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Business Segments - Segment Operating Profit (Details) - USD ($)
$ in Millions
3 Months Ended 9 Months Ended
Sep. 30, 2020
Sep. 30, 2019
Sep. 30, 2020
Sep. 30, 2019
Segment Reporting Information [Line Items]        
Operating Income (Loss) $ 112.3 $ 163.0 $ 415.6 $ 396.0
Corporate and Other Operating Profit (Loss) From:        
Income (Loss) from Change in Fair Value of Equity and Convertible Securities 45.2 9.8 (1.0) 99.7
Impairment Losses     (20.0) (12.1)
Loss from Early Extinguishment of Debt 0.0 (5.8) 0.0 (5.8)
Income before Income Taxes 152.1 161.5 389.5 504.7
Operating Segments        
Segment Reporting Information [Line Items]        
Operating Income (Loss) 123.3 166.1 353.0 400.0
Operating Segments | Specialty Property & Casualty Insurance        
Segment Reporting Information [Line Items]        
Operating Income (Loss) 149.9 98.6 309.4 277.4
Operating Segments | Preferred Property & Casualty Insurance        
Segment Reporting Information [Line Items]        
Operating Income (Loss) (41.8) 26.5 (18.0) 36.2
Operating Segments | Life & Health Insurance        
Segment Reporting Information [Line Items]        
Operating Income (Loss) 15.2 41.0 61.6 86.4
Corporate and Other        
Segment Reporting Information [Line Items]        
Operating Income (Loss) (11.0) (3.1) 62.6 (4.0)
Corporate and Other Operating Profit (Loss) From:        
Partial Satisfaction of Judgment 0.0 0.0 89.4 20.1
Other (11.0) (3.1) (26.8) (24.1)
Segment Reconciling Items        
Corporate and Other Operating Profit (Loss) From:        
Income (Loss) from Change in Fair Value of Equity and Convertible Securities 45.2 9.8 (1.0) 99.7
Net Realized Gains on Sales of Investments 10.0 1.7 38.2 39.1
Impairment Losses (1.0) (1.8) (20.0) (12.1)
Acquisition Related Transaction, Integration and Other Costs (14.4) (5.4) (43.3) (12.2)
Loss from Early Extinguishment of Debt $ 0.0 $ (5.8) $ 0.0 $ (5.8)