<?xml version="1.0" encoding="UTF-8"?>

<!--XBRL Document Created with the Workiva Platform-->
<!--Copyright 2026 Workiva-->
<!--r:019e1ddf-511a-796d-88a9-7320a3e7bbc6,g:0abb39b6-3658-446c-abd2-9a81d9a8a1fc-->
<xs:schema xmlns:xs="http://www.w3.org/2001/XMLSchema" xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:hg="http://www.hamiltongroup.com/20260630" xmlns:xbrli="http://www.xbrl.org/2003/instance" xmlns:dtr-types="http://www.xbrl.org/dtr/type/2024-01-31" xmlns:xbrldt="http://xbrl.org/2005/xbrldt" attributeFormDefault="unqualified" elementFormDefault="qualified" targetNamespace="http://www.hamiltongroup.com/20260630">
  <xs:import namespace="http://fasb.org/srt/2026" schemaLocation="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd"/>
  <xs:import namespace="http://fasb.org/us-gaap/2026" schemaLocation="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd"/>
  <xs:import namespace="http://www.xbrl.org/2003/instance" schemaLocation="http://www.xbrl.org/2003/xbrl-instance-2003-12-31.xsd"/>
  <xs:import namespace="http://www.xbrl.org/2003/linkbase" schemaLocation="http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd"/>
  <xs:import namespace="http://www.xbrl.org/dtr/type/2024-01-31" schemaLocation="https://www.xbrl.org/dtr/type/2024-01-31/types.xsd"/>
  <xs:import namespace="http://xbrl.org/2005/xbrldt" schemaLocation="http://www.xbrl.org/2005/xbrldt-2005.xsd"/>
  <xs:import namespace="http://xbrl.sec.gov/country/2026" schemaLocation="https://xbrl.sec.gov/country/2026/country-2026.xsd"/>
  <xs:import namespace="http://xbrl.sec.gov/dei/2026" schemaLocation="https://xbrl.sec.gov/dei/2026/dei-2026.xsd"/>
  <xs:import namespace="http://xbrl.sec.gov/ecd/2026" schemaLocation="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd"/>
  <xs:annotation>
    <xs:appinfo>
      <link:linkbaseRef xmlns:xlink="http://www.w3.org/1999/xlink" xlink:arcrole="http://www.w3.org/1999/xlink/properties/linkbase" xlink:href="hg-20260630_pre.xml" xlink:role="http://www.xbrl.org/2003/role/presentationLinkbaseRef" xlink:type="simple"/>
      <link:linkbaseRef xmlns:xlink="http://www.w3.org/1999/xlink" xlink:arcrole="http://www.w3.org/1999/xlink/properties/linkbase" xlink:href="hg-20260630_def.xml" xlink:role="http://www.xbrl.org/2003/role/definitionLinkbaseRef" xlink:type="simple"/>
      <link:linkbaseRef xmlns:xlink="http://www.w3.org/1999/xlink" xlink:arcrole="http://www.w3.org/1999/xlink/properties/linkbase" xlink:href="hg-20260630_lab.xml" xlink:role="http://www.xbrl.org/2003/role/labelLinkbaseRef" xlink:type="simple"/>
      <link:linkbaseRef xmlns:xlink="http://www.w3.org/1999/xlink" xlink:arcrole="http://www.w3.org/1999/xlink/properties/linkbase" xlink:href="hg-20260630_cal.xml" xlink:role="http://www.xbrl.org/2003/role/calculationLinkbaseRef" xlink:type="simple"/>
      <link:roleType id="Cover" roleURI="http://www.hamiltongroup.com/role/Cover">
        <link:definition>0000001 - Document - Cover</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="UnauditedCondensedConsolidatedBalanceSheets" roleURI="http://www.hamiltongroup.com/role/UnauditedCondensedConsolidatedBalanceSheets">
        <link:definition>9952151 - Statement - Unaudited Condensed Consolidated Balance Sheets</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="UnauditedCondensedConsolidatedBalanceSheetsParenthetical" roleURI="http://www.hamiltongroup.com/role/UnauditedCondensedConsolidatedBalanceSheetsParenthetical">
        <link:definition>9952152 - Statement - Unaudited Condensed Consolidated Balance Sheets (Parenthetical)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="UnauditedCondensedConsolidatedStatementsofOperationsandComprehensiveIncomeLoss" roleURI="http://www.hamiltongroup.com/role/UnauditedCondensedConsolidatedStatementsofOperationsandComprehensiveIncomeLoss">
        <link:definition>9952153 - Statement - Unaudited Condensed Consolidated Statements of Operations and Comprehensive Income (Loss)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="UnauditedCondensedConsolidatedStatementsofShareholdersEquity" roleURI="http://www.hamiltongroup.com/role/UnauditedCondensedConsolidatedStatementsofShareholdersEquity">
        <link:definition>9952154 - Statement - Unaudited Condensed Consolidated Statements of Shareholders' Equity</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="UnauditedCondensedConsolidatedStatementsofCashFlows" roleURI="http://www.hamiltongroup.com/role/UnauditedCondensedConsolidatedStatementsofCashFlows">
