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Business Segments - Segment Revenues (Details) - USD ($)
$ in Millions
3 Months Ended 9 Months Ended
Sep. 30, 2019
Sep. 30, 2018
Sep. 30, 2019
Sep. 30, 2018
Segment Reporting Information [Line Items]        
Earned Premiums $ 1,135.2 $ 1,052.9 $ 3,326.6 $ 2,320.8
Net Investment Income 91.7 92.0 270.4 249.6
Other Income 7.2 37.8 31.8 40.2
Total Revenues 1,243.8 1,195.5 3,755.5 2,630.4
Income from Change in Fair Value of Equity and Convertible Securities 9.8 11.0 99.7 12.1
Net Impairment Losses Recognized in Earnings (1.8) (1.8) (12.1) (2.3)
Operating Segments        
Segment Reporting Information [Line Items]        
Total Revenues 1,233.0 1,146.8 3,604.6 2,573.1
Operating Segments | Preferred Property & Casualty Insurance        
Segment Reporting Information [Line Items]        
Earned Premiums 191.0 184.0 565.1 541.9
Net Investment Income 12.0 20.1 32.6 47.8
Total Revenues 203.0 204.1 597.7 589.7
Operating Segments | Specialty Property & Casualty Insurance        
Segment Reporting Information [Line Items]        
Earned Premiums 783.4 711.2 2,278.7 1,309.6
Net Investment Income 28.8 20.7 79.2 40.8
Other Income 4.4 0.9 6.2 1.6
Total Revenues 816.6 732.8 2,364.1 1,352.0
Operating Segments | Life & Health Insurance        
Segment Reporting Information [Line Items]        
Earned Premiums 160.8 157.7 482.8 469.3
Net Investment Income 49.7 51.0 154.4 159.2
Other Income 2.9 1.2 5.6 2.9
Total Revenues 213.4 209.9 642.8 631.4
Segment Reconciling Items        
Segment Reporting Information [Line Items]        
Income from Change in Fair Value of Equity and Convertible Securities 9.8 11.0 99.7 12.1
Net Realized Gains on Sales of Investments 1.7 3.6 39.1 10.0
Net Impairment Losses Recognized in Earnings (1.8) (1.8) (12.1) (2.3)
Other $ 1.1 $ 35.9 $ 24.2 $ 37.5