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RELATED PARTY TRANSACTIONS (Details) - USD ($)
$ in Thousands
7 Months Ended 12 Months Ended
Jul. 31, 2018
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Related Party Transaction [Line Items]        
Other investments   $ 770,923 $ 787,787  
Ceded premiums   2,409,243 2,251,103 $ 1,529,130
Ceded losses and loss expenses   1,602,000 1,565,000 1,010,000
Insurance and reinsurance balances payable   1,349,082 1,338,991  
Stone Point Group        
Related Party Transaction [Line Items]        
Fees paid to related party   3,000 2,000 2,000
NXT Capital II        
Related Party Transaction [Line Items]        
Other investments   11,000    
NXT Capital III        
Related Party Transaction [Line Items]        
Other investments   19,000    
NXT Capital        
Related Party Transaction [Line Items]        
Fees paid to related party     1,000 1,000
Freedom Consumer Credit Fund, LLC Series B        
Related Party Transaction [Line Items]        
Fees paid to related party   3,000 2,000 1,000
Other investments   52,000    
Stone Point Trident Fund VIII        
Related Party Transaction [Line Items]        
Other investments   71,000    
Chairman        
Related Party Transaction [Line Items]        
Fees paid to related party   400 500 500
Significant influence        
Related Party Transaction [Line Items]        
Other investments   410,000 450,000  
Harrington Re        
Related Party Transaction [Line Items]        
Ceded premiums   247,000 194,000 213,000
Ceded losses and loss expenses   157,000 142,000 119,000
Reinsurance recoverable on unpaid and paid losses   518,000 363,000  
Insurance and reinsurance balances payable   159,000 115,000  
Ventures Re        
Related Party Transaction [Line Items]        
Ceded premiums   192,000 182,000 107,000
Ceded losses and loss expenses   140,000 138,000 $ 126,000
Reinsurance recoverable on unpaid and paid losses   199,000 186,000  
Insurance and reinsurance balances payable   $ 46,000 $ 67,000  
Stone Point Group | NXT Capital        
Related Party Transaction [Line Items]        
Percentage ownership by related parties 43.00%      
Stone Point Group | Pantheon        
Related Party Transaction [Line Items]        
Percentage ownership by related parties   14.50%