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Fair Value Measurements - Reconciliation of Level 3 Inputs (Details) - USD ($)
$ in Millions
 12 Months Ended
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]      
Liability for unpaid claims and claims adjustment expense amount ceded   $ 125.5 $ (85.8)
Amount classified within accrued expenses and other payables $ (5.7) (52.5)  
Recurring      
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]      
Debt Instrument, Accrued Interest and Payables, Fair Value Disclosure 4.6 42.4  
Silverton 2017 | Recurring | Level 3      
Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]      
Balance at the beginning of the period 86.6    
Distributed to third parties (86.4)    
Total change in fair value included in the statement of operations 4.4    
Balance at the end of the period 4.6 86.6  
Silverton 2016 | Recurring | Level 3      
Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]      
Balance at the beginning of the period 86.6 223.4  
Distributed to third parties   (115.6)  
Total change in fair value included in the statement of operations   (21.2)  
Balance at the end of the period   86.6 $ 223.4
Third party      
Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]      
Amount classified within accrued expenses and other payables $ (4.6) $ (42.4)