<PAGE>
                                                                   EXHIBIT 10.16



December 20, 2005

VIA HAND DELIVERY
PERSONAL AND CONFIDENTIAL

Mr. Paul B. Healy
210 West 90th Street, Apartment 7J
New York, NY 10024

         RE: RESIGNATION FROM HOLLINGER INTERNATIONAL INC.

Dear Paul:

You have advised Hollinger International Inc. (the "Company") of your
resignation of employment, effective as of December 31, 2005 (the Effective
Date"). Upon the execution of this Agreement, the Employment Agreement, dated as
of January 26, 2005, between you and the Company will terminate and be of no
further force or effect. In consideration of you providing consulting services
to the Company for a period of nine months from the Effective Date, the Company
desires to provide you with certain payments and benefits, as are described
below. This letter sets forth the terms and conditions of your separation and
the consideration to be given to you in connection therewith, the receipt and
sufficiency of which the Company (together with its parent corporations,
affiliates, past and present officers, directors, stockholders, agents,
employees, publications, legal representatives, successors, and assigns,
hereinafter collectively referred to as, the "Company") and you hereby
acknowledge:

1.       EFFECT OF RESIGNATION

         As of the Effective Date, you will no longer be an employee of the
         Company. Except as otherwise agreed by the Company, you shall
         relinquish all titles, positions and authorities that you held during
         your employment, with respect to the Company and each and every
         subsidiary or affiliate of the Company with which you have held
         positions as an officer and/or director. You agree to provide execute
         any and all documents necessary to effect your resignation from all
         such positions. It is understood that there are some indirect
         subsidiaries of the Company with respect to which it may be difficult
         to affect a change in Board membership by the Effective Date. In such
         circumstances, you agree to remain as a member of the Board and to
         cooperate with the Company and each such subsidiary until such time as
         the Company determines it appropriate for you to resign from such
         position.


<PAGE>

Paul B. Healy
December 20, 2005
Page 2


2.       EFFECTIVE DATE OF RESIGNATION:

         December 31, 2005 (the "Effective Date"). You shall continue to perform
         your regular duties and the attendant responsibilities and
         accountabilities until the Effective Date.

3.       SEPARATION BENEFITS:

         You have the right to receive a lump sum payment for any accrued,
         unused vacation time, reduced by all applicable taxes, regardless of
         whether you sign this agreement. Your separation will be considered
         voluntary for purposes of unemployment compensation and any pension
         rights you may have under the Company's plan(s). In consideration of
         your resignation, your full cooperation with the Company in the
         resolution and investigation of all remaining open issues relating to
         the Company and in executing such further documentation as is deemed
         reasonably necessary in the opinion of the Company and you to effect
         your separation; and your agreement to the terms of the Release and
         other obligations set forth below, we will grant you the following:

         o    SALARY CONTINUATION. From the Effective Date until September 30,
              2006 (the "Severance Period") you shall continue to receive your
              regular biweekly compensation, less all customary and applicable
              withholding.

         o    BONUS PAYMENT. The Company shall pay you your target bonus for
              calendar year 2005, totaling Two Hundred Seventy Thousand Dollars
              ($270,000.00), and representing 75% of your 2005 base salary of
              $360,000.00. The Company shall make this payment as promptly as is
              reasonably practicable following the execution of this Agreement,
              and will endeavor to make the payment on or before December 30,
              2005. Monies received under this provision shall be reduced by all
              applicable local, state and federal income tax withholding,
              payable upon the lapse of all applicable waiting periods herein.

         o    STOCK OPTIONS. During the Severance Period, the Company agrees
              that any and all unvested and unexpired stock options that had
              been previously granted to you shall continue to vest in
              accordance with their vesting schedules, except that no event
              giving rise to an acceleration of vesting (such as a change in
              control) shall accelerate the vesting of any of your stock
              options. Your ability to exercise vested options shall expire
              thirty (30) days following the end of the Severance Period, unless
              otherwise agreed by the Company.

         o    HEALTH AND DENTAL INSURANCE. If you so elect, the Company will
              continue to provide you, at company expense, with health and
              dental insurance at a level consistent with that provided to
              employees of the Company until September 30, 2006 unless you
              earlier attain insurance through a new job position. You agree to
              nootify the Company upon the event that you obtain replacement

<PAGE>
Paul B. Healy
December 20, 2005
Page 3


         coverage. You will be responsible for the employee portion of the
         premiums for that period.

