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Goodwill and Intangible Assets - Summary of intangible assets by major class (Details) - USD ($)
$ in Thousands
Dec. 31, 2020
Dec. 31, 2019
Schedule of Goodwill And Intangible Assets [Line Items]    
Gross balance $ 1,180,860 $ 1,161,336
Intangible assets with a finite life, accumulated amortization (489,828) (419,294)
Goodwill and intangible assets, accumulated foreign currency translation and other adjustments 1,831 (3,959)
Goodwill and intangible assets, net balance 692,863 738,083
Intangible liability - unfavorable service contract    
Schedule of Goodwill And Intangible Assets [Line Items]    
Gross balance (9,533) (9,533)
Intangible assets with a finite life, accumulated amortization 9,147 8,657
Goodwill and intangible assets, accumulated foreign currency translation and other adjustments 0 0
Goodwill and intangible assets, net balance (386) (876)
Intangible assets with a finite life    
Schedule of Goodwill And Intangible Assets [Line Items]    
Intangible assets with a finite life, accumulated amortization (489,828)  
Goodwill and intangible assets, accumulated foreign currency translation and other adjustments 3,922  
Intangible assets with a finite life | Acquired insurance contracts    
Schedule of Goodwill And Intangible Assets [Line Items]    
Gross balance 451,505 452,470
Intangible assets with a finite life, accumulated amortization (381,349) (336,559)
Goodwill and intangible assets, accumulated foreign currency translation and other adjustments 284 310
Goodwill and intangible assets, net balance 70,440 116,221
Intangible assets with a finite life | Operating platform    
Schedule of Goodwill And Intangible Assets [Line Items]    
Gross balance 52,674 52,674
Intangible assets with a finite life, accumulated amortization (44,347) (39,571)
Goodwill and intangible assets, accumulated foreign currency translation and other adjustments 60 (259)
Goodwill and intangible assets, net balance 8,387 12,844
Intangible assets with a finite life | Distribution relationships    
Schedule of Goodwill And Intangible Assets [Line Items]    
Gross balance 285,141 243,838
Intangible assets with a finite life, accumulated amortization (71,383) (50,542)
Goodwill and intangible assets, accumulated foreign currency translation and other adjustments 3,450 212
Goodwill and intangible assets, net balance 217,208 193,508
Intangible assets with a finite life | Other    
Schedule of Goodwill And Intangible Assets [Line Items]    
Gross balance 5,134 5,134
Intangible assets with a finite life, accumulated amortization (1,896) (1,279)
Goodwill and intangible assets, accumulated foreign currency translation and other adjustments 127 70
Goodwill and intangible assets, net balance 3,365 3,925
Goodwill    
Schedule of Goodwill And Intangible Assets [Line Items]    
Gross balance 318,043 331,448
Goodwill and intangible assets, accumulated foreign currency translation and other adjustments (3,414) (4,897)
Goodwill and intangible assets, net balance 314,629 326,551
Intangible assets with an indefinite life    
Schedule of Goodwill And Intangible Assets [Line Items]    
Goodwill and intangible assets, accumulated foreign currency translation and other adjustments 1,323  
Intangible assets with an indefinite life | Insurance licenses    
Schedule of Goodwill And Intangible Assets [Line Items]    
Gross balance 55,981 63,390
Goodwill and intangible assets, accumulated foreign currency translation and other adjustments 0 0
Goodwill and intangible assets, net balance 55,981 63,390
Intangible assets with an indefinite life | Syndicate capacity    
Schedule of Goodwill And Intangible Assets [Line Items]    
Gross balance 21,915 21,915
Goodwill and intangible assets, accumulated foreign currency translation and other adjustments 1,324 605
Goodwill and intangible assets, net balance $ 23,239 $ 22,520