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Segment Reporting - Summary of the Schedule of the Company's gross written premiums based on the location of the insured risk (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Segment Reporting Information [Line Items]      
Gross written premiums $ 3,442.4 $ 3,446.9 $ 3,360.9
Australia/Asia      
Segment Reporting Information [Line Items]      
Gross written premiums 215.9 175.9 167.3
Caribbean      
Segment Reporting Information [Line Items]      
Gross written premiums 9.3 7.7 17.6
Europe      
Segment Reporting Information [Line Items]      
Gross written premiums 82.8 92.6 94.5
United Kingdom      
Segment Reporting Information [Line Items]      
Gross written premiums 295.7 290.1 258.3
United States & Canada      
Segment Reporting Information [Line Items]      
Gross written premiums 2,003.9 1,875.9 1,729.3
Worldwide excluding United States      
Segment Reporting Information [Line Items]      
Gross written premiums 63.0 70.1 88.1
Worldwide including United States      
Segment Reporting Information [Line Items]      
Gross written premiums 614.9 775.8 868.6
Others      
Segment Reporting Information [Line Items]      
Gross written premiums $ 156.9 $ 158.8 $ 137.2