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RELATED PARTY TRANSACTIONS (Details) - USD ($)
$ in Thousands
12 Months Ended
Jun. 29, 2021
Dec. 31, 2022
Dec. 31, 2021
Dec. 31, 2020
Related Party Transaction [Line Items]        
Other investments   $ 996,751 $ 947,982  
Ceded premiums   2,951,539 2,759,360 $ 2,490,529
Ceded losses and loss expenses   1,754,000 1,782,000 1,914,000
Insurance and reinsurance balances payable   1,522,764 1,324,620  
Stone Point Group        
Related Party Transaction [Line Items]        
Fees paid to related party   2,000 2,000 3,000
Freedom Consumer Credit Fund, LLC Series B        
Related Party Transaction [Line Items]        
Fees paid to related party   2,000 3,000 2,000
Other investments   39,000    
Stone Point Trident Fund VIII        
Related Party Transaction [Line Items]        
Fees paid to related party   2,000 4,000 1,000
Other investments   82,000    
Stone Point Trident VIII Co-Invest        
Related Party Transaction [Line Items]        
Other investments   26,000    
Trident IX L.P. ("Trident IX")        
Related Party Transaction [Line Items]        
Fees paid to related party   1,000 0 0
Other investments   9,000    
Rialto Real Estate Fund IV-Property        
Related Party Transaction [Line Items]        
Fees paid to related party   2,000 1,000 0
Other investments   17,000    
Stone Point Credit Corporation        
Related Party Transaction [Line Items]        
Fees paid to related party   300 0 0
Other investments   18,000    
Stone Point Credit Corporation Bond        
Related Party Transaction [Line Items]        
Other investments   17,000    
Income earned from related party   600    
Sound Point Capital Bond        
Related Party Transaction [Line Items]        
Other investments   6,000    
Gordon Brothers        
Related Party Transaction [Line Items]        
Other investments   24,000    
Chairman        
Related Party Transaction [Line Items]        
Fees paid to related party       400
Significant influence        
Related Party Transaction [Line Items]        
Other investments   462,000 555,000  
Harrington Re        
Related Party Transaction [Line Items]        
Ceded premiums   324,000 283,000 256,000
Ceded losses and loss expenses   234,000 188,000 $ 187,000
Reinsurance recoverable on unpaid and paid losses   819,000 717,000  
Insurance and reinsurance balances payable   220,000 $ 189,000  
Senior Unsecured Notes Due 2031 | Investment In Related Party        
Related Party Transaction [Line Items]        
Other investments $ 10,000      
Related party transaction floating rate (as a percent) 7.25%      
Rialto Real Estate IV-Property        
Related Party Transaction [Line Items]        
Other investments   $ 40,000    
Stone Point Group | Pantheon        
Related Party Transaction [Line Items]        
Percentage ownership by related parties   14.50%