        <link:definition>9952155 - Statement - Unaudited Condensed Consolidated Statements of Cash Flows</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="Organization" roleURI="http://www.hamiltongroup.com/role/Organization">
        <link:definition>9952156 - Disclosure - Organization</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SummaryofSignificantAccountingPolicies" roleURI="http://www.hamiltongroup.com/role/SummaryofSignificantAccountingPolicies">
        <link:definition>9952157 - Disclosure - Summary of Significant Accounting Policies</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="Investments" roleURI="http://www.hamiltongroup.com/role/Investments">
        <link:definition>9952158 - Disclosure - Investments</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="FairValue" roleURI="http://www.hamiltongroup.com/role/FairValue">
        <link:definition>9952159 - Disclosure - Fair Value</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="VariableInterestEntities" roleURI="http://www.hamiltongroup.com/role/VariableInterestEntities">
        <link:definition>9952160 - Disclosure - Variable Interest Entities</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="Reinsurance" roleURI="http://www.hamiltongroup.com/role/Reinsurance">
        <link:definition>9952161 - Disclosure - Reinsurance</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ReserveforLossesandLossAdjustmentExpenses" roleURI="http://www.hamiltongroup.com/role/ReserveforLossesandLossAdjustmentExpenses">
        <link:definition>9952162 - Disclosure - Reserve for Losses and Loss Adjustment Expenses</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SegmentReporting" roleURI="http://www.hamiltongroup.com/role/SegmentReporting">
        <link:definition>9952163 - Disclosure - Segment Reporting</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="DebtandCreditFacilities" roleURI="http://www.hamiltongroup.com/role/DebtandCreditFacilities">
        <link:definition>9952164 - Disclosure - Debt and Credit Facilities</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ShareCapital" roleURI="http://www.hamiltongroup.com/role/ShareCapital">
        <link:definition>9952165 - Disclosure - Share Capital</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="EarningsPerShare" roleURI="http://www.hamiltongroup.com/role/EarningsPerShare">
        <link:definition>9952166 - Disclosure - Earnings Per Share</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SummaryofSignificantAccountingPoliciesPolicies" roleURI="http://www.hamiltongroup.com/role/SummaryofSignificantAccountingPoliciesPolicies">
        <link:definition>9955511 - Disclosure - Summary of Significant Accounting Policies (Policies)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="InvestmentsTables" roleURI="http://www.hamiltongroup.com/role/InvestmentsTables">
        <link:definition>9955512 - Disclosure - Investments (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="FairValueTables" roleURI="http://www.hamiltongroup.com/role/FairValueTables">
        <link:definition>9955513 - Disclosure - Fair Value (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="VariableInterestEntitiesTables" roleURI="http://www.hamiltongroup.com/role/VariableInterestEntitiesTables">
        <link:definition>9955514 - Disclosure - Variable Interest Entities (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ReinsuranceTables" roleURI="http://www.hamiltongroup.com/role/ReinsuranceTables">
        <link:definition>9955515 - Disclosure - Reinsurance (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ReserveforLossesandLossAdjustmentExpensesTables" roleURI="http://www.hamiltongroup.com/role/ReserveforLossesandLossAdjustmentExpensesTables">
        <link:definition>9955516 - Disclosure - Reserve for Losses and Loss Adjustment Expenses (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SegmentReportingTables" roleURI="http://www.hamiltongroup.com/role/SegmentReportingTables">
        <link:definition>9955517 - Disclosure - Segment Reporting (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="DebtandCreditFacilitiesTables" roleURI="http://www.hamiltongroup.com/role/DebtandCreditFacilitiesTables">
