-----BEGIN PRIVACY-ENHANCED MESSAGE-----
Proc-Type: 2001,MIC-CLEAR
Originator-Name: webmaster@www.sec.gov
Originator-Key-Asymmetric:
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 TWSM7vrzLADbmYQaionwg5sDW3P6oaM5D3tdezXMm7z1T+B+twIDAQAB
MIC-Info: RSA-MD5,RSA,
 A8b6o2vNsVlCjt4vfcoXRtU5jsID1wBsrMj0o+bNfa8mL+LOMMF6lF8ZoE8wAzyO
 Vv9HTPVmsKeqjP0p2qUJXA==

<SEC-DOCUMENT>0001181431-09-027155.txt : 20090527
<SEC-HEADER>0001181431-09-027155.hdr.sgml : 20090527
<ACCEPTANCE-DATETIME>20090527105805
ACCESSION NUMBER:		0001181431-09-027155
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20090522
FILED AS OF DATE:		20090527
DATE AS OF CHANGE:		20090527

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Callahan Kevin R
		CENTRAL INDEX KEY:			0001316464

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	000-50795
		FILM NUMBER:		09853578

	MAIL ADDRESS:	
		STREET 1:		3959 N LINCOLN AVE
		CITY:			CHICAGO
		STATE:			IL
		ZIP:			60613

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
		FISCAL YEAR END:			1231

	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>rrd243978.xml
<DESCRIPTION>FORM 4
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0303</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2009-05-22</periodOfReport>

    <notSubjectToSection16>0</notSubjectToSection16>

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

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001316464</rptOwnerCik>
            <rptOwnerName>Callahan Kevin R</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>1</isDirector>
            <isOfficer>1</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
            <officerTitle>Chief Executive Officer</officerTitle>
        </reportingOwnerRelationship>
    </reportingOwner>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock, $0.01 par value</value>
            </securityTitle>
            <transactionDate>
                <value>2009-05-22</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>P</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>10000</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>3.582</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>130000</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <ownerSignature>
        <signatureName>/s/ Kevin R. Callahan</signatureName>
        <signatureDate>2009-05-27</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
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