4.       CONSULTING:

         During the Severance Period, you agree to provide to the Company and
         its subsidiaries and affiliates, on an as-needed basis, consulting
         services relating to the Company's investor relations and corporate
         development activities. In requesting your services from time to time,
         the Company shall make reasonable efforts to accommodate your schedule
         and the requirements of your employer. The services that shall be
         required of you shall include, but not be limited to, assisting your
         successor in the assumption of your prior responsibilities, making
         introductions to investors and others as needed for a successful
         transition, and providing such additional reasonable assistance to
         ensure a smooth transition of responsibilities. The Company agrees to
         reimburse you for all reasonable out-of-pocket expenses associated with
         the provision of these consulting services to the Company, subject to
         the provision of detailed invoices for all expenses so incurred. The
         Company shall also provide to you such reasonable support services as
         you may require from time to time in connection with your consulting
         services.

         You agree to return to the Company any and all confidential and
         proprietary information you have acquired regarding the Company,
         including information about the Company's personnel, policies,
         publications, business practices, strategic plans, advertisers,
         customers, suppliers, distributors, readers, financial forecasts,
         production data, marketing techniques, promotional plans, and financial
         information, and to hold in the strictest confidence, except as
         required by applicable law, and not to disclose any of said information
         to anyone, and to refrain from making any statements or representations
         to any employee of the Company or to its customers, suppliers,
         competitors or the public at large which might disparage or have a
         detrimental effect on the Company's business, operations, public image,
         reputation or its relations with advertisers, customers, suppliers,
         employees, lenders, competitors, or other business associates.

5.       RETURN OF COMPANY PROPERTY:

         The Company agrees that you shall be entitled to retain any personal
         computing equipment provided to you by the Company, including any PCs
         and laptops, subject to the condition that the Company be permitted to
         remove from such equipment all proprietary software and documents. You
         may also retain the Blackberry provided to you by the Company, subject
         to the same condition set forth immediately above. All other property
         of the Company which you have in your possession including, but not
         limited to, all access cards, facility keys and credit cards, shall be
         returned to the Company by the Effective Date, except as otherwise
         agreed to between you and the Company.

<PAGE>
Paul B. Healy
December 20, 2005
Page 4


6.       CONTINUATION OF INSURANCE:

         COBRA requires that, in certain cases, terminated employees be allowed
         to continue their medical and dental insurance beyond their separation
         date at their own expense. An explanation of your rights, if any, under
         this law will be sent to you under separate cover at a future date.

7.       RELEASE:

         You hereby agree (except for any vested benefits to which you are
         entitled under the Company's pension or 401(k) plans, including the
         anticipated March 2006 Company match with respect to your 401(k) Plan
         account, and any rights you may have under COBRA or other insurance
         policies the Company may have) to WAIVE any and all rights in
         connection with, and to fully RELEASE and forever discharge the

         Company from, any and all torts, contracts, claims, suits, actions,
         causes of action, demands, rights, damages, costs, expenses, attorneys
         fees, and compensation in any form whatsoever, whether now known or
         unknown, which you have (up through and including the date hereof)
         against the Company on account of or in any way growing out of your
         employment by the Company or your separation, including but not limited
         to, any and all claims for damages or injury to any entity, person,
         property or reputation arising there from, claims for wages, employment
         benefits, tort claims and claims under Title VII of the Civil Rights
         Act of 1964, the Civil Rights Act of 1991, the Civil Rights Act of
         1866, the Employee Retirement Income Security Act of 1974, the National
         Labor Relations Act, the Fair Labor Standards Act, the Rehabilitation
         Act of 1973, the Family and Medical Leave Act of 1993, the Americans
         with Disabilities Act of 1990, the Illinois Human Rights Act, the
         Illinois Wage Payment and Collection Act, the Cook County Human Rights
         Ordinance, the Chicago Human Rights Ordinance and any other federal,
         state or local law, statute, ordinance, guideline, regulation, order or
         common-law principle of any state relating to employment, employment
         contracts, wrongful discharge or any other matter.

