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Reinsurance - Summary of Assumed and Ceded Reinsurance on Premiums Written, Premiums Earned and Insurance Losses and Loss Adjustment Expenses (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
Premiums written:                              
Direct                         $ 1,951.2 $ 1,812.4 $ 1,733.8
Assumed                         1,495.7 1,548.5 1,413.2
Ceded                         (1,364.9) (1,148.4) (553.3)
Net premiums written                         2,082.0 2,212.5 2,593.7
Premiums earned:                              
Direct                         1,940.5 1,757.4 1,768.4
Assumed                         1,593.9 1,451.8 1,317.9
Ceded                         (1,319.7) (902.6) (449.0)
Net premiums earned $ 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
Insurance losses and loss adjustment expenses:                              
Direct                         1,458.9 1,673.6 1,091.9
Assumed                         1,196.1 1,399.9 699.6
Ceded                         (1,082.0) (1,078.8) (215.4)
Net insurance 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