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Commitments and Contingencies - Narrative (Details) - USD ($)
$ in Thousands
12 Months Ended
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2015
Other Commitments [Line Items]      
Additional investment commitment - other investments $ 82,600    
Commitment To Invest In Limited Partnerships Time Period 6 years 6 months    
Commitment To Invest In Closed End Funds Limited Partnerships And Investment Vehicles $ 308,000    
Commitment To Invest In Closed End Funds Limited Partnerships Time Period 5 years 1 month 6 days    
Operating Leases, Rent Expense, Net $ 76,300 $ 68,000 $ 71,100
Sale Leaseback Transaction, Net Book Value 55,700 55,500  
Sale Leaseback Transaction, Amount Due under Financing Arrangement 94,200 89,900  
Sale Leaseback Transaction, Deferred Gain, Net 16,900    
Total minimum future lease payments $ 133,377    
Branch Profit Tax On Taxable Income Percentage 30.00%    
Letter of credit facility      
Other Commitments [Line Items]      
Available letter of credit facilities - in use $ 2,549,226 $ 2,345,293  
Collateralized by certain assets of the Company's investment portfolio 54.20% 48.60%  
Shareholders' equity | Credit concentration risk      
Other Commitments [Line Items]      
Maximum percentage of ceded written premium 5.00%    
Property and casualty operations | Gross written premium | Credit concentration risk      
Other Commitments [Line Items]      
Maximum percentage of ceded written premium 10.00%