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                                                                   Exhibit 10.10


                       MANAGEMENT STOCK PURCHASE AGREEMENT


         This Management Stock Purchase Agreement (the "Agreement") is entered
into as of December 15, 2000, by and between Liberty Group Publishing, Inc., a
Delaware corporation (the "Company"), Green Equity Investors II, L.P., a
Delaware limited partnership ("Green II"), Green Equity Investors III, L.P., a
Delaware limited partnership ("Green III"), and Gene Hall (hereinafter referred
to as the "Management Investor"). Capitalized terms used but not defined herein
shall have the meanings ascribed to them in the Stockholders Agreement referred
to below.

         WHEREAS, Management Investor is a key employee of the Company or one of
its subsidiaries and, accordingly, as an incentive to the Management Investor,
the Company desires to issue and sell uncertificated shares of the Company's
common stock, par value $0.01 per share (the "Common Stock") to the Management
Investor as set forth herein; and

         WHEREAS, Management Investor desires to purchase such shares of Common
Stock as set forth herein;

         NOW, THEREFORE, in consideration of the premises and for other good and
valuable consideration, the receipt and adequacy of which is hereby
acknowledged, the parties hereto agree as follows:

         1. Purchase of Common Stock.

            (a) The Company agrees to issue and sell to the Management Investor,
and the Management Investor agrees to purchase from the Company, on the date
hereof, 5,794 shares of Common Stock (the "Equity"), for a purchase price equal
to $15.00 per share. The Equity shall be issued and sold to the Management
Investor free and clear of all liens, other than restrictions and legends
pursuant to federal or state securities laws, the Amended and Restated
Management Subscription and Stockholders Agreement dated as of February 1, 2000,
by and between Management Investor, the Company and Green II, as amended by that
certain Master Amendment dated as of April 18, 2000 pursuant to which Green III
became a party to such agreement (the "Stockholders Agreement") and the Pledge
Agreement referred to below. For avoidance of doubt, the Equity shall be
considered to be "Common Stock" for all purposes of the Stockholders Agreement.
The Equity issued hereunder shall be uncertificated shares and shall be subject
to all of the terms and restrictions contained in the Stockholders Agreement,
including, without limitation: Section 3 (Transfer of Stock); Section 7
(Piggyback Registration Rights); Section 8 (Tag-Along Rights) and Section 9
(Drag-Along Sales), except that the provisions of Section 4 (Company "Call"
Option) shall not apply to the Equity. Subject to the limitations set forth in
Section 2 of the Stockholders Agreement, the Management Investor shall be
entitled, upon written request to the Company, to have a certificate issued to
him or her representing the Equity issued hereunder.

            (b) The Management Investor may pay 65% of the aggregate purchase
price for the Equity by issuing to the Company a non-recourse promissory note in
the form attached hereto as EXHIBIT A and the balance of the aggregate purchase
price for the Equity by issuing to the Company a full recourse promissory note
in the form attached hereto as EXHIBIT B
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(collectively, the "Equity Notes"). The percentage of the principal and accrued
interest under the Equity Notes equal to the percentage of the Equity held by
the Management Investor and sold in any Sales Event (as hereinafter defined)
shall become due and payable upon the consummation of such Sale Event. The
entire principal amount and accrued interest under the Equity Notes shall become
due and payable on December 31, 2025. The Equity Notes shall be secured by a
pledge of the Equity pursuant to the Pledge Agreement in the form attached
hereto as EXHIBIT C. A "Sale Event" shall mean any sale of all or a portion of
the Equity by the Management Investor.

            (c) Any of Green II, Green III or the Company (or any combination of
the foregoing, collectively the "Optionee") shall have the option to repurchase
the Equity, at a price of $15.00 per share of Common Stock to be repurchased, if
the aggregate internal rate of return ("IRR") realized by Green III on the
Common Stock and the shares of Series B 10% Junior Redeemable Cumulative
Preferred Stock of the Company, par value $0.01 per share ("Junior Preferred
Stock") purchased by Green III pursuant to that certain Stock Purchase
Agreement, dated as of April 18, 2000, between the Company and Green III (the
"Green III Equity") does not equal or exceed twenty-five percent (25%) (the "IRR
Threshold") under the circumstances described below (the "Investment Performance
Repurchase Right").


