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Business Segments - Segment Operating Profit (Details) - USD ($)
$ in Millions
3 Months Ended 12 Months Ended
Dec. 31, 2018
Sep. 30, 2018
Jun. 30, 2018
Mar. 31, 2018
Dec. 31, 2017
Sep. 30, 2017
Jun. 30, 2017
Mar. 31, 2017
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Segment Reporting Information [Line Items]                      
Operating Income (Loss)                 $ 286.2 $ 118.9 $ 3.1
Equity Securities, FV-NI $ (64.3)       $ 0.0       (64.3) 0.0 0.0
Net Realized Gains on Sales of Investments                 26.4 56.5 33.1
Net Impairment Losses Recognized in Earnings (2.2) $ (1.8) $ 0.0 $ (0.5) (3.8) $ (2.9) $ (2.6) $ (5.0) (4.5) (14.3) (32.7)
Income (Loss) from Continuing Operations before Income Taxes 6.1 $ 80.5 $ 45.5 $ 67.0 44.2 $ 68.3 $ 52.1 $ (3.5) 199.1 161.1 3.5
Operating Segments [Member]                      
Segment Reporting Information [Line Items]                      
Operating Income (Loss)                 290.1 142.6 34.8
Operating Segments [Member] | Preferred Property & Casualty Insurance [Member]                      
Segment Reporting Information [Line Items]                      
Operating Income (Loss)                 28.6 (78.1) 15.8
Operating Segments [Member] | Specialty Property & Casualty Insurance [Member]                      
Segment Reporting Information [Line Items]                      
Operating Income (Loss)                 145.6 80.5 (27.7)
Operating Segments [Member] | Life and Health Insurance [Member]                      
Segment Reporting Information [Line Items]                      
Operating Income (Loss)                 115.9 140.2 46.7
Corporate, Non-Segment [Member]                      
Segment Reporting Information [Line Items]                      
Operating Income (Loss)                 (3.9) (23.7) (31.7)
Segment Reconciling Items [Member]                      
Segment Reporting Information [Line Items]                      
Equity Securities, FV-NI (64.3)       0.0       (64.3) 0.0 0.0
Net Realized Gains on Sales of Investments                 26.4 56.5 33.1
Net Impairment Losses Recognized in Earnings                 (4.5) (14.3) (32.7)
Business Acquisition, Transaction Costs $ (44.7)       $ 0.0       $ (44.7) $ 0.0 $ 0.0