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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
 12 Months Ended
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Segment Reporting Information [Line Items]        
Gross written premiums $ 3,442.4 $ 3,446.9 $ 3,360.9  
Net written premiums 2,427.9 2,082.0 2,212.5  
Gross earned premiums 3,422.4 3,534.4 3,209.2  
Net earned premium 2,293.3 2,214.7 2,306.6  
Losses and loss adjustment expenses 1,679.7 1,573.0 1,994.7  
Amortization of deferred policy acquisition costs 412.7 371.6 400.5  
General and administrative expenses 341.5 357.7 411.2  
Underwriting income (loss) (140.6) (87.6) (499.8)  
Corporate expenses (54.5) (56.8) (58.3)  
Non-operating expenses (125.6) (77.2) (32.7)  
Net investment income 197.3 198.2 189.0  
Realized and unrealized investment gains 97.1 110.0 148.9  
Realized and unrealized investment losses (10.9) (174.7) (28.4)  
Realized loss on debt extinguishment (5.5) (8.6) 0.0  
Change in fair value of loan notes issued by variable interest entities (3.1) (4.4) 21.2  
Change in fair value of derivatives (144.2) (31.8) 27.7  
Interest expense on long term debt (20.2) (25.9) (29.5)  
Net realized and unrealized foreign exchange (losses) (11.8) (3.5) (23.9)  
Other income 4.9 9.0 8.9  
Other expenses (1.7) (2.7) (4.9)  
(Loss) from operations before income tax (218.8) (156.0) (281.8)  
Income tax (expense)/benefit (22.9) 10.2 15.4  
Net (loss) (241.7) (145.8) (266.4)  
Losses and loss adjustment expenses 6,951.8 7,074.2 6,749.5 $ 5,319.9
Net Reserves for Losses and LAE $ 4,632.0 $ 4,996.6 $ 5,234.3 $ 4,759.2
Ratios        
Loss ratio 73.20% 71.00% 86.50%  
Policy acquisition expense ratio 18.00% 16.80% 17.40%  
General and administrative expense ratio 22.70% 22.20% 21.80%  
Expense ratio 40.70% 39.00% 39.20%  
Combined ratio 113.90% 110.00% 125.70%  
Non-operating expenses related to Merger Agreement $ 103.4 $ 39.0    
Non-operating expenses related to Effectiveness And Efficiency Program 22.2 37.5 $ 15.2  
Non-operating expenses related to impairment charges on lease assets 12.3      
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 1,251.1 1,182.9 1,250.0  
Net earned premium 1,255.2 1,256.4 1,206.1  
Losses and loss adjustment expenses 2,605.9 2,843.6 2,917.1  
Net Reserves for Losses and LAE $ 2,605.9 $ 2,843.6 $ 2,917.1  
Ratios        
Loss ratio 73.10% 73.80% 92.60%  
Policy acquisition expense ratio 21.10% 20.80% 19.50%  
General and administrative expense ratio 8.90% 9.40% 13.00%  
Expense ratio 30.00% 30.20% 32.50%  
Combined ratio 103.10% 104.00% 125.10%  
Insurance        
Segment Reporting Information [Line Items]        
Net written premiums $ 1,176.8 $ 899.1 $ 962.5  
Net earned premium 1,038.1 958.3 1,100.5  
Losses and loss adjustment expenses 2,026.1 2,153.0 2,317.2  
Net Reserves for Losses and LAE $ 2,026.1 $ 2,153.0 $ 2,317.2  
Ratios        
Loss ratio 73.40% 67.40% 79.80%  
Policy acquisition expense ratio 14.20% 11.60% 15.00%  
General and administrative expense ratio 22.10% 25.00% 23.10%  
Expense ratio 36.30% 36.60% 38.10%  
Combined ratio 109.70% 104.00% 117.90%  
Operating Segments | Reinsurance        
Segment Reporting Information [Line Items]        
Gross written premiums $ 1,485.5 $ 1,495.7 $ 1,548.5  
Net written premiums 1,251.1 1,182.9 1,250.0  
Gross earned premiums 1,494.9 1,593.9 1,451.8  
Net earned premium 1,255.2 1,256.4 1,206.1  
Losses and loss adjustment expenses 917.9 927.0 1,116.4  
Amortization of deferred policy acquisition costs 264.9 260.9 235.5  
General and administrative expenses 111.7 118.5 157.3  
Underwriting income (loss) (39.3) (50.0) (303.1)  
Operating Segments | Insurance        
Segment Reporting Information [Line Items]        
Gross written premiums 1,956.9 1,951.2 1,812.4  
Net written premiums 1,176.8 899.1 962.5  
Gross earned premiums 1,927.5 1,940.5 1,757.4  
Net earned premium 1,038.1 958.3 1,100.5  
Losses and loss adjustment expenses 761.8 646.0 878.3  
Amortization of deferred policy acquisition costs 147.8 110.7 165.0  
General and administrative expenses 229.8 239.2 253.9  
Underwriting income (loss) $ (101.3) $ (37.6) $ (196.7)