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Held for Sale and Discontinued Operations - (Details) - USD ($)
$ / shares in Units, $ in Millions
3 Months Ended 9 Months Ended
Sep. 28, 2017
Sep. 30, 2018
Sep. 30, 2017
Sep. 30, 2018
Sep. 30, 2017
Sep. 28, 2017
Dec. 31, 2017
Discontinued Operations [Line Items}              
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold       $ 0.0 $ 1,131.0    
Gain (loss) from sale of discontinued operations, net of tax     $ 554.3 (17.2) 552.7    
Net (loss) income from discontinued operations   $ 0.0 (15.2) 0.0 20.5    
OneBeacon              
Discontinued Operations [Line Items}              
Sale of stock, price per share $ 18.10         $ 18.10  
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold $ 1,300.0            
Gain (loss) from sale of discontinued operations, net of tax $ 554.6            
Net (loss) income from discontinued operations     (15.2)     $ 20.5  
Discontinued Operations | OneBeacon              
Discontinued Operations [Line Items}              
Net (loss) income from discontinued operations     (15.2)   20.5    
Discontinued Operations | Tranzact              
Discontinued Operations [Line Items}              
Gain (loss) from sale of discontinued operations, net of tax         (1.0)    
Discontinued Operations | Sirius Group              
Discontinued Operations [Line Items}              
Gain (loss) from sale of discontinued operations, net of tax   (17.3) (0.2) 0.1 (0.8)    
Net (loss) income from discontinued operations     $ 0.0   $ 0.0    
Connecticut | Discontinued Operations, Held-for-sale              
Discontinued Operations [Line Items}              
Assets held for sale   3.3   3.3     $ 3.3
Swedish Tax Authority | Discontinued Operations | Sirius Group              
Discontinued Operations [Line Items}              
Gain (loss) from sale of discontinued operations, net of tax   (17.3)   (17.2)      
Swedish Tax Authority | Sirius Group              
Discontinued Operations [Line Items}              
Loss contingency, estimate of possible loss   $ 17.3   $ 17.3