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Commitments and Contingencies - Schedule of Company's Restricted Assets (Details) - USD ($)
$ in Millions
 12 Months Ended
Dec. 31, 2018
Dec. 31, 2017
Sep. 19, 2018
May 01, 2018
Schedule of Fair Value of Separate Accounts by Major Category of Investment [Line Items]        
Total restricted assets $ 4,419.2 $ 4,638.8    
Other investments (equity method) $ 102.5 $ 0.0    
Total as percent of investable assets 56.40% 53.40%    
Securities and cash as collateral secured letters of credit $ 771.1 $ 658.5    
Affiliated transactions        
Schedule of Fair Value of Separate Accounts by Major Category of Investment [Line Items]        
Total restricted assets 1,033.9 1,455.0    
Third party        
Schedule of Fair Value of Separate Accounts by Major Category of Investment [Line Items]        
Total restricted assets 2,511.7 2,425.3    
Letters of credit / guarantees        
Schedule of Fair Value of Separate Accounts by Major Category of Investment [Line Items]        
Total restricted assets 771.1 658.5    
Limited Partner | Real estate fund        
Schedule of Fair Value of Separate Accounts by Major Category of Investment [Line Items]        
Total restricted assets 0.0 100.0    
Other investments (equity method) $ 102.5 $ 0.0 $ 13.8 $ 86.2