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Reserves (Roll Forward of Claims and Benefits Payable) (Details) - USD ($)
$ in Millions
6 Months Ended
Jun. 30, 2018
Jun. 30, 2017
May 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]          
Claims and benefits payable, at beginning of period $ 3,782.2 $ 3,301.2      
Less: Reinsurance ceded and other (3,193.3) (2,718.2)      
Net claims and benefits payable, at beginning of period 588.9 583.0      
Acquired reserves as of Acquisition Date       $ 142.9 $ 0.0
Incurred losses and loss adjustment expenses related to:          
Current year 938.1 856.3      
Prior years (30.6) (60.0)      
Total incurred losses and loss adjustment expenses 907.5 796.3      
Paid losses and loss adjustment expenses related to:          
Current year 624.6 556.0      
Prior years 336.4 262.8      
Total paid losses and loss adjustment expenses 961.0 818.8      
Net claims and benefits payable, at end of period 678.3 560.5      
Reinsurance ceded and other 3,193.3 2,718.2   3,193.3 2,718.2
Claims and benefits payable, at end of period 3,503.1 3,093.3      
Claims and benefits payable 3,503.1 3,301.2   $ 3,782.2 $ 3,301.2
Plus: Reinsurance ceded and other $ 2,824.8 $ 2,532.8      
TWG Holdings Limited          
Paid losses and loss adjustment expenses related to:          
Reinsurance ceded and other     $ 280.6    
Claims and benefits payable     $ 423.5