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<H5 align="left" style="page-break-before:always"><A HREF="#toc">Table of Contents</A></H5><P>
<DIV style="font-family: 'Times New Roman',Times,serif">

<DIV align="center" style="font-size: 10pt; margin-top: 12pt">As filed with the Securities and Exchange Commission on August&nbsp;8, 2008</DIV>


<DIV align="right" style="font-size: 10pt; margin-top: 12pt; margin-bottom: 6pt">Registration No.&nbsp;333-<U>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</U>
</DIV>


<DIV style="width: 100%; border-bottom: 2pt solid black; font-size: 1pt">&nbsp;</DIV>
<DIV style="width: 100%; border-bottom: 1pt solid black; font-size: 1pt">&nbsp;</DIV>






<DIV align="center" style="font-size: 14pt; margin-top: 12pt"><B>UNITED STATES<BR>
SECURITIES AND EXCHANGE COMMISSION</B>
</DIV>

<DIV align="center" style="font-size: 12pt"><B>WASHINGTON, D.C. 20549</B>
</DIV>

<DIV align="center" style="font-size: 18pt; margin-top: 12pt"><B>FORM S-8</B>
</DIV>


<DIV align="center" style="font-size: 12pt; margin-top: 12pt"><B>REGISTRATION STATEMENT UNDER THE<BR>
SECURITIES ACT OF 1933</B>
</DIV>

<DIV align="center" style="font-size: 24pt; margin-top: 12pt"><B>HCC Insurance Holdings, Inc.</B>
</DIV>

<DIV align="center" style="font-size: 10pt">(Exact name of registrant as specified in its charter)</DIV>


<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
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    <TD width="47%">&nbsp;</TD>
</TR>
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<TR valign="bottom">
    <TD align="center" valign="top"><B>Delaware</B><BR>
(State of Incorporation)
</TD>
    <TD>&nbsp;</TD>
    <TD align="center" valign="top"><B>76-0336636</B><BR>
(I.R.S. Employer Identification No.)</TD>
</TR>
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</TABLE>
</DIV>

<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
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<TR valign="bottom">
    <TD width="47%">&nbsp;</TD>
    <TD width="5%">&nbsp;</TD>
    <TD width="47%">&nbsp;</TD>
</TR>
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<TR valign="bottom">
    <TD align="center" valign="top"><B>13403 Northwest Freeway, Houston, Texas</B><BR>
(Address of Principal Executive Offices)
</TD>
    <TD>&nbsp;</TD>
    <TD align="center" valign="top"><B>77040</B><BR>
(Zip code)</TD>
</TR>
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</TABLE>
</DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><B>HCC INSURANCE HOLDINGS, INC.<BR>
2008 FLEXIBLE INCENTIVE PLAN</B><BR>
(Full title of the plan)</DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><B>James L. Simmons,<BR>
Vice President and Corporate Secretary<BR>
13403 Northwest Freeway<BR>
Houston, Texas 77040<BR>
(713)&nbsp;690-7300</B></DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt">(Name and address and telephone<BR>
number, including area code,<BR>
of agent for service)</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a
non-accelerated filer or a smaller reporting company. See definition of &#147;large accelerated filer&#148;,
&#147;accelerated filer&#148; and &#147;smaller reporting company&#148; in Rule&nbsp;12b-2 of the Exchange Act. (Check one):
</DIV>



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    <TD width="3%">&nbsp;</TD>
    <TD width="22%">&nbsp;</TD>
</TR>
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<TR valign="bottom">
    <TD align="center" valign="top">Large accelerated filer <FONT face="Wingdings">&#254;</FONT>
</TD>
    <TD>&nbsp;</TD>
    <TD align="center" valign="top">Accelerated filer <FONT face="Wingdings">&#111;</FONT>
</TD>
    <TD>&nbsp;</TD>
    <TD align="center" valign="top">Non-accelerated filer <FONT face="Wingdings">&#111;</FONT>
</TD>
    <TD>&nbsp;</TD>
    <TD align="center" valign="top" nowrap>Smaller reporting company <FONT face="Wingdings">&#111;</FONT></TD>
</TR>
<TR valign="bottom">
    <TD align="center" valign="top">&nbsp;
</TD>
    <TD>&nbsp;</TD>
    <TD align="center" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="center" valign="top" nowrap>(Do not check if a smaller reporting company)</TD>
    <TD>&nbsp;</TD>
    <TD align="center" valign="top">&nbsp;</TD>
</TR>
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</TABLE>
</DIV>
<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><B>CALCULATION OF REGISTRATION FEE</B></DIV>

<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
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    <TD width="1%">&nbsp;</TD>
    <TD width="17%">&nbsp;</TD>

    <TD width="1%">&nbsp;</TD>
</TR><TR style="font-size: 1px" valign="bottom">
    <TD nowrap align="left" colspan="15" style="border-bottom: 3px double #000000">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">    <TD width="1%">&nbsp;</TD>

    <TD nowrap align="center">Title of Each</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Proposed</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Proposed</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">    <TD width="1%">&nbsp;</TD>

    <TD nowrap align="center">Class Of</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Maximum</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Maximum</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">    <TD width="1%">&nbsp;</TD>

    <TD nowrap align="center">Securities</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Amount</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Offering</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Aggregate</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Amount of</TD>
    <TD width="1%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">    <TD width="1%">&nbsp;</TD>

    <TD nowrap align="center">To Be</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">To Be</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Price</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Offering</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Registration</TD>
    <TD width="1%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">    <TD width="1%">&nbsp;</TD>

    <TD nowrap align="center">Registered</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Registered (1)</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Per Unit</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Price</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Fee</TD>
    <TD width="1%">&nbsp;</TD>
</TR>

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    <TD width="1%" style="border-top: 2px solid #000000">&nbsp;</TD>
                    <TD style="border-top: 2px solid #000000"><DIV style="margin-left:15px; text-indent:-15px">Common Shares</DIV></TD>
    <TD style="border-right: 2px solid #000000; border-top: 2px solid #000000">&nbsp;</TD>
    <TD style="border-top: 2px solid #000000">&nbsp;</TD>
    <TD align="center" valign="top" style="border-top: 2px solid #000000">14,094,993</TD>
    <TD style="border-right: 2px solid #000000; border-top: 2px solid #000000">&nbsp;</TD>
    <TD style="border-top: 2px solid #000000">&nbsp;</TD>
    <TD align="center" valign="top" style="border-top: 2px solid #000000">$22.82(2)</TD>
    <TD style="border-right: 2px solid #000000; border-top: 2px solid #000000">&nbsp;</TD>
    <TD style="border-top: 2px solid #000000">&nbsp;</TD>
    <TD nowrap align="center" valign="top" style="border-top: 2px solid #000000">$321,647,740.26 (2)(3)</TD>
    <TD style="border-right: 2px solid #000000; border-top: 2px solid #000000">&nbsp;</TD>
    <TD style="border-top: 2px solid #000000">&nbsp;</TD>
    <TD align="center" valign="top" style="border-top: 2px solid #000000">$12,640.76(3)</TD>
    <TD width="1%" style="border-top: 2px solid #000000">&nbsp;</TD>
</TR>
<TR style="font-size: 1px" valign="bottom">
    <TD nowrap align="left" colspan="15" style="border-top: 3px double #000000">&nbsp;</TD>
</TR>

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</TABLE>
</DIV>


<DIV align="left">
<DIV style="font-size: 3pt; margin-top: 16pt; width: 18%; border-top: 0px solid #000000">&nbsp;</DIV>
</DIV>

