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Reclassifications from Accumulated Other Comprehensive Income - Schedule of Accumulated Other Comprehensive Income Reclassification (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
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]                              
(Loss)/income from operations before income tax $ (143.6) $ (30.6) $ (16.2) $ 34.4 $ (195.1) $ (263.0) $ 77.0 $ 99.3 $ (74.1) $ 100.5 $ 66.2 $ 116.9 $ (156.0) $ (281.8) $ 209.5
Income tax benefit/(expense) (3.2) 15.5 1.5 (3.6) 10.2 9.2 (1.2) (2.8) 2.6 (4.9) (1.3) (2.5) 10.2 15.4 (6.1)
General, administrative and corporate expenses (100.1) (160.4) (110.2) (121.0) (150.1) (110.9) (119.9) (121.3) (128.9) (125.0) (116.4) (119.8) (491.7) (502.2) (490.1)
Income (Loss), Including Portion Attributable to Noncontrolling Interest, before Tax                         (145.8) (266.4) 203.4
Net (loss)/income $ (146.8) $ (15.1) $ (14.7) $ 30.8 $ (184.9) $ (253.8) $ 75.8 $ 96.5 $ (71.5) $ 95.6 $ 64.9 $ 114.4 (145.8) (266.4) $ 203.4
Reclassification out of Accumulated Other Comprehensive Income                              
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]                              
Income (Loss), Including Portion Attributable to Noncontrolling Interest, before Tax                         (5.5) 7.2  
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                         6.7 10.7  
Realized (losses) on sale of securities                         (11.9) (6.7)  
(Loss)/income from operations before income tax                         (5.2) 4.0  
Income tax benefit/(expense)                         0.7 (0.4)  
Net (loss)/income                         (4.5) 3.6  
Foreign currency translation adjustments | Reclassification out of Accumulated Other Comprehensive Income                              
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]                              
Income tax benefit/(expense)                         0.2 (0.8)  
General, administrative and corporate expenses                         (1.2) 4.4  
Income (Loss), Including Portion Attributable to Noncontrolling Interest, before Tax                         $ (1.0) $ 3.6