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Fair Value Measurements - Loan Notes Issued by Variable Interest Entities (Details) - USD ($)
$ in Millions
3 Months Ended 9 Months Ended 12 Months Ended
Sep. 30, 2018
Sep. 30, 2017
Sep. 30, 2018
Sep. 30, 2017
Dec. 31, 2017
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]          
Gross written premiums $ 873.2 $ 852.5 $ 2,843.8 $ 2,672.6  
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   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   325.0
Fair Value, Measurements, Recurring          
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]          
Total 6,837.2   6,837.2   7,485.4
Loan notes held by third parties         44.2
Fair Value, Measurements, Recurring | Level 3          
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]          
Total (12.3)   (12.3)   (86.6)
Loan notes held by third parties         44.2
Fair Value, Measurements, Recurring | Level 3 | Silverton 2016          
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]          
Total         86.6
Amount of Level 3 liabilities settled   1.4   115.9  
Total change in fair value included in the statement of operations   $ (9.8)   $ (3.6)  
Fair Value, Measurements, Recurring | Level 3 | Silverton 2017          
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]          
Total 12.3   12.3    
Amount of Level 3 liabilities settled 14.7   78.4    
Total change in fair value included in the statement of operations 1.7   4.1    
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 12.3   12.3   42.4
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 $ 12.3   $ 12.3   $ 42.4
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