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Commitments and Contingencies - Additional Information (Details)
$ / shares in Units, £ in Millions, SFr in Millions, $ in Millions, $ in Millions, $ in Millions, $ in Millions
12 Months Ended
Dec. 31, 2018
USD ($)
Investment
Dec. 31, 2017
USD ($)
Investment
Mar. 31, 2019
$ / shares
Dec. 31, 2018
GBP (£)
Investment
Dec. 31, 2018
AUD ($)
Investment
Dec. 31, 2018
CHF (SFr)
Investment
Dec. 31, 2018
CAD ($)
Investment
Dec. 31, 2018
SGD ($)
Investment
Sep. 19, 2018
USD ($)
May 01, 2018
USD ($)
Dec. 31, 2017
GBP (£)
Investment
Dec. 31, 2017
AUD ($)
Investment
Dec. 31, 2017
CHF (SFr)
Investment
Dec. 31, 2017
CAD ($)
Investment
Dec. 31, 2017
SGD ($)
Investment
Restricted Cash And Collateral [Line Items]                              
Restricted assets $ 4,419.2 $ 4,638.8                          
Other investments (equity method) $ 102.5 $ 0.0                          
Total as percent of investable assets 56.40% 53.40%                          
Investable assets held by the Company $ 7,800.0 $ 8,700.0                          
Investable assets held by insurance regulators $ 503.2 458.7                          
Minimum capital required | £       £ 0.4             £ 0.4        
Percentage of reinsurance liabilities 100.00%     100.00% 100.00% 100.00% 100.00% 100.00%              
Reinsurance liabilities $ 1,311.4 1,268.4                          
Assets held-in-trust 1,336.4 1,350.9                          
Regulatory deposits 6.0 6.0                          
Deposit with states 6.1 6.1                          
Rental and premises expenses 27.3 26.3                          
Depreciation for fixed assets 29.7 34.6                          
Accumulated depreciation $ 175.8 $ 146.2                          
Number of investments | Investment 2 2   2 2 2 2 2     2 2 2 2 2
Us Multi Beneficiary Trust Fund                              
Restricted Cash And Collateral [Line Items]                              
Minimum trust fund $ 20.0                            
Assets held-in-trust 1,112.4 $ 1,333.6                          
Us Surplus Lines Trust Fund                              
Restricted Cash And Collateral [Line Items]                              
Assets held-in-trust $ 198.8 195.0                          
Canadian Trust Fund                              
Restricted Cash And Collateral [Line Items]                              
Assets held-in-trust             $ 152.7             $ 169.9  
Australian Trust Fund                              
Restricted Cash And Collateral [Line Items]                              
Assets held-in-trust         $ 209.3             $ 198.7      
Swiss Trust Fund                              
Restricted Cash And Collateral [Line Items]                              
Assets held-in-trust | SFr           SFr 9.0             SFr 9.8    
Singapore Trust Fund                              
Restricted Cash And Collateral [Line Items]                              
Assets held-in-trust               $ 135.9             $ 120.6
Bermuda                              
Restricted Cash And Collateral [Line Items]                              
Percentage of reinsurance liabilities 100.00%     100.00% 100.00% 100.00% 100.00% 100.00%              
Reinsurance liabilities $ 647.8 895.5                          
Limited Partner | Real estate fund                              
Restricted Cash And Collateral [Line Items]                              
Restricted assets 0.0 100.0                          
Other investments (equity method) $ 102.5 $ 0.0             $ 13.8 $ 86.2          
Subsequent Event                              
Restricted Cash And Collateral [Line Items]                              
Business acquisition, share price | $ / shares     $ 42.75