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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, 2018
Dec. 31, 2017
Dec. 31, 2016
Segment Reporting Information [Line Items]      
Gross written premiums $ 3,446.9 $ 3,360.9 $ 3,147.0
Australia/Asia      
Segment Reporting Information [Line Items]      
Gross written premiums 175.9 167.3 140.5
Caribbean      
Segment Reporting Information [Line Items]      
Gross written premiums 7.7 17.6 14.3
Europe      
Segment Reporting Information [Line Items]      
Gross written premiums 92.6 94.5 109.7
United Kingdom      
Segment Reporting Information [Line Items]      
Gross written premiums 290.1 258.3 231.4
United States & Canada      
Segment Reporting Information [Line Items]      
Gross written premiums 1,875.9 1,729.3 1,597.0
Worldwide excluding United States      
Segment Reporting Information [Line Items]      
Gross written premiums 70.1 88.1 90.7
Worldwide including United States      
Segment Reporting Information [Line Items]      
Gross written premiums 775.8 868.6 837.2
Others      
Segment Reporting Information [Line Items]      
Gross written premiums $ 158.8 $ 137.2 $ 126.2