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Discontinued Operations (Summary of Discontinued Chaucer Business) (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
Revenues                      
Premiums                 $ 4,254.4 $ 3,980.4 $ 3,789.5
Net investment income                 267.4 243.9 231.6
Total revenues $ 1,102.8 $ 1,166.6 $ 1,133.4 $ 1,091.5 $ 1,092.5 $ 1,085.9 $ 1,053.3 $ 1,036.2 4,494.3 4,267.9 4,053.9
Losses and operating expenses                      
Losses and LAE                 2,724.6 2,579.6 2,546.0
Amortization of deferred acquisition costs                 891.8 840.7 803.6
Other operating expenses                 522.1 509.5 498.6
Total losses and expenses                 4,211.8 3,975.0 3,987.9
Other items:                      
Interest expense                 (45.1) (45.2) (51.4)
Net realized and unrealized investment gains (losses)                 (50.7) 21.1 10.2
Income tax expense                 (43.5) (76.8) 1.0
Income (loss) from Chaucer business, net of taxes                 0.1 (16.8) (1.0)
Chaucer [Member]                      
Revenues                      
Premiums                 850.0 [1] 853.0 838.6
Net investment income                 54.9 [1] 52.0 45.7
Other income                 7.5 [1] 6.7 7.1
Total revenues                 912.4 [1] 911.7 891.4
Losses and operating expenses                      
Losses and LAE                 515.5 [1] 549.5 419.3
Amortization of deferred acquisition costs                 252.5 [1] 245.9 231.6
Other operating expenses                 115.0 [1] 109.2 113.7
Total losses and expenses                 883.0 [1] 904.6 764.6
Income from Chaucer business before income taxes and other items (previously presented as Chaucer's operating income)                 29.4 [1] 7.1 126.8
Other items:                      
Interest expense                 (3.8) [1] (3.3) (3.5)
Net realized and unrealized investment gains (losses)                 (1.3) [1] 2.6 (1.6)
Other income                 0.4 [1] 2.2 4.6
Income from Chaucer business before income taxes                 24.7 [1] 8.6 126.3
Income tax expense                 (4.7) [1] (21.7) (37.2)
Income (loss) from Chaucer business, net of taxes                 $ 20.0 [1] $ (13.1) $ 89.1
[1] 2018 reflects the results of operations for the period in which THG owned Chaucer, which concluded with the sale of the Chaucer business on December 28, 2018.