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Business Segments - Segment Net Operating Income (Details) - USD ($)
$ in Millions
 3 Months Ended 6 Months Ended
Jun. 30, 2020
Jun. 30, 2019
Jun. 30, 2020
Jun. 30, 2019
Segment Reporting Information [Line Items]        
Segment Net Operating Income $ 79.2 $ 91.5 $ 242.1 $ 190.4
Net Income 126.1 122.1 190.1 277.4
Operating Segments        
Segment Reporting Information [Line Items]        
Segment Net Operating Income 84.5 81.2 185.3 186.7
Operating Segments | Specialty Property & Casualty Insurance        
Segment Reporting Information [Line Items]        
Segment Net Operating Income 67.5 62.7 127.6 142.3
Operating Segments | Preferred Property & Casualty Insurance        
Segment Reporting Information [Line Items]        
Segment Net Operating Income 0.9 5.2 19.3 8.0
Operating Segments | Life & Health Insurance        
Segment Reporting Information [Line Items]        
Segment Net Operating Income 16.1 13.3 38.4 36.4
Corporate and Other        
Segment Reporting Information [Line Items]        
Segment Net Operating Income (5.3) 10.3 56.8 3.7
Partial Satisfaction of Judgment 0.0 15.9 70.6 15.9
Other (5.3) (5.6) (13.8) (12.2)
Segment Reconciling Items        
Segment Reporting Information [Line Items]        
Change in Fair Value of Equity and Convertible Securities 56.6 20.1 (36.5) 71.0
Net Realized Gains on Sales of Investments 9.3 16.8 22.3 29.5
Impairment Losses (5.5) (5.3) (15.0) (8.1)
Acquisition Related Transaction, Integration and Other Costs $ (13.5) $ (1.0) $ (22.8) $ (5.4)