        <link:definition>9955518 - Disclosure - Debt and Credit Facilities (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ShareCapitalTables" roleURI="http://www.hamiltongroup.com/role/ShareCapitalTables">
        <link:definition>9955519 - Disclosure - Share Capital (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="EarningsPerShareTables" roleURI="http://www.hamiltongroup.com/role/EarningsPerShareTables">
        <link:definition>9955520 - Disclosure - Earnings Per Share (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="InvestmentsScheduleofFixedMaturityandShortTermInvestmentsDetails" roleURI="http://www.hamiltongroup.com/role/InvestmentsScheduleofFixedMaturityandShortTermInvestmentsDetails">
        <link:definition>9955521 - Disclosure - Investments - Schedule of Fixed Maturity and Short-Term Investments (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="InvestmentsScheduleofContractualMaturitiesofFixedMaturitySecuritiesDetails" roleURI="http://www.hamiltongroup.com/role/InvestmentsScheduleofContractualMaturitiesofFixedMaturitySecuritiesDetails">
        <link:definition>9955522 - Disclosure - Investments - Schedule of Contractual Maturities of Fixed Maturity Securities (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="InvestmentsScheduleofOwnershipPercentageinTwoSigmaFundsDetails" roleURI="http://www.hamiltongroup.com/role/InvestmentsScheduleofOwnershipPercentageinTwoSigmaFundsDetails">
        <link:definition>9955523 - Disclosure - Investments - Schedule of Ownership Percentage in Two Sigma Funds (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="InvestmentsScheduleofInvestmentsinTwoSigmaFundsDetails" roleURI="http://www.hamiltongroup.com/role/InvestmentsScheduleofInvestmentsinTwoSigmaFundsDetails">
        <link:definition>9955524 - Disclosure - Investments - Schedule of Investments in Two Sigma Funds (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="InvestmentsScheduleofCertainInvestmentsDetails" roleURI="http://www.hamiltongroup.com/role/InvestmentsScheduleofCertainInvestmentsDetails">
        <link:definition>9955525 - Disclosure - Investments - Schedule of Certain Investments (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="InvestmentsNarrativeDetails" roleURI="http://www.hamiltongroup.com/role/InvestmentsNarrativeDetails">
        <link:definition>9955526 - Disclosure - Investments - Narrative (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="InvestmentsScheduleofRealizedandUnrealizedGainsLossesonInvestmentsandNetInvestmentIncomeLossDetails" roleURI="http://www.hamiltongroup.com/role/InvestmentsScheduleofRealizedandUnrealizedGainsLossesonInvestmentsandNetInvestmentIncomeLossDetails">
        <link:definition>9955527 - Disclosure - Investments - Schedule of Realized and Unrealized Gains (Losses) on Investments and Net Investment Income (Loss) (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="InvestmentsNetRealizedGainsLossesonInvestmentsDetails" roleURI="http://www.hamiltongroup.com/role/InvestmentsNetRealizedGainsLossesonInvestmentsDetails">
        <link:definition>9955528 - Disclosure - Investments - Net Realized Gains (Losses) on Investments (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="InvestmentsNetUnrealizedGainsLossesonInvestmentsDetails" roleURI="http://www.hamiltongroup.com/role/InvestmentsNetUnrealizedGainsLossesonInvestmentsDetails">
        <link:definition>9955529 - Disclosure - Investments - Net Unrealized Gains (Losses) on Investments (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="FairValueDetails" roleURI="http://www.hamiltongroup.com/role/FairValueDetails">
        <link:definition>9955530 - Disclosure - Fair Value (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="VariableInterestEntitiesScheduleofActivityintheNonControllingInterestDetails" roleURI="http://www.hamiltongroup.com/role/VariableInterestEntitiesScheduleofActivityintheNonControllingInterestDetails">
        <link:definition>9955531 - Disclosure - Variable Interest Entities - Schedule of Activity in the Non-Controlling Interest (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="VariableInterestEntitiesScheduleofTotalAssetsandTotalLiabilitiesofTSHamiltonFundDetails" roleURI="http://www.hamiltongroup.com/role/VariableInterestEntitiesScheduleofTotalAssetsandTotalLiabilitiesofTSHamiltonFundDetails">
