SEPARATION AGREEMENT

      This Separation Agreement (this “ Agreement ”) by and between Journal Register Company, a Delaware corporation (the “ Company ”) and Robert M. Jelenic (the “ Executive ”), is dated as of October 12, 2007.

      WHEREAS, the Executive has been serving the Company as its Chairman and Chief Executive Officer and is party to an Amended and Restated Employment Agreement with the Company dated September 27, 2006 (the “ Employment Agreement ”); and

      WHEREAS, the Company and the Executive have agreed that it is in the best interests of the Company and the Executive for the Executive to resign, and they wish to set forth their mutual agreement as to the terms and conditions of such resignation;

     NOW, THEREFORE, the Company and the Executive hereby agree as follows:

      1. Resignation . Effective as of November 1, 2007 (the “ Resignation Date ”), the Executive hereby resigns from his employment with the Company, from his position as a member of the Board of Directors of the Company, and from all other positions he holds as an officer or member of the board of directors of any of the Company’s subsidiaries or affiliates (the Company and all of its subsidiaries and affiliates are hereinafter referred to collectively as the “ Affiliated Entities ”).

     2. Compensation Matters .

      (a) Severance Payment . Subject to the Executive’s execution and non-revocation of the release of claims set forth in Section 5 hereof and of the release of claims contemplated by Section 5(e) hereof (the “ Final Release ”), the Company shall, as soon as practicable following the six-month anniversary of the Resignation Date, pay to the Executive a lump sum in cash of $4,763,909 (plus interest thereon from the Resignation Date through the six-month anniversary thereof (such six-month period, the “ 409A Delay Period ”) at the applicable federal rate (the “ Applicable Federal Rate ”) provided for in Section 7872(f)(2)(A) of the Internal Revenue Code of 1986 (the “ Code ”)).

      (b) Benefits Continuation . Until the third anniversary of the Resignation Date, the Company shall continue to provide the Executive and his family with employee life, group life, accidental death or dismemberment and disability insurance benefits on the same terms and conditions as provided to the Executive as of the Resignation Date or as in effect from time to time, as if the Executive had remained employed during that period, subject to the Executive’s payment of such employee contributions, co-payments and similar charges; provided , however , that (i) in no event shall the amount of the Executive’s premium payments under this sentence be determined on terms less favorable than the most favorable terms provided to any senior executive officer of the Company, (ii) such continued benefits shall become secondary to the extent the Executive becomes re-employed and becomes eligible for substantially comparable benefits from another employer, and (iii) in the event that it is determined that receipt of any such continued benefit during the 409A Delay Period would subject the Executive to taxation under Section 409A of the Code, the Executive shall pay all premiums with respect to the applicable benefit during the 409A Delay Period, and shall be reimbursed by the Company as soon as practicable following the conclusion of the 409A Delay Period for all payments so made (plus interest thereon from the applicable payment date through

the conclusion of the 409A Delay Period at the Applicable Federal Rate). Until the third anniversary of the Resignation Date, the Company shall continue to (x) provide the Executive with use of his Company-owned automobile (the “ Car ”) on the same terms and conditions as provided to the Executive as of immediately prior to the Resignation Date and related insurance coverage, and (y) pay the Executive’s dues payments at the Jasna Polana Country Club (the “ Club ”) with respect to which it currently pays such dues, provided , that the Executive shall pay all dues to the Club with respect to the 409A Delay Period, and shall be reimbursed by the Company as soon as practicable following the conclusion of the 409A Delay Period for all payments so made (plus interest thereon from the applicable payment date through the conclusion of the 409A Delay Period at the Applicable Federal Rate), and, provided , further , that the Executive shall pay the Company a quarterly premium of $3000 to lease the Car during the 409A Delay Period, payable quarterly in arrears, and shall be reimbursed by the Company as soon as practicable following the conclusion of the 409A Delay Period for all payments so made (plus interest thereon from the applicable payment date through the conclusion of the 409A Delay Period at the Applicable Federal Rate).

      (c) Lifetime Medical Benefits . Following the Resignation Date, the Company shall provide the Executive and his spouse with the following benefits (the “ Post-Retirement Health Benefits ”) during the remaining lifetime of the Executive and the remaining lifetime of the Executive’s surviving spouse (if he has a surviving spouse): (x) health benefits (including medical, prescription, dental and vision coverage, if and to the extent applicable) with similar coverage to the coverage provided to the Executive as of the Resignation Date, which may be made under the plans provided to the Company’s executive officers, or (y) benefits under separate arrangements that provide coverage similar to the health benefits described in clause (x), taking into account in determining similarity the benefits provided and the costs and tax consequences to the Executive and his spouse. The Executive’s percentage contribution toward the cost of the Post-Retirement Health Benefits shall be the same percentage contribution as in effect on the Resignation Date. In all cases, the Post-Retirement Health Benefits shall be made secondary to any other benefits to which the Executive and his spouse may be entitled under another employer-provided plan or a governmental plan such as Medicare. The amount of Post-Retirement Health Benefits provided in any given calendar year shall not affect the amount of Post-Retirement Health Benefits provided in any other calendar year, and the Executive’s (and his spouse’s) right to Post-Retirement Health Benefits may not be liquidated or exchanged for any other benefit. The parties anticipate that the Post-Retirement Health Benefits will initially be provided through COBRA coverage (without payment for the 2% administrative surcharge), and thereafter be provided either through a insurance policy or by adding the Executive to a self-funded retiree medical plan sponsored by a subsidiary of the Company. Within 90 days of the Resignation Date, the Company will provide the Executive with an outline of the current benefit program and an overview of the Company’s intended plan of implementation of the Post-Retirement Health Benefits.

