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HOLLINGER INTERNATIONAL PUBLISHING INC.

9% Senior Notes due 2010

Unconditionally Guaranteed by

HOLLINGER INTERNATIONAL INC.

INDENTURE

Dated as of December 23, 2002

WACHOVIA TRUST COMPANY, NATIONAL ASSOCIATION,

Trustee

TABLE OF CONTENTS

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SCHEDULE 1 — Permitted Indebtedness
EXHIBIT A — Form of Note
EXHIBIT B — Form of Transfer Certificate for Transfer to QIB
EXHIBIT C — Form of Certificate to be Delivered in Connection with Transfers Pursuant to Regulation S
EXHIBIT D — Form of Rule 144 Certification

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CROSS-REFERENCE TABLE

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     INDENTURE, dated as of December 23, 2002, among HOLLINGER INTERNATIONAL PUBLISHING INC., a Delaware corporation (as more fully defined below, “Publishing”), HOLLINGER INTERNATIONAL INC., a Delaware corporation (as more fully defined below, “Hollinger International”), and WACHOVIA TRUST COMPANY, NATIONAL ASSOCIATION, as trustee (the “Trustee”).

RECITALS OF PUBLISHING

     Publishing has duly authorized the execution and delivery of this Indenture to provide for the issuance of its unsecured senior notes, to be issued pursuant to Articles II and III hereof or a supplemental indenture (each a “Note” and collectively the “Notes”).

     Hollinger International has duly authorized the issuance of a guarantee (the “Guarantee”) of the Notes, of substantially the tenor as hereinafter set forth, and to provide therefor, Hollinger International has duly authorized the execution and delivery of this Indenture in its capacity as Guarantor hereunder;

     This Indenture is subject to, and shall be governed by, the provisions of the Trust Indenture Act that are required to be part of and to govern indentures qualified under the Trust Indenture Act; and

     All acts and things necessary have been done to make (i) the Notes, when executed by Publishing and authenticated and delivered hereunder and duly issued by Publishing, the valid obligations of Publishing and (ii) this Indenture a valid agreement of Publishing and Hollinger International in accordance with the terms of this Indenture.

     NOW, THEREFORE, in consideration of the premises and the purchase of the Notes by the Holders thereof, it is mutually covenanted and agreed, for the equal and proportionate benefit of all Holders of the Notes, as follows:

ARTICLE I

Definitions and Other Provisions of General Application

     SECTION 1.01. Definitions. For all purposes of this Indenture, except as otherwise expressly provided or unless the context otherwise requires:

	(a) the terms defined in this Article have the meanings assigned to them in this Article, and include the plural as well as the singular;
	(b) all other terms used herein which are defined in the Trust Indenture Act, either directly or by reference therein, have the meanings assigned to them therein;
	(c) all accounting terms not otherwise defined herein have the meanings assigned to them in accordance with GAAP;

	(d) the words “herein”, “hereof” and “hereunder” and other words of similar import refer to this Indenture as a whole and not to any particular Article, Section or other subdivision; and

	(e) all references to $, US$, dollars or United States dollars shall refer to the lawful currency of the United States of America.

     The following terms shall have the meanings set forth in this Section:

     “Acceleration Right” means a right, which at the time is immediately exercisable (without further notice or lapse of time), by the holders or a trustee to cause the acceleration of the maturity of Indebtedness of Publishing or a Restricted Subsidiary having an aggregate principal amount outstanding of at least $7,500,000.

     “Acquired Indebtedness” means Indebtedness of a Person (including an Unrestricted Subsidiary) (i) existing at the time such Person becomes a Restricted Subsidiary or (ii) assumed in connection with the acquisition of assets from such Person, in each case, other than Indebtedness Incurred in connection with, or in contemplation of, such Person becoming a Restricted Subsidiary or such acquisition. Acquired Indebtedness will be deemed to be Incurred on the date of the related acquisition of assets from any Person or the date the acquired Person becomes a Restricted Subsidiary.

     “Additional Note Board Resolutions” means resolutions duly adopted by the Board of Directors of Publishing and delivered to the Trustee in an Officers’ Certificate providing for the issuance of Additional Notes.

