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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 9 Months Ended
Sep. 30, 2018
Sep. 30, 2017
Sep. 30, 2018
Sep. 30, 2017
Dec. 31, 2017
Dec. 31, 2016
Underwriting Revenues            
Gross written premiums $ 873.2 $ 852.5 $ 2,843.8 $ 2,672.6    
Net written premiums 578.9 607.4 1,700.4 1,872.3    
Gross earned premiums 973.6 913.3 2,661.7 2,414.3    
Net earned premiums 623.2 652.5 1,676.2 1,795.6    
Underwriting Expenses            
Losses and loss adjustment expenses 431.1 776.2 1,051.7 1,450.5    
Amortization of deferred policy acquisition costs 101.0 105.4 277.7 315.4    
General and administrative expenses 93.4 92.2 273.7 304.3    
Underwriting (loss)/income (2.3) (321.3) 73.1 (274.6)    
Corporate expenses (16.0) (13.5) (45.7) (38.3)    
Non-operating income (expense) (51.0) (5.2) (72.2) (9.5)    
Net investment income 48.0 46.4 145.7 141.5    
Realized and unrealized investment gains 1.8 29.9 105.9 130.1    
Realized and unrealized investment losses (2.7) (12.4) (165.2) (24.4)    
Realized loss on debt extinguishment     (8.6)      
Change in fair value of loan notes issued by variable interest entities (1.7) 9.8 (4.1) 3.6    
Change in fair value of derivatives 7.2 4.5 (15.4) 25.2    
Interest expense on long term debt (5.4) (7.4) (20.4) (22.2)    
Net realized and unrealized foreign exchange losses (9.5) 8.4 (9.0) (21.1)    
Other income 1.4 (2.2) 5.6 5.0    
Net other expense   (2.2)        
Other expenses (0.4)   (2.1) (2.0)    
(Loss) from operations before income tax (30.6) (263.0) (12.4) (86.7)    
Net reserves for loss and loss adjustment expenses $ 4,959.1 $ 5,121.1 $ 4,959.1 $ 5,121.1 $ 5,234.3 $ 4,759.2
Ratios            
Loss ratio 69.20% 119.00% 62.70% 80.80%    
Policy acquisition expense ratio 16.20% 16.20% 16.60% 17.60%    
General and administrative expense ratio 25.70% 17.00% 23.40% 19.60%    
Expense ratio 41.90% 33.20% 40.00% 37.20%    
Combined ratio 111.10% 152.20% 102.70% 118.00%    
Non-operating expenses related to Effectiveness and Efficiency Program $ 11.1 $ 4.1 $ 31.5 $ 4.1    
Non-operating expenses related to Merger Agreement 38.6   38.6      
Reinsurance            
Underwriting Revenues            
Gross written premiums 396.4 431.5 1,345.9 1,332.4    
Net written premiums 356.4 363.6 1,048.3 1,097.3    
Gross earned premiums 475.3 464.0 1,216.5 1,112.2    
Net earned premiums 388.5 382.0 960.0 932.2    
Underwriting Expenses            
Losses and loss adjustment expenses 281.5 502.2 615.4 797.9    
Amortization of deferred policy acquisition costs 75.7 61.5 194.4 174.4    
General and administrative expenses 34.7 32.8 94.2 117.4    
Underwriting (loss)/income (3.4) (214.5) 56.0 (157.5)    
Net reserves for loss and loss adjustment expenses $ 2,829.1 $ 2,865.8 $ 2,829.1 $ 2,865.8    
Ratios            
Loss ratio 72.50% 131.50% 64.10% 85.60%    
Policy acquisition expense ratio 19.50% 16.10% 20.30% 18.70%    
General and administrative expense ratio 8.90% 8.60% 9.80% 12.60%    
Expense ratio 28.40% 24.70% 30.10% 31.30%    
Combined ratio 100.90% 156.20% 94.20% 116.90%    
Insurance            
Underwriting Revenues            
Gross written premiums $ 476.8 $ 421.0 $ 1,497.9 $ 1,340.2    
Net written premiums 222.5 243.8 652.1 775.0    
Gross earned premiums 498.3 449.3 1,445.2 1,302.1    
Net earned premiums 234.7 270.5 716.2 863.4    
Underwriting Expenses            
Losses and loss adjustment expenses 149.6 274.0 436.3 652.6    
Amortization of deferred policy acquisition costs 25.3 43.9 83.3 141.0    
General and administrative expenses 58.7 59.4 179.5 186.9    
Underwriting (loss)/income 1.1 (106.8) 17.1 (117.1)    
Net reserves for loss and loss adjustment expenses $ 2,130.0 $ 2,255.3 $ 2,130.0 $ 2,255.3    
Ratios            
Loss ratio 63.70% 101.30% 60.90% 75.60%    
Policy acquisition expense ratio 10.80% 16.20% 11.60% 16.30%    
General and administrative expense ratio 25.00% 22.00% 25.10% 21.60%    
Expense ratio 35.80% 38.20% 36.70% 37.90%    
Combined ratio 99.50% 139.50% 97.60% 113.50%