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SEGMENT INFORMATION - Summary of Underwriting Results of Reportable Segments (Details)
$ in Thousands
 12 Months Ended
Dec. 31, 2023
USD ($)
reportableSegment
Dec. 31, 2022
USD ($)
Dec. 31, 2021
USD ($)
Dec. 31, 2020
USD ($)
Segment Reporting [Abstract]        
Number of reportable segments | reportableSegment 2      
Segment Information [Line Items]        
Gross premiums written $ 8,356,525 $ 8,214,595 $ 7,685,984  
Net premiums written 5,102,325 5,263,056 4,926,624  
Net premiums earned 5,083,781 5,160,326 4,709,850  
Other insurance related income (loss) 22,495 13,073 23,295  
Net losses and loss expenses (3,393,102) (3,242,410) (3,008,783)  
Acquisition costs (1,000,945) (1,022,017) (921,834)  
Underwriting-related general and administrative expenses (684,446) (680,343) (663,304)  
Net investment income 611,742 418,829 454,301  
Net investment gains (losses) (74,630) (456,789) 134,279  
Foreign exchange (losses) gains (58,115) 157,945 (315)  
Interest expense and financing costs (68,421) (63,146) (62,302)  
Reorganization expenses (28,997) (31,426) 0  
Amortization of value of business acquired 0 0 (3,854)  
Amortization of intangible assets (10,917) (10,917) (12,424)  
Income before income taxes and interest in income of equity method investments 398,445 243,125 648,909  
Income tax expense (26,316) (22,037) (62,384)  
Interest in income of equity method investments 4,163 1,995 32,084  
Net income 376,292 223,083 618,609  
Preferred share dividends 30,250 30,250 30,250  
Net income available to common shareholders 346,042 192,833 588,359  
Goodwill and intangible assets 287,684 298,601 309,518 $ 324,288
Operating Segments        
Segment Information [Line Items]        
Gross premiums written 8,356,525 8,214,595 7,685,984  
Net premiums written 5,102,325 5,263,056 4,926,624  
Net premiums earned 5,083,781 5,160,326 4,709,850  
Other insurance related income (loss) 22,495 13,073 23,295  
Net losses and loss expenses (3,393,102) (3,242,410) (3,008,783)  
Acquisition costs (1,000,945) (1,022,017) (921,834)  
Underwriting-related general and administrative expenses (551,467) (550,289) (536,834)  
Underwriting income (loss) $ 160,762 $ 358,683 $ 265,694  
Net losses and loss expenses ratio 66.70% 62.80% 63.90%  
Acquisition cost ratio 19.70% 19.80% 19.60%  
General and administrative expense ratio 13.50% 13.20% 14.00%  
Combined ratio 99.90% 95.80% 97.50%  
Goodwill and intangible assets $ 287,684 $ 298,601 $ 309,518  
Operating Segments | Insurance        
Segment Information [Line Items]        
Gross premiums written 6,140,764 5,585,581 4,863,232  
Net premiums written 3,758,720 3,377,906 2,894,885  
Net premiums earned 3,461,700 3,134,155 2,651,339  
Other insurance related income (loss) (198) 559 1,662  
Net losses and loss expenses (2,080,001) (1,785,854) (1,514,998)  
Acquisition costs (648,463) (577,838) (484,344)  
Underwriting-related general and administrative expenses (472,094) (443,704) (429,282)  
Underwriting income (loss) $ 260,944 $ 327,318 $ 224,377  
Net losses and loss expenses ratio 60.10% 57.00% 57.10%  
Acquisition cost ratio 18.70% 18.40% 18.30%  
General and administrative expense ratio 13.70% 14.20% 16.20%  
Combined ratio 92.50% 89.60% 91.60%  
Goodwill and intangible assets $ 287,684 $ 298,601 $ 309,518  
Operating Segments | Reinsurance        
Segment Information [Line Items]        
Gross premiums written 2,215,761 2,629,014 2,822,752  
Net premiums written 1,343,605 1,885,150 2,031,739  
Net premiums earned 1,622,081 2,026,171 2,058,511  
Other insurance related income (loss) 22,693 12,514 21,633  
Net losses and loss expenses (1,313,101) (1,456,556) (1,493,785)  
Acquisition costs (352,482) (444,179) (437,490)  
Underwriting-related general and administrative expenses (79,373) (106,585) (107,552)  
Underwriting income (loss) $ (100,182) $ 31,365 $ 41,317  
Net losses and loss expenses ratio 81.00% 71.90% 72.60%  
Acquisition cost ratio 21.70% 21.90% 21.30%  
General and administrative expense ratio 4.90% 5.30% 5.10%  
Combined ratio 107.60% 99.10% 99.00%  
Goodwill and intangible assets $ 0 $ 0 $ 0  
Significant Reconciling Items        
Segment Information [Line Items]        
Net investment income 611,742 418,829 454,301  
Net investment gains (losses) (74,630) (456,789) 134,279  
Foreign exchange (losses) gains (58,115) 157,945 (315)  
Interest expense and financing costs (68,421) (63,146) (62,302)  
Reorganization expenses (28,997) (31,426) 0  
Amortization of value of business acquired 0 0 (3,854)  
Amortization of intangible assets (10,917) (10,917) (12,424)  
Corporate        
Segment Information [Line Items]        
Underwriting-related general and administrative expenses $ (132,979) $ (130,054) $ (126,470)