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Reserve for Losses and Loss Adjustment Expenses - Average Annual Percentage Payouts of Incurred Claims (Details)
Dec. 31, 2019
Casualty Reinsurance  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Year 1 21.10%
Year 2 16.40%
Year 3 12.20%
Year 4 8.90%
Year 5 6.40%
Year 6 5.30%
Year 7 4.30%
Year 8 3.60%
Year 9 3.50%
Year 10 3.20%
Fronting and Programs | Specialty Admitted Insurance  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Year 1 18.70%
Year 2 22.40%
Year 3 24.30%
Year 4 16.10%
Year 5 10.50%
Year 6 5.30%
Excluding Commercial Auto | E&S  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Year 1 9.50%
Year 2 15.70%
Year 3 17.20%
Year 4 18.50%
Year 5 14.50%
Year 6 8.00%
Year 7 5.40%
Year 8 3.80%
Year 9 2.00%
Year 10 1.10%
Commercial Auto | E&S  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Year 1 20.40%
Year 2 38.10%
Year 3 16.00%
Year 4 14.10%
Year 5 7.20%
Year 6 2.60%
Year 7 1.50%
Individual Risk Workers' Compensation | Specialty Admitted Insurance  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Year 1 27.90%
Year 2 30.90%
Year 3 16.00%
Year 4 10.20%
Year 5 7.20%
Year 6 1.20%
Year 7 1.70%
Year 8 0.90%
Year 9 0.10%
Year 10 1.30%