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Proc-Type: 2001,MIC-CLEAR
Originator-Name: webmaster@www.sec.gov
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MIC-Info: RSA-MD5,RSA,
 LUQCGzUOfYczdvwZM729li78F6wMXFrGgh1orwGuKtSoWB08A524Byf3FcSHxjKT
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<SEC-DOCUMENT>0001181431-10-030326.txt : 20100601
<SEC-HEADER>0001181431-10-030326.hdr.sgml : 20100531
<ACCEPTANCE-DATETIME>20100601123945
ACCESSION NUMBER:		0001181431-10-030326
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20100527
FILED AS OF DATE:		20100601
DATE AS OF CHANGE:		20100601

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			FLAGG JAMES C
		CENTRAL INDEX KEY:			0001207713

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-13790
		FILM NUMBER:		10868790

ISSUER:		

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			HCC INSURANCE HOLDINGS INC/DE/
		CENTRAL INDEX KEY:			0000888919
		STANDARD INDUSTRIAL CLASSIFICATION:	FIRE, MARINE & CASUALTY INSURANCE [6331]
		IRS NUMBER:				760336636
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	BUSINESS ADDRESS:	
		STREET 1:		13403 NORTHWEST FRWY
		CITY:			HOUSTON
		STATE:			TX
		ZIP:			77040-6094
		BUSINESS PHONE:		7136907300

	MAIL ADDRESS:	
		STREET 1:		13403 NORTHWEST FREEWAY
		CITY:			HOUSTON
		STATE:			TX
		ZIP:			77040
</SEC-HEADER>
<DOCUMENT>
<TYPE>4
<SEQUENCE>1
<FILENAME>rrd277362.xml
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0303</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2010-05-27</periodOfReport>

    <notSubjectToSection16>0</notSubjectToSection16>

    <issuer>
        <issuerCik>0000888919</issuerCik>
        <issuerName>HCC INSURANCE HOLDINGS INC/DE/</issuerName>
        <issuerTradingSymbol>HCC</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001207713</rptOwnerCik>
            <rptOwnerName>FLAGG JAMES C</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>C/O HCC INSURANCE HOLDINGS, INC.</rptOwnerStreet1>
            <rptOwnerStreet2>13403 NORTHWEST FREEWAY</rptOwnerStreet2>
            <rptOwnerCity>HOUSTON</rptOwnerCity>
            <rptOwnerState>TX</rptOwnerState>
            <rptOwnerZipCode>77040</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>1</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
        </reportingOwnerRelationship>
    </reportingOwner>

    <nonDerivativeTable>
        <nonDerivativeHolding>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>9211</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeHolding>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2010-05-27</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>A</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>3158</value>
                    <footnoteId id="F1"/>
                </transactionShares>
                <transactionPricePerShare>
                    <value>25.33</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>12369</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <derivativeTable>
        <derivativeHolding>
            <securityTitle>
                <value>Option to Purchase</value>
                <footnoteId id="F2"/>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>30.85</value>
            </conversionOrExercisePrice>
            <exerciseDate>
                <value>2007-01-05</value>
            </exerciseDate>
            <expirationDate>
                <value>2011-01-05</value>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>12500</value>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>12500</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </derivativeHolding>
    </derivativeTable>

    <footnotes>
        <footnote id="F1">As part of the HCC Board of Directors compensation package, each non-employee Director receives a grant of HCC Common Stock in the amount of the number of shares determined by dividing $80,000 by the closing price on the date of the Annual Meeting of Shareholders.  The Annual Meeting of Shareholders was Thursday, May 27, 2010.</footnote>
        <footnote id="F2">Option to purchase granted pursuant to the 2004 Flexibe Incentive Plan.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>Randy D. Rinicella as Attorney in Fact for James C. Flagg</signatureName>
        <signatureDate>2010-06-01</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
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