        <link:definition>9955532 - Disclosure - Variable Interest Entities - Schedule of Total Assets and Total Liabilities of TS Hamilton Fund (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ReinsuranceNarrativeDetails" roleURI="http://www.hamiltongroup.com/role/ReinsuranceNarrativeDetails">
        <link:definition>9955533 - Disclosure - Reinsurance - Narrative (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ReinsuranceNarrativeDetails_1" roleURI="http://www.hamiltongroup.com/role/ReinsuranceNarrativeDetails_1">
        <link:definition>9955533 - Disclosure - Reinsurance - Narrative (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ReinsuranceScheduleofRollforwardofProvisionofCompanysPremiumsReceivableDetails" roleURI="http://www.hamiltongroup.com/role/ReinsuranceScheduleofRollforwardofProvisionofCompanysPremiumsReceivableDetails">
        <link:definition>9955534 - Disclosure - Reinsurance - Schedule of Rollforward of Provision of Company's Premiums Receivable (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ReinsuranceScheduleofRollforwardofProvisionofCompanysReinsuranceRecoverableDetails" roleURI="http://www.hamiltongroup.com/role/ReinsuranceScheduleofRollforwardofProvisionofCompanysReinsuranceRecoverableDetails">
        <link:definition>9955535 - Disclosure - Reinsurance - Schedule of Rollforward of Provision of Company's Reinsurance Recoverable (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ReinsuranceScheduleofPaidandUnpaidLossesandLossAdjustmentExpensesRecoverableDetails" roleURI="http://www.hamiltongroup.com/role/ReinsuranceScheduleofPaidandUnpaidLossesandLossAdjustmentExpensesRecoverableDetails">
        <link:definition>9955536 - Disclosure - Reinsurance - Schedule of Paid and Unpaid Losses and Loss Adjustment Expenses Recoverable (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ReserveforLossesandLossAdjustmentExpensesScheduleofReconciliationofUnpaidLossesandLossAdjustmentExpensesDetails" roleURI="http://www.hamiltongroup.com/role/ReserveforLossesandLossAdjustmentExpensesScheduleofReconciliationofUnpaidLossesandLossAdjustmentExpensesDetails">
        <link:definition>9955537 - Disclosure - Reserve for Losses and Loss Adjustment Expenses - Schedule of Reconciliation of Unpaid Losses and Loss Adjustment Expenses (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ReserveforLossesandLossAdjustmentExpensesNarrativeDetails" roleURI="http://www.hamiltongroup.com/role/ReserveforLossesandLossAdjustmentExpensesNarrativeDetails">
        <link:definition>9955538 - Disclosure - Reserve for Losses and Loss Adjustment Expenses - Narrative (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ReserveforLossesandLossAdjustmentExpensesNarrativeDetails_1" roleURI="http://www.hamiltongroup.com/role/ReserveforLossesandLossAdjustmentExpensesNarrativeDetails_1">
        <link:definition>9955538 - Disclosure - Reserve for Losses and Loss Adjustment Expenses - Narrative (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SegmentReportingScheduleofSegmentReportingInformationDetails" roleURI="http://www.hamiltongroup.com/role/SegmentReportingScheduleofSegmentReportingInformationDetails">
        <link:definition>9955539 - Disclosure - Segment Reporting - Schedule of Segment Reporting Information (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SegmentReportingScheduleofGrossPremiumsWrittenbyGeographicalLocationofSubsidiariesDetails" roleURI="http://www.hamiltongroup.com/role/SegmentReportingScheduleofGrossPremiumsWrittenbyGeographicalLocationofSubsidiariesDetails">
        <link:definition>9955540 - Disclosure - Segment Reporting - Schedule of Gross Premiums Written by Geographical Location of Subsidiaries (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="DebtandCreditFacilitiesNarrativeDetails" roleURI="http://www.hamiltongroup.com/role/DebtandCreditFacilitiesNarrativeDetails">
        <link:definition>9955541 - Disclosure - Debt and Credit Facilities - Narrative (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="DebtandCreditFacilitiesScheduleofCompanyComplianceDetails" roleURI="http://www.hamiltongroup.com/role/DebtandCreditFacilitiesScheduleofCompanyComplianceDetails">
        <link:definition>9955542 - Disclosure - Debt and Credit Facilities - Schedule of Company Compliance (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="DebtandCreditFacilitiesScheduleofCreditFacilitiesDetails" roleURI="http://www.hamiltongroup.com/role/DebtandCreditFacilitiesScheduleofCreditFacilitiesDetails">
