-----BEGIN PRIVACY-ENHANCED MESSAGE-----
Proc-Type: 2001,MIC-CLEAR
Originator-Name: webmaster@www.sec.gov
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MIC-Info: RSA-MD5,RSA,
 B9E/zq8MDEUb0RUjR5M+GFn0oEPZul65H+5e1dNJ2yXjTGLCLqVhZMsaRD8oCt3z
 IOgCkIloj+KLlR22RHBn6w==

<SEC-DOCUMENT>0001181431-08-062491.txt : 20081118
<SEC-HEADER>0001181431-08-062491.hdr.sgml : 20081118
<ACCEPTANCE-DATETIME>20081118150441
ACCESSION NUMBER:		0001181431-08-062491
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20081114
FILED AS OF DATE:		20081118
DATE AS OF CHANGE:		20081118

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Bondi Robert
		CENTRAL INDEX KEY:			0001382174

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	000-50795
		FILM NUMBER:		081198128

	BUSINESS ADDRESS:	
		BUSINESS PHONE:		972-728-3445

	MAIL ADDRESS:	
		STREET 1:		6640 SOUTH CICERO AVENUE
		CITY:			BEDFORD PARK
		STATE:			IL
		ZIP:			60638

ISSUER:		

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			AFFIRMATIVE INSURANCE HOLDINGS INC
		CENTRAL INDEX KEY:			0001282543
		STANDARD INDUSTRIAL CLASSIFICATION:	FIRE, MARINE & CASUALTY INSURANCE [6331]
		IRS NUMBER:				752770432
		STATE OF INCORPORATION:			DE

	BUSINESS ADDRESS:	
		STREET 1:		4450 SOJOURN DRIVE
		STREET 2:		SUITE 500
		CITY:			ADDISON
		STATE:			TX
		ZIP:			75001
		BUSINESS PHONE:		972-728-6300

	MAIL ADDRESS:	
		STREET 1:		4450 SOJOURN DRIVE
		STREET 2:		SUITE 500
		CITY:			ADDISON
		STATE:			TX
		ZIP:			75001
</SEC-HEADER>
<DOCUMENT>
<TYPE>4
<SEQUENCE>1
<FILENAME>rrd223871.xml
<DESCRIPTION>FORM 4
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0303</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2008-11-14</periodOfReport>

    <notSubjectToSection16>0</notSubjectToSection16>

    <issuer>
        <issuerCik>0001282543</issuerCik>
        <issuerName>AFFIRMATIVE INSURANCE HOLDINGS INC</issuerName>
        <issuerTradingSymbol>AFFM</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001382174</rptOwnerCik>
            <rptOwnerName>Bondi Robert</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>4450 SOJOURN DRIVE</rptOwnerStreet1>
            <rptOwnerStreet2>SUITE 500</rptOwnerStreet2>
            <rptOwnerCity>ADDISON</rptOwnerCity>
            <rptOwnerState>TX</rptOwnerState>
            <rptOwnerZipCode>75001</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>0</isDirector>
            <isOfficer>1</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
            <officerTitle>EVP &amp; Chief Operating Officer</officerTitle>
        </reportingOwnerRelationship>
    </reportingOwner>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock, $0.01 par value</value>
            </securityTitle>
            <transactionDate>
                <value>2008-11-14</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>10000</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>1.30</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>52273</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock, $0.01 par value</value>
            </securityTitle>
            <transactionDate>
                <value>2008-11-17</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>2300</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>1.34</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>54573</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock, $0.01 par value</value>
            </securityTitle>
            <transactionDate>
                <value>2008-11-17</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>400</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>1.33</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>54973</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock, $0.01 par value</value>
            </securityTitle>
            <transactionDate>
                <value>2008-11-17</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>346</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>1.29</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>55319</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock, $0.01 par value</value>
            </securityTitle>
            <transactionDate>
                <value>2008-11-17</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>1954</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>1.25</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>57273</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <ownerSignature>
        <signatureName>/s/ Robert A. Bondi</signatureName>
        <signatureDate>2008-11-18</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
-----END PRIVACY-ENHANCED MESSAGE-----