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Reclassifications from Accumulated Other Comprehensive Income - Schedule of Accumulated Other Comprehensive Income Reclassification (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]      
(Loss) from operations before income tax $ (218.8) $ (156.0) $ (281.8)
Income tax (expense)/benefit (22.9) 10.2 15.4
General, administrative and corporate expenses (521.6) (491.7) (502.2)
Net (loss) (241.7) (145.8) (266.4)
Net (loss) (241.7) (145.8) $ (266.4)
Reclassification out of Accumulated Other Comprehensive Income      
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]      
Net (loss) (2.8) (5.5)  
Available for sale securities | Reclassification out of Accumulated Other Comprehensive Income      
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]      
Available for sale securities — gross realized gains (14.4) 6.7  
Realized gains/(losses) on sale of securities 7.6 (11.9)  
(Loss) from operations before income tax (6.8) (5.2)  
Income tax (expense)/benefit 0.0 0.7  
Net (loss) (6.8) (4.5)  
Foreign currency translation adjustments | Reclassification out of Accumulated Other Comprehensive Income      
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]      
Income tax (expense)/benefit (0.8) 0.2  
General, administrative and corporate expenses 4.8 (1.2)  
Net (loss) $ 4.0 $ (1.0)