<TABLE width="100%" border="0" cellpadding="0" cellspacing="0" style="font-size: 10pt">
<TR>
    <TD width="3%"></TD>
    <TD width="1%"></TD>
    <TD width="96"></TD>
</TR>

<TR valign="top">
    <TD nowrap align="left">(1)</TD>
    <TD>&nbsp;</TD>
    <TD>Pursuant to Rule&nbsp;416 under the Securities Act of 1933, this registration statement also
covers an indeterminate number of shares as may be required to cover possible adjustments
under the Plan by reason of any stock dividend, stock split, share combination, exchange of
shares, recapitalization, merger, consolidation, separate reorganization or the like of or by
the Registrant.</TD>
</TR>

<TR style="font-size: 3pt"><TD>&nbsp;</TD></TR>

<TR valign="top">
    <TD nowrap align="left">(2)</TD>
    <TD>&nbsp;</TD>
    <TD>Estimated solely for the purposes of calculating the registration fee pursuant to Rule
457(h), based on the
average of the high and low prices of the Common Stock of the Registrant on the New York
Stock Exchange on August&nbsp;1, 2008, which was $22.82.</TD>
</TR>

<TR style="font-size: 3pt"><TD>&nbsp;</TD></TR>

<TR valign="top">
    <TD nowrap align="left">(3)</TD>
    <TD>&nbsp;</TD>
    <TD>Shares to be offered or sold under the HCC Insurance Holdings, Inc. 2008 Flexible Incentive
Plan include 1,423,351 shares that were previously available for grant under the HCC Insurance
Holdings, Inc. 2004 Flexible Incentive Plan. The Registrant previously registered such shares
for issuance pursuant to such prior plan on a Form S-8 registration statement (File No.
333-121907) filed with the Securities and Exchange Commission on January&nbsp;7, 2005. The
Registrant is concurrently filing a post-effective amendment to deregister such shares from
the Form S-8 registration statement filed with respect to such prior plan, and accordingly,
pursuant to Instruction&nbsp;E of Form S-8 and Interpretation 89 under Section&nbsp;G of the Division of
Corporation Finance&#146;s Manual of Publicly Available Telephone Interpretations dated July&nbsp;1997,
the associated registration fee of $5,494.93 previously paid on those 1,423,351 shares under
the prior Form S-8 registration statement (File No.&nbsp;333-121907) is hereby carried forward to
cover the applicable registration fees under this Registration Statement.</TD>
</TR>

</TABLE>



<DIV style="width: 100%; border-bottom: 1pt solid black; margin-top: 10pt; font-size: 1pt">&nbsp;</DIV>
<DIV style="width: 100%; border-bottom: 2pt solid black; font-size: 1pt">&nbsp;</DIV>









<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

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<DIV style="font-family: 'Times New Roman',Times,serif">


<!-- TOC -->
<A name="toc"><DIV align="CENTER" style="page-break-before:always"><U><B>TABLE OF CONTENTS</B></U></DIV></A>

<P><CENTER>
<TABLE border="0" width="90%" cellpadding="0" cellspacing="0">
<TR>
	<TD width="3%"></TD>
	<TD width="3%"></TD>
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	<TD width="76%"></TD>
</TR>
<TR><TD colspan="9"><A HREF="#000">PART II</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#001">Item&nbsp;3. Incorporation of Documents by Reference</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#002">Item&nbsp;4. Description of Securities</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#003">Item&nbsp;5. Interests of Named Experts and Counsel</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#004">Item&nbsp;6. Indemnification of Directors and Officers</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#005">Item&nbsp;7. Exemption from Registration Claimed</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#006">Item&nbsp;8. Exhibits</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#007">Item&nbsp;9. Undertakings</A></TD></TR>
<TR><TD colspan="9"><A HREF="#008">SIGNATURES</A></TD></TR>
<TR><TD colspan="9"><A HREF="#009">Exhibit&nbsp;Index</A></TD></TR>
<TR><TD colspan="9"><A HREF="h59397exv4w1.htm">2008 Flexible Incentive Plan</A></TD></TR>
<TR><TD colspan="9"><A HREF="h59397exv5w1.htm">Opinion of Haynes & Boone, LLP</A></TD></TR>
<TR><TD colspan="9"><A HREF="h59397exv23w1.htm">Consent of PricewaterhouseCoopers LLP</A></TD></TR>
<TR><TD colspan="9"><A HREF="h59397exv24w1.htm">Powers of Attorney</A></TD></TR>
</TABLE>
</CENTER>
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<H5 align="left" style="page-break-before:always"><A HREF="#toc">Table of Contents</A></H5><P>



<DIV align="center" style="font-size: 10pt; margin-top: 18pt"><B>EXPLANATORY NOTE</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;This Registration Statement on Form S-8 is filed by HCC Insurance Holdings, Inc., a Delaware
corporation (the &#147;Registrant&#148;), relating to 14,094,993 of its shares of common stock, par value
$1.00 per share (the &#147;Common Stock&#148;), issuable to eligible directors, officers, other employees,
and consultants of the Registrant and its subsidiaries under the Registrant&#146;s 2008 Flexible
Incentive Plan (the &#147;Plan&#148;), which was approved by the Registrant&#146;s shareholders at the Annual
Meeting of Shareholders held May&nbsp;14, 2008. The Registrant is registering 14,094,993 shares of
Common Stock on this Form S-8 because the Plan authorizes the issuance of (i)&nbsp;4,000,000 shares,
<I>plus </I>(ii)&nbsp;97,765 shares of Common Stock that were authorized for issuance under the HCC Insurance
Holdings, Inc. 2001 Flexible Incentive Plan, as amended (the &#147;First Prior Plan&#148;) and that as of May
14, 2008, remained available for issuance under the First Prior Plan, <I>plus </I>(iii)&nbsp;2,925,627 shares
of Common Stock that were subject to outstanding awards under the First Prior Plan on May&nbsp;14, 2008
(which are included in the Plan to the extent that on or after May&nbsp;14, 2008 such shares represented
by awards are cancelled, forfeited, surrendered, or terminated, expire unexercised, or are settled
without delivery of shares), <I>plus </I>(iv)&nbsp;1,423,351 shares of Common Stock that were authorized for
issuance under the HCC Insurance Holdings, Inc. 2004 Flexible Incentive Plan, as amended (the
&#147;Second Prior Plan&#148;) and that as of May&nbsp;14, 2008, remained available for issuance under the Second
Prior Plan, <I>plus </I>(v)&nbsp;5,648,250 shares of Common Stock that were subject to outstanding awards under
the Second Prior Plan on May&nbsp;14, 2008 (which are included in the Plan to the extent that on or
after May&nbsp;14, 2008 such shares represented by awards are cancelled, forfeited, surrendered, or
terminated, expire unexercised, or are settled without delivery of shares).
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Documents containing the information specified in Part&nbsp;I of Form S-8 have been and/or will be
sent or given to employees as specified by Rule&nbsp;428(b)(1) of the Securities Act. In accordance
with the instructions to Part&nbsp;I of Form S-8, such documents will not be filed with the Securities
and Exchange Commission (the &#147;Commission&#148;) either as part of this Registration Statement or as
prospectuses or prospectus supplements pursuant to Rule&nbsp;424 under the Securities Act. These
documents and the documents incorporated by reference pursuant to Item&nbsp;3 of Part&nbsp;II of this
Registration Statement, taken together, constitute the prospectus as required by Section&nbsp;10(a) of
the Securities Act.
</DIV>
<!-- link1 "PART II" -->
<DIV align="left"><A NAME="000"></A></DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 18pt"><B>PART II</B>
</DIV>