                        (i) General. The Investment Performance Repurchase Right
            will be available to the Optionee (x) upon each occasion on which it
            disposes (including by way of a distribution to its partners) of a
            portion (or all) of the Common Stock included in the Green III
            Equity prior to the eighth anniversary of the ------- date hereof
            and (y) with respect to any Equity for which the Investment
            Performance Repurchase Right has not terminated prior to the eighth
            anniversary of the date hereof, upon the eighth anniversary of the
            date hereof.

                        (ii) Valuation. Each time the Investment Performance
            Repurchase Right is available to the Optionee, all of the Green III
            Equity (Common Stock and Junior Preferred Stock) will be valued for
            purposes of determining whether the IRR Threshold has been achieved.
            In the case of an event described in clause (x), the shares disposed
            of by Green III will be valued at the price received by Green III in
            the disposition (or, in the case of a disposition to Green III's
            partners, at the price attributed to it in such distribution). If
            Junior Preferred Stock is not disposed of in the transaction, it
            will be valued at an amount equal to its liquidation preference plus
            accrued and unpaid dividends. In the event the Investment
            Performance Repurchase Right is exercised at the eighth anniversary
            instead of upon a disposition event, for purposes of calculating the
            IRR, the value of the Green III Equity shall be the same as the
            valuation most recently used by Green III pursuant to its governing
            documents.

                        (iii) Partial or Total Extinguishment of Investment
            Performance Repurchase Right. If and to the extent the IRR Threshold
            is achieved in the disposition, the Investment Performance
            Repurchase Right shall terminate as to the percentage of the Equity
            equal to the percentage of the Common Stock included in the Green
            III Equity sold in the disposition event, and if such IRR Threshold
            is not achieved, such percentage of the Equity will be subject to



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            repurchase. All of the Equity as to which the Investment Performance
            Repurchase Right has not theretofore terminated in accordance with
            this paragraph will remain subject to the Investment Performance
            Repurchase Right.

                        (iv) Time Repurchase Right. In the event that, prior to
            January 1, 2004, the Management Investor's employment with Liberty
            Group Operating, Inc., a Delaware corporation and wholly-owned
            subsidiary of the Company ("Operating"), is terminated for any
            reason (including without limitation Voluntary Termination, Just
            Cause Dismissal, Involuntary Termination Without Cause or the
            retirement, death or Permanent Disability of the Management
            Investor), the Optionee shall have the option to repurchase the
            Equity at a price of $15.00 per share of Common Stock (the "Time
            Repurchase Right"). The Time Repurchase Right shall terminate with
            respect to one-third of the Equity on each of January 1, 2002 and
            January 1, 2003 and with respect to the balance of such Equity on
            January 1, 2004, so long as Management Investor is employed by
            Operating on such date, and with respect to all of the Equity on a
            Liquidity Event (as hereinafter defined), so long as the Management
            Investor is employed by Operating immediately prior to such
            Liquidity Event. The partial or complete extinguishment of the Time
            Repurchase Right will not affect the Investment Performance
            Repurchase Right, which will only expire as set forth above.

            (d) The Optionee must exercise the Investment Performance Repurchase
Right, if at all, by written notice to the Management Investor within thirty
(30) days after a triggering event described above. To the extent not exercised
within such thirty (30) day period, the Investment Performance Repurchase Right
shall terminate with respect to such triggering event. The Optionee must
exercise its Time Repurchase Right, if at all, by written notice to the
Management Investor within thirty (30) days after the Management Investor's
employment with Operating is terminated. To the extent not exercised within such
thirty (30) day period, the Time Repurchase Right shall terminate.

            (e) The Management Investor agrees that until the repurchase rights
set forth above have expired or been exercised, he shall in no event dispose of
the Equity subject to such repurchase rights without the prior written consent
of the Company.