     “Additional Note Supplemental Indenture” means a supplement to this Indenture duly executed and delivered by Publishing, each Guarantor and the Trustee pursuant to Article IX providing for the issuance of Additional Notes.

     “Additional Notes” means additional Notes of up to an amount equal to the difference between (i) $450 million and (i) the aggregate principal amount of Notes originally issued as of the Issue Date and any Notes originally issued after the Issue Date pursuant to Section 3.12, such difference to exclude the aggregate principal amount of any replacement Notes and any Exchange Notes as specified in the relevant Additional Note Board Resolutions or Additional Note Supplemental Indenture issued therefor in accordance with this Indenture.

     “Affiliate” means, with respect to any specified Person, (i) any other Person directly or indirectly controlling or controlled by or under direct or indirect common control with such specified Person or (ii) any other Person that owns, directly or indirectly, 10% or more of such Person’s equity ownership or Voting Stock or any officer or director of any such Person or other Person or with respect to any natural Person, any person having a relationship with such Person by blood, marriage or adoption not more remote than first cousin. For the purposes of this definition, “control” when used with respect to any specified Person means the power to direct the management and policies of such Person directly or indirectly, whether through ownership of voting securities, by contract or otherwise; and the terms “controlling” and “controlled” have meanings correlative to the foregoing.

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     “Agent” means Wachovia Bank, N.A., the administrative agent under the Senior Credit Facility, and its successors and assigns in such capacity.

     “Asset Sale” means any sale, issuance, conveyance, transfer, lease or other disposition (including, without limitation, by way of merger, consolidation or sale and leaseback transaction but not the grant of a pledge or security interest) (collectively, a “transfer”), directly or indirectly, in one or a series of related transactions, of (i) any Capital Stock of any Restricted Subsidiary; (ii) all or substantially all of the properties and assets of any division or line of business of Publishing or any of its Restricted Subsidiaries; or (iii) any other properties or assets (other than cash) of Publishing or any Restricted Subsidiary, other than in the ordinary course of business. For the purposes of this definition, the term “Asset Sale” shall not include (A) any transfer of properties and assets, in a single transaction or series of related transactions, that is governed by the provisions of Article VIII, (B) any transfer of properties and assets from any Restricted Subsidiary to Publishing in accordance with the terms of this Indenture, (C) any transfer of properties and assets, in a single transaction or series of related transactions, having a market value of less than $5,000,000 (it being understood that if the market value of the properties or assets being transferred exceeds $5,000,000, the entire value and not just the portion in excess of $5,000,000, shall be deemed to have been the subject of an Asset Sale), (D) any transfer of properties and assets which are obsolete (in the case of equipment) to Publishing’s and its Restricted Subsidiaries’ businesses, (E) any transfer of properties and assets to any Restricted Subsidiary, and (F) any transfer of properties and assets from any Restricted Subsidiary to any other Restricted Subsidiary.

     “Average Life to Stated Maturity” means, as of the date of determination with respect to any Indebtedness, the quotient obtained by dividing (i) the sum of the products of (a) the number of years from the date of determination to the date or dates of each successive scheduled principal payment of such Indebtedness multiplied by (b) the amount of each such principal payment by (ii) the sum of all such principal payments.

     “Bankruptcy Law” means Title 11 of the United States Code, as amended, or any similar United States federal or state or foreign law relating to bankruptcy, insolvency, receivership, winding-up, liquidation, reorganization or relief of debtors or any amendment to, succession to or change in any such law.

     “Board of Directors” means the board of directors of Publishing or any duly authorized committee of such board.

     “Board Resolution” means a copy of a resolution certified by an officer of Publishing to have been duly adopted by such Board of Directors of Publishing or a duly authorized committee of such board and to be in full force and effect on the date of such certification, and delivered to the Trustee.

     “Business Day” means each Monday, Tuesday, Wednesday, Thursday and Friday which is not a day on which banking institutions in The City of New York, or the city in which the principal corporate trust office of the Trustee is located (initially Wilmington, Delaware), are authorized or obligated by law or executive order to close.

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     “Business Opportunities Agreement” means the Business Opportunities Agreement dated as of February 7, 1996, between Hollinger Inc. and Hollinger International and any amendment, modification, or supplement thereto or restatement thereof and any similar agreements entered into after the date of the original issuance of the Notes in accordance with the terms of this Indenture.

