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Claim and Claim Adjustment Expense Reserves - Schedule of Historical Claims Duration (Detail) - CNA Financial [Member]
Dec. 31, 2018
Medical Professional Liability [Member]  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Average Annual Percentage Payout of Claims in Year 1 3.80%
Average Annual Percentage Payout of Claims in Year 2 19.70%
Average Annual Percentage Payout of Claims in Year 3 24.30%
Average Annual Percentage Payout of Claims in Year 4 20.10%
Average Annual Percentage Payout of Claims in Year 5 12.10%
Average Annual Percentage Payout of Claims in Year 6 7.20%
Average Annual Percentage Payout of Claims in Year 7 4.50%
Average Annual Percentage Payout of Claims in Year 8 2.50%
Average Annual Percentage Payout of Claims in Year 9 1.00%
Average Annual Percentage Payout of Claims in Year 10 2.90%
Total 98.10%
Other Professional Liability and Management Liability [Member]  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Average Annual Percentage Payout of Claims in Year 1 6.20%
Average Annual Percentage Payout of Claims in Year 2 21.50%
Average Annual Percentage Payout of Claims in Year 3 21.30%
Average Annual Percentage Payout of Claims in Year 4 17.40%
Average Annual Percentage Payout of Claims in Year 5 10.70%
Average Annual Percentage Payout of Claims in Year 6 6.40%
Average Annual Percentage Payout of Claims in Year 7 5.80%
Average Annual Percentage Payout of Claims in Year 8 2.90%
Average Annual Percentage Payout of Claims in Year 9 3.30%
Average Annual Percentage Payout of Claims in Year 10 2.10%
Total 97.60%
Surety [Member]  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Average Annual Percentage Payout of Claims in Year 1 21.60%
Average Annual Percentage Payout of Claims in Year 2 37.90%
Average Annual Percentage Payout of Claims in Year 3 21.00%
Average Annual Percentage Payout of Claims in Year 4 7.90%
Average Annual Percentage Payout of Claims in Year 5 2.10%
Average Annual Percentage Payout of Claims in Year 6 1.60%
Average Annual Percentage Payout of Claims in Year 7 (1.70%)
Average Annual Percentage Payout of Claims in Year 8 (0.50%)
Total 89.90%
Commercial Auto [Member]  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Average Annual Percentage Payout of Claims in Year 1 28.00%
Average Annual Percentage Payout of Claims in Year 2 23.00%
Average Annual Percentage Payout of Claims in Year 3 18.50%
Average Annual Percentage Payout of Claims in Year 4 14.20%
Average Annual Percentage Payout of Claims in Year 5 9.30%
Average Annual Percentage Payout of Claims in Year 6 3.10%
Average Annual Percentage Payout of Claims in Year 7 1.30%
Average Annual Percentage Payout of Claims in Year 8 0.30%
Average Annual Percentage Payout of Claims in Year 9 0.20%
Average Annual Percentage Payout of Claims in Year 10 0.70%
Total 98.60%
General Liability [Member]  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Average Annual Percentage Payout of Claims in Year 1 4.30%
Average Annual Percentage Payout of Claims in Year 2 15.90%
Average Annual Percentage Payout of Claims in Year 3 19.50%
Average Annual Percentage Payout of Claims in Year 4 20.50%
Average Annual Percentage Payout of Claims in Year 5 15.70%
Average Annual Percentage Payout of Claims in Year 6 8.00%
Average Annual Percentage Payout of Claims in Year 7 5.60%
Average Annual Percentage Payout of Claims in Year 8 3.20%
Average Annual Percentage Payout of Claims in Year 9 1.60%
Average Annual Percentage Payout of Claims in Year 10 0.80%
Total 95.10%
Workers' Compensation [Member]  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Average Annual Percentage Payout of Claims in Year 1 13.70%
Average Annual Percentage Payout of Claims in Year 2 21.10%
Average Annual Percentage Payout of Claims in Year 3 13.90%
Average Annual Percentage Payout of Claims in Year 4 10.60%
Average Annual Percentage Payout of Claims in Year 5 7.50%
Average Annual Percentage Payout of Claims in Year 6 4.40%
Average Annual Percentage Payout of Claims in Year 7 4.40%
Average Annual Percentage Payout of Claims in Year 8 3.20%
Average Annual Percentage Payout of Claims in Year 9 2.50%
Average Annual Percentage Payout of Claims in Year 10 1.20%
Total 82.50%