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RELATED PARTY TRANSACTIONS (Details) - USD ($)
$ in Thousands
 3 Months Ended 12 Months Ended
Sep. 22, 2023
Jun. 29, 2021
Dec. 31, 2023
Dec. 31, 2023
Dec. 31, 2022
Dec. 31, 2021
Dec. 31, 2020
Related Party Transaction [Line Items]              
Other investments     $ 949,413 $ 949,413 $ 996,751    
Net premiums earned       5,083,781 5,160,326 $ 4,709,850  
Acquisition costs       1,000,945 1,022,017 921,834  
Net losses and loss expenses       3,393,102 3,242,410 3,008,783  
Reinsurance recoverable on unpaid claims     6,323,083 6,323,083 5,831,172 5,017,611 $ 4,496,641
Reinsurance recoverable on paid losses and loss expenses     575,847 575,847 539,676    
Ceded premiums       3,254,200 2,951,539 2,759,360  
Ceded losses and loss expenses       1,754,000 1,754,000 1,782,000  
Insurance and reinsurance balances payable     1,792,719 1,792,719 1,609,924    
Loan advance       349,842 105,822 82,870  
Loan balance receivable     305,222 305,222 87,160    
Related Party              
Related Party Transaction [Line Items]              
Other investments     424,000 424,000 462,000    
Ceded premiums       107,000 88,000 74,000  
Related Party | SKY Harbor Capital Management, LLC              
Related Party Transaction [Line Items]              
Income earned       3,000 2,000 2,000  
Related Party | Freedom              
Related Party Transaction [Line Items]              
Income earned       1,000 2,000 3,000  
Other investments     17,000 17,000      
Related Party | Stone Point Trident Fund VIII              
Related Party Transaction [Line Items]              
Income earned       2,000 2,000 4,000  
Other investments     87,000 87,000      
Related Party | Stone Point Trident VIII Co-Invest              
Related Party Transaction [Line Items]              
Other investments     26,000 26,000      
Related Party | Trident IX L.P. ("Trident IX")              
Related Party Transaction [Line Items]              
Income earned       1,000 1,000 0  
Other investments     24,000 24,000      
Related Party | Rialto Real Estate IV-Property              
Related Party Transaction [Line Items]              
Other investments     43,000 43,000      
Related Party | Rialto Real Estate Fund IV-Property              
Related Party Transaction [Line Items]              
Income earned       2,000 2,000 1,000  
Other investments     19,000 19,000      
Related Party | Stone Point Credit Corporation              
Related Party Transaction [Line Items]              
Income earned       500 300 0  
Other investments     18,000 18,000      
Related Party | Sound Point Capital Bond              
Related Party Transaction [Line Items]              
Other investments     5,000 5,000      
Related Party | Gordon Brothers              
Related Party Transaction [Line Items]              
Income earned       100 100    
Other investments     9,000 9,000      
Related Party | Eagle Point Credit Management, LLC              
Related Party Transaction [Line Items]              
Income earned       0      
Other investments     7,000 7,000      
Related Party | Aspida Holdings, Ltd              
Related Party Transaction [Line Items]              
Income earned       0      
Other investments     6,000 6,000      
Related Party | Monarch Point Re              
Related Party Transaction [Line Items]              
Income earned       100      
Other investments     22,000 22,000      
Net premiums earned $ 119,000            
Acquisition costs 33,000            
Net losses and loss expenses $ 7,000            
Reinsurance recoverable on unpaid claims     76,000 76,000      
Reinsurance recoverable on paid losses and loss expenses     4,000 4,000      
Ceded premiums       287,000      
Ceded losses and loss expenses       37,000      
Reinsurance recoverable on unpaid and paid losses     37,000 37,000      
Insurance and reinsurance balances payable     166,000 166,000      
Non-cash repayment of advance       72,000      
Related Party | Harrington Re              
Related Party Transaction [Line Items]              
Ceded premiums       298,000 324,000 283,000  
Ceded losses and loss expenses       229,000 234,000 $ 188,000  
Reinsurance recoverable on unpaid and paid losses     933,000 933,000 819,000    
Insurance and reinsurance balances payable     219,000 219,000 220,000    
Investment In Related Party | Senior Unsecured Notes Due 2031              
Related Party Transaction [Line Items]              
Other investments   $ 10,000          
Related party transaction floating rate (as a percent)   7.25%          
Loan Agreement With Monarch Point Re | Related Party | Monarch Point Re              
Related Party Transaction [Line Items]              
Loan advance       297,000      
Non-cash repayment of advance       72,000      
Loan balance receivable     225,000 225,000      
Other Commitment     $ 16,000 16,000      
Loan Agreement With Monarch Point Re | Related Party | Monarch Point Re | Minimum              
Related Party Transaction [Line Items]              
Related party transaction floating rate (as a percent)     5.70%        
Loan Agreement With Monarch Point Re | Related Party | Monarch Point Re | Maximum              
Related Party Transaction [Line Items]              
Related party transaction floating rate (as a percent)     5.85%        
Stone Pointe Credit Corporation Bonds | Related Party | Stone Point Credit Corporation              
Related Party Transaction [Line Items]              
Income earned       1,000 $ 600    
Other investments     $ 18,000 $ 18,000      
Stone Point Group | Related Party | Pantheon              
Related Party Transaction [Line Items]              
Percentage ownership by related parties       14.50%