<DIV align="center" style="font-size: 10pt"><B>INFORMATION REQUIRED IN THE REGISTRATION STATEMENT</B></DIV>


<!-- link2 "Item&nbsp;3. Incorporation of Documents by Reference" -->
<DIV align="left"><A NAME="001"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;3. Incorporation of Documents by Reference.</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The following documents (as filed with the Securities and Exchange Commission (the
&#147;Commission&#148;) by the Registrant) are incorporated by reference in this Registration Statement:
</DIV>


<DIV style="margin-top: 6pt">
<TABLE width="100%" border="0" cellpadding="0" cellspacing="0" style="font-size: 10pt">

<TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
    <TD width="4%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(a)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>The registrant&#146;s latest annual report on Form 10-K for the period ended
December&nbsp;31, 2007, as filed with the Commission on February&nbsp;29, 2008;</TD>
</TR>

<TR>
    <TD style="font-size: 6pt">&nbsp;</TD>
</TR><TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
        <TD width="4%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(b)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>The registrant&#146;s quarterly report on Form 10-Q for the quarter ended March&nbsp;31,
2008, as filed with the Commission on May&nbsp;9, 2008;</TD>
</TR>

<TR>
    <TD style="font-size: 6pt">&nbsp;</TD>
</TR><TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
      <TD width="4%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(c)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>The registrant&#146;s current reports on Form 8-K, as filed with the Commission on
January&nbsp;1, 2008, January&nbsp;9, 2008, February&nbsp;11, 2008 (relating to a litigation
settlement), March&nbsp;17, 2008, April&nbsp;2, 2008, April&nbsp;3, 2008, April&nbsp;3, 2008, June&nbsp;24, 2008
and July&nbsp;22, 2008;</TD>
</TR>

<TR>
    <TD style="font-size: 6pt">&nbsp;</TD>
</TR><TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
       <TD width="4%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(d)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>The description of common stock contained in the Registrant&#146;s Prospectus
Supplement filed with the Commission on November&nbsp;22, 2005 (Registration No.&nbsp;333-58350),
including any future amendment or report filed for the purpose of updating such
description; and</TD>
</TR>

<TR>
    <TD style="font-size: 6pt">&nbsp;</TD>
</TR><TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
       <TD width="4%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(e)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>All documents subsequently filed by the Registrant with the Commission pursuant
to Sections&nbsp;13(a), 13(c), 14, and 15(d) of the Exchange Act prior to the filing of a
post-effective amendment which indicates that all securities offered have been sold or
which deregisters all securities then remaining unsold, shall be deemed to be
incorporated by reference in this Registration Statement and to be part hereof from the
date of filing of such documents.</TD>
</TR>

</TABLE>
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Any statement contained herein or in a document incorporated or deemed to be incorporated by
reference herein shall be deemed to be modified or superseded for purposes of this Registration
Statement to the extent that a
</DIV>





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<DIV style="font-family: 'Times New Roman',Times,serif">



<DIV align="left" style="font-size: 10pt; margin-top: 6pt">statement contained herein or in any other subsequently filed
document that also is or is deemed to be incorporated herein by reference modifies or supersedes
such earlier statement. Any statement so modified or superseded shall not be deemed, except as so
modified or superseded, to constitute a part of this Registration Statement. The Registrant&#146;s
Exchange Act file number with the Commission is 1-13790.
</DIV>

<!-- link2 "Item&nbsp;4. Description of Securities" -->
<DIV align="left"><A NAME="002"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;4. Description of Securities.</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Not applicable.
</DIV>

<!-- link2 "Item&nbsp;5. Interests of Named Experts and Counsel" -->
<DIV align="left"><A NAME="003"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;5. Interests of Named Experts and Counsel.</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Not applicable.
</DIV>

<!-- link2 "Item&nbsp;6. Indemnification of Directors and Officers" -->
<DIV align="left"><A NAME="004"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;6. Indemnification of Directors and Officers.</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The Registrant is incorporated under the laws of the State of Delaware. Section&nbsp;145 of the
General Corporation Law of the State of Delaware (&#147;Section&nbsp;145&#148;) provides that a Delaware
corporation may indemnify any person who was or is a party or is threatened to be made a party to
any threatened, pending or completed action, suit or proceeding, whether civil, criminal,
administrative or investigative, by reason of the fact that such person is or was an officer,
director, employee or agent of such corporation, or is or was serving at the request of such
corporation as a director, officer, employee or agent of another corporation, partnership, joint
venture, trust or enterprise, including an employee benefit plan. The indemnity may include
expenses (including attorneys&#146; fees), judgments, fines and amounts paid in settlement actually and
reasonably incurred by such person in connection with such action, suit or proceeding, provided
that such person acted in good faith and in a manner he reasonably believed to be in or not opposed
to the corporation&#146;s best interests and, with respect to any criminal action or proceeding, had no
reasonable cause to believe that his conduct was unlawful, except that no indemnification shall be
made in connection with any action or suit by or in the right of the corporation to procure a
judgment in its favor in respect of any claim, issue, or matter as to which such person shall have
been adjudged to be liable to the corporation unless and only to the extent that the Court of
Chancery or the court in which such action or suit was brought shall determine upon application
that, despite the adjudication of liability but in view of all the circumstances of the case, such
person is fairly and reasonably entitled to indemnity for such expenses that such court deems
proper. The termination of any action, suit, or proceeding by judgment, order, settlement,
conviction or upon a plea of <I>nolo contendere </I>or its equivalent, shall not, of itself, create a
presumption that the person did not act in good faith and in a manner which he reasonably believed
to be in or not opposed to the best interests of the corporation, and, with respect to any criminal
action or proceeding, had reasonable cause to believe that his conduct was unlawful.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Section&nbsp;145 also provides that to the extent that a director, officer, employee or agent of
the corporation has been successful on the merits or otherwise in defense of any action, suit or
proceeding referred to above, or in defense of any claim, issue or matter therein, the corporation
must indemnify him against expenses (including attorneys&#146; fees) actually and reasonably incurred by
him in connection therewith.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Section&nbsp;145 further provides that any indemnification (unless ordered by a court) must be made
only as authorized in the specific case upon a determination that indemnification of the director,
officer, employee or agent is proper in the circumstances because he has met the applicable
standard of conduct set forth above. Such determination must be made (i)&nbsp;by a majority vote of the
directors who were not parties to such action, suit or proceeding, even though less than a quorum,
or (ii)&nbsp;if there are no such directors, or if such directors so direct, by independent legal
counsel in a written opinion, or (iii)&nbsp;by the stockholders.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Section&nbsp;145 also provides that expenses (including attorneys&#146; fees) incurred by an officer or
director in defending or settling any civil, criminal, administrative or investigative action, suit
or proceeding may be paid by the corporation in advance of the final disposition of such action,
suit or proceeding, upon receipt of an undertaking by or on behalf of such director or officer to
repay such amount if it is ultimately determined that he is not entitled to be indemnified by the
corporation.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Section&nbsp;145 further provides that the indemnification and advancement of expenses provided by,
or granted pursuant to, Section&nbsp;145 shall not exclude any other rights to which a person seeking
indemnification or advancement of expenses may be entitled under any bylaw, agreement, vote of
stockholders or disinterested
</DIV>




<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

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<H5 align="left" style="page-break-before:always"><A HREF="#toc">Table of Contents</A></H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif">



