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Business Segments - Segment Operating Profit (Details) - USD ($)
$ in Millions
3 Months Ended
Mar. 31, 2021
Mar. 31, 2020
Segment Reporting Information [Line Items]    
Operating Income (Loss) $ 75.9 $ 202.8
Corporate and Other Operating Income (Loss) From:    
Income (Loss) from Change in Fair Value of Equity and Convertible Securities 52.2 (117.8)
Impairment Losses (4.0) (12.0)
Income before Income Taxes 121.6 77.7
Operating Segments    
Segment Reporting Information [Line Items]    
Operating Income (Loss) 87.4 124.5
Operating Segments | Specialty Property & Casualty Insurance    
Segment Reporting Information [Line Items]    
Operating Income (Loss) 85.2 75.0
Operating Segments | Preferred Property & Casualty Insurance    
Segment Reporting Information [Line Items]    
Operating Income (Loss) 3.0 23.0
Operating Segments | Life & Health Insurance    
Segment Reporting Information [Line Items]    
Operating Income (Loss) (0.8) 26.5
Corporate and Other    
Segment Reporting Information [Line Items]    
Operating Income (Loss) (11.5) 78.3
Corporate and Other Operating Income (Loss) From:    
Partial Satisfaction of Judgment 0.0 89.4
Other (11.5) (11.1)
Segment Reconciling Items    
Corporate and Other Operating Income (Loss) From:    
Income (Loss) from Change in Fair Value of Equity and Convertible Securities 52.2 (117.8)
Net Realized Gains on Sales of Investments 13.8 16.5
Impairment Losses (4.0) (12.0)
Acquisition Related Transaction, Integration and Other Costs $ (16.3) $ (11.8)