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Related Party Transactions - KaylaRe (Details) - USD ($)
$ in Thousands
3 Months Ended 12 Months Ended
May 14, 2018
Dec. 15, 2016
Dec. 31, 2019
Sep. 30, 2019
Jun. 30, 2019
Mar. 31, 2019
Dec. 31, 2018
Sep. 30, 2018
Jun. 30, 2018
Mar. 31, 2018
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
May 13, 2018
Dec. 31, 2016
Related Party Transaction [Line Items]                              
Ownership percentage     47.40%       47.40%       47.40% 47.40%      
Fee income due to Enstar Limited                       $ 1,453 $ 2,679    
Transactions under KaylaRe-StarStone QS:                              
Ceded, premiums earned                     $ (267,197) (330,136) (434,166)    
Net incurred losses and LAE     $ 121,416 $ 222,417 $ 216,338 $ 312,404 $ 187,698 $ 153,974 $ 92,819 $ 19,534 872,575 454,025 193,551    
Acquisition costs     $ 95,026 $ 50,282 $ 66,855 $ 93,788 $ 55,106 $ 54,242 $ 53,334 $ 30,108 $ 305,951 192,790 96,906    
KaylaRe                              
Related Party Transaction [Line Items]                              
Initial capital raise   $ 620,000                          
KaylaRe | Starstone                              
Related Party Transaction [Line Items]                              
Percentage reinsured of certain businesses                     35.00%        
KaylaRe | Fitzwilliam | Subsidiaries                              
Related Party Transaction [Line Items]                              
Ceded reinsurance receivables                             $ 177,200
KaylaRe Transactions With Starstone                              
Transactions under KaylaRe-StarStone QS:                              
Ceded, premiums earned                       (52,651) (234,079)    
Net incurred losses and LAE                       31,654 155,433    
Acquisition costs                       18,774 99,500    
KaylaRe Transactions With Fitzwilliam | Subsidiaries                              
Transactions under Fitzwilliam reinsurance agreement:                              
Profit Commission                       0 18,843    
Affiliated entity | KaylaRe                              
Transactions under Fitzwilliam reinsurance agreement:                              
Total net earnings (loss)                       $ (770) $ 42,376    
KaylaRe                              
Related Party Transaction [Line Items]                              
Ownership percentage                           48.20%  
KaylaRe                              
Related Party Transaction [Line Items]                              
Number of Enstar ordinary shares issued (shares) 2,007,017                            
Ordinary Shares | KaylaRe                              
Related Party Transaction [Line Items]                              
Number of Enstar ordinary shares issued (shares) 1,501,778                            
Ordinary Shares | KaylaRe | Hillhouse                              
Related Party Transaction [Line Items]                              
Number of Enstar ordinary shares issued (shares) 1,204,353                            
Ordinary Shares | KaylaRe | Trident                              
Related Party Transaction [Line Items]                              
Number of Enstar ordinary shares issued (shares) 285,986                            
Series E non-voting convertible ordinary shares | KaylaRe                              
Related Party Transaction [Line Items]                              
Number of Enstar ordinary shares issued (shares) 505,239                            
Series E non-voting convertible ordinary shares | KaylaRe | Hillhouse                              
Related Party Transaction [Line Items]                              
Number of Enstar ordinary shares issued (shares) 505,239                            
Series E non-voting convertible ordinary shares | KaylaRe | Minority Shareholder                              
Related Party Transaction [Line Items]                              
Number of Enstar ordinary shares issued (shares) 11,439