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Business Segments - Segment Operating Profit (Details) - USD ($)
$ in Millions
3 Months Ended 6 Months Ended
Jun. 30, 2019
Jun. 30, 2018
Jun. 30, 2019
Jun. 30, 2018
Segment Reporting Information [Line Items]        
Operating Income (Loss) $ 109.6 $ 44.9 $ 233.0 $ 115.3
Operating Costs and Expenses [Abstract]        
Income from Change in Fair Value of Equity and Convertible Securities 25.5 0.4 89.9 1.1
Net Impairment Losses Recognized in Earnings (6.7) 0.0 (10.3) (0.5)
Income from Continuing Operations before Income Taxes 148.5 45.5 343.2 112.5
Operating Segments        
Segment Reporting Information [Line Items]        
Operating Income (Loss) 101.9 53.3 233.9 129.2
Operating Segments | Preferred Property & Casualty Insurance        
Segment Reporting Information [Line Items]        
Operating Income (Loss) 6.4 (8.7) 9.7 7.9
Operating Segments | Specialty Property & Casualty Insurance        
Segment Reporting Information [Line Items]        
Operating Income (Loss) 79.4 28.2 178.8 57.2
Operating Segments | Life & Health Insurance        
Segment Reporting Information [Line Items]        
Operating Income (Loss) 16.1 33.8 45.4 64.1
Corporate and Other        
Segment Reporting Information [Line Items]        
Operating Income (Loss) 7.7 (8.4) (0.9) (13.9)
Operating Costs and Expenses [Abstract]        
Partial Satisfaction of Judgment 20.1 0.0 20.1 0.0
Other (12.4) (8.4) (21.0) (13.9)
Segment Reconciling Items        
Operating Costs and Expenses [Abstract]        
Income from Change in Fair Value of Equity and Convertible Securities 25.5 0.4 89.9 1.1
Net Realized Gains on Sales of Investments 21.3 3.8 37.4 6.4
Net Impairment Losses Recognized in Earnings (6.7) 0.0 (10.3) (0.5)
Acquisition Related Transaction, Integration and Other Costs $ (1.2) $ (3.6) $ (6.8) $ (9.8)