            (f) For purposes of this Agreement, a "Liquidity Event" shall mean
the earliest of (i) the consummation of a Change of Control, (ii) the
consummation of an initial public offering in which gross proceeds to the
Company equal or exceed $35,000,000 and (iii) the commencement of the public
trading of the Company's Common Stock on any national securities exchange,
including, but not limited to, the NASDAQ National Market System. A "Change of
Control" shall be deemed to have occurred if at any time after the date hereof
(i) Operating sells or otherwise disposes of all or substantially all of its
assets, except for a sale or disposition to Kenneth L. Serota ("Serota") or an
entity controlled, directly or indirectly, by Serota or (ii) Green II no longer
owns 50% or more of the voting shares of stock of the Company or the Company no
longer owns, directly or indirectly, at least 95% of the voting securities of
Operating, other than as a result of a public offering of the securities of the
Company registered


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under the Securities Act of 1933, as amended (the "Act"), or an acquisition by
Serota or an entity controlled, directly or indirectly, by Serota.

         2. Management Investor Representations.

            (a) Investment Risk. The Management Investor represents and
acknowledges that (i) as a result of the Management Investor's (A) existing
relationship with the Company and by virtue of being an executive of Operating,
and (B) experience in financial matters, the Management Investor is properly
able to evaluate the capital structure of the Company, the business of the
Company and its subsidiaries and the risks inherent therein; (ii) the Management
Investor has been given the opportunity to obtain any additional information or
documents from and to ask questions, and receive answers of, the officers and
representatives of the Company and its subsidiaries to the extent necessary to
evaluate the merits and risks related to an investment in the Company; (iii) the
Management Investor has been and will be, to the extent the Management Investor
deems necessary, advised by legal counsel of the Management Investor's choice at
Management Investor's expense in connection with this Agreement and the issuance
and sale of the Equity hereunder, (iv) the purchase or issuance of the Equity
hereunder will be consistent, in both nature and amount, with the Management
Investor's overall investment program and financial condition, and the
Management Investor's financial condition will be such that the Management
Investor will be able to bear the economic risk of holding unregistered Common
Stock for which there is no market and to suffer a complete loss of the
Management Investor's investment therein and (v) the Management Investor is an
"accredited investor" as that term is defined in Rule 501(a)(3) under the Act.
The Management Investor further acknowledges that investment in the Equity
hereunder involves significant risks and that these risks include, without
limitation, the fact that the Company has a leveraged financial structure.

            (b) Purchase for Investment.

                        (i) The Management Investor represents and warrants
            that: (A) the Equity will be acquired for the Management Investor's
            own account for investment, without any present intention of selling
            or further distributing the same and the Management Investor will
            not have any reason to anticipate any change in the Management
            Investor's circumstances or any other particular occasion or event
            which would cause the Management Investor to sell any of the Equity
            and (B) the Management Investor is fully aware that in agreeing to
            sell or issue such Common Stock to the Management Investor the
            Company will be relying upon the truth and accuracy of these
            representations and warranties. The Management Investor agrees that
            the Management Investor will not sell or otherwise dispose of any of
            the Equity except in compliance with the Securities Act, the rules
            and regulations of the Securities and Exchange Commission
            thereunder, the relevant state securities laws applicable to the
            Management Investor's action and the terms of this Agreement and the
            Stockholders Agreement.

                        (ii) Subject to the restrictions provided in the
            Stockholders Agreement, the Management Investor agrees that prior to
            making any disposition of any of the Equity acquired hereunder
            (other than a disposition to the Company, Green II or Green III),
            the Management Investor will give not less than 10 days' advance
            written notice to the


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            Company describing the manner of such proposed disposition. The
            Management Investor further agrees that the Management Investor will
            not effect such proposed disposition until either (A) the Management
            Investor has provided to the Company, if so requested by the
            Company, an opinion of counsel reasonably satisfactory in form and
            substance to the Company that such proposed disposition is exempt
            from registration under the Act and any applicable state securities
            laws or (B) a registration statement under the Act covering such
            proposed disposition has been filed by the Company under the Act and
            has become effective and compliance with applicable state securities
            laws has been effected.