     “Capital Lease Obligation” of any Person means any obligation of such Person and its subsidiaries on a consolidated basis under any capital lease of real or personal property which, in accordance with GAAP, has been recorded as a capitalized lease obligation.

     “Capital Stock” of any Person means any and all shares, interests, participations or other equivalents (however designated) of such Person’s capital stock and options, warrants or other rights to acquire such Person’s capital stock.

     “Cash Equivalents” means (i) any evidence of Indebtedness with a maturity of 180 days or less issued or directly and fully guaranteed or insured by the United States of America or any agency or instrumentality thereof (provided, that the full faith and credit of the United States of America is pledged in support thereof); (ii) certificates of deposit or acceptances with a maturity of 180 days or less of any financial institution that is a member of the Federal Reserve System having combined capital and surplus and undivided profits of not less than $500,000,000; (iii) commercial paper with a maturity of 180 days or less issued by a corporation that is not an Affiliate of Publishing organized under the laws of any state of the United States or the District of Columbia and rated A-1 (or higher) according to S&P or P-1 (or higher) according to Moody’s or at least an equivalent rating category of another nationally recognized securities rating agency; (iv) any money market deposit accounts issued or offered by a domestic commercial bank having capital and surplus in excess of $500,000,000; and (v) repurchase agreements and reverse repurchase agreements relating to marketable direct obligations issued or unconditionally guaranteed by the government of the United States of America or issued by any agency thereof and backed by the full faith and credit of the United States of America, in each case maturing within 180 days from the date of acquisition; provided, that the terms of such agreements comply with the guidelines set forth in the Federal Financial Agreements of Depository Institutions with Securities Dealers and Others, as adopted by the Comptroller of the Currency on October 31, 1985.

     “Certificated Note” means any Note issued in registered certificated form (other than a Global Note), which shall be substantially in the form of Exhibit A, with appropriate legends as specified in Section 3.05 and Exhibit A.

     “Change of Control” means the occurrence of any of the following:

(a) there is a report filed on Schedule 13D, 14D-1 or 14D-1F (or any successor schedule, form or report) pursuant to the Exchange Act, disclosing that any person (for purposes of this definition, as the term “person” is used in Section 13(d)(3) or Section 14(d)(2) of the Exchange Act or any successor provision to either of the foregoing), other than any person consisting solely of Lord Black (or his heirs, executors or legal representatives) and his Affiliates, has become the beneficial owner (as the term “beneficial owner” is defined under Rule 13d-3 or any successor rule or regulation

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promulgated under the Exchange Act) of Voting Stock representing 50% or more of the total voting power attached to all Voting Stock of Hollinger Inc., Hollinger International or Publishing then outstanding; provided, however, that a person shall not be deemed to be the beneficial owner of, or to own beneficially, (i) any securities tendered pursuant to a tender or exchange offer made by or on behalf of such person or any of such person’s Affiliates until such tendered securities are accepted for purchase or exchange thereunder, or (ii) any securities if such beneficial ownership (A) arises solely as a result of a revocable proxy delivered in response to a proxy or consent solicitation made pursuant to applicable law, and (B) is not also then reportable on Schedule 13D (or any successor schedule) under the Exchange Act;