<DIV align="left" style="font-size: 10pt; margin-top: 6pt">directors or otherwise, both as to action in his official capacity
and as to action in another capacity while holding such office.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Article&nbsp;IX of the Registrant&#146;s certificate of incorporation, as amended, requires the
Registrant to indemnify the Registrant&#146;s directors and officers to the extent permitted under
Section&nbsp;145.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Article&nbsp;VII of the Registrant&#146;s amended and restated bylaws also provides that the Registrant
shall indemnify any person who was or is a party or is threatened to be made a party to any
threatened, pending, or completed action, suit, or proceeding whether civil, criminal,
administrative, or investigative, by reason of the fact that he is or was a director or officer of
the Registrant, or is or was serving at the request of the Registrant as a director, officer,
employee or agent of another corporation, partnership, joint venture, trust, or other enterprise,
in accordance with provisions corresponding to Section&nbsp;145. The determination of whether a person
is entitled to indemnification is to be made, unless ordered by a court: (i)&nbsp;by a majority vote of
a quorum consisting of directors who at the time of the vote are not parties to the proceeding;
(ii)&nbsp;if such quorum cannot be obtained, or even if obtainable a quorum of disinterested directors
so directs, by independent legal counsel in a written opinion; or (iii)&nbsp;by the stockholders of the
Registrant. Further, the Registrant&#146;s bylaws provide that any person, other than an officer or
director, who was or is a party or is threatened to be made a party to any threatened, pending, or
completed action, suit or proceeding, whether civil, criminal, administrative, or investigative, by
reason of the fact that he is or was an employee or agent of the Registrant, or was serving at the
request of the Registrant as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust, or other enterprise, and who desires indemnification shall make
written application for such indemnification to the Board of Directors for its determination that
indemnification is appropriate, and if so, to what extent.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Section&nbsp;145 further provides that a corporation may purchase and maintain insurance on behalf
of any person who is or was a director, officer, employee or agent of the corporation, or is or was
serving at the request of the corporation as a director, officer, employee or agent of another
corporation, partnership, joint venture, trust or other enterprise against any liability asserted
against him and incurred by him in any such capacity, or arising out of his status as such, whether
or not the corporation would have the authority to indemnify him against such liability and
expenses under the provisions described in the preceding paragraphs. The Registrant maintains
liability insurance covering its directors and officers.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Section&nbsp;102(b)(7) of the General Corporation Law of the State of Delaware permits a Delaware
corporation to include a provision in its certificate of incorporation eliminating or limiting the
personal liability of a director to the corporation or its stockholders for monetary damages for
breach of fiduciary duty as a director, except (i)&nbsp;for any breach of the director&#146;s duty of loyalty
to the corporation or its stockholders, (ii)&nbsp;for acts or omissions not in good faith or which
involve intentional misconduct or a knowing violation of law, (iii)&nbsp;pursuant to Section&nbsp;174 of the
General Corporation Law of the State of Delaware (providing for liability of directors for unlawful
payment of dividends or unlawful stock purchases or redemptions), or (iv)&nbsp;for any transaction from
which the director derived an improper personal benefit. Article&nbsp;X of the Registrant&#146;s Certificate
of Incorporation eliminates liability of directors of the Registrant to the Registrant or its
shareholders for monetary damages for breach of fiduciary duty to the extent permitted by
Section&nbsp;102(b)(7) of the General Corporation Law of the State of Delaware.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The foregoing discussion is qualified in its entirety by reference to the General Corporation
Law of the State of Delaware and the Registrant&#146;s Certificate of Incorporation and Bylaws.
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The Registrant also maintains indemnity insurance pursuant to which its directors and officers
are indemnified against losses under certain circumstances as a result of claims brought against
the directors and officers in their capacities as such.
</DIV>

<!-- link2 "Item&nbsp;7. Exemption from Registration Claimed" -->
<DIV align="left"><A NAME="005"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;7. Exemption from Registration Claimed.</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Not applicable.
</DIV>

<!-- link2 "Item&nbsp;8. Exhibits" -->
<DIV align="left"><A NAME="006"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;8. Exhibits.</B>
</DIV>


<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

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<P><HR noshade><P>
<H5 align="left" style="page-break-before:always"><A HREF="#toc">Table of Contents</A></H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif">



<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head -->
<TR valign="bottom">
    <TD width="5%">&nbsp;</TD>
    <TD width="3%">&nbsp;</TD>
    <TD width="92%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">
    <TD nowrap align="left" style="border-bottom: 1px solid #000000"><B>Exhibit Number</B></TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center" style="border-bottom: 1px solid #000000"><B>Description</B></TD>
</TR>

<!-- End Table Head -->
<!-- Begin Table Body -->
<TR valign="bottom">
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">4.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">HCC Insurance Holdings, Inc. 2008 Flexible Incentive Plan.</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">5.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Opinion of Haynes &#038; Boone, LLP as to the legality of the
securities being registered &#151; filed herewith.</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">23.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Consent of PricewaterhouseCoopers LLP, independent
certified public accountants &#151; filed herewith.</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">23.2
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Consent of Haynes &#038; Boone, LLP (included in the opinion
filed as Exhibit&nbsp;5.1 to this Registration Statement).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">24.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Powers of Attorney &#150; filed herewith.</TD>
</TR>
<!-- End Table Body -->
</TABLE>
</DIV>

<!-- link2 "Item&nbsp;9. Undertakings" -->
<DIV align="left"><A NAME="007"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;9. Undertakings.</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The undersigned Registrant hereby undertakes:
</DIV>

<DIV style="margin-top: 6pt">
<TABLE width="100%" border="0" cellpadding="0" cellspacing="0" style="font-size: 10pt">

<TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
    <TD width="2%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(a)(1)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>To file, during any period in which offers or sales are being made, a post-effective
amendment to this Registration Statement:</TD>
</TR>

</TABLE>
</DIV>

<DIV style="margin-top: 6pt">
<TABLE width="100%" border="0" cellpadding="0" cellspacing="0" style="font-size: 10pt">

<TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
    <TD width="6%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(i)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>To include any prospectus required by Section&nbsp;10(a)(3) of the
Securities Act of 1933;</TD>
</TR>

<TR>
    <TD style="font-size: 6pt">&nbsp;</TD>
</TR><TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
    <TD width="6%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(ii)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>To reflect in the prospectus any facts or events arising after
the effective date of the registration statement (or the most recent
post-effective amendment thereof) which, individually or in the aggregate,
represent a fundamental change in the information set forth in the registration
statement. Notwithstanding the foregoing, any increase or decrease in volume of
securities offered (if the total dollar value of securities offered would not
exceed that which was registered) and any deviation from the low or high end of
the estimated maximum offering range may be reflected in the form of prospectus
filed with the Commission pursuant to Rule 424(b) if, in the aggregate, the
changes in volume and price represent no more than 20% change in the maximum
aggregate offering price set forth in the &#147;Calculation of Registration Fee&#148;
table in the effective registration statement; and</TD>
</TR>

<TR>
    <TD style="font-size: 6pt">&nbsp;</TD>
</TR><TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
    <TD width="6%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(iii)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>To include any information with respect to the plan of
distribution not previously disclosed in this Registration Statement or any
material change to such information in the Registration Statement;</TD>
</TR>

</TABLE>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt; margin-left: 6%"><I>provided, however</I>, that paragraphs (a)(1)(i) and (a)(1)(ii) of this section do not
apply if the information required to be included in a post-effective amendment by
those paragraphs is contained in reports filed with or furnished to the Commission
by the registrant pursuant to section 13 or section 15(d) of the Securities Exchange
Act of 1934 that are incorporated by reference in the registration statement;
</DIV>

<DIV style="margin-top: 6pt">
<TABLE width="100%" border="0" cellpadding="0" cellspacing="0" style="font-size: 10pt">

<TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
        <TD width="3%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(2)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>That, for the purpose of determining any liability under the Securities Act
of 1933, each such post-effective amendment shall be deemed to be a new registration
statement relating to the securities offered therein, and the offering of such
securities at that time shall be deemed to be the initial bona fide offering thereof.</TD>
</TR>

<TR>
    <TD style="font-size: 6pt">&nbsp;</TD>
</TR><TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
       <TD width="3%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(3)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>To remove from registration by means of a post-effective amendment any of
the securities being registered which remain unsold at the termination of the
offering.</TD>
</TR>
</table>
</div>
<DIV style="margin-top: 6pt">
<TABLE width="100%" border="0" cellpadding="0" cellspacing="0" style="font-size: 10pt">

<TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
    <TD width="2%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(b)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>The undersigned registrant hereby undertakes that, for purposes of determining
any liability under the Securities Act of 1933, each filing of the registrant&#146;s annual
report pursuant to section 13(a) or section 15(d) of the Securities Exchange Act of
1934 (and, where applicable, each filing of an</TD>
</TR>

</TABLE>
</DIV>
<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

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<H5 align="left" style="page-break-before:always"><A HREF="#toc">Table of Contents</A></H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif">


<DIV style="margin-top: 6pt"><TABLE width="100%" border="0" cellpadding="0" cellspacing="0" style="font-size: 10pt">


<TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
    <TD width="2%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>employee benefit plan&#146;s annual report
pursuant to section 15(d) of the Securities Exchange Act of 1934) that is incorporated
by reference in the registration statement shall be deemed to be a new registration
statement relating to the securities offered therein, and the offering of such
securities at that time shall be deemed to be the initial bona fide offering thereof.</TD>
</TR>

<TR>
    <TD style="font-size: 6pt">&nbsp;</TD>
</TR><TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
    <TD width="2%" style="background: transparent">&nbsp;</TD>
    <TD width="3%" nowrap align="left">(c)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>Insofar as indemnification for liabilities arising under the Securities Act of
1933 may be permitted to directors, officers and controlling persons of the registrant
pursuant to the foregoing provisions, or otherwise, the registrant has been advised
that in the opinion of the Securities and Exchange Commission such indemnification is
against public policy as expressed in the Act and is, therefore, unenforceable. In the
event that a claim for indemnification against such liabilities (other than the payment
by the registrant of expenses incurred or paid by a director, officer or controlling
person of the registrant in the successful defense of any action, suit or proceeding)
is asserted by such director, officer or controlling person in connection with the
securities being registered, the registrant will, unless in the opinion of its counsel
the matter has been settled by controlling precedent, submit to a court of appropriate
jurisdiction the question whether such indemnification by it is against public policy
as expressed in the Act and will be governed by the final adjudication of such issue.</TD>
</TR>


</TABLE>
</DIV>
<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

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<H5 align="left" style="page-break-before:always"><A HREF="#toc">Table of Contents</A></H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif">


<DIV style="margin-top: 6pt"><TABLE width="100%" border="0" cellpadding="0" cellspacing="0" style="font-size: 10pt">



</TABLE>
</DIV>
<!-- link1 "SIGNATURES" -->
<DIV align="left"><A NAME="008"></A></DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 18pt"><B>SIGNATURES</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Pursuant to the requirements of the Securities Act of 1933, the Registrant certifies that it
has reasonable grounds to believe that it meets all of the requirements for filing on Form&nbsp;S-8 and
has duly caused this Registration Statement to be signed on its behalf by the undersigned,
thereunto duly authorized, in the City of Houston, State of Texas, on August&nbsp;8, 2008.
</DIV>


<TABLE width="100%" border="0" cellspacing="0" cellpadding="0" style="font-size: 10pt">
<TR>
    <TD width="48%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="35%">&nbsp;</TD>
    <TD width="15%">&nbsp;</TD>
</TR>
<TR>
    <TD valign="top" align="left">&nbsp;</TD>
    <TD colspan="3" align="left">HCC INSURANCE HOLDINGS, INC.<BR>
(Registrant)<BR>
&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">&nbsp;</TD>
    <TD valign="top">By:&nbsp;&nbsp;</TD>
    <TD colspan="2" style="border-bottom: 1px solid #000000" align="left"><FONT style="font-variant: SMALL-CAPS">/s/ Frank J. Bramanti</FONT>
&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD colspan="2" align="left">Frank J. Bramanti,&nbsp;<br>Chief Executive Officer</TD>
    <TD>&nbsp;</TD>
</TR><TR>
    <TD align="left">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD colspan="2" align="left">&nbsp;</TD>
    <TD>&nbsp;</TD>
</TR>
<TR>
    <TD colspan="5">&nbsp;</TD>
</TR>
</TABLE>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Pursuant to the Securities Act of 1933, this Registration Statement has been signed below by
the following persons and in the capacities and on the dates indicated.
</DIV>

<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head -->
<TR valign="bottom">
    <TD width="35%">&nbsp;</TD>
    <TD width="2%">&nbsp;</TD>
    <TD width="35%">&nbsp;</TD>
    <TD width="2%">&nbsp;</TD>
    <TD width="25%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">
    <TD nowrap align="left" style="border-bottom: 1px solid #000000">SIGNATURE</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="left" style="border-bottom: 1px solid #000000">TITLE</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="left" style="border-bottom: 1px solid #000000">DATE</TD>
</TR>

<!-- End Table Head -->
<!-- Begin Table Body -->
<TR valign="bottom">
    <TD align="left" valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Frank J. Bramanti</FONT>
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Frank J. Bramanti
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Chief Executive Officer and Director<br>
(Principal Executive Officer)
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD align="left" valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Patrick B. Collins</FONT> *
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Patrick B. Collins
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">J. Robert Dickerson</FONT> *
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
J. Robert Dickerson
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008&nbsp;</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Walter M. Duer</FONT> *
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Walter M. Duer
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008&nbsp;</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD align="left" valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Edward H. Ellis, Jr.</FONT>
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Edward H. Ellis, Jr.
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Executive Vice President,<br>
Chief Financial Officer and Director<br>
(Principal Financial Officer and<br>
Principal Accounting Officer)
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">James C. Flagg, Ph.D.</FONT> *
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
James C. Flagg, Ph.D.
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008&nbsp;</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Allan W. Fulkerson</FONT> *
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Allan W. Fulkerson
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008&nbsp;</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">John N. Molbeck, Jr.</FONT> *
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
John N. Molbeck, Jr.
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">President, Chief Operating Officer<br>
and Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">James E. Oesterreicher</FONT> *
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
James E. Oesterreicher
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008&nbsp;</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Michael A. F. Roberts</FONT> *
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Michael A. F. Roberts
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008&nbsp;</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Christopher J. B. Williams</FONT>*
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px"><DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Christopher J. B. Williams
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Scott W. Wise</FONT> *
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Scott W. Wise
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">August&nbsp;8, 2008&nbsp;</TD>
</TR>
<!-- End Table Body -->
</TABLE>
</DIV>

<DIV align="left">
<DIV style="font-size: 3pt; margin-top: 16pt; width: 18%; border-top: 1px solid #000000">&nbsp;</DIV>
</DIV>

<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head -->
<TR valign="bottom" style="font-size: 1px">
    <TD width="3%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="50%">&nbsp;</TD>
    <TD width="1%">&nbsp;</TD>
    <TD width="40%">&nbsp;</TD>
</TR>
<!-- End Table Head -->
<!-- Begin Table Body -->
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">*By
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">/s/ <FONT style="font-variant: SMALL-CAPS">Edward H. Ellis, Jr.</FONT>
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Edward H. Ellis, Jr.,
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;<I>Attorney in Fact</I></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<!-- End Table Body -->
</TABLE>
</DIV>



