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Segment Information - Narrative (Details) - segment
12 Months Ended
Dec. 31, 2019
Jan. 01, 2019
Dec. 31, 2018
Jan. 01, 2018
Segment Reporting Information [Line Items]        
Number of reportable segments 5      
Number of operating segments 5      
Syndicate 1729        
Segment Reporting Information [Line Items]        
Proportion of capital provided to support Lloyd's syndicate (percent)   61.00% 62.00%  
Workers' Compensation Insurance        
Segment Reporting Information [Line Items]        
Alternative market solutions percentage ceded 100.00%      
Syndicate 6131        
Segment Reporting Information [Line Items]        
Proportion of capital provided to support Lloyd's syndicate (percent)       100.00%