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Claim, Claim Adjustment Expense and Future Policy Benefit Reserves - Schedule of Historical Claims Duration (Detail) - CNA Financial Corporation [Member]
Dec. 31, 2019
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 20.00%
Average Annual Percentage Payout of Claims in Year 3 24.30%
Average Annual Percentage Payout of Claims in Year 4 19.40%
Average Annual Percentage Payout of Claims in Year 5 12.40%
Average Annual Percentage Payout of Claims in Year 6 7.80%
Average Annual Percentage Payout of Claims in Year 7 5.10%
Average Annual Percentage Payout of Claims in Year 8 3.10%
Average Annual Percentage Payout of Claims in Year 9 1.10%
Average Annual Percentage Payout of Claims in Year 10 0.80%
Total 97.80%
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 6.60%
Average Annual Percentage Payout of Claims in Year 2 22.60%
Average Annual Percentage Payout of Claims in Year 3 21.70%
Average Annual Percentage Payout of Claims in Year 4 16.90%
Average Annual Percentage Payout of Claims in Year 5 10.50%
Average Annual Percentage Payout of Claims in Year 6 6.00%
Average Annual Percentage Payout of Claims in Year 7 4.90%
Average Annual Percentage Payout of Claims in Year 8 3.30%
Average Annual Percentage Payout of Claims in Year 9 3.80%
Average Annual Percentage Payout of Claims in Year 10 0.70%
Total 97.00%
Surety [Member]  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Average Annual Percentage Payout of Claims in Year 1 20.00%
Average Annual Percentage Payout of Claims in Year 2 44.50%
Average Annual Percentage Payout of Claims in Year 3 21.00%
Average Annual Percentage Payout of Claims in Year 4 4.40%
Average Annual Percentage Payout of Claims in Year 5 2.20%
Average Annual Percentage Payout of Claims in Year 6 0.90%
Average Annual Percentage Payout of Claims in Year 7 (2.50%)
Average Annual Percentage Payout of Claims in Year 8 (1.10%)
Average Annual Percentage Payout of Claims in Year 10 1.60%
Total 91.00%
Commercial Auto [Member]  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Average Annual Percentage Payout of Claims in Year 1 28.60%
Average Annual Percentage Payout of Claims in Year 2 24.00%
Average Annual Percentage Payout of Claims in Year 3 18.60%
Average Annual Percentage Payout of Claims in Year 4 14.30%
Average Annual Percentage Payout of Claims in Year 5 9.40%
Average Annual Percentage Payout of Claims in Year 6 3.20%
Average Annual Percentage Payout of Claims in Year 7 1.50%
Average Annual Percentage Payout of Claims in Year 8 0.40%
Total 100.00%
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 15.80%
Average Annual Percentage Payout of Claims in Year 3 19.00%
Average Annual Percentage Payout of Claims in Year 4 20.10%
Average Annual Percentage Payout of Claims in Year 5 15.70%
Average Annual Percentage Payout of Claims in Year 6 8.70%
Average Annual Percentage Payout of Claims in Year 7 6.00%
Average Annual Percentage Payout of Claims in Year 8 2.50%
Average Annual Percentage Payout of Claims in Year 9 1.50%
Average Annual Percentage Payout of Claims in Year 10 1.60%
Total 95.20%
Workers' Compensation [Member]  
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]  
Average Annual Percentage Payout of Claims in Year 1 14.10%
Average Annual Percentage Payout of Claims in Year 2 21.40%
Average Annual Percentage Payout of Claims in Year 3 13.90%
Average Annual Percentage Payout of Claims in Year 4 10.30%
Average Annual Percentage Payout of Claims in Year 5 7.00%
Average Annual Percentage Payout of Claims in Year 6 3.70%
Average Annual Percentage Payout of Claims in Year 7 2.90%
Average Annual Percentage Payout of Claims in Year 8 2.70%
Average Annual Percentage Payout of Claims in Year 9 1.40%
Average Annual Percentage Payout of Claims in Year 10 0.80%
Total 78.20%