<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

<!-- PAGEBREAK -->
<P><HR noshade><P>
<H5 align="left" style="page-break-before:always"><A HREF="#toc">Table of Contents</A></H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif">



<!-- link1 "Exhibit&nbsp;Index" -->
<DIV align="left"><A NAME="009"></A></DIV>
<DIV align="center" style="font-size: 10pt; margin-top: 18pt"><B>Exhibit&nbsp;Index</B>
</DIV>

<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head -->
<TR valign="bottom">
    <TD width="5%">&nbsp;</TD>
    <TD width="3%">&nbsp;</TD>
    <TD width="92%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">
    <TD nowrap align="left"><B>Exhibit Number</B></TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center"><B>Description</B></TD>
</TR>

<!-- End Table Head -->
<!-- Begin Table Body -->
<TR valign="bottom">
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">4.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">HCC Insurance Holdings, Inc. 2008 Flexible Incentive Plan.</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">5.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Opinion of Haynes &#038; Boone, LLP as to the legality of the
securities being registered &#151; filed herewith.</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">23.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Consent of PricewaterhouseCoopers LLP, independent
certified public accountants &#151; filed herewith.</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">23.2
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Consent of Haynes &#038; Boone, LLP (included in the opinion
filed as Exhibit&nbsp;5.1 to this Registration Statement).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD align="center" valign="top"><DIV style="margin-left:0px; text-indent:-0px">24.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Powers of Attorney &#151; filed herewith.</TD>
</TR>
<!-- End Table Body -->
</TABLE>
</DIV>


<P align="center" style="font-size: 10pt"><!-- Folio -->&nbsp;<!-- /Folio -->
</DIV>

