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Fair Value Measurements - Loan Notes Issued by Variable Interest Entities (Details) - USD ($)
$ in Millions
 3 Months Ended 12 Months Ended
Mar. 31, 2019
Mar. 31, 2018
Dec. 31, 2018
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Gross written premiums $ 1,013.8 $ 1,116.8  
Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Gross written premiums 61.1   $ 61.1
Reserve for losses 61.9   61.9
Loan notes held by third parties 325.0   325.0
Minimum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Gross written premiums 50.1   50.1
Reserve for losses 4.2   4.2
Loan notes held by third parties 325.0   325.0
Fair Value, Measurements, Recurring      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Total 6,662.0   6,667.2
Fair Value, Measurements, Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Total (5.9)   (4.6)
Fair Value, Measurements, Recurring | Level 3 | Silverton 2016      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Total     4.6
Amount of Level 3 liabilities settled   45.8  
Total change in fair value included in the statement of operations   $ (1.0)  
Fair Value, Measurements, Recurring | Level 3 | Silverton 2017      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Total 5.9    
Amount of Level 3 liabilities settled 0.2    
Total change in fair value included in the statement of operations 1.5    
Accrued expenses and other payables | Fair Value, Measurements, Recurring      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Loan notes held by third parties 5.9   4.6
Accrued expenses and other payables | Fair Value, Measurements, Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Loan notes held by third parties $ 5.9   $ 4.6
Measurement Input, Expected Term | Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Contract period 365 days   365 days