      (d) Equity Compensation Awards . In consideration of the Executive’s promises set forth in Section 4(a) below, the Company hereby agrees that, effective as of the date the Final Release becomes irrevocable, (i) the 192,500 restricted stock units previously granted to the Executive shall vest in full and be settled for shares of Company common stock, and (ii) all outstanding stock options held by the Executive shall remain exercisable until the earlier of (x) the expiration of the original term of the applicable option or (y) the third anniversary of the Resignation Date (such stock options shall otherwise be governed by the terms of the applicable plan and award agreement pursuant to which they were granted).

      (e) Vested Benefits . Within 15 days following the Resignation Date, the Company shall pay the Executive any accrued but unpaid base salary and vacation pay, and, within 30 days of the Resignation Date (or, if later, of the date of submission of the actual invoice), shall reimburse the Executive in accordance with the Company’s policies for any reimbursable expenses incurred through the Resignation Date. The Company acknowledges that the Executive will have 36 days of accrued but unpaid vacation as of the Resignation Date (less any vacation days used between the date hereof and the Resignation Date). Nothing in this Agreement shall prevent or limit the Executive’s continuing or future participation in any plan, program, policy or practice provided by the Company or the Affiliated Entities and for which the Executive may qualify (including, without limitation, the Company’s 401(k) Savings and Retirement Plan for West State Street Employees and 401(k) Excess/Deferred Compensation Plan), nor shall anything herein limit or otherwise affect such rights as the Executive may have under any other contract or agreement with the Company or the Affiliated Entities, in each case, except to the extent modified by this Agreement. Amounts that are vested benefits or that the Executive is otherwise entitled to receive under any plan, policy, practice or program of or any other contract with the Company or the Affiliated Entities (including, without limitation, the Company’s 401(k) Savings and Retirement Plan for West State Street Employees and 401(k) Excess/Deferred Compensation Plan) at or subsequent to the Resignation Date shall be payable in accordance with such plan, policy, practice or program or contract or agreement, except to the extent modified by this Agreement.

      (f) Secretarial Benefits . Until December 31, 2009, the Company shall provide the Executive with continued secretarial and information technology support from the individuals who were serving as the Executive’s secretary and information technology support immediately before the Resignation Date, or from a suitable replacement(s) on the Company’s payroll if such individual(s) cease(s) to be employed by the Company or the Executive and the Company agree to another suitable replacement, in any case at no charge to the Executive.

      (g) Transfers of Ownership . As soon as practicable following the Resignation Date, the Company shall (i) sell to the Executive, for $1.00 each, the Company-owned personal computer, printer and fax machine and other similar items being used by the Executive immediately before such date (provided that the Company may arrange for removal from the hard drive of said computer any of its proprietary software and confidential and proprietary information), and (ii) transfer to the Executive, for $1.00, the Club membership held by the Company. As soon as practicable following the third anniversary of the Resignation Date, the Company shall sell the Car to the Executive for $1.00.

      (h) Split Dollar Insurance Arrangement . In consideration of the Executive’s promises set forth in Sections 4 and 5 herein, the Company hereby agrees that it will not exercise its discretion pursuant to Section 6 of the Split Dollar Agreement between the Company and the Executive, dated January 1, 2001, to terminate such agreement, provided , that the Executive acknowledges that the foregoing shall in no way constitute a waiver of the Company’s right to receive a return of the cash surrender value or insurance proceeds, as applicable, thereunder (up to the amount of premium paid by the Company) upon the ultimate termination or settlement of the underlying insurance policy. The Executive shall have the right to maintain the insurance provided under the Split Dollar Agreement at his sole cost and expense following the Resignation Date, as well as the right to terminate the insurance arrangement at any time. The Executive further acknowledges that by mutual agreement the Company in 2001

- 3 -

ceased to pay any premiums on the insurance policy that is the subject of such arrangement, and that the Company has no further obligations to make any such premium payments.

      (i) Waiver Payment . In consideration of the Executive’s waiver of certain outplacement and perquisite benefits to which the Executive would otherwise be entitled under the Employment Agreement, the Company shall, as soon as practicable following the conclusion of the 409A Delay Period, pay $55,000 (plus interest thereon from the Resignation Date through the conclusion of the 409A Delay Period at the Applicable Federal Rate) to the Executive.

      3. Consulting and Cooperation . The Executive shall make himself available to render consulting services to the Company from the Resignation Date through the third anniversary thereof, as may be reasonably requested by the Company at mutually convenient times and places; provided , that in no event shall the Executive be required to provide consulting services in excess of 10 hours per month (it being understood that in the event that the Company desires additional hours, the Company and Executive will in good faith negotiate an appropriate rate of compensation for such additional hours). The Executive shall make himself reasonably available to the Company following the Resignation Date to assist the Affiliated Entities, as may be reasonably requested by the Company at mutually convenient times and places, with respect to pending and future litigations, arbitrations, governmental investigations or other dispute resolutions relating to matters that arose during the Executive’s employment with the Company. The Company will reimburse the Executive at a reasonable rate of compensation determined in good faith for assistance provided pursuant to the preceding sentence. The Company will reimburse the Executive for all reasonable expenses and costs he may incur as a result of providing assistance under this Section 3, upon