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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, 2017
Jun. 30, 2016
Jun. 30, 2017
Jun. 30, 2016
Dec. 31, 2016
Dec. 31, 2015
Underwriting Revenues            
Gross written premiums $ 822.1 $ 801.7 $ 1,820.1 $ 1,777.4    
Net written premiums 578.7 724.8 1,264.9 1,524.5    
Gross earned premiums 749.7 784.5 1,501.0 1,536.9    
Net earned premiums 562.0 680.8 1,143.1 1,343.9    
Underwriting Expenses            
Losses and loss adjustment expenses 346.1 442.2 674.3 799.6    
Amortization of deferred policy acquisition costs 96.3 126.7 210.0 256.9    
General and administrative expenses 106.4 96.3 212.1 199.0    
Underwriting income 13.2 15.6 46.7 88.4    
Corporate expenses (11.4) (20.1) (24.8) (37.2)    
Non-operating expenses (2.1)   (4.3)      
Net investment income 47.4 48.0 95.1 97.5    
Realized and unrealized investment gains 49.0 45.1 100.2 110.7    
Realized and unrealized investment losses (7.0) (8.3) (12.0) (28.9)    
Change in fair value of loan notes issued by variable interest entities (3.3) 0.5 (6.2) (3.9)    
Change in fair value of derivatives 17.6 (0.4) 20.7 (7.6)    
Interest expense on long term debt (7.4) (7.4) (14.8) (14.8)    
Net realized and unrealized foreign exchange losses (20.6) (5.3) (29.5) (21.0)    
Other income 3.6 (0.5) 7.2 0.9    
Other expenses (2.0) (1.0) (2.0) (1.0)    
Income from operations before income tax 77.0 66.2 176.3 183.1    
Net reserves for loss and loss adjustment expenses $ 4,792.0 $ 4,771.1 $ 4,792.0 $ 4,771.1 $ 4,759.2 $ 4,583.4
Ratios            
Loss ratio 61.60% 65.00% 59.00% 59.50%    
Policy acquisition expense ratio 17.10% 18.60% 18.40% 19.10%    
General and administrative expense ratio 21.30% 17.10% 21.10% 17.60%    
Expense ratio 38.40% 35.70% 39.50% 36.70%    
Combined ratio 100.00% 100.70% 98.50% 96.20%    
Reinsurance            
Underwriting Revenues            
Gross written premiums $ 335.6 $ 332.6 $ 900.9 $ 850.2    
Net written premiums 285.5 306.8 733.7 756.3    
Gross earned premiums 320.6 329.8 648.2 636.6    
Net earned premiums 272.7 299.4 550.2 579.7    
Underwriting Expenses            
Losses and loss adjustment expenses 152.6 181.1 295.7 315.6    
Amortization of deferred policy acquisition costs 53.4 50.7 112.9 110.1    
General and administrative expenses 40.7 39.1 84.6 83.2    
Underwriting income 26.0 28.5 57.0 70.8    
Net reserves for loss and loss adjustment expenses $ 2,445.0 $ 2,474.6 $ 2,445.0 $ 2,474.6    
Ratios            
Loss ratio 56.00% 60.50% 53.70% 54.40%    
Policy acquisition expense ratio 19.60% 16.90% 20.50% 19.00%    
General and administrative expense ratio 14.90% 13.10% 15.40% 14.40%    
Expense ratio 34.50% 30.00% 35.90% 33.40%    
Combined ratio 90.50% 90.50% 89.60% 87.80%    
Insurance            
Underwriting Revenues            
Gross written premiums $ 486.5 $ 469.1 $ 919.2 $ 927.2    
Net written premiums 293.2 418.0 531.2 768.2    
Gross earned premiums 429.1 454.7 852.8 900.3    
Net earned premiums 289.3 381.4 592.9 764.2    
Underwriting Expenses            
Losses and loss adjustment expenses 193.5 261.1 378.6 484.0    
Amortization of deferred policy acquisition costs 42.9 76.0 97.1 146.8    
General and administrative expenses 65.7 57.2 127.5 115.8    
Underwriting income (12.8) (12.9) (10.3) 17.6    
Net reserves for loss and loss adjustment expenses $ 2,347.0 $ 2,296.5 $ 2,347.0 $ 2,296.5    
Ratios            
Loss ratio 66.90% 68.50% 63.90% 63.30%    
Policy acquisition expense ratio 14.80% 19.90% 16.40% 19.20%    
General and administrative expense ratio 22.70% 15.00% 21.50% 15.20%    
Expense ratio 37.50% 34.90% 37.90% 34.40%    
Combined ratio 104.40% 103.40% 101.80% 97.70%