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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
 12 Months Ended
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Premiums written:      
Direct $ 1,956.9 $ 1,951.2 $ 1,812.4
Assumed 1,485.5 1,495.7 1,548.5
Ceded (1,014.5) (1,364.9) (1,148.4)
Net premiums written 2,427.9 2,082.0 2,212.5
Premiums earned:      
Direct 1,927.5 1,940.5 1,757.4
Assumed 1,494.9 1,593.9 1,451.8
Ceded (1,129.1) (1,319.7) (902.6)
Net premiums earned 2,293.3 2,214.7 2,306.6
Insurance losses and loss adjustment expenses:      
Direct 1,415.5 1,458.9 1,673.6
Assumed 1,147.9 1,196.1 1,399.9
Ceded (883.7) (1,082.0) (1,078.8)
Net insurance losses and loss adjustment expenses $ 1,679.7 $ 1,573.0 $ 1,994.7