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Business Segments - Segment Operating Profit (Details) - USD ($)
$ in Millions
3 Months Ended 12 Months Ended
Dec. 31, 2019
Sep. 30, 2019
Jun. 30, 2019
Mar. 31, 2019
Dec. 31, 2018
Sep. 30, 2018
Jun. 30, 2018
Mar. 31, 2018
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Segment Reporting Information [Line Items]                      
Segment Operating Profit (Loss)                 $ 518.8 $ 286.2 $ 118.9
Income (Loss) from Change in Fair Value of Equity and Convertible Securities $ 39.2 $ 9.8 $ 25.5 $ 64.4 $ (76.4) $ 11.0 $ 0.4 $ 0.7 138.9 (64.3) 0.0
Net Impairment Losses Recognized in Earnings (1.7) (1.8) (6.7) (3.6) (2.2) (1.8) 0.0 (0.5) (13.8) (4.5) (14.3)
Loss from Early Extinguishment of Debt 0.0 (5.8) 0.0 0.0         (5.8) 0.0 0.0
Income from Continuing Operations before Income Taxes $ 156.9 $ 161.5 $ 148.5 $ 194.7 $ 6.1 $ 80.5 $ 45.5 $ 67.0 661.6 199.1 161.1
Operating Segments                      
Segment Reporting Information [Line Items]                      
Segment Operating Profit (Loss)                 530.1 290.1 142.6
Operating Segments | Specialty Property & Casualty Insurance                      
Segment Reporting Information [Line Items]                      
Segment Operating Profit (Loss)                 355.9 145.6 80.5
Operating Segments | Preferred Property & Casualty Insurance                      
Segment Reporting Information [Line Items]                      
Segment Operating Profit (Loss)                 52.3 28.6 (78.1)
Operating Segments | Life & Health Insurance                      
Segment Reporting Information [Line Items]                      
Segment Operating Profit (Loss)                 121.9 115.9 140.2
Corporate, Non-Segment                      
Segment Reporting Information [Line Items]                      
Segment Operating Profit (Loss)                 (11.3) (3.9) (23.7)
Partial Satisfaction of Judgment                 20.1 35.7 0.0
Other                 (31.4) (39.6) (23.7)
Segment Reconciling Items                      
Segment Reporting Information [Line Items]                      
Income (Loss) from Change in Fair Value of Equity and Convertible Securities                 138.9 (64.3) 0.0
Net Realized Gains on the Sales of Investments                 41.9 26.4 56.5
Net Impairment Losses Recognized in Earnings                 (13.8) (4.5) (14.3)
Acquisition Related Transaction, Integration and Other Costs                 $ (18.4) $ (44.7) $ 0.0