         Release of Age Discrimination Claims. In further consideration of the
         promises made by the Company in this Agreement, you specifically
         release the Company from all claims or rights you may have as of the
         date you sign this Agreement arising under the Age Discrimination in
         Employment Act of 1967, as amended, 29 U.S.C. Sec. 621, et seq. You
         further agree that:

         (a)      your waiver of rights under this release is knowing and
                  voluntary and in compliance with the Older Workers Benefit
                  Protection Act of 1990 (OWBPA);

         (b)      you understand the terms of this release;


<PAGE>
Paul B. Healy
December 20, 2005
Page 5


         (c)      the consideration provided in Paragraph 3 represents
                  consideration over and above that to which you otherwise would
                  be entitled, that the consideration would not have been
                  provided had you not signed this release, and that the
                  consideration is in exchange for the signing of this release;

         (d)      the Company is hereby advising you in writing to consult with
                  your attorney prior to executing this release;

         (e)      the Company is giving you a period of twenty-one days within
                  which to consider this release;

         (f)      following your execution of this release you have seven (7)
                  days in which to revoke this release by written notice. To be
                  effective, the revocation must be made in writing and
                  delivered to and received by Pamela A. Davidson, Assistant
                  Corporate Counsel, Hollinger International Publishing Inc.,
                  350 North Orleans, 10 South, Chicago, Illinois 60654, no later
                  than 4:00 p.m. on the seventh day after you execute this
                  release. An attempted revocation not actually received by Ms.
                  Davidson before the revocation deadline will not be effective;
                  and

         (g)      this entire Agreement shall be void and of no force and effect
                  if you choose to so revoke, and if you choose not to so revoke
                  this Agreement shall then become fully effective and
                  enforceable.

         This Section does not waive rights or claims that may arise under the
         ADEA after the date you sign this Agreement. In addition, nothing in
         this agreement shall in any way affect your right to the
         indemnification and expense advancement to the extent provided by the
         Company's bylaws and Articles of Incorporation. Your right to such
         indemnification and advancement shall relate to, but not be limited to,
         your continuing cooperation with the Company, the Special Committee of
         the Company's Board of Directors, and governmental authorities.

9.       ACKNOWLEDGMENT; NO ADMISSION; CONFIDENTIALITY:

         You hereby represent and warrant that: (a) you have no pending claims
         against the Company with any municipal, state, federal or other
         governmental or non-governmental entity; and (b) you will not file any
         claims with respect to any events occurring on or before the date
         hereof. You also acknowledge and agree that by entering into this
         Agreement you can never make claim or demand upon or sue the Company
         for any reason whatsoever relating to anything that has happened
         through the date hereof.

         Both the Company and you acknowledge and agree that this Agreement does
         not constitute, is not intended to be, and shall not be construed,
         interpreted or treated in any respect as, an admission of liability or
         wrongdoing by either party for any


<PAGE>
Paul B. Healy
December 20, 2005
Page 6


         purpose whatsoever. Further, each of us acknowledge and agree that
         there has been no determination that either party has violated any
         federal, state or local law, statute, ordinance, guideline, regulation,
         order or common-law principle.

10.      CONTINUING OBLIGATIONS:

         Should you damage the reputation, good will or competitive position of
         the Company, or if you cause, directly or indirectly, any other key
         executive employee of the Company to terminate his or her employment
         with the Company (except that you shall be permitted to respond to
         unsolicited requests for references), then the Company will be entitled
         to reimbursement from you of the full amount of separation pay and
         other compensation that you have received under this Agreement through
         the date of such action by you, and the Company will also be entitled
         to obtain injunctive relief against your continuing any such action.

         You also understand and agree that in the event you, your heirs,
         spouse, family members, executors, or administrators attempt to
         institute or do institute any charge, claim, suit or action against the
         Company in violation of this Agreement, you shall be obligated, as an
         express condition of bringing such action, to tender back to the
         Company the full amount of separation pay and other compensation that
         you have received under this Agreement; and you further agree that you
         will pay all of the Company's costs, expenses and fees of defending
         against such action, including among other things, reasonable
         attorney's fees. This paragraph does not grant you an option to return
         the money and institute an action. Instead this paragraph merely
         creates an additional term and condition precedent to bringing an
         action regardless of the fact that such action is expressly barred by
         this Agreement, and is without merit.

