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Reserves for Losses and Loss Adjustment Expenses - Reconciliation of Beginning and Ending Consolidated Loss and Loss Adjustment Expenses ("LAE") Reserves (Details) - USD ($)
$ in Millions
 3 Months Ended 12 Months Ended
Mar. 31, 2019
Mar. 31, 2018
Dec. 31, 2018
Dec. 31, 2017
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]        
Provision for losses and LAE at the start of the year $ 7,074.2 $ 6,749.5 $ 6,749.5  
Net loss and LAE at the start of the year 4,996.6 5,234.3 5,234.3  
Provision for losses and LAE for claims incurred:        
Current year 304.2 347.9 1,684.1  
Prior years 7.6 (37.7) (111.1)  
Total incurred 311.8 310.2 1,573.0  
Losses and LAE payments for claims incurred:        
Current year (7.1) (7.4) (285.7)  
Prior years (474.8) (483.7) (1,441.0)  
Total paid (481.9) (491.1) (1,726.7)  
Foreign exchange losses/(gains) 50.9 14.7 (84.0)  
Net losses and LAE reserves at period end 4,877.4 5,068.1 4,996.6  
Plus reinsurance recoverable on unpaid losses at period end 2,122.9 1,611.3 2,077.6 $ 1,515.2
Provision for losses and LAE at the end of the relevant period $ 7,000.3 $ 6,679.4 $ 7,074.2