        <link:definition>9955543 - Disclosure - Debt and Credit Facilities - Schedule of Credit Facilities (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ShareCapitalScheduleofShareCapitalDetails" roleURI="http://www.hamiltongroup.com/role/ShareCapitalScheduleofShareCapitalDetails">
        <link:definition>9955544 - Disclosure - Share Capital - Schedule of Share Capital (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ShareCapitalScheduleofCommonStockAuthorizedDetails" roleURI="http://www.hamiltongroup.com/role/ShareCapitalScheduleofCommonStockAuthorizedDetails">
        <link:definition>9955545 - Disclosure - Share Capital - Schedule of Common Stock Authorized (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ShareCapitalScheduleofCommonStockIssuedandOutstandingDetails" roleURI="http://www.hamiltongroup.com/role/ShareCapitalScheduleofCommonStockIssuedandOutstandingDetails">
        <link:definition>9955546 - Disclosure - Share Capital - Schedule of Common Stock Issued and Outstanding (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ShareCapitalNarrativeDetails" roleURI="http://www.hamiltongroup.com/role/ShareCapitalNarrativeDetails">
        <link:definition>9955547 - Disclosure - Share Capital - Narrative (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ShareCapitalShareRepurchaseInformationDetails" roleURI="http://www.hamiltongroup.com/role/ShareCapitalShareRepurchaseInformationDetails">
        <link:definition>9955548 - Disclosure - Share Capital - Share Repurchase Information (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="EarningsPerShareDetails" roleURI="http://www.hamiltongroup.com/role/EarningsPerShareDetails">
        <link:definition>9955549 - Disclosure - Earnings Per Share (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
    </xs:appinfo>
  </xs:annotation>
  <xs:element id="hg_GainLossOnInvestmentsAndNetInvestmentIncome" abstract="false" name="GainLossOnInvestmentsAndNetInvestmentIncome" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_DividendsCommonStockCashIncludingAccruedDividendEquivalentsOnUnvestedAwards" abstract="false" name="DividendsCommonStockCashIncludingAccruedDividendEquivalentsOnUnvestedAwards" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_IncreaseDecreaseInReinsuranceRecoverablePaidClaimsAndClaimsAdjustments" abstract="false" name="IncreaseDecreaseInReinsuranceRecoverablePaidClaimsAndClaimsAdjustments" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_IncreaseDecreaseInReinsuranceRecoverableUnpaidLossesAndLossAdjustmentExpenses" abstract="false" name="IncreaseDecreaseInReinsuranceRecoverableUnpaidLossesAndLossAdjustmentExpenses" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_ProceedsRelatedToChangeInReceivablesForInvestmentsSold" abstract="false" name="ProceedsRelatedToChangeInReceivablesForInvestmentsSold" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_PaymentsRelatedToChangeInPayablesForInvestmentsPurchased" abstract="false" name="PaymentsRelatedToChangeInPayablesForInvestmentsPurchased" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_ProceedsFromPaymentsForFromContributionsToAdditionalPaidInCapital" abstract="false" name="ProceedsFromPaymentsForFromContributionsToAdditionalPaidInCapital" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_AlternativeInvestmentsTableTextBlock" abstract="false" name="AlternativeInvestmentsTableTextBlock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:textBlockItemType"/>
  <xs:element id="hg_ScheduleOfRealizedAndUnrealizedGainsLossesOnInvestmentsAndNetInvestmentIncomeLossTableTextBlock" abstract="false" name="ScheduleOfRealizedAndUnrealizedGainsLossesOnInvestmentsAndNetInvestmentIncomeLossTableTextBlock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:textBlockItemType"/>
  <xs:element id="hg_ScheduleOfShareRepurchaseProgramActivityTableTextBlock" abstract="false" name="ScheduleOfShareRepurchaseProgramActivityTableTextBlock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:textBlockItemType"/>
