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Claim and Claim Adjustment Expense Reserves - Net Prior Year Loss Reserve Development in Property and Casualty Operations (Details) - USD ($)
$ in Millions
3 Months Ended 6 Months Ended
Jun. 30, 2023
Jun. 30, 2022
Jun. 30, 2023
Jun. 30, 2022
Net Prior Year Development [Abstract]        
Total pretax (favorable) unfavorable development $ 18 $ 27 $ 31 $ 15
Medical professional liability        
Net Prior Year Development [Abstract]        
Total pretax (favorable) unfavorable development 1 9 9
Other professional liability and management liability        
Net Prior Year Development [Abstract]        
Total pretax (favorable) unfavorable development (1) 13 (1) 13
Surety        
Net Prior Year Development [Abstract]        
Total pretax (favorable) unfavorable development (7) (19) (7) (28)
Commercial auto        
Net Prior Year Development [Abstract]        
Total pretax (favorable) unfavorable development 11 21 11 21
General liability        
Net Prior Year Development [Abstract]        
Total pretax (favorable) unfavorable development 70 41 70 41
Workers’ compensation        
Net Prior Year Development [Abstract]        
Total pretax (favorable) unfavorable development (96) (82) (98) (84)
Property and other        
Net Prior Year Development [Abstract]        
Total pretax (favorable) unfavorable development 6 (12) 12 (21)
Other insurance operations        
Net Prior Year Development [Abstract]        
Total pretax (favorable) unfavorable development 35 64 35 64
Other insurance operations | CNA Financial        
Net Prior Year Development [Abstract]        
Total pretax (favorable) unfavorable development 35 64 35 64
Commercial Property and Casualty Operations | CNA Financial        
Net Prior Year Development [Abstract]        
Total pretax (favorable) unfavorable development $ (17) $ (37) $ (4) $ (49)