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Acquisitions - Additional Information (Details)
3 Months Ended 6 Months Ended
Oct. 30, 2019
USD ($)
Dec. 27, 2018
USD ($)
May 14, 2018
USD ($)
$ / shares
shares
Jun. 30, 2018
USD ($)
Jun. 30, 2018
USD ($)
Dec. 31, 2019
USD ($)
Dec. 31, 2018
USD ($)
May 13, 2018
Dec. 31, 2017
USD ($)
Business Acquisition [Line Items]                  
Asbestos and environmental liabilities           $ 2,259,600,000 $ 1,839,700,000    
Goodwill           $ 114,807,000 $ 114,807,000   $ 73,071,000
Ownership percentage           47.40% 47.40%    
Morse TEC                  
Business Acquisition [Line Items]                  
Asbestos and environmental liabilities $ 700,000,000                
Cash paid 0                
Intangible assets acquired 0                
Goodwill 0                
Gain on bargain purchase $ 0                
Maiden Re                  
Business Acquisition [Line Items]                  
Cash paid   $ 286,375,000              
Goodwill   $ 0              
KaylaRe                  
Business Acquisition [Line Items]                  
Goodwill     $ 41,736,000            
Number of Enstar ordinary shares issued (shares) | shares     2,007,017            
Closing price of shares (dollars per share) | $ / shares     $ 206.65            
Ownership percentage acquired     51.80%            
Price-to-book multiple     1.05            
Gain recognized on remeasurement of previously held equity method investment to fair value       $ 16,000,000.0 $ 16,007,000        
Loss on settlement of preexisting relationships       $ 15,600,000 $ 15,600,000        
Ordinary Shares | KaylaRe                  
Business Acquisition [Line Items]                  
Number of Enstar ordinary shares issued (shares) | shares     1,501,778            
Series E non-voting convertible ordinary shares | KaylaRe                  
Business Acquisition [Line Items]                  
Number of Enstar ordinary shares issued (shares) | shares     505,239            
KaylaRe                  
Business Acquisition [Line Items]                  
Ownership percentage               48.20%