  <xs:element id="hg_OtherAssetBackedSecuritiesMember" abstract="true" name="OtherAssetBackedSecuritiesMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingAccumulatedGrossUnrealizedGainBeforeTax" abstract="false" name="DebtSecuritiesTradingAccumulatedGrossUnrealizedGainBeforeTax" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingAccumulatedGrossUnrealizedLossBeforeTax" abstract="false" name="DebtSecuritiesTradingAccumulatedGrossUnrealizedLossBeforeTax" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_FixedMaturitiesExcludingMortgageBackedAndAssetBackedSecuritiesMember" abstract="true" name="FixedMaturitiesExcludingMortgageBackedAndAssetBackedSecuritiesMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingAmortizedCostMaturityAllocatedAndSingleMaturityDateYearOne" abstract="false" name="DebtSecuritiesTradingAmortizedCostMaturityAllocatedAndSingleMaturityDateYearOne" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingAmortizedCostMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" abstract="false" name="DebtSecuritiesTradingAmortizedCostMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingAmortizedCostMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" abstract="false" name="DebtSecuritiesTradingAmortizedCostMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingAmortizedCostMaturityAllocatedAndSingleMaturityDateAfterYear10" abstract="false" name="DebtSecuritiesTradingAmortizedCostMaturityAllocatedAndSingleMaturityDateAfterYear10" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingMaturityWithoutSingleMaturityDateAmortizedCost" abstract="false" name="DebtSecuritiesTradingMaturityWithoutSingleMaturityDateAmortizedCost" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne" abstract="false" name="DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" abstract="false" name="DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" abstract="false" name="DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10" abstract="false" name="DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_DebtSecuritiesTradingMaturityWithoutSingleMaturityDateFairValue" abstract="false" name="DebtSecuritiesTradingMaturityWithoutSingleMaturityDateFairValue" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_TwoSigmaSpectrumPortfolioLLCSTVMember" abstract="true" name="TwoSigmaSpectrumPortfolioLLCSTVMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_TwoSigmaEquitySpectrumPortfolioLLCESTVMember" abstract="true" name="TwoSigmaEquitySpectrumPortfolioLLCESTVMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_TwoSigmaAbsoluteReturnPortfolioLLCATVMember" abstract="true" name="TwoSigmaAbsoluteReturnPortfolioLLCATVMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_TwoSigmaFuturesPortfolioLLCFTVMember" abstract="true" name="TwoSigmaFuturesPortfolioLLCFTVMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_TwoSigmaHorizonPortfolioLLCHTVMember" abstract="true" name="TwoSigmaHorizonPortfolioLLCHTVMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_TwoSigmaNavigatorPortfolioLLCNTVMember" abstract="true" name="TwoSigmaNavigatorPortfolioLLCNTVMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_TwoSigmaKuiperPortfolioLLCKTVMember" abstract="true" name="TwoSigmaKuiperPortfolioLLCKTVMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_AlternativeInvestmentOwnershipPercentage" abstract="false" name="AlternativeInvestmentOwnershipPercentage" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_InvestmentOwnedAccumulatedGrossUnrealizedGainLossBeforeTax" abstract="false" name="InvestmentOwnedAccumulatedGrossUnrealizedGainLossBeforeTax" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_StateStreetTreasuryObligationsMoneyMarketFundMember" abstract="true" name="StateStreetTreasuryObligationsMoneyMarketFundMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_U.S.TreasurySecuritiesMaturing20262056Member" abstract="true" name="U.S.TreasurySecuritiesMaturing20262056Member" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_U.S.TreasurySecuritiesMaturing20272056Member" abstract="true" name="U.S.TreasurySecuritiesMaturing20272056Member" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_InvestmentTypeConcentrationRiskMember" abstract="true" name="InvestmentTypeConcentrationRiskMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_TwoSigmaHamiltonFundLLCMember" abstract="true" name="TwoSigmaHamiltonFundLLCMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_CapitalRequirementsMember" abstract="true" name="CapitalRequirementsMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_TrustAccountsMember" abstract="true" name="TrustAccountsMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_UnderwritingObligationsMember" abstract="true" name="UnderwritingObligationsMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_HamiltonReMember" abstract="true" name="HamiltonReMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_OtherCommitmentsWithdrawalStructureAxis" abstract="true" name="OtherCommitmentsWithdrawalStructureAxis" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrldt:dimensionItem" type="xbrli:stringItemType"/>
