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Subsequent Events Subsequent Events - Narrative (Details)
$ in Millions
12 Months Ended
Mar. 02, 2020
USD ($)
Jan. 01, 2020
USD ($)
Dec. 31, 2019
USD ($)
Dec. 31, 2018
USD ($)
Dec. 31, 2017
USD ($)
Subsequent Event [Line Items]          
Coverage     $ 2,319.8 $ 2,077.6 $ 1,515.2
Interest rate, compounded     0.25    
Enstar | Subsequent Event          
Subsequent Event [Line Items]          
Coverage $ 800.0        
Second coverage 300.0        
Ceded premiums payable   $ 800.0      
Interest rate, compounded   0.0375      
Enstar | Minimum | Subsequent Event          
Subsequent Event [Line Items]          
Reinsurance retention policy, amount retained 3,800.0        
Enstar | Maximum | Subsequent Event          
Subsequent Event [Line Items]          
Reinsurance retention policy, amount retained 4,600.0        
Reinsurance retention policy, second amount retained $ 4,800.0