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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, 2020
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Segment Reporting [Abstract]        
Non-operating expenses related to impairment charges on lease assets $ 12.9 $ 12.3    
Segment Reporting Information [Line Items]        
Gross written premiums 3,703.6 3,442.4 $ 3,446.9  
Net written premiums 2,582.9 2,427.9 2,082.0  
Gross earned premiums 3,643.5 3,422.4 3,534.4  
Net earned premium 2,532.6 2,293.3 2,214.7  
Losses and loss adjustment expenses 1,840.8 1,679.7 1,573.0  
Amortization of deferred policy acquisition costs 465.7 412.7 371.6  
General and administrative expenses 308.0 341.5 357.7  
Underwriting income (loss) (81.9) (140.6) (87.6)  
Corporate Expenses (70.2) (54.5) (56.8)  
Non-operating expenses (32.7) (125.6) (77.2)  
Net investment income 154.6 197.3 198.2  
Realized and unrealized investment gains 98.5 97.1 110.0  
Debt Securities, Gain (Loss) (27.4) (10.9) (174.7)  
Realized loss on debt extinguishment 0.0 (5.5) (8.6)  
Change in fair value of loan notes issued by variable interest entities 0.0 (3.1) (4.4)  
Change in fair value of derivatives (65.1) (144.2) (31.8)  
Interest Expense, Debt (33.9) (20.2) (25.9)  
Net realized and unrealized foreign exchange (losses) (12.4) (11.8) (3.5)  
Other income (1) 49.8 [1] 4.9 9.0  
Other expenses 10.8 1.7 2.7  
(Loss) from operations before income taxes (31.5) (218.8) (156.0)  
Income Tax Expense (Benefit) (8.6) (22.9) 10.2  
Net (loss) (40.1) (241.7) (145.8)  
Losses and loss adjustment expenses 7,165.3 6,951.8 7,074.2 $ 6,749.5
Liability for Unpaid Claims and Claims Adjustment Expense, Net, Total $ 3,970.1 $ 4,632.0 $ 4,996.6 $ 5,234.3
Ratios        
Loss ratio 72.70% 73.20% 71.00%  
Policy acquisition expense ratio 18.40% 18.00% 16.80%  
General and administrative expense ratio 16.20% 22.70% 22.20%  
Expense ratio 34.60% 40.70% 39.00%  
Combined ratio 107.30% 113.90% 110.00%  
Non-operating expenses related to severance, retention awards and other non-recurring costs $ 18.2      
Non-operating expenses related to impairment charges on lease assets 12.9 $ 12.3    
Non-operating expenses related to other non-recurring expenses 1.6      
Non-operating expenses related to Merger Agreement   103.4 $ 39.0  
Non-operating expenses related to Effectiveness And Efficiency Program   22.2 37.5  
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 1,302.1 1,251.1 1,182.9  
Net earned premium 1,292.1 1,255.2 1,256.4  
Losses and loss adjustment expenses 2,095.7 2,605.9 2,843.6  
Liability for Unpaid Claims and Claims Adjustment Expense, Net, Total $ 2,095.7 $ 2,605.9 $ 2,843.6  
Ratios        
Loss ratio 74.20% 73.10% 73.80%  
Policy acquisition expense ratio 19.00% 21.10% 20.80%  
General and administrative expense ratio 8.60% 8.90% 9.40%  
Expense ratio 27.60% 30.00% 30.20%  
Combined ratio 101.80% 103.10% 104.00%  
Insurance        
Segment Reporting Information [Line Items]        
Net written premiums $ 1,280.8 $ 1,176.8 $ 899.1  
Net earned premium 1,240.5 1,038.1 958.3  
Losses and loss adjustment expenses 1,874.4 2,026.1 2,153.0  
Liability for Unpaid Claims and Claims Adjustment Expense, Net, Total $ 1,874.4 $ 2,026.1 $ 2,153.0  
Ratios        
Loss ratio 71.10% 73.40% 67.40%  
Policy acquisition expense ratio 17.70% 14.20% 11.60%  
General and administrative expense ratio 15.90% 22.10% 25.00%  
Expense ratio 33.60% 36.30% 36.60%  
Combined ratio 104.70% 109.70% 104.00%  
Operating Segments | Reinsurance        
Segment Reporting Information [Line Items]        
Gross written premiums $ 1,660.8 $ 1,485.5 $ 1,495.7  
Net written premiums 1,302.1 1,251.1 1,182.9  
Gross earned premiums 1,616.4 1,494.9 1,593.9  
Net earned premium 1,292.1 1,255.2 1,256.4  
Losses and loss adjustment expenses 958.6 917.9 927.0  
Amortization of deferred policy acquisition costs 246.0 264.9 260.9  
General and administrative expenses 110.8 111.7 118.5  
Underwriting income (loss) (23.3) (39.3) (50.0)  
Operating Segments | Insurance        
Segment Reporting Information [Line Items]        
Gross written premiums 2,042.8 1,956.9 1,951.2  
Net written premiums 1,280.8 1,176.8 899.1  
Gross earned premiums 2,027.1 1,927.5 1,940.5  
Net earned premium 1,240.5 1,038.1 958.3  
Losses and loss adjustment expenses 882.2 761.8 646.0  
Amortization of deferred policy acquisition costs 219.7 147.8 110.7  
General and administrative expenses 197.2 229.8 239.2  
Underwriting income (loss) $ (58.6) $ (101.3) $ (37.6)  
[1]     2020 includes the gain on sale of our renewal rights on our surety insurance book of business to a third party, totaling $43.1 million.