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Income Taxes - Tax Effects of Deferred Tax Assets and Deferred Tax Liabilities (Details) - USD ($) $ in Millions | Dec. 31, 2020 | Dec. 31, 2019
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Income Tax Disclosure [Abstract] |  |
Share-based payments | $ 0.0 | $ 0.3
Operating loss carryforwards | 119.6 | 121.5
Insurance reserves: Losses and loss adjustment expenses | 7.9 | 5.0
Accrued expenses | 6.4 | 7.1
Unearned premiums | 17.6 | 15.3
Deferred policy acquisition costs | 0.0 | 0.1
Office properties and equipment | 12.7 | 16.8
Operating lease liability | 17.7 | 21.5
Other temporary differences | 2.5 | 6.1
Total deferred tax assets | 184.4 | 193.7
Less valuation allowance | (138.9) | (149.2)
Deferred tax assets, net of valuation allowance | 45.5 | 44.5
Unrealized (gains) on investments | (2.7) | (2.7)
Intangible assets | (20.1) | (1.6)
Deferred policy acquisition costs | (8.4) | (16.4)
Operating lease assets | (12.3) | (19.9)
Other temporary differences | (2.0) | (3.9)
Total deferred tax (liabilities) | (45.5) | (44.5)
Deferred Tax Assets, Net | $ 0.0 | $ 0.0

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