         Should you breach any other term of this Agreement, including but not
         limited to filing any claim which you have agreed to release and waive
         under this Agreement or breaching any of the provisions of this
         Agreement, the Company will be entitled to recover damages for such
         breach and also to obtain injunctive relief against further breach by
         you.

         If the Company or you at any time believe that the other party has
         breached any term of this Agreement, the party claiming a breach shall
         promptly notify the other of the specific basis for that belief, and
         the other party will have a period of ten (10) days within which to
         cure any breach (if cure is possible) or to otherwise respond to the
         claim of breach.


<PAGE>
Paul B. Healy
December 20, 2005
Page 7


11.      ARBITRATION OF DISPUTES; PAYMENT OF EXPENSES:

         Any controversy or claim arising out of or relating to this Agreement,
         or the breach thereof, shall be settled by arbitration proceedings
         conducted in accordance with the commercial rules of the American
         Arbitration Association ("AAA") as then in effect. Any arbitration
         shall be held in Chicago, Illinois. The arbitrator shall be selected by
         joint agreement of the Company and you, but if such agreement is not
         reached within seven (7) days of the date of the request for
         arbitration, the selection shall be made by the AAA in accordance with
         its commercial rules. Judgment upon any award rendered by the
         arbitrator may be entered in any court having jurisdiction. The costs
         and expenses of the arbitrator and all costs and expenses of experts,
         attorneys, witnesses and other parties reasonably incurred by the
         prevailing party shall be borne by the party that does not prevail in
         such arbitration or in any court proceeding relating to enforcement of
         this Agreement.

         The existence and execution of this Agreement shall not be considered,
         and shall not be admissible in any proceeding, as an admission by the
         Company of any liability, error, violation or omission. You acknowledge
         that nothing contained in this Agreement or any other agreement or
         instrument delivered by the Company to you shall constitute an
         admission that the Company is in any way liable to you or has in any
         way violated any law. You further acknowledge that no precedent,
         practice, policy or usage shall be established by this Agreement or the
         Company's offer of benefits herein.

12.      GOVERNING LAW:

         This Agreement shall be governed by the laws of the State of New York


<PAGE>
Paul B. Healy
December 20, 2005
Page 8


13.      ACKNOWLEDGMENT/REVOCATION:

         You hereby acknowledge (a) that the Company has given you a period of
         at least twenty one (21) days in which to review and consider this
         Agreement; (b) that the Company has advised, and does hereby in writing
         advise, you to consult with an attorney before signing this Agreement;
         (c) that you have read this Agreement in its entirety; (d) that you
         have had at least twenty one (21) days in which to confer with your own
         attorney for assistance and advice concerning this Agreement; (e) that
         you understand the terms of this Agreement; (f) that you understand
         that the terms of this Agreement are legally enforceable; (g) that you
         have entered into this Agreement freely, voluntarily, knowingly and
         willingly and were in no manner coerced into signing it; (h) that
         neither this Agreement nor the discussion and negotiation leading to it
         are or were, in any manner, discriminatory; (i) that you were, and
         hereby are, encouraged to discuss any questions, problems, or issues
         concerning this Agreement with the Company BEFORE signing it; (j) that
         you are waiving rights and claims you may have in exchange for
         consideration in addition to things of value to which you are already
         entitled; and (k) that after signing this Agreement you have a period
         of seven (7) days in which to revoke your agreement, however, any such
         revocation must be in writing and must be addressed to Pamela A.
         Davidson, Assistant Corporate Counsel, Hollinger International, 350
         North Orleans, 10 South, Chicago, Illinois 60654.

Paul, please indicate your understanding and acceptance of this Agreement by
executing both copies below, and retaining one fully executed original for your
files and returning one fully executed original to me.

                                              Very truly yours,

                                              HOLLINGER INTERNATIONAL INC.



                                              By:
                                                 -------------------------------
                                                Gordon Paris, Chairman and CEO


I hereby accept the terms of this Agreement
and agree to abide by the provisions hereof:


--------------------------
Paul B. Healy

                                              Dated:
                                                    ----------------------------