                        (iii) The Management Investor acknowledges that no
            trading market for the Equity exists currently or is expected to
            exist at any time in the foreseeable future and that, as a result,
            the Management Investor may be unable to sell any of the Equity
            acquired hereunder for an indefinite period. Further, the Company
            has no obligation to register any of the Equity, except as expressly
            provided in Section 7 of the Stockholders Agreement.

                        (iv) The Management Investor acknowledges and agrees
            that nothing herein, including the opportunity to make an equity
            investment in the Company, shall be deemed to create any implication
            concerning the adequacy of the Management Investor's services to
            Operating or its subsidiaries or shall be construed as an agreement
            by the Company or its subsidiaries, express or implied, to employ
            the Management Investor or contract for the Management Investor's
            services, to restrict the right of Operating to discharge the
            Management Investor or cease contracting for the Management
            Investor's services or to modify, extend or otherwise affect in any
            manner whatsoever the terms of any employment agreement or contract
            for services which may exist between the Management Investor and the
            Company or its subsidiaries.

                  3. Notices. All notices or other communications under this
         Agreement shall be given in writing and shall be deemed duly given and
         received on the third full business day following the day of the
         mailing thereof by registered or certified mail or when delivered
         personally or sent by facsimile transmission as follows:

            (a) if to the Company, at its principal executive offices at the
time of the giving of such notice, or at such other place as the Company shall
have designated by notice as herein provided to the Management Investor,
Attention: Kenneth L. Serota;

            (b) if to the Management Investor, at the address of the Management
Investor as it appears on the signature page to this Agreement or at such other
place as the Management Investor shall have designated by notice as herein
provided to the Company;

            (c) if to Green II or Green III, at their principal executive
offices at the time of the giving of such notice, or at such other place as
Green II or Green III shall have designated by notice as herein provided to the
Company.

         4. Specific Performance. Due to the fact that the securities of the
Company cannot be readily purchased or sold in the open market and because
damages to the Company and its subsidiaries will be difficult to ascertain and
remedies at law to the Company and its subsidiaries


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will be inadequate and for other reasons, the parties will be irreparably
damaged in the event that this Agreement is not specifically enforced. In the
event of a breach or threatened breach of the terms, covenants and/or conditions
of this Agreement by any of the parties hereto, the other parties shall, in
addition to all other remedies, be entitled (without any bond or other security
being required) to a temporary and/or permanent injunction, without showing any
actual damage or that monetary damages would not provide an adequate remedy,
and/or a decree for specific performance, in accordance with the provisions
hereof.

         5. Miscellaneous.

            (a) This Agreement, and the Stockholders Agreement, constitutes the
entire agreement of the parties with respect to the subject matter hereof and
may not be modified or amended except by a written agreement signed by the
Company, Green II, Green III and the Management Investor.

            (b) No waiver of any breach or default hereunder shall be considered
valid unless in writing, and no such waiver shall be deemed a waiver of any
subsequent breach or default of the same or similar nature. Anything in this
Agreement to the contrary notwithstanding, any waiver, consent or other
instrument under or pursuant to this Agreement signed by, or binding upon, the
Management Investor shall be valid and binding upon any and all persons or
entities (other than the Company, Green II and Green III) who may, at any time,
have or claim any rights under or pursuant to this Agreement in respect of the
Equity acquired hereunder.

            (c) Except as otherwise expressly provided herein, this Agreement
shall be binding upon and inure to the benefit of the Company, Green II and
Green III and their respective successors and assigns and the Management
Investor and the Management Investor's heirs, personal representatives,
successors and assigns; provided, however, that nothing contained herein shall
be construed as granting the Management Investor the right to transfer any of
the Equity acquired hereunder except in accordance with this Agreement and the
Stockholders Agreement and any transferee shall hold the Equity having only
those rights and being subject to the restrictions provided for in this
Agreement and the Stockholders Agreement.

            (d) If any provision of this Agreement shall be invalid or
unenforceable, such invalidity or unenforceability shall attach only to such
provision and shall not in any manner affect or render invalid or unenforceable
any other severable provision of this Agreement, and this Agreement shall be
carried out as if any such invalid or unenforceable provision were not contained
herein.

