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Income Taxes - Tax Effects of Deferred Tax Assets and Deferred Tax Liabilities (Details) - USD ($) $ in Millions | Dec. 31, 2018 | Dec. 31, 2017
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Income Tax Disclosure [Abstract] |  |
Share-based payments | $ 2.2 | $ 4.0
Operating loss carryforwards | 126.4 | 102.5
Loss reserves | 5.0 | 4.3
Unrealized losses on investments | 0.8 | 0.0
Accrued expenses | 7.9 | 7.9
Foreign tax credit carryforwards | 3.8 | 4.0
Unearned premiums | 15.5 | 11.8
Deferred policy acquisition costs | 0.0 | 5.9
Office properties and equipment | 11.1 | 8.0
Other temporary differences | 3.3 | 2.9
Total gross deferred tax assets | 176.0 | 151.3
Less valuation allowance | (111.9) | (104.8)
Net deferred tax assets | 64.1 | 46.5
Intangible assets (other) | (2.5) | (2.0)
Deferred policy acquisition costs | (18.5) | (14.5)
Quota share losses | (0.6) | 0.0
Loss portfolio transfer costs | (6.1) | 0.0
Other temporary differences | (1.0) | (1.7)
Total gross deferred tax (liabilities) | (28.7) | (18.2)
Deferred Tax Assets, Net | $ 35.4 | $ 28.3

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