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Business Segments - Segment Revenues (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]                      
Earned Premiums $ 1,145.8 $ 1,135.2 $ 1,116.6 $ 1,074.8 $ 1,063.6 $ 1,052.9 $ 658.1 $ 609.8 $ 4,472.4 $ 3,384.4 $ 2,350.0
Net Investment Income 93.9 91.7 96.0 82.7 91.3 92.0 78.4 79.2 364.3 340.9 327.2
Other Income 3.7 7.2 22.7 1.9 2.0 37.8 1.2 1.2 35.5 42.2 4.0
Total Revenues 1,283.7 1,243.8 1,275.4 1,236.3 1,094.7 1,195.5 741.9 693.0 5,039.2 3,725.1 2,723.4
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)
Operating Segments                      
Segment Reporting Information [Line Items]                      
Total Revenues                 4,845.9 3,726.9 2,675.0
Operating Segments | Specialty Property & Casualty Insurance                      
Segment Reporting Information [Line Items]                      
Earned Premiums                 3,078.4 2,027.4 1,005.7
Net Investment Income                 107.5 63.4 39.2
Other Income                 7.0 2.4 1.1
Total Revenues                 3,192.9 2,093.2 1,046.0
Operating Segments | Preferred Property & Casualty Insurance                      
Segment Reporting Information [Line Items]                      
Earned Premiums                 750.3 730.7 730.3
Net Investment Income                 44.1 61.8 58.9
Total Revenues                 794.4 792.5 789.2
Operating Segments | Life & Health Insurance                      
Segment Reporting Information [Line Items]                      
Earned Premiums                 643.7 626.3 614.0
Net Investment Income                 206.4 210.9 223.2
Other Income                 8.5 4.0 2.6
Total Revenues                 858.6 841.2 839.8
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)
Other                 $ 26.3 $ 40.6 $ 6.2