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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 12 Months Ended
Dec. 31, 2018
Sep. 30, 2018
Jun. 30, 2018
Mar. 31, 2018
Dec. 31, 2017
Sep. 30, 2017
Jun. 30, 2017
Mar. 31, 2017
Dec. 31, 2016
Sep. 30, 2016
Jun. 30, 2016
Mar. 31, 2016
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2015
Segment Reporting Information [Line Items]                                
Gross written premiums                         $ 3,446.9 $ 3,360.9 $ 3,147.0  
Net written premiums                         2,082.0 2,212.5 2,593.7  
Gross earned premiums                         3,534.4 3,209.2 3,086.3  
Net earned premium $ 538.5 $ 623.2 $ 519.5 $ 533.5 $ 511.0 $ 652.5 $ 562.0 $ 581.1 $ 612.4 $ 681.0 $ 680.8 $ 663.1 2,214.7 2,306.6 2,637.3  
Losses and loss adjustment expenses 521.3 431.1 310.4 310.2 544.2 776.2 346.1 328.2 387.3 389.2 442.2 357.4 1,573.0 1,994.7 1,576.1  
Amortization of deferred policy acquisition costs 93.9 101.0 85.9 90.8 85.1 105.4 96.3 113.7 141.1 130.9 126.7 130.2 371.6 400.5 528.9  
General and administrative expenses                         357.7 411.2 406.6  
Underwriting income (loss)                         (87.6) (499.8) 125.7  
Corporate expenses                         (56.8) (58.3) (73.8)  
Non-operating expenses                         (77.2) (32.7) (9.7)  
Net investment income 52.5 48.0 50.4 47.3 47.5 46.4 47.4 47.7 43.2 46.4 48.0 49.5 198.2 189.0 187.1  
Realized and unrealized investment gains 4.1 1.8 3.5 100.6 18.8 29.9 49.0 51.2 (29.0) 26.7 45.1 65.6 110.0 148.9 108.4  
Realized and unrealized investment losses (9.5) (2.7) (24.2) (138.3) (4.0) (12.4) (7.0) (5.0) (29.1) (5.2) (8.3) (20.6) (174.7) (28.4) (63.2)  
Realized loss on debt extinguishment 0.0 0.0 8.6 0.0                 8.6 0.0 0.0  
Change in fair value of loan notes issued by variable interest entities (0.3) (1.7) (3.4) 1.0 17.6 9.8 (3.3) (2.9) (3.4) (9.8) 0.5 (4.4) (4.4) 21.2 (17.1)  
Change in fair value of derivatives (16.4) 7.2 (46.1) 23.5 2.5 4.5 17.6 3.1 (17.6) 0.6 (0.4) (7.2) (31.8) 27.7 (24.6)  
Interest expense on long term debt (5.5) (5.4) (7.6) (7.4) (7.3) (7.4) (7.4) (7.4) (7.4) (7.3) (7.4) (7.4) (25.9) (29.5) (29.5)  
Net realized and unrealized foreign exchange (losses) 5.5 (9.5) 5.2 (4.7) (2.8) 8.4 (20.6) (8.9) 12.0 10.8 (5.3) (15.7) (3.5) (23.9) 1.8  
Other income 3.4 1.4 2.1 2.1 3.9 (2.2) 3.6 3.6 3.3 1.5 (0.5) 1.4 9.0 8.9 5.7  
Other expenses                         (2.7) (4.9) (1.3)  
(Loss)/income from operations before income tax (143.6) (30.6) (16.2) 34.4 (195.1) (263.0) 77.0 99.3 (74.1) 100.5 66.2 116.9 (156.0) (281.8) 209.5  
Income tax benefit/(expense) (3.2) 15.5 1.5 (3.6) 10.2 9.2 (1.2) (2.8) 2.6 (4.9) (1.3) (2.5) 10.2 15.4 (6.1)  
Net (loss)/income (146.8) $ (15.1) $ (14.7) $ 30.8 (184.9) $ (253.8) $ 75.8 $ 96.5 (71.5) $ 95.6 $ 64.9 $ 114.4 (145.8) (266.4) 203.4  
Losses and loss adjustment expenses 7,074.2       6,749.5       5,319.9       7,074.2 6,749.5 5,319.9 $ 4,938.2
Net Reserves for Losses and LAE 4,996.6       5,234.3       4,759.2       $ 4,996.6 $ 5,234.3 $ 4,759.2 $ 4,583.4
Ratios                                
Loss ratio                         71.00% 86.50% 59.80%  
Policy acquisition expense ratio                         16.80% 17.40% 20.10%  
General and administrative expense ratio                         22.20% 21.80% 18.60%  
Expense ratio                         39.00% 39.20% 38.70%  
Combined ratio                         110.00% 125.70% 98.50%  