</BODY>
</HTML>
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sv8
Table of Contents
As filed with the Securities and Exchange Commission on August 8, 2008
Registration No. 333-
UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, D.C. 20549
FORM S-8
REGISTRATION STATEMENT UNDER THE
SECURITIES ACT OF 1933
HCC Insurance Holdings, Inc.
(Exact name of registrant as specified in its charter)
Delaware
(State of Incorporation)
76-0336636
(I.R.S. Employer Identification No.)
13403 Northwest Freeway, Houston, Texas
(Address of Principal Executive Offices)
77040
(Zip code)
HCC INSURANCE HOLDINGS, INC.
2008 FLEXIBLE INCENTIVE PLAN
(Full title of the plan)
James L. Simmons,
Vice President and Corporate Secretary
13403 Northwest Freeway
Houston, Texas 77040
(713) 690-7300
(Name and address and telephone
number, including area code,
of agent for service)
Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a
non-accelerated filer or a smaller reporting company. See definition of "large accelerated filer",
"accelerated filer" and "smaller reporting company" in Rule 12b-2 of the Exchange Act. (Check one):
Large accelerated filer
þ
Accelerated filer
o
Non-accelerated filer
o
Smaller reporting company
o
(Do not check if a smaller reporting company)
CALCULATION OF REGISTRATION FEE
Title of Each
Proposed
Proposed
Class Of
Maximum
Maximum
Securities
Amount
Offering
Aggregate
Amount of
To Be
To Be
Price
Offering
Registration
Registered
Registered (1)
Per Unit
Price
Fee
Common Shares
14,094,993
$22.82(2)
$321,647,740.26 (2)(3)
$12,640.76(3)
(1)
Pursuant to Rule 416 under the Securities Act of 1933, this registration statement also
covers an indeterminate number of shares as may be required to cover possible adjustments
under the Plan by reason of any stock dividend, stock split, share combination, exchange of
shares, recapitalization, merger, consolidation, separate reorganization or the like of or by
the Registrant.
(2)
Estimated solely for the purposes of calculating the registration fee pursuant to Rule
457(h), based on the
average of the high and low prices of the Common Stock of the Registrant on the New York
Stock Exchange on August 1, 2008, which was $22.82.
(3)
Shares to be offered or sold under the HCC Insurance Holdings, Inc. 2008 Flexible Incentive
Plan include 1,423,351 shares that were previously available for grant under the HCC Insurance
Holdings, Inc. 2004 Flexible Incentive Plan. The Registrant previously registered such shares
for issuance pursuant to such prior plan on a Form S-8 registration statement (File No.
333-121907) filed with the Securities and Exchange Commission on January 7, 2005. The
Registrant is concurrently filing a post-effective amendment to deregister such shares from
the Form S-8 registration statement filed with respect to such prior plan, and accordingly,
pursuant to Instruction E of Form S-8 and Interpretation 89 under Section G of the Division of
Corporation Finance's Manual of Publicly Available Telephone Interpretations dated July 1997,
the associated registration fee of $5,494.93 previously paid on those 1,423,351 shares under
the prior Form S-8 registration statement (File No. 333-121907) is hereby carried forward to
cover the applicable registration fees under this Registration Statement.
TABLE OF CONTENTS
PART II
Item 3. Incorporation of Documents by Reference
Item 4. Description of Securities
Item 5. Interests of Named Experts and Counsel
Item 6. Indemnification of Directors and Officers
Item 7. Exemption from Registration Claimed
Item 8. Exhibits
Item 9. Undertakings
SIGNATURES
Exhibit Index
2008 Flexible Incentive Plan
Opinion of Haynes & Boone, LLP
Consent of PricewaterhouseCoopers LLP
Powers of Attorney
Table of Contents
EXPLANATORY NOTE
This Registration Statement on Form S-8 is filed by HCC Insurance Holdings, Inc., a Delaware
corporation (the "Registrant"), relating to 14,094,993 of its shares of common stock, par value
$1.00 per share (the "Common Stock"), issuable to eligible directors, officers, other employees,
and consultants of the Registrant and its subsidiaries under the Registrant's 2008 Flexible
Incentive Plan (the "Plan"), which was approved by the Registrant's shareholders at the Annual
Meeting of Shareholders held May 14, 2008. The Registrant is registering 14,094,993 shares of
Common Stock on this Form S-8 because the Plan authorizes the issuance of (i) 4,000,000 shares,
plus
(ii) 97,765 shares of Common Stock that were authorized for issuance under the HCC Insurance
Holdings, Inc. 2001 Flexible Incentive Plan, as amended (the "First Prior Plan") and that as of May
14, 2008, remained available for issuance under the First Prior Plan,
plus
(iii) 2,925,627 shares
of Common Stock that were subject to outstanding awards under the First Prior Plan on May 14, 2008
(which are included in the Plan to the extent that on or after May 14, 2008 such shares represented
by awards are cancelled, forfeited, surrendered, or terminated, expire unexercised, or are settled
without delivery of shares),
plus
(iv) 1,423,351 shares of Common Stock that were authorized for
issuance under the HCC Insurance Holdings, Inc. 2004 Flexible Incentive Plan, as amended (the
"Second Prior Plan") and that as of May 14, 2008, remained available for issuance under the Second
Prior Plan,
plus
(v) 5,648,250 shares of Common Stock that were subject to outstanding awards under
the Second Prior Plan on May 14, 2008 (which are included in the Plan to the extent that on or
after May 14, 2008 such shares represented by awards are cancelled, forfeited, surrendered, or
terminated, expire unexercised, or are settled without delivery of shares).
Documents containing the information specified in Part I of Form S-8 have been and/or will be
sent or given to employees as specified by Rule 428(b)(1) of the Securities Act. In accordance
with the instructions to Part I of Form S-8, such documents will not be filed with the Securities
and Exchange Commission (the "Commission") either as part of this Registration Statement or as
prospectuses or prospectus supplements pursuant to Rule 424 under the Securities Act. These
documents and the documents incorporated by reference pursuant to Item 3 of Part II of this
Registration Statement, taken together, constitute the prospectus as required by Section 10(a) of
the Securities Act.
PART II
INFORMATION REQUIRED IN THE REGISTRATION STATEMENT
Item 3. Incorporation of Documents by Reference.
The following documents (as filed with the Securities and Exchange Commission (the
"Commission") by the Registrant) are incorporated by reference in this Registration Statement:
(a)
The registrant's latest annual report on Form 10-K for the period ended
December 31, 2007, as filed with the Commission on February 29, 2008;
(b)
The registrant's quarterly report on Form 10-Q for the quarter ended March 31,
2008, as filed with the Commission on May 9, 2008;
(c)
The registrant's current reports on Form 8-K, as filed with the Commission on
January 1, 2008, January 9, 2008, February 11, 2008 (relating to a litigation
settlement), March 17, 2008, April 2, 2008, April 3, 2008, April 3, 2008, June 24, 2008
and July 22, 2008;
(d)
The description of common stock contained in the Registrant's Prospectus
Supplement filed with the Commission on November 22, 2005 (Registration No. 333-58350),
including any future amendment or report filed for the purpose of updating such
description; and
(e)
All documents subsequently filed by the Registrant with the Commission pursuant
to Sections 13(a), 13(c), 14, and 15(d) of the Exchange Act prior to the filing of a
post-effective amendment which indicates that all securities offered have been sold or
which deregisters all securities then remaining unsold, shall be deemed to be
incorporated by reference in this Registration Statement and to be part hereof from the
date of filing of such documents.
Any statement contained herein or in a document incorporated or deemed to be incorporated by
reference herein shall be deemed to be modified or superseded for purposes of this Registration
Statement to the extent that a
Table of Contents
statement contained herein or in any other subsequently filed
document that also is or is deemed to be incorporated herein by reference modifies or supersedes
such earlier statement. Any statement so modified or superseded shall not be deemed, except as so
modified or superseded, to constitute a part of this Registration Statement. The Registrant's
Exchange Act file number with the Commission is 1-13790.
Item 4. Description of Securities.
Not applicable.
Item 5. Interests of Named Experts and Counsel.
Not applicable.
Item 6. Indemnification of Directors and Officers.
The Registrant is incorporated under the laws of the State of Delaware. Section 145 of the
General Corporation Law of the State of Delaware ("Section 145") provides that a Delaware
corporation may indemnify any person who was or is a party or is threatened to be made a party to
any threatened, pending or completed action, suit or proceeding, whether civil, criminal,
administrative or investigative, by reason of the fact that such person is or was an officer,
director, employee or agent of such corporation, or is or was serving at the request of such
corporation as a director, officer, employee or agent of another corporation, partnership, joint
venture, trust or enterprise, including an employee benefit plan. The indemnity may include
expenses (including attorneys' fees), judgments, fines and amounts paid in settlement actually and
reasonably incurred by such person in connection with such action, suit or proceeding, provided
that such person acted in good faith and in a manner he reasonably believed to be in or not opposed
to the corporation's best interests and, with respect to any criminal action or proceeding, had no
reasonable cause to believe that his conduct was unlawful, except that no indemnification shall be
made in connection with any action or suit by or in the right of the corporation to procure a
judgment in its favor in respect of any claim, issue, or matter as to which such person shall have
been adjudged to be liable to the corporation unless and only to the extent that the Court of
Chancery or the court in which such action or suit was brought shall determine upon application
that, despite the adjudication of liability but in view of all the circumstances of the case, such
person is fairly and reasonably entitled to indemnity for such expenses that such court deems
proper. The termination of any action, suit, or proceeding by judgment, order, settlement,
conviction or upon a plea of
nolo contendere
or its equivalent, shall not, of itself, create a
presumption that the person did not act in good faith and in a manner which he reasonably believed
to be in or not opposed to the best interests of the corporation, and, with respect to any criminal
action or proceeding, had reasonable cause to believe that his conduct was unlawful.
Section 145 also provides that to the extent that a director, officer, employee or agent of
the corporation has been successful on the merits or otherwise in defense of any action, suit or
proceeding referred to above, or in defense of any claim, issue or matter therein, the corporation
must indemnify him against expenses (including attorneys' fees) actually and reasonably incurred by
him in connection therewith.
Section 145 further provides that any indemnification (unless ordered by a court) must be made
only as authorized in the specific case upon a determination that indemnification of the director,
officer, employee or agent is proper in the circumstances because he has met the applicable
standard of conduct set forth above. Such determination must be made (i) by a majority vote of the
directors who were not parties to such action, suit or proceeding, even though less than a quorum,
or (ii) if there are no such directors, or if such directors so direct, by independent legal
counsel in a written opinion, or (iii) by the stockholders.
Section 145 also provides that expenses (including attorneys' fees) incurred by an officer or
director in defending or settling any civil, criminal, administrative or investigative action, suit