	(b) there is a report filed or required to be filed with any securities commission or securities regulatory authority in Canada, disclosing that any offeror (as the term “offeror” is defined in Section 89(1) of Securities Act (Ontario) for the purpose of Section 101 of such Securities Act or any successor provision of the foregoing) other than any person consisting solely of Lord Black (or his heirs, executors or legal representatives) and his Affiliates, has acquired beneficial ownership (within the meaning of the Securities Act (Ontario)) of, or the power to exercise control or direction over, or securities convertible into, any voting or equity shares of Hollinger Inc. that together with such offeror’s securities (as the term “offeror’s securities” is defined in Section 89(1) of the Securities Act (Ontario) or any successor provision thereto in relation to the voting or equity shares of Hollinger Inc.), would constitute Voting Stock of Hollinger Inc. representing 50% or more of the total voting power attached to all Voting Stock of Hollinger Inc. then outstanding;
	(c) Hollinger International shall cease to own, directly or indirectly, 50% or more of the Voting Stock of Publishing (other than upon a merger or consolidation of Hollinger International with or into Publishing that is otherwise permitted in accordance with the terms of this Indenture);
	(d) there is consummated a consolidation (involving a business combination) or merger of Publishing or Hollinger International, as the case may be, (i) in which Publishing or Hollinger International, as the case may be, is not the continuing or surviving corporation or (ii) pursuant to which any Voting Stock of Publishing or Hollinger International, as the case may be, would be reclassified, changed or converted into or exchanged for cash, securities or other property, other than (in each case) a consolidation or merger of Publishing or Hollinger International, as the case may be, in which the holders of the Voting Stock of Publishing or Hollinger International, as the case may be, immediately prior to the consolidation or merger have, directly or indirectly, 50% or more of the Voting Stock of the continuing or surviving corporation immediately after such transaction;
	(e) during any period of 12 consecutive months, individuals who at the beginning of such period constituted the Board of Directors of Hollinger International or Publishing (together with any new directors whose election by such Board of Directors, or whose nomination for election by the stockholders of Hollinger International or Publishing, as the case may be, was approved by a vote of at least a majority of the

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	directors then still in office who were either directors at the beginning of such period or whose election or nomination for election was previously so approved) cease for any reason to constitute a majority of such Board of Directors then in office; or
	(f) Lord Black (or his heirs, executors and legal representatives) and his Affiliates cease to beneficially own and control the voting of, directly or indirectly, Voting Stock of Publishing or Hollinger International representing a greater percentage of the total voting power attached to the Voting Stock of Publishing or Hollinger International than the percentage beneficially owned and controlled, directly or indirectly, by any other single shareholder of Publishing or Hollinger International together with its Affiliates (a “Designated Transaction”) and there shall occur a Rating Decline.

     “Collateral” means any property, assets, proceeds or other items that may be pledged as security for the Notes, whether pursuant to Section 10.11 or otherwise.

     “Commission” means the Securities and Exchange Commission, as from time to time constituted, created under the Exchange Act, or if at any time after the execution of this Indenture such Commission is not existing and performing the duties now assigned to it under the Trust Indenture Act, then the body performing such duties at such time.

     “Consolidated Assets” means, with respect to Publishing, the total assets shown on the balance sheet of Publishing and its Restricted Subsidiaries, as determined on a consolidated basis in accordance with GAAP, as of Publishing’s latest full fiscal quarter.

     “Consolidated Cash Flow Ratio” means, as at any date of determination, the ratio of (i) the aggregate amount of Indebtedness of Publishing and the Restricted Subsidiaries on a Consolidated basis outstanding as at such date to (ii) the Operating Cash Flow of Publishing and the Restricted Subsidiaries (determined on a Consolidated basis) for the most recently completed period of four consecutive fiscal quarters of Publishing; provided that for the purpose of determining the Consolidated Cash Flow Ratio, the Indebtedness and Operating Cash Flow of Restricted Subsidiaries that are not Wholly Owned Restricted Subsidiaries shall be determined in accordance with the actual percentage of Publishing’s common equity interest in such Restricted Subsidiary on the date of determination of the Consolidated Cash Flow Ratio (thus, for example, in the case of a Restricted Subsidiary in which Publishing owns a 51% common equity interest, 51% each of such Restricted Subsidiary’s Indebtedness and Operating Cash Flow would be included in the calculation of Publishing’s aggregate Indebtedness and Operating Cash Flow, respectively).

     “Consolidated Interest Expense” means, with respect to any period, the sum of (i) the interest expense of Publishing and the Restricted Subsidiaries for such period, determined on a Consolidated basis in accordance with GAAP, including, without limitation, (a) amortization of debt discount, (b) the net payments, if any, under interest rate contracts (including amortization of discounts), (c) the interest portion of any deferred payment obligation and (d) accrued interest, plus (ii) the interest component of Capital Lease Obligations paid, accrued and/or scheduled to be paid or accrued by Publishing and the Restricted Subsidiaries during such period, and all capitalized interest of Publishing and the Restricted Subsidiaries, in each case as determined on a Consolidated basis in accordance with GAAP.