  <xs:element id="hg_OtherCommitmentsWithdrawalStructureDomain" abstract="true" name="OtherCommitmentsWithdrawalStructureDomain" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_SubSeriesAInterestsMember" abstract="true" name="SubSeriesAInterestsMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_SubSeriesBInterestsMember" abstract="true" name="SubSeriesBInterestsMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_ManagementAndServiceFeesIncentiveRatePercentageReduction" abstract="false" name="ManagementAndServiceFeesIncentiveRatePercentageReduction" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_ManagementAndServicesFeesIncentiveRateCumulativeNetProfitsRecoveryHurdlePercentage" abstract="false" name="ManagementAndServicesFeesIncentiveRateCumulativeNetProfitsRecoveryHurdlePercentage" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_ManagementAndServicesFeesIncentiveRateExcessProfitsPercentage" abstract="false" name="ManagementAndServicesFeesIncentiveRateExcessProfitsPercentage" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_ManagementAndServicesFeesIncentiveRateNetProfitsHurdlePercentage" abstract="false" name="ManagementAndServicesFeesIncentiveRateNetProfitsHurdlePercentage" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_IncentiveFeeExpenseIncome" abstract="false" name="IncentiveFeeExpenseIncome" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_OtherCommitmentMinimumInvestmentCommitment" abstract="false" name="OtherCommitmentMinimumInvestmentCommitment" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_OtherCommitmentMinimumInvestmentCommitmentPercentageOfNetTangibleAssets" abstract="false" name="OtherCommitmentMinimumInvestmentCommitmentPercentageOfNetTangibleAssets" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_OtherCommitmentsCapitalAccountWithdrawalNoticePeriod" abstract="false" name="OtherCommitmentsCapitalAccountWithdrawalNoticePeriod" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="xbrli:durationItemType"/>
  <xs:element id="hg_OtherCommitmentsCapitalAccountWithdrawalMonthlyWithdrawalMaximum" abstract="false" name="OtherCommitmentsCapitalAccountWithdrawalMonthlyWithdrawalMaximum" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_TSHamiltonFundMember" abstract="true" name="TSHamiltonFundMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_OtherInvestmentsNettingMember" abstract="true" name="OtherInvestmentsNettingMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_FixedMaturitiesAndShortTermInvestmentsMember" abstract="true" name="FixedMaturitiesAndShortTermInvestmentsMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_NetRealizedAndUnrealizedGainsLossesOnInvestmentsAbstract" abstract="true" name="NetRealizedAndUnrealizedGainsLossesOnInvestmentsAbstract" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:stringItemType"/>
  <xs:element id="hg_NoncontrollingInterestIncreaseDecreaseFromIncentiveAllocation" abstract="false" name="NoncontrollingInterestIncreaseDecreaseFromIncentiveAllocation" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_WithdrawalPayable" abstract="false" name="WithdrawalPayable" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_VariableInterestEntityNetAssetsLiabilities" abstract="false" name="VariableInterestEntityNetAssetsLiabilities" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_ReinsurerOneMember" abstract="true" name="ReinsurerOneMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_ReinsurerTwoMember" abstract="true" name="ReinsurerTwoMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_ReinsurerThreeMember" abstract="true" name="ReinsurerThreeMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_LiabilityForClaimsAndClaimsAdjustmentExpenseAmortizationOfDeferredGain" abstract="false" name="LiabilityForClaimsAndClaimsAdjustmentExpenseAmortizationOfDeferredGain" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_RelatedPartyTransactionRiskTransferCapacity" abstract="false" name="RelatedPartyTransactionRiskTransferCapacity" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_CreditRatingMajorRatingAgenciesAxis" abstract="true" name="CreditRatingMajorRatingAgenciesAxis" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrldt:dimensionItem" type="xbrli:stringItemType"/>
