Exhibit 10.1

STOCK REPURCHASE AGREEMENT

This Stock Repurchase Agreement (the “Agreement”) is entered into as of this
     day of August, 2011, by and between Affirmative Insurance Holdings, Inc., a
Delaware corporation, with one of its principal places of business located at
4450 Sojourn Drive, Addison, Texas 75001 (the “Company”), and the undersigned
stockholder of the Company (“Stockholder”).

Recitals:

WHEREAS, on March 18, 2011, Stockholder and the Company entered into a
Restricted Stock Award Agreement (“RSAA”) (a true and correct copy of which is
attached hereto), whereby the Company granted an award of                     
Thousand (            ) shares of the Company’s $0.01 par value per share Common
Stock to Stockholder, subject to certain restrictions, including restrictions on
time and performance vesting and dividend rights (the “Restricted Shares”); and

WHEREAS, after due consideration by both Stockholder and the Company, the
parties hereto have agreed that the Company will repurchase all of the
Restricted Shares from Stockholder upon the terms and subject to the conditions
set forth in this Agreement.

Agreement:

NOW, THEREFORE, in consideration of the premises and the benefits to be received
by each of the parties, as well as the covenants and promises contained herein
and other good and valuable consideration, the receipt and sufficiency of which
is hereby acknowledged, the parties hereto agree as follows:

1. Repurchase of Restricted Shares. On the terms and subject to the conditions
set forth in this Agreement, the Company agrees to purchase from Stockholder and
Stockholder agrees to sell, transfer, convey and deliver to the Company all of
his right, title and interest in and to all of his Restricted Shares at the
stated price of one cent ($0.01) per share (the par value per share of the
Company’s Common Stock).

2. Payment for Restricted Shares. The total purchase price for the shares of
Restricted Shares shall be                              dollars ($        ) (the
“Purchase Price”). Upon receipt of the Purchase Price, Stockholder irrevocably
appoints any officer of the Company as his attorney-in-fact to take possession
of the Restricted Shares and reflect the Company’s ownership of the same on the
books of the Company.

3. Ownership. Subject to the vesting and other restrictions otherwise set forth
in the RSAA, Stockholder represents and warrants that he is the owner of record
of all right, title and interest in and to the Restricted Shares.

4. Corporate Good Standing. The Company represents and warrants that the Company
is a corporation, duly organized, validly existing, and in good standing under
the laws of the State of Delaware.

5. Authority/Binding Effect. Stockholder and the Company each have the requisite
power and authority, corporate or otherwise, to execute and deliver this
Agreement, to perform their respective obligations under this Agreement and to
consummate the transaction contemplated hereby. All requisite action, corporate
or otherwise, has been taken to authorize the execution, delivery and
performance by

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Stockholder and the Company of this Agreement and the consummation of the
transaction contemplated hereby, and, with respect to the Company, no other
proceedings on the part of the Company are necessary to authorize the execution,
delivery and performance of this Agreement and the consummation of the
transaction contemplated hereby. This Agreement has been duly executed and
delivered by both the Stockholder and the Company and constitutes the legal,
valid and binding obligations of Stockholder and the Company, enforceable
against Stockholder and the Company in accordance with its terms. Stockholder
specifically authorizes the Company’s stock transfer agent to remit any
certificate(s) representing the Restricted Stock to the Company or, in the
alternative, to update its electronic books and records to reflect the instant
share repurchase by the Company. Stockholder further specifically acknowledges
and agrees that Stockholder: (a) has been afforded ample time and opportunity to
review the terms of this Agreement; (b) understands the terms and conditions set
forth in this Agreement; and (c) has been afforded sufficient time and
opportunity to consult with his personal attorney(s), accountant(s) and/or other
professionals regarding the terms of this Agreement before signing the same and
becoming a party hereto.

6. No Conflicts; Consents. The execution, delivery and performance by
Stockholder and the Company of this Agreement, and the consummation of the
transaction contemplated hereby do not: (a) with respect to the Company,
conflict with or result in a violation or breach of, or default under, any
provision of the Company’s organizational documents; or (b) conflict with or
result in a violation or breach of any provision of any law or governmental
order applicable to Stockholder or the Company. No consent, approval, permit,
governmental order, declaration or filing with, or notice to, any governmental
authority is required by or with respect to Stockholder or the Company in
connection with the execution and delivery of this Agreement and the
consummation of the transactions contemplated hereby (except for any filings
that may be required by the U.S. Securities and Exchange Commission as a result
of obligations under Section 13 or Section 16 of the Securities Exchange Act of
1934, as amended (the “Exchange Act”)) .

7. Further Assurances. Each party hereto shall use its commercially reasonable
efforts to execute all documents necessary or desirable to effect the
transaction contemplated hereunder, including but not limited to any ancillary
notices with respect to the revocation/termination of the irrevocable proxy
granted by Stockholder to New Affirmative LLC in connection with the original
issuance of his Restricted Shares in March 2011, as well as any documentation
required as may be required by the Company’s transfer agent to verify and/or
otherwise document the transaction set forth in this Agreement.

8. Successors and Assigns. This Agreement shall be binding upon and inure to the
benefit of the parties hereto and their respective permitted successors and
assigns.

9. Entire Agreement, Amendment. This Agreement constitutes the entire agreement
between the Company and Stockholder with respect to the transaction contemplated
hereby, supersedes all prior or contemporaneous negotiations, communications,
discussions and correspondence concerning the subject matter hereof, and may be
amended or modified only with the written consent of the Company and
Stockholder.

10. Severability. If any provision of this Agreement shall be prohibited by or
invalid under applicable law, such provision shall be ineffective only to the
extent of such prohibition or invalidity without invalidating the remainder of
such provision or any remaining provisions of this Agreement.

11. Governing Law. This Agreement shall be governed by and construed in
accordance with the laws of the State of Delaware without giving effect to its
conflict of law principles. If any provision of this Agreement is determined by
a court of law to be illegal or unenforceable, then such provision will be
enforced to the maximum extent possible and the other provisions will remain
fully effective and enforceable.

 

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12. Counterparts. This Agreement may be executed in separate counterparts,
either of which, when so executed, shall be deemed to be an original and both of
which, when taken together, shall constitute but one and the same agreement.
Signatures of the parties transmitted by facsimile or .pdf shall be deemed to be
their originals for all purposes.

13. Recitals. The recitals of this Agreement are hereby incorporated into the
body of this Agreement by reference.

WITH THE INTENT TO BE LEGALLY BOUND HEREBY, the above terms and conditions are
hereby agreed to and accepted as of the day and year first written above.

 

AFFIRMATIVE INSURANCE HOLDINGS, INC.

 

By: Title: STOCKHOLDER

 

Name:

 

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