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Property and Casualty Insurance Reserves - Reserve Activity (Details) - USD ($)
$ in Millions
6 Months Ended
Jun. 30, 2019
Jun. 30, 2018
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]    
Gross of Reinsurance and Indemnification at Beginning of Year $ 1,874.9  
Incurred Losses and LAE Related to:    
Incurred Losses and LAE Related to Prior Years (34.6) $ 1.6
Paid Losses and LAE Related to:    
Property and Casualty Insurance Reserves - Gross of Reinsurance at End of Period 1,911.9  
Property, Liability and Casualty Insurance Product Line    
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]    
Gross of Reinsurance and Indemnification at Beginning of Year 1,874.9 1,016.8
Less Reinsurance and Indemnification Recoverables at Beginning of Year 101.9 53.1
Property and Casualty Insurance Reserves - Net of Reinsurance at Beginning of Year 1,773.0 963.7
Property and Casualty Insurance Reserves Acquired, Net of Reinsurance 3.6 0.0
Incurred Losses and LAE Related to:    
Incurred Losses and LAE Related to Prior Years (34.6) 1.6
Total Incurred Losses and LAE 1,384.8 743.9
Paid Losses and LAE Related to:    
Paid Losses and LAE Related to Prior Years 698.5 363.3
Total Paid Losses and LAE 1,335.1 698.4
Property and Casualty Insurance Reserves - Net of Reinsurance at End of Period 1,826.3 1,009.2
Plus Reinsurance Recoverables at End of Period 85.6 50.5
Property and Casualty Insurance Reserves - Gross of Reinsurance at End of Period 1,911.9 1,059.7
Property, Liability and Casualty Insurance Product Line | Continuing Operations    
Incurred Losses and LAE Related to:    
Incurred Losses and LAE Related to Current Year 1,419.4 742.3
Incurred Losses and LAE Related to Prior Years (34.6) 2.0
Paid Losses and LAE Related to:    
Paid Losses and LAE Related to Current Year 636.6 335.1
Paid Losses and LAE Related to Prior Years 696.9 361.6
Property, Liability and Casualty Insurance Product Line | Discontinued Operations    
Incurred Losses and LAE Related to:    
Incurred Losses and LAE Related to Prior Years 0.0 (0.4)
Paid Losses and LAE Related to:    
Paid Losses and LAE Related to Prior Years $ 1.6 $ 1.7