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Segment Reporting - Summary of Gross and Net Written and Earned Premiums, Underwriting Results, Ratios and Reserves for Each of Company's Business Segments (Details) - USD ($)
$ in Millions
 3 Months Ended 6 Months Ended
Jun. 30, 2018
Jun. 30, 2017
Jun. 30, 2018
Jun. 30, 2017
Dec. 31, 2017
Dec. 31, 2016
Underwriting Revenues            
Gross written premiums $ 853.8 $ 822.1 $ 1,970.6 $ 1,820.1    
Net written premiums 486.0 578.7 1,121.5 1,264.9    
Gross earned premiums 845.5 749.7 1,688.1 1,501.0    
Net earned premiums 519.5 562.0 1,053.0 1,143.1    
Underwriting Expenses            
Losses and loss adjustment expenses 310.4 346.1 620.6 674.3    
Amortization of deferred policy acquisition costs 85.9 96.3 176.7 210.0    
General and administrative expenses 85.1 106.4 180.3 212.1    
Underwriting income 38.1 13.2 75.4 46.7    
Corporate expenses (16.0) (11.4) (29.7) (24.8)    
Nonoperating Income (Expense) (9.1) (2.1) (21.2) (4.3)    
Net investment income 50.4 47.4 97.7 95.1    
Realized and unrealized investment gains 3.5 49.0 104.1 100.2    
Realized and unrealized investment losses (24.2) (7.0) (162.5) (12.0)    
Realized loss on the debt extinguishment (8.6) 0.0 (8.6) 0.0    
Change in fair value of loan notes issued by variable interest entities (3.4) (3.3) (2.4) (6.2)    
Change in fair value of derivatives (46.1) 17.6 (22.6) 20.7    
Interest expense on long term debt (7.6) (7.4) (15.0) (14.8)    
Net realized and unrealized foreign exchange gains 5.2 (20.6) 0.5 (29.5)    
Other income 2.1 3.6 4.2 7.2    
Other expenses (0.5) (2.0) (1.7) (2.0)    
(Loss)/income from operations before income tax (16.2) 77.0 18.2 176.3    
Net reserves for loss and loss adjustment expenses $ 4,876.4 $ 4,792.0 $ 4,876.4 $ 4,792.0 $ 5,234.3 $ 4,759.2
Ratios            
Loss ratio 59.70% 61.60% 58.90% 59.00%    
Policy acquisition expense ratio 16.50% 17.10% 16.80% 18.40%    
General and administrative expense ratio 21.20% 21.30% 22.00% 21.10%    
Expense ratio 37.70% 38.40% 38.80% 39.50%    
Combined ratio 97.40% 100.00% 97.70% 98.50%    
Non-operating expenses related to Effectiveness and Efficiency Program $ 8.6   $ 20.4      
Reinsurance            
Underwriting Revenues            
Gross written premiums 326.0 $ 335.6 949.5 $ 900.9    
Net written premiums 266.9 285.5 691.9 733.7    
Gross earned premiums 366.2 320.6 741.2 648.2    
Net earned premiums 289.0 272.7 571.5 550.2    
Underwriting Expenses            
Losses and loss adjustment expenses 167.0 152.6 333.9 295.7    
Amortization of deferred policy acquisition costs 62.8 53.4 118.7 112.9    
General and administrative expenses 27.9 40.7 59.5 84.6    
Underwriting income 31.3 26.0 59.4 57.0    
Net reserves for loss and loss adjustment expenses $ 2,744.1 $ 2,445.0 $ 2,744.1 $ 2,445.0    
Ratios            
Loss ratio 57.80% 56.00% 58.40% 53.70%    
Policy acquisition expense ratio 21.70% 19.60% 20.80% 20.50%    
General and administrative expense ratio 9.70% 14.90% 10.40% 15.40%    
Expense ratio 31.40% 34.50% 31.20% 35.90%    
Combined ratio 89.20% 90.50% 89.60% 89.60%    
Insurance            
Underwriting Revenues            
Gross written premiums $ 527.8 $ 486.5 $ 1,021.1 $ 919.2    
Net written premiums 219.1 293.2 429.6 531.2    
Gross earned premiums 479.3 429.1 946.9 852.8    
Net earned premiums 230.5 289.3 481.5 592.9    
Underwriting Expenses            
Losses and loss adjustment expenses 143.4 193.5 286.7 378.6    
Amortization of deferred policy acquisition costs 23.1 42.9 58.0 97.1    
General and administrative expenses 57.2 65.7 120.8 127.5    
Underwriting income 6.8 (12.8) 16.0 (10.3)    
Net reserves for loss and loss adjustment expenses $ 2,132.3 $ 2,347.0 $ 2,132.3 $ 2,347.0    
Ratios            
Loss ratio 62.20% 66.90% 59.50% 63.90%    
Policy acquisition expense ratio 10.00% 14.80% 12.00% 16.40%    
General and administrative expense ratio 24.80% 22.70% 25.10% 21.50%    
Expense ratio 34.80% 37.50% 37.10% 37.90%    
Combined ratio 97.00% 104.40% 96.60% 101.80%