adjustment expenses, net of reinsurance 192,961 107,377 41,467              
Commercial Auto | Excess and Surplus Lines | Accident year 2018                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 230,220 255,881                
Cumulative paid losses and loss adjustment expenses, net of reinsurance 119,099 45,136                
Commercial Auto | Excess and Surplus Lines | Accident year 2019                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 262,306                  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 44,225                  
Excluding Commercial Auto | Excess and Surplus Lines                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 1,185,370                  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 625,534                  
All outstanding losses and loss adjustment expenses prior to 2010, net of reinsurance 8,978                  
Total outstanding losses and loss adjustment expenses, net of reinsurance 568,814                  
Excluding Commercial Auto | Excess and Surplus Lines | Accident year 2010                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 69,594 71,312 70,913 70,294 69,964 69,080 73,035 78,117 80,569 78,424
Cumulative paid losses and loss adjustment expenses, net of reinsurance 65,915 65,246 64,214 61,307 57,371 52,071 45,641 35,812 26,418 13,673
Excluding Commercial Auto | Excess and Surplus Lines | Accident year 2011                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 105,173 106,536 106,643 106,130 106,381 106,564 114,473 119,927 111,190  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 101,728 99,798 98,684 94,998 90,884 81,696 72,732 53,109 27,684  
Excluding Commercial Auto | Excess and Surplus Lines | Accident year 2012                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 103,061 101,271 99,619 97,306 96,497 97,829 98,672 97,908    
Cumulative paid losses and loss adjustment expenses, net of reinsurance 94,588 88,812 82,545 74,869 63,216 49,604 33,757 6,944    
Excluding Commercial Auto | Excess and Surplus Lines | Accident year 2013                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 82,732 83,855 82,830 81,009 85,433 96,064 96,729      
Cumulative paid losses and loss adjustment expenses, net of reinsurance 71,035 66,553 59,641 44,421 30,382 14,509 3,867      
Excluding Commercial Auto | Excess and Surplus Lines | Accident year 2014                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 88,904 84,074 82,232 90,267 104,092 114,942        
Cumulative paid losses and loss adjustment expenses, net of reinsurance 71,549 58,774 43,891 28,212 16,969 3,412        
Excluding Commercial Auto | Excess and Surplus Lines | Accident year 2015                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 103,688 102,434 104,847 113,417 126,443          
Cumulative paid losses and loss adjustment expenses, net of reinsurance 73,455 55,911 34,801 17,164 4,048          
Excluding Commercial Auto | Excess and Surplus Lines | Accident year 2016                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 126,971 126,050 125,093 138,507            
Cumulative paid losses and loss adjustment expenses, net of reinsurance 70,105 46,045 22,852 5,180            
Excluding Commercial Auto | Excess and Surplus Lines | Accident year 2017                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 132,136 131,897 144,349              
Cumulative paid losses and loss adjustment expenses, net of reinsurance 42,764 22,956 5,290              
Excluding Commercial Auto | Excess and Surplus Lines | Accident year 2018                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 158,458 167,004                
Cumulative paid losses and loss adjustment expenses, net of reinsurance 26,160 6,000                
Excluding Commercial Auto | Excess and Surplus Lines | Accident year 2019                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 214,653                  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 8,235                  
Fronting and Programs | Specialty Admitted Insurance                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 91,751                  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 43,424                  
All outstanding losses and loss adjustment expenses prior to 2010, net of reinsurance 48,327                  
Total outstanding losses and loss adjustment expenses, net of reinsurance 48,727                  
Fronting and Programs | Specialty Admitted Insurance | Accident year 2013                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 52 52 52 52 52 80 104      
Cumulative paid losses and loss adjustment expenses, net of reinsurance 52 52 52 52 52 52 28      
Fronting and Programs | Specialty Admitted Insurance | Accident year 2014                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 3,083 3,228 3,425 3,818 3,468 3,460        
Cumulative paid losses and loss adjustment expenses, net of reinsurance 2,916 2,854 2,728 2,369 1,687 883        
