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Losses and Loss Expenses Payable Losses and Loss Expenses Payable - Schedule of Activity in Liability for Unpaid Losses and Loss Expenses Payable (Details) - USD ($)
$ in Millions
3 Months Ended 9 Months Ended
Sep. 30, 2018
Sep. 30, 2017
Sep. 30, 2018
Sep. 30, 2017
Dec. 31, 2017
Dec. 31, 2016
Losses and Loss Expenses Payable [Abstract]            
Liability for Claims and Claims Adjustment Expense, Property Casualty Liability $ 1,198.7 $ 1,280.8 $ 1,198.7 $ 1,280.8 $ 1,255.6 $ 1,181.6
Reinsurance Recoverables, Including Reinsurance Premium Paid 5.0 4.9 5.0 4.9 3.1 3.6
Liability for Unpaid Claims and Claims Adjustment Expense, Net 1,193.7 1,275.9 1,193.7 1,275.9 $ 1,252.5 $ 1,178.0
Current Year Claims and Claims Adjustment Expense     678.7 752.8    
Prior Year Claims and Claims Adjustment Expense     57.6 (34.6)    
Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims $ 191.0 $ 253.5 621.1 718.2    
Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Current Year     314.1 302.0    
Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Prior Years     365.8 318.3    
Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid     $ 679.9 $ 620.3