Non-operating expenses related to Effectiveness And Efficiency Program                         $ 37.5 $ 15.2    
Non-operating expenses related to Merger Agreement                         39.0      
Non-operating expenses related to retention costs                         11.3      
Write back of buy out provision                         (14.1)      
Reinsurance                                
Segment Reporting Information [Line Items]                                
Net written premiums                         1,182.9 1,250.0 $ 1,269.2  
Net earned premium                         1,256.4 1,206.1 1,181.9  
Losses and loss adjustment expenses 2,843.6       2,917.1       2,462.1       2,843.6 2,917.1 2,462.1  
Net Reserves for Losses and LAE 2,843.6       2,917.1       2,462.1       $ 2,843.6 $ 2,917.1 $ 2,462.1  
Ratios                                
Loss ratio                         73.80% 92.60% 55.70%  
Policy acquisition expense ratio                         20.80% 19.50% 19.20%  
General and administrative expense ratio                         9.40% 13.00% 15.10%  
Expense ratio                         30.20% 32.50% 34.30%  
Combined ratio                         104.00% 125.10% 90.00%  
Insurance                                
Segment Reporting Information [Line Items]                                
Net written premiums                         $ 899.1 $ 962.5 $ 1,324.5  
Net earned premium                         958.3 1,100.5 1,455.4  
Losses and loss adjustment expenses 2,153.0       2,317.2       2,297.1       2,153.0 2,317.2 2,297.1  
Net Reserves for Losses and LAE $ 2,153.0       $ 2,317.2       $ 2,297.1       $ 2,153.0 $ 2,317.2 $ 2,297.1  
Ratios                                
Loss ratio                         67.40% 79.80% 63.10%  
Policy acquisition expense ratio                         11.60% 15.00% 20.80%  
General and administrative expense ratio                         25.00% 23.10% 15.70%  
Expense ratio                         36.60% 38.10% 36.50%  
Combined ratio                         104.00% 117.90% 99.60%  
Operating Segments | Reinsurance                                
Segment Reporting Information [Line Items]                                
Gross written premiums                         $ 1,495.7 $ 1,548.5 $ 1,413.2  
Net written premiums                         1,182.9 1,250.0 1,269.2  
Gross earned premiums                         1,593.9 1,451.8 1,317.9  
Net earned premium                         1,256.4 1,206.1 1,181.9  
Losses and loss adjustment expenses                         927.0 1,116.4 657.9  
Amortization of deferred policy acquisition costs                         260.9 235.5 226.4  
General and administrative expenses                         118.5 157.3 178.2  
Underwriting income (loss)                         (50.0) (303.1) 119.4  
Operating Segments | Insurance                                
Segment Reporting Information [Line Items]                                
Gross written premiums                         1,951.2 1,812.4 1,733.8  
Net written premiums                         899.1 962.5 1,324.5  
Gross earned premiums                         1,940.5 1,757.4 1,768.4  
Net earned premium                         958.3 1,100.5 1,455.4  
Losses and loss adjustment expenses                         646.0 878.3 918.2  
Amortization of deferred policy acquisition costs                         110.7 165.0 302.5  
General and administrative expenses                         239.2 253.9 228.4  
Underwriting income (loss)                         $ (37.6) $ (196.7) $ 6.3