  <xs:element id="hg_CreditRatingMajorRatingAgenciesDomain" abstract="true" name="CreditRatingMajorRatingAgenciesDomain" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_AOrBetterRatingMember" abstract="true" name="AOrBetterRatingMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_BelowARatingMember" abstract="true" name="BelowARatingMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_CatastropheLossesMember" abstract="true" name="CatastropheLossesMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_AttritionalLossesMember" abstract="true" name="AttritionalLossesMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_CasualtyLinesMember" abstract="true" name="CasualtyLinesMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_SpecialtyContractsMember" abstract="true" name="SpecialtyContractsMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_PropertyContractsMember" abstract="true" name="PropertyContractsMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_BaltimoreBridgeMember" abstract="true" name="BaltimoreBridgeMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_MiddleEastConflictMember" abstract="true" name="MiddleEastConflictMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_CaliforniaWildfiresMember" abstract="true" name="CaliforniaWildfiresMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_UkrainianConflictMember" abstract="true" name="UkrainianConflictMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_InternationalSegmentMember" abstract="true" name="InternationalSegmentMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_BermudaSegmentMember" abstract="true" name="BermudaSegmentMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_UnderwritingIncomeLossNet" abstract="false" name="UnderwritingIncomeLossNet" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="hg_AttritionalLossRatioCurrentYear" abstract="false" name="AttritionalLossRatioCurrentYear" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_AttritionalLossRatioPriorYearDevelopment" abstract="false" name="AttritionalLossRatioPriorYearDevelopment" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_CatastropheLossRatioCurrentYear" abstract="false" name="CatastropheLossRatioCurrentYear" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_CatastropheLossRatioPriorYearDevelopment" abstract="false" name="CatastropheLossRatioPriorYearDevelopment" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_TermLoanMember" abstract="true" name="TermLoanMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_UncommittedSecuredLetterOfCreditFacilityMember" abstract="true" name="UncommittedSecuredLetterOfCreditFacilityMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_UnsecuredFacilityMember" abstract="true" name="UnsecuredFacilityMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_UBSLetterOfCreditFacilityMember" abstract="true" name="UBSLetterOfCreditFacilityMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_UnsecuredFacilityLloydsMember" abstract="true" name="UnsecuredFacilityLloydsMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_FixedIncomePortfolioMember" abstract="true" name="FixedIncomePortfolioMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_UnclassifiedCommonClassMember" abstract="true" name="UnclassifiedCommonClassMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_CommonStockSharesAuthorizedConversionOfConvertibleSecurities" abstract="false" name="CommonStockSharesAuthorizedConversionOfConvertibleSecurities" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="hg_OpenMarketRepurchasesMember" abstract="true" name="OpenMarketRepurchasesMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="hg_CommonStockVotingRightsClassAAndClassBLimitationAsAPercent" abstract="false" name="CommonStockVotingRightsClassAAndClassBLimitationAsAPercent" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="hg_StockConvertedDuringPeriodSharesConversionOfConvertibleSecurities" abstract="false" name="StockConvertedDuringPeriodSharesConversionOfConvertibleSecurities" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
</xs:schema>