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     “Consolidated Net Income (Loss)” of Publishing and the Restricted Subsidiaries means, for any period, the Consolidated net income (or loss (and treating a loss as a negative number)) of Publishing and the Restricted Subsidiaries for such period as determined in accordance with GAAP, adjusted by (a) excluding, without duplication, to the extent included in calculating such Consolidated Net Income (or Loss), (i) all extraordinary gains and losses, (ii) the portion of Consolidated net income (or loss) of Publishing and its Restricted Subsidiaries allocable to Investments in unconsolidated Persons (other than Unrestricted Subsidiaries) to the extent that cash dividends or distributions have not actually been received by such Person or one of its Restricted Subsidiaries, (iii) the portion of Consolidated net income (or loss) of Publishing and its Restricted Subsidiaries allocable to Publishing’s Unrestricted Subsidiaries (or to payments received therefrom), (iv) the net income (or loss) of any Person acquired during the specified period attributable to any period prior to the date of such acquisition, (v) any gain or loss, realized upon the termination of any employee pension benefit plan, (vi) aggregate gains and losses (less all fees and expenses relating thereto) in respect of dispositions of assets (including without limitation sales of shares of Unrestricted Subsidiaries or unconsolidated Persons and noncash writeoffs of assets (provided, that there are no continuing cash expenses related to such writeoffs)) other than in the ordinary course of business, (vii) the net income of any Restricted Subsidiary to the extent that the declaration of dividends or similar distributions by that Restricted Subsidiary of that income is not at the time permitted, directly or indirectly, by operation of the terms of its charter or any agreement, instrument, judgment, decree, order, statute, rule or governmental regulations applicable to that Restricted Subsidiary or its stockholders, (viii) any gain from the collection of proceeds of life insurance policies, (ix) any gain arising from the acquisition of any securities, or the extinguishment, under GAAP, of any Indebtedness of Publishing or one of its Restricted Subsidiaries, (x) aggregate gains or losses relating to foreign currency transactions or translations and (xi) redundancy costs relating to the elimination of jobs. In calculating the Operating Cash Flow of Publishing and its Restricted Subsidiaries, the Consolidated Net Income of Restricted Subsidiaries that are not Wholly Owned Restricted Subsidiaries will be included only to the extent of Publishing’s common equity interest in such Restricted Subsidiaries, as provided in the definition of Operating Cash Flow.

     “Consolidated Net Worth” means the common and preferred stockholders’ equity of Publishing and its Restricted Subsidiaries (exclusive of any redeemable capital stock), as determined on a Consolidated basis and in accordance with GAAP.

     “Consolidated Tangible Assets” means the total assets appearing on a Consolidated balance sheet of Publishing and its Restricted Subsidiaries less, without duplication, each of the following: (i) all applicable depreciation, amortization and other valuation reserves, (ii) all other intangible assets and deferred charges, (iii) deferred income tax assets (to the extent recorded as an asset) and (iv) all investments in unconsolidated subsidiaries (including all Unrestricted Subsidiaries).

     “Consolidation” means, with respect to any Person, the consolidation of the accounts of such Person and each of its subsidiaries if and to the extent the accounts of such Person and each of its subsidiaries would normally be consolidated with those of such Person, all in accordance with GAAP; provided, however, that the accounts of any Unrestricted Subsidiary shall not be consolidated with Publishing but instead the interest of Publishing or any Restricted

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Subsidiary therein will be accounted for as an investment on an equity basis. The term “Consolidated” shall have a correlative meaning.

     “Corporate Trust Office” means the office of the Trustee or an affiliate or agent thereof at which at any particular time the corporate trust business for the purposes of this Indenture shall be principally administered, which office at the date of execution of this Indenture is located at 920 King Street, Suite 102, Wilmington, DE 19801.

     “CST Real Estate” means the real estate, including land, building and fixtures, located at 401 North Wabash Avenue, Chicago, Illinois, where Publishing currently maintains its headquarters, and all improvements thereon.

     “CST Real Estate Transaction” means the sale or other disposition (other than to an Affiliate), including contribution to a new joint venture entity, of all or any portion of the interest of Publishing or a Restricted Subsidiary in the CST Real Estate.

