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Schedule III - Supplementary Insurance Information (Details) - USD ($)
$ in Thousands
 12 Months Ended
Dec. 31, 2020
Dec. 31, 2019
Dec. 31, 2018
Supplementary Insurance Information, by Segment [Line Items]      
Deferred Acquisition Costs $ 622,053 $ 581,863 $ 511,573
Reverse for Losses and Loss Adjustment Expenses 16,398,997 13,611,313 13,119,090
Unearned Premium Reserves 3,501,359 3,056,735 2,517,612
Premiums Earned 8,681,513 7,403,686 6,931,699
Net Investment Income 642,465 647,139 581,183
Incurred Loss and Loss Adjustment Expenses 6,550,837 4,922,898 5,651,403
Amortization of Deferred Acquisition Costs 1,873,250 1,703,726 1,519,030
Other Operating Expenses 511,237 440,899 371,541
Net Written Premium 9,116,983 7,824,424 7,414,428
Domestic Country [Member]      
Supplementary Insurance Information, by Segment [Line Items]      
Deferred Acquisition Costs 341,836 358,108 334,818
Reverse for Losses and Loss Adjustment Expenses 9,501,573 7,823,095 8,154,003
Unearned Premium Reserves 2,206,378 2,014,712 1,695,208
Premiums Earned 5,123,460 4,383,837 4,167,619
Net Investment Income 341,797 320,923 287,002
Incurred Loss and Loss Adjustment Expenses 3,920,837 2,761,871 3,849,982
Amortization of Deferred Acquisition Costs 1,063,266 1,007,282 835,823
Other Operating Expenses 409,912 348,861 288,933
Net Written Premium 5,313,490 4,605,731 4,350,157
International Country [Member]      
Supplementary Insurance Information, by Segment [Line Items]      
Deferred Acquisition Costs 85,678 66,183 54,253
Reverse for Losses and Loss Adjustment Expenses 2,781,210 2,655,458 2,209,202
Unearned Premium Reserves 430,227 344,222 261,611
Premiums Earned 1,752,244 1,475,669 1,439,882
Net Investment Income 37,208 37,297 34,965
Incurred Loss and Loss Adjustment Expenses 1,074,727 1,193,816 992,704
Amortization of Deferred Acquisition Costs 399,908 342,400 364,010
Other Operating Expenses 45,757 41,690 39,042
Net Written Premium 1,854,813 1,551,753 1,458,745
Bermuda Country [Member]      
Supplementary Insurance Information, by Segment [Line Items]      
Deferred Acquisition Costs 194,539 157,572 122,502
Reverse for Losses and Loss Adjustment Expenses 4,116,214 3,132,760 2,755,885
Unearned Premium Reserves 864,754 697,801 560,793
Premiums Earned 1,805,809 1,544,180 1,324,198
Net Investment Income 263,460 288,919 259,216
Incurred Loss and Loss Adjustment Expenses 1,555,273 967,211 808,717
Amortization of Deferred Acquisition Costs 410,076 354,044 319,197
Other Operating Expenses 55,568 50,348 43,566
Net Written Premium $ 1,948,680 $ 1,666,940 $ 1,605,526