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Intangible Assets and Goodwill - Summary of Changes in Intangible Assets (Details) - USD ($)
$ in Millions
 3 Months Ended 6 Months Ended
Jan. 19, 2016
Jun. 30, 2018
Jun. 30, 2017
Jun. 30, 2018
Jun. 30, 2017
Finite and Indefinite Lived Intangible Assets [Roll Forward]          
Amortization   $ (0.5) $ (1.1) $ (0.9) $ (2.0)
Goodwill [Roll Forward]          
Goodwill, Beginning of the period   3.9 26.0 3.9 24.2
Goodwill, Additions   0.0 0.0 0.0 1.8
Goodwill, End of the period   3.9 26.0 3.9 26.0
Intangible assets and goodwill, Beginning of the period   27.5 80.5 27.9 79.6
Intangible Assets and Goodwill, Acquired   0.0 0.0 0.0 1.8
Intangible assets and goodwill, End of the period   27.0 79.4 27.0 79.4
Trademark          
Finite and Indefinite Lived Intangible Assets [Roll Forward]          
Intangible Assets, Beginning of the period   2.8 6.4 2.9 6.6
Intangible Assets, Additions   0.0 0.0 0.0 0.0
Amortization   (0.1) (0.1) (0.2) (0.3)
Intangible Assets, End of the period $ 4.0 2.7 6.3 2.7 6.3
Insurance Licenses          
Finite and Indefinite Lived Intangible Assets [Roll Forward]          
Intangible Assets, Beginning of the period   16.7 16.7 16.7 16.7
Intangible Assets, Additions   0.0 0.0 0.0 0.0
Amortization   0.0 0.0 0.0 0.0
Intangible Assets, End of the period   16.7 16.7 16.7 16.7
Agency Relationships          
Finite and Indefinite Lived Intangible Assets [Roll Forward]          
Intangible Assets, Beginning of the period   2.2 25.8 2.3 26.2
Intangible Assets, Additions   0.0 0.0 0.0 0.0
Amortization   (0.2) (0.7) (0.3) (1.1)
Intangible Assets, End of the period 25.0 2.0 25.1 2.0 25.1
Non-compete Agreements          
Finite and Indefinite Lived Intangible Assets [Roll Forward]          
Intangible Assets, Beginning of the period   0.6 3.1 0.7 3.3
Intangible Assets, Additions 2.9 0.0 0.0 0.0 0.0
Amortization   (0.1) (0.1) (0.2) (0.3)
Intangible Assets, End of the period   0.5 3.0 0.5 3.0
Consulting Relationships          
Finite and Indefinite Lived Intangible Assets [Roll Forward]          
Intangible Assets, Beginning of the period   0.0 0.9 0.0 0.9
Intangible Assets, Additions   0.0 0.0 0.0 0.0
Amortization   0.0 (0.1) 0.0 (0.1)
Intangible Assets, End of the period $ 1.0 0.0 0.8 0.0 0.8
Contractual Rights          
Finite and Indefinite Lived Intangible Assets [Roll Forward]          
Intangible Assets, Beginning of the period   1.3 1.6 1.4 1.7
Intangible Assets, Additions   0.0 0.0 0.0 0.0
Amortization   (0.1) (0.1) (0.2) (0.2)
Intangible Assets, End of the period   $ 1.2 $ 1.5 $ 1.2 $ 1.5