            (e) Except as set forth in Section 4, arbitration shall be the
exclusive remedy for resolving any dispute or controversy between the Company,
Green II or Green III and the Management Investor under this Agreement. Such
arbitration shall be conducted in accordance with the then most applicable rules
of the American Arbitration Association. The arbitrator shall be empowered to
grant only such relief as would be available in a court of law. In the event of
any conflict between this Agreement and the rules of the American Arbitration
Association, the provisions of this Agreement shall be determinative. If the
parties are unable to agree upon an arbitrator, they shall select a single
arbitrator from a list of seven arbitrators designated by the


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office of the American Arbitration Association having responsibility for the
city in which the Management Investor last resided while employed by the Company
or its subsidiaries, all of whom shall be retired judges who are actively
involved in hearing private cases or members of the National Academy of
Arbitrators. If the parties are unable to agree upon an arbitrator from such
list, they shall each strike names alternatively from the list, with the first
to strike being determined by lot. After each party has used three strikes, the
remaining name on the list shall be the arbitrator. The fees and expenses of the
arbitrator shall initially be borne equally by the parties; provided, however,
that each party shall initially be responsible for the fees and expenses of its
own representatives and witnesses. If the parties cannot agree upon a location
for the arbitration, the arbitrator shall determine the location. Judgment may
be entered on the award of the arbitrator in any court having jurisdiction. The
prevailing party in the arbitration proceeding, as determined by the arbitrator,
and in any enforcement or other court proceedings, shall be entitled to the
extent provided by law to reimbursement from the other party for all of the
prevailing party's costs (including but not limited to the arbitrator's
compensation), expenses and reasonable attorneys' fees.

            (f) Should any party to this Agreement be required to commence any
litigation concerning any provision of this Agreement or the rights and duties
of the parties hereunder, the prevailing party in such proceeding shall be
entitled, in addition to such other relief as may be granted, to the reasonable
attorneys' fees and court costs incurred by reason of such litigation.

            (g) The section headings contained herein are for the purposes of
convenience only and are not intended to define or limit the contents of said
sections.

            (h) Words in the singular shall be read and construed as though in
the plural and words in the plural shall be read and construed as though in the
singular in all cases where they would so apply.

            (i) This Agreement may be executed in one or more counterparts, each
of which shall be fully effective as an original and all of which together shall
constitute one and the same instrument.

            (j) The Management Investor hereby irrevocably and unconditionally
consents to the jurisdiction of any Delaware State court or federal court of the
United States sitting in the State of Delaware in any action or proceeding
relating to this Agreement and consents to service of process in connection
therewith by the delivery of notice to such Management Investor's address set
forth in this Agreement.

            (k) This Agreement shall be deemed to be a contract under the laws
of the State of Delaware and for all purposes shall be construed and enforced in
accordance with the internal laws of said state without regard to the principles
of conflicts of law.


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            IN WITNESS WHEREOF, the parties have executed this Management Stock
Purchase Agreement as of the first date written above.

                                        LIBERTY GROUP PUBLISHING, INC.


                                        By:   /s/  Kenneth L. Serota
                                            ------------------------------------
                                        Name:
                                              ----------------------------------
                                        Its:
                                             -----------------------------------


                                        GREEN EQUITY INVESTORS II, L.P.
                                        By: Grand Avenue Capital Partners, L.P.,
                                            its General Partner
                                        By: Grand Avenue Capital Corporation,
                                            its General Partner


                                        By:    /s/  Peter J. Nolan
                                            ------------------------------------
                                        Name:
                                              ----------------------------------


                                        GREEN EQUITY INVESTORS III, L.P.
                                        By: GEI Capital III, LLC , its General
                                            Partner


                                        By:    /s/  Peter J. Nolan
                                            ------------------------------------
                                        Name:
                                              ----------------------------------


                                        MANAGEMENT INVESTOR


                                        By:    /s/  Gene Hall
                                            ------------------------------------
                                        Name:
                                              ----------------------------------
                                        Address:
                                                --------------------------------



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