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Acquisitions - Purchase Price and Fair Value of Assets Acquired (Details)
$ / shares in Units, $ in Thousands
3 Months Ended 6 Months Ended
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
USD ($)
Dec. 31, 2017
USD ($)
Purchase Price                
Excess of purchase price over fair value of net assets acquired         $ 114,807 $ 114,807   $ 73,071
Fair Value of Previously Held Equity Method Investment                
Carrying value of previously held equity method investment prior to the close of the transaction         $ 326,277 $ 204,507    
Maiden Re                
Purchase Price                
Cash paid $ 286,375              
Adjustment for the fair value of preexisting relationships 10,273              
Purchase price 296,648              
Net assets acquired at fair value 296,648              
Excess of purchase price over fair value of net assets acquired $ 0              
KaylaRe                
Purchase Price                
Adjustment for the fair value of preexisting relationships   $ 37,169            
Value of ordinary shares issued   414,750            
Fair value of previously held equity method investment   336,137            
Purchase price   788,056            
Net assets acquired at fair value   746,320            
Excess of purchase price over fair value of net assets acquired   $ 41,736            
Fair Value of Enstar Ordinary Shares Issued                
Number of Enstar ordinary shares issued (shares) | shares   2,007,017            
Closing price of shares (dollars per share) | $ / shares   $ 206.65            
Fair value of Enstar ordinary shares issued to shareholders of KaylaRe   $ 414,750            
Fair Value of Previously Held Equity Method Investment                
Price-to-book multiple   1.05            
Fair value of previously held equity method investment prior to the close of the transaction   $ 336,137            
Gain recognized on remeasurement of previously held equity method investment to fair value     $ 16,000 $ 16,007        
KaylaRe                
Fair Value of Previously Held Equity Method Investment                
Carrying value of previously held equity method investment prior to the close of the transaction             $ 320,130