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Reserves - Schedule of Most Significant Claims and Benefits Payable (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2015
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]        
Claims and benefits payable, at beginning of year $ 1,266.1 $ 1,412.9 $ 1,719.9  
Less: Reinsurance ceded and other (1,179.2) (1,255.1) (1,401.8) $ (384.3)
Net claims and benefits payable, at beginning of year 11.0 11.1 1,335.6  
Incurred losses and loss adjustment expenses related to:        
Current year 63.4 32.0 181.6  
Prior year's interest 0.0 0.0 9.4  
Prior years 0.0 (0.1) (40.4)  
Total incurred losses and loss adjustment expenses 63.4 31.9 150.6  
Paid losses and loss adjustment expenses related to:        
Current year 56.6 29.0 177.2  
Prior years 6.5 3.0 1,297.9  
Total paid losses and loss adjustment expenses 63.1 32.0 1,475.1  
Net claims and benefits payable, at end of year 11.3 11.0 11.1  
Plus: Reinsurance ceded and other 1,179.2 1,255.1 1,401.8 $ 384.3
Claims and benefits payable, at end of year $ 1,190.5 $ 1,266.1 $ 1,412.9