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Taxation (Tables) | 12 Months Ended
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Dec. 31, 2019
Income Tax Disclosure [Abstract] |
Schedule of Income before Income Tax, Domestic and Foreign | The following is a summary of the Company’s income (loss) before taxes allocated between domestic and foreign operations:
| Year ended December 31, | 2019 |  | 2018 |  | 2017 |
| Domestic |  |  |  |  |  |
| Bermuda | $ | 861,068 |  |  | $ | 349,959 |  |  | $ | (262,827 | ) |
| Foreign |  |  |  |  |  |
| U.S. | 102,724 |  |  | (56,261 | ) |  | (11,897 | ) |
| Australia | 3,390 |  |  | — |  |  | — |  |
| Switzerland | 14,255 |  |  | 166 |  |  | — |  |
| Ireland | (388 | ) |  | 551 |  |  | 617 |  |
| Singapore | (6,334 | ) |  | (3,226 | ) |  | (12,421 | ) |
| U.K. | (7,233 | ) |  | (28,574 | ) |  | (41,656 | ) |
| Income (loss) before taxes | $ | 967,482 |  |  | $ | 262,615 |  |  | $ | (328,184 | ) |
Schedule of Components of Income Tax (Expense) Benefit | Income tax (expense) benefit is comprised as follows:
| Year ended December 31, 2019 | Current |  | Deferred |  | Total |
| Total income tax expense | $ | (2,128 | ) |  | $ | (15,087 | ) |  | $ | (17,215 | ) |
| Year ended December 31, 2018 |  |  |  |  |  |
| Total income tax (expense) benefit | $ | (1,668 | ) |  | $ | 7,970 |  |  | $ | 6,302 |  |
| Year ended December 31, 2017 |  |  |  |  |  |
| Total income tax expense | $ | (844 | ) |  | $ | (25,643 | ) |  | $ | (26,487 | ) |
Schedule of Effective Income Tax Rate Reconciliation | A reconciliation of the difference between the provision for income taxes and the expected tax provision at the weighted average tax rate is as follows:
| Year ended December 31, | 2019 |  | 2018 |  | 2017 |
| Expected income tax (expense) benefit | $ | (22,874 | ) |  | $ | 17,697 |  |  | $ | 14,216 |  |
| Nondeductible expenses | (7,059 | ) |  | (370 | ) |  | (276 | ) |
| Change in valuation allowance | (5,481 | ) |  | (5,255 | ) |  | (11,718 | ) |
| Withholding tax | (665 | ) |  | (1,831 | ) |  | (216 | ) |
| Effect of change in tax rate | (262 | ) |  | (708 | ) |  | (38,083 | ) |
| Non-taxable foreign exchange gains (losses) | (4 | ) |  | 586 |  |  | 2,574 |  |
| Tax exempt income | 400 |  |  | 944 |  |  | 3,794 |  |
| Transfer pricing | 2,503 |  |  | (2,481 | ) |  | (11 | ) |
| GAAP to statutory accounting difference | 6,553 |  |  | — |  |  | — |  |
| Foreign branch adjustments | 7,315 |  |  | — |  |  | — |  |
| U.S. base erosion and anti-abuse tax | — |  |  | (1,271 | ) |  | — |  |
| Other | 2,359 |  |  | (1,009 | ) |  | 3,233 |  |
| Income tax (expense) benefit | $ | (17,215 | ) |  | $ | 6,302 |  |  | $ | (26,487 | ) |
Schedule of Deferred Tax Assets and Liabilities | The tax effects of temporary differences that give rise to significant portions of the deferred tax assets and deferred tax liabilities are presented below:
| At December 31, | 2019 |  | 2018 |
| Deferred tax assets |  |  |  |
| Tax loss and credit carryforwards | $ | 111,835 |  |  | $ | 60,395 |  |
| Unearned premiums | 14,430 |  |  | 10,108 |  |
| Deferred finance charges | 10,160 |  |  | 14,646 |  |
| Reserve for claims and claim expenses | 8,984 |  |  | 17,345 |  |
| Accrued expenses | 7,196 |  |  | 4,292 |  |
| Deferred underwriting results | 4,033 |  |  | 3,514 |  |
| Premiums receivable | 3,412 |  |  | — |  |
| Investments | — |  |  | 4,427 |  |
|  | 160,050 |  |  | 114,727 |  |
| Deferred tax liabilities |  |  |  |
| Deferred acquisition expenses | (16,296 | ) |  | (11,801 | ) |
| VOBA | (12,673 | ) |  | — |  |
| Investments | (6,468 | ) |  | — |  |
| Intangible assets | (2,891 | ) |  | — |  |
| Amortization and depreciation | (2,133 | ) |  | (2,992 | ) |
|  | (40,461 | ) |  | (14,793 | ) |
| Net deferred tax asset before valuation allowance | 119,589 |  |  | 99,934 |  |
| Valuation allowance | (75,685 | ) |  | (35,271 | ) |
| Net deferred tax asset | $ | 43,904 |  |  | $ | 64,663 |  |

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