or proceeding may be paid by the corporation in advance of the final disposition of such action,
suit or proceeding, upon receipt of an undertaking by or on behalf of such director or officer to
repay such amount if it is ultimately determined that he is not entitled to be indemnified by the
corporation.
Section 145 further provides that the indemnification and advancement of expenses provided by,
or granted pursuant to, Section 145 shall not exclude any other rights to which a person seeking
indemnification or advancement of expenses may be entitled under any bylaw, agreement, vote of
stockholders or disinterested
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directors or otherwise, both as to action in his official capacity
and as to action in another capacity while holding such office.
Article IX of the Registrant's certificate of incorporation, as amended, requires the
Registrant to indemnify the Registrant's directors and officers to the extent permitted under
Section 145.
Article VII of the Registrant's amended and restated bylaws also provides that the Registrant
shall indemnify any person who was or is a party or is threatened to be made a party to any
threatened, pending, or completed action, suit, or proceeding whether civil, criminal,
administrative, or investigative, by reason of the fact that he is or was a director or officer of
the Registrant, or is or was serving at the request of the Registrant as a director, officer,
employee or agent of another corporation, partnership, joint venture, trust, or other enterprise,
in accordance with provisions corresponding to Section 145. The determination of whether a person
is entitled to indemnification is to be made, unless ordered by a court: (i) by a majority vote of
a quorum consisting of directors who at the time of the vote are not parties to the proceeding;
(ii) if such quorum cannot be obtained, or even if obtainable a quorum of disinterested directors
so directs, by independent legal counsel in a written opinion; or (iii) by the stockholders of the
Registrant. Further, the Registrant's bylaws provide that any person, other than an officer or
director, who was or is a party or is threatened to be made a party to any threatened, pending, or
completed action, suit or proceeding, whether civil, criminal, administrative, or investigative, by
reason of the fact that he is or was an employee or agent of the Registrant, or was serving at the
request of the Registrant as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust, or other enterprise, and who desires indemnification shall make
written application for such indemnification to the Board of Directors for its determination that
indemnification is appropriate, and if so, to what extent.
Section 145 further provides that a corporation may purchase and maintain insurance on behalf
of any person who is or was a director, officer, employee or agent of the corporation, or is or was
serving at the request of the corporation as a director, officer, employee or agent of another
corporation, partnership, joint venture, trust or other enterprise against any liability asserted
against him and incurred by him in any such capacity, or arising out of his status as such, whether
or not the corporation would have the authority to indemnify him against such liability and
expenses under the provisions described in the preceding paragraphs. The Registrant maintains
liability insurance covering its directors and officers.
Section 102(b)(7) of the General Corporation Law of the State of Delaware permits a Delaware
corporation to include a provision in its certificate of incorporation eliminating or limiting the
personal liability of a director to the corporation or its stockholders for monetary damages for
breach of fiduciary duty as a director, except (i) for any breach of the director's duty of loyalty
to the corporation or its stockholders, (ii) for acts or omissions not in good faith or which
involve intentional misconduct or a knowing violation of law, (iii) pursuant to Section 174 of the
General Corporation Law of the State of Delaware (providing for liability of directors for unlawful
payment of dividends or unlawful stock purchases or redemptions), or (iv) for any transaction from
which the director derived an improper personal benefit. Article X of the Registrant's Certificate
of Incorporation eliminates liability of directors of the Registrant to the Registrant or its
shareholders for monetary damages for breach of fiduciary duty to the extent permitted by
Section 102(b)(7) of the General Corporation Law of the State of Delaware.
The foregoing discussion is qualified in its entirety by reference to the General Corporation
Law of the State of Delaware and the Registrant's Certificate of Incorporation and Bylaws.
The Registrant also maintains indemnity insurance pursuant to which its directors and officers
are indemnified against losses under certain circumstances as a result of claims brought against
the directors and officers in their capacities as such.
Item 7. Exemption from Registration Claimed.
Not applicable.
Item 8. Exhibits.
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Exhibit Number
Description
4.1
HCC Insurance Holdings, Inc. 2008 Flexible Incentive Plan.
5.1
Opinion of Haynes & Boone, LLP as to the legality of the
securities being registered — filed herewith.
23.1
Consent of PricewaterhouseCoopers LLP, independent
certified public accountants — filed herewith.
23.2
Consent of Haynes & Boone, LLP (included in the opinion
filed as Exhibit 5.1 to this Registration Statement).
24.1
Powers of Attorney – filed herewith.
Item 9. Undertakings.
The undersigned Registrant hereby undertakes:
(a)(1)
To file, during any period in which offers or sales are being made, a post-effective
amendment to this Registration Statement:
(i)
To include any prospectus required by Section 10(a)(3) of the
Securities Act of 1933;
(ii)
To reflect in the prospectus any facts or events arising after
the effective date of the registration statement (or the most recent
post-effective amendment thereof) which, individually or in the aggregate,
represent a fundamental change in the information set forth in the registration
statement. Notwithstanding the foregoing, any increase or decrease in volume of
securities offered (if the total dollar value of securities offered would not
exceed that which was registered) and any deviation from the low or high end of
the estimated maximum offering range may be reflected in the form of prospectus
filed with the Commission pursuant to Rule 424(b) if, in the aggregate, the
changes in volume and price represent no more than 20% change in the maximum
aggregate offering price set forth in the "Calculation of Registration Fee"
table in the effective registration statement; and
(iii)
To include any information with respect to the plan of
distribution not previously disclosed in this Registration Statement or any
material change to such information in the Registration Statement;
provided, however
, that paragraphs (a)(1)(i) and (a)(1)(ii) of this section do not
apply if the information required to be included in a post-effective amendment by
those paragraphs is contained in reports filed with or furnished to the Commission
by the registrant pursuant to section 13 or section 15(d) of the Securities Exchange
Act of 1934 that are incorporated by reference in the registration statement;
(2)
That, for the purpose of determining any liability under the Securities Act
of 1933, each such post-effective amendment shall be deemed to be a new registration
statement relating to the securities offered therein, and the offering of such
securities at that time shall be deemed to be the initial bona fide offering thereof.
(3)
To remove from registration by means of a post-effective amendment any of
the securities being registered which remain unsold at the termination of the
offering.
(b)
The undersigned registrant hereby undertakes that, for purposes of determining
any liability under the Securities Act of 1933, each filing of the registrant's annual
report pursuant to section 13(a) or section 15(d) of the Securities Exchange Act of
1934 (and, where applicable, each filing of an
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employee benefit plan's annual report
pursuant to section 15(d) of the Securities Exchange Act of 1934) that is incorporated
by reference in the registration statement shall be deemed to be a new registration
statement relating to the securities offered therein, and the offering of such
securities at that time shall be deemed to be the initial bona fide offering thereof.
(c)
Insofar as indemnification for liabilities arising under the Securities Act of
1933 may be permitted to directors, officers and controlling persons of the registrant
pursuant to the foregoing provisions, or otherwise, the registrant has been advised
that in the opinion of the Securities and Exchange Commission such indemnification is
against public policy as expressed in the Act and is, therefore, unenforceable. In the
event that a claim for indemnification against such liabilities (other than the payment
by the registrant of expenses incurred or paid by a director, officer or controlling
person of the registrant in the successful defense of any action, suit or proceeding)
is asserted by such director, officer or controlling person in connection with the
securities being registered, the registrant will, unless in the opinion of its counsel
the matter has been settled by controlling precedent, submit to a court of appropriate
jurisdiction the question whether such indemnification by it is against public policy
as expressed in the Act and will be governed by the final adjudication of such issue.
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SIGNATURES
Pursuant to the requirements of the Securities Act of 1933, the Registrant certifies that it
has reasonable grounds to believe that it meets all of the requirements for filing on Form S-8 and
has duly caused this Registration Statement to be signed on its behalf by the undersigned,
thereunto duly authorized, in the City of Houston, State of Texas, on August 8, 2008.
HCC INSURANCE HOLDINGS, INC.
(Registrant)
By:
/s/ Frank J. Bramanti
Frank J. Bramanti,
Chief Executive Officer
Pursuant to the Securities Act of 1933, this Registration Statement has been signed below by
the following persons and in the capacities and on the dates indicated.
SIGNATURE
TITLE
DATE
/s/
Frank J. Bramanti
Frank J. Bramanti
Chief Executive Officer and Director
(Principal Executive Officer)
August 8, 2008
/s/
Patrick B. Collins
*
Patrick B. Collins
Director
August 8, 2008
/s/
J. Robert Dickerson
*
J. Robert Dickerson
Director
August 8, 2008
/s/
Walter M. Duer
*
Walter M. Duer
Director
August 8, 2008
/s/
Edward H. Ellis, Jr.
Edward H. Ellis, Jr.
Executive Vice President,
Chief Financial Officer and Director
(Principal Financial Officer and
Principal Accounting Officer)
August 8, 2008
/s/
James C. Flagg, Ph.D.
*
James C. Flagg, Ph.D.
Director
August 8, 2008
/s/
Allan W. Fulkerson
*
Allan W. Fulkerson
Director
August 8, 2008
/s/
John N. Molbeck, Jr.
*
John N. Molbeck, Jr.
President, Chief Operating Officer
and Director
August 8, 2008
/s/
James E. Oesterreicher
*
James E. Oesterreicher
Director
August 8, 2008
/s/
Michael A. F. Roberts
*
Michael A. F. Roberts
Director
August 8, 2008
/s/
Christopher J. B. Williams
*
Director
August 8, 2008
Christopher J. B. Williams
/s/
Scott W. Wise
*
Scott W. Wise
Director
August 8, 2008
*By
/s/
Edward H. Ellis, Jr.
Edward H. Ellis, Jr.,
Attorney in Fact
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Exhibit Index
Exhibit Number
Description
4.1
HCC Insurance Holdings, Inc. 2008 Flexible Incentive Plan.
5.1
Opinion of Haynes & Boone, LLP as to the legality of the
securities being registered — filed herewith.
23.1
Consent of PricewaterhouseCoopers LLP, independent
certified public accountants — filed herewith.
23.2
Consent of Haynes & Boone, LLP (included in the opinion
filed as Exhibit 5.1 to this Registration Statement).
24.1
Powers of Attorney — filed herewith.