Fronting and Programs | Specialty Admitted Insurance | Accident year 2015                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 8,384 8,974 9,358 9,632 7,136          
Cumulative paid losses and loss adjustment expenses, net of reinsurance 7,329 6,919 6,165 4,666 2,058          
Fronting and Programs | Specialty Admitted Insurance | Accident year 2016                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 15,522 14,682 15,670 11,542            
Cumulative paid losses and loss adjustment expenses, net of reinsurance 10,732 6,888 5,123 1,894            
Fronting and Programs | Specialty Admitted Insurance | Accident year 2017                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 25,201 24,271 21,229              
Cumulative paid losses and loss adjustment expenses, net of reinsurance 13,065 6,682 1,223              
Fronting and Programs | Specialty Admitted Insurance | Accident year 2018                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 20,677 21,758                
Cumulative paid losses and loss adjustment expenses, net of reinsurance 4,972 885                
Fronting and Programs | Specialty Admitted Insurance | Accident year 2019                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 18,832                  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 4,358                  
Individual Risk Workers' Compensation | Specialty Admitted Insurance                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 205,237                  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 167,741                  
All outstanding losses and loss adjustment expenses prior to 2010, net of reinsurance 1,039                  
Total outstanding losses and loss adjustment expenses, net of reinsurance 43,191                  
Individual Risk Workers' Compensation | Specialty Admitted Insurance | Accident year 2010                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 27,099 27,099 27,098 27,590 28,938 28,963 30,373 30,464 28,736 27,209
Cumulative paid losses and loss adjustment expenses, net of reinsurance 26,365 26,358 26,352 26,345 25,477 25,210 23,898 21,805 16,245 $ 7,157
Individual Risk Workers' Compensation | Specialty Admitted Insurance | Accident year 2011                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 36,593 36,593 36,594 37,455 38,311 38,999 40,154 41,421 37,834  
Cumulative paid losses and loss adjustment expenses, net of reinsurance 34,638 34,614 34,334 34,287 34,240 33,204 29,021 23,127 $ 10,123  
Individual Risk Workers' Compensation | Specialty Admitted Insurance | Accident year 2012                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 28,186 28,186 28,174 28,255 29,689 31,490 32,420 32,116    
Cumulative paid losses and loss adjustment expenses, net of reinsurance 26,994 26,963 26,932 26,897 26,435 24,755 20,308 $ 9,222    
Individual Risk Workers' Compensation | Specialty Admitted Insurance | Accident year 2013                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 10,909 10,909 10,907 11,578 12,786 13,668 12,525      
Cumulative paid losses and loss adjustment expenses, net of reinsurance 10,337 10,309 10,263 10,246 9,846 8,723 $ 4,487      
Individual Risk Workers' Compensation | Specialty Admitted Insurance | Accident year 2014                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 12,704 12,704 13,890 14,620 16,652 16,638        
Cumulative paid losses and loss adjustment expenses, net of reinsurance 12,282 12,282 12,236 12,041 10,648 $ 4,633        
Individual Risk Workers' Compensation | Specialty Admitted Insurance | Accident year 2015                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 17,626 18,376 19,741 21,274 20,938          
Cumulative paid losses and loss adjustment expenses, net of reinsurance 15,901 15,889 15,118 13,285 $ 6,604          
Individual Risk Workers' Compensation | Specialty Admitted Insurance | Accident year 2016                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 15,800 18,050 20,299 21,678            
Cumulative paid losses and loss adjustment expenses, net of reinsurance 12,432 12,135 10,227 $ 4,664            
Individual Risk Workers' Compensation | Specialty Admitted Insurance | Accident year 2017                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 19,779 22,071 24,869              
Cumulative paid losses and loss adjustment expenses, net of reinsurance 14,285 12,782 $ 6,546              
Individual Risk Workers' Compensation | Specialty Admitted Insurance | Accident year 2018                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 16,288 16,432                
Cumulative paid losses and loss adjustment expenses, net of reinsurance 9,034 $ 4,497                
Individual Risk Workers' Compensation | Specialty Admitted Insurance | Accident year 2019                    
Claims Development [Line Items]                    
Incurred losses and loss adjustment expenses, net of reinsurance 20,253                  
Cumulative paid losses and loss adjustment expenses, net of reinsurance $ 5,473