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Goodwill and Other Intangible Assets - Narrative (Details) - USD ($)
$ in Thousands
12 Months Ended
Sep. 30, 2016
Feb. 01, 2016
Jul. 24, 2015
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2015
Dec. 31, 2014
Goodwill [Line Items]              
Goodwill       $ 1,234,150 $ 1,213,524 $ 1,213,630 $ 415,936
Goodwill, acquired during period         14,084 807,381  
Gross goodwill       2,600,000 2,600,000    
Accumulated impairment loss on goodwill       1,400,000 1,400,000    
Finite-Lived Intangible Assets, Gross       354,200 347,200    
Finite-Lived Intangible Assets, Accumulated Amortization       $ 61,600 39,800    
Acquired Finite-lived Intangible Assets, Weighted Average Useful Life       16 years 8 months 12 days      
Finite-lived Intangible Assets Acquired         28,948 315,000  
Indefinite-lived Intangible Assets Acquired         8,000 $ 673,000  
Insurance Segment              
Goodwill [Line Items]              
Goodwill       $ 492,300 483,600    
Reinsurance Segment              
Goodwill [Line Items]              
Goodwill       $ 741,900 $ 730,000    
New Energy Risk Inc. [Member]              
Goodwill [Line Items]              
Goodwill, acquired during period     $ 13,400        
Brooklyn Underwriting Pty Limited and Brooklyn IT Pty Limited [Member]              
Goodwill [Line Items]              
Finite-lived Intangible Assets Acquired $ 22,900            
Allied International Holdings, Inc.              
Goodwill [Line Items]              
Goodwill, acquired during period   $ 14,100          
Finite-lived Intangible Assets Acquired   6,000          
Indefinite-lived Intangible Assets Acquired   8,000          
Allied International Holdings, Inc. | Insurance Segment              
Goodwill [Line Items]              
Goodwill, acquired during period   $ 14,100