     “Cumulative Credit” means (x) the Operating Cash Flow of Publishing and the Restricted Subsidiaries (determined on a Consolidated basis) from and after October 1, 2002 to the end of the fiscal quarter immediately preceding the date of the proposed Restricted Payment, or, if such Operating Cash Flow for such period is negative, minus the amount by which such Operating Cash Flow is negative, less (y) 150% of Publishing’s cumulative Consolidated Interest Expense for such period.

     “Currency Agreements” means one or more of the following agreements which shall be entered into with one or more financial institutions: foreign exchange contracts, currency swap agreements or other similar agreements or arrangements designed to protect against fluctuations in currency values.

     “Default” means any event which is, or after notice or passage of time or both would be, an Event of Default.

     “Designated Transaction” shall have the meaning assigned to such term in paragraph (f) of the “Change of Control” definition.

     “Distribution Compliance Period” means, in respect of any Regulation S Global Note, the 40 consecutive days beginning on and including the later of (a) the day on which any Notes represented thereby are offered to persons other than distributors (as defined in Regulation S under the Securities Act) pursuant to Regulation S and (b) the issue date for such Notes.

     “Dollar Equivalent” means with respect to any monetary amount in a currency other than U.S. dollars, at any time of determination thereof, the amount of U.S. dollars obtained by converting such foreign currency involved in such computation into U.S. dollars at the spot rate for the purchase of U.S. dollars with the applicable foreign currency as published in The Wall Street Journal in the “Exchange Rates” column under the heading “Currency Trading” on the date two Business Days prior to such determination.

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     “DTC” means The Depository Trust Company, its nominees and their respective successors and assigns, or such other depositary institution hereinafter appointed by Publishing that is a clearing agency registered under the Exchange Act.

     “Event of Default” has the meaning specified in Article V.

     “Exchange Act” means the Securities Exchange Act of 1934, as amended.

     “Exchange Notes” means debt securities of Publishing, guaranteed by Hollinger International, substantially identical in all material respects to the Notes (except that the additional interest provisions and the transfer restrictions pertaining to the Notes will be modified or eliminated, as appropriate), to be issued pursuant to this Indenture.

     “Exchange Offer Registration Statement” shall have the meaning assigned to such term in the Issue Date Registration Rights Agreement and any other Registration Rights Agreement.

     “FDTH” means First DT Holdings Limited, a corporation under the laws of England and its successors and assigns.

     “Generally Accepted Accounting Principles” or “GAAP” means generally accepted accounting principles in the United States, consistently applied, which are in effect on the date of this Indenture.

     “Global Note” means any Note issued in registered certificated form to DTC (or its nominee), as depositary for the beneficial owners thereof, which shall be substantially in the form of Exhibit A, with appropriate legends as specified in Section 3.05 and Exhibit A.

     “Guarantee” means the guarantee by Hollinger International and, if the context requires, by any Restricted Subsidiary of the Indenture Obligations.

     “Guaranteed Debt” of any Person means, without duplication, all Indebtedness of any other Person referred to in the definition of Indebtedness guaranteed directly or indirectly in any manner by such Person, or in effect guaranteed directly or indirectly by such Person through an agreement (i) to pay or purchase such Indebtedness or to advance or supply funds for the payment or purchase of such Indebtedness (or to indemnify another Person for the costs thereof), (ii) to purchase, sell or lease (as lessee or lessor) property, or to purchase or sell services, primarily for the purpose of enabling the debtor to make payment of such Indebtedness or to assure the holder of such Indebtedness against loss, (iii) to supply funds to, or in any other manner invest in, the debtor (including any agreement to pay for property or services without requiring that such property be received or such services be rendered), (iv) to maintain working capital or equity capital of the debtor, or otherwise to maintain the net worth, solvency or other financial condition of the debtor or (v) otherwise to assure a creditor against loss, provided, that the term “guarantee” shall not include endorsements for collection or deposit, in either case in the ordinary course of business.

     “Guarantor” means any guarantor of the Notes in accordance with the terms of this Indenture, including Hollinger International.

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     “Holder” means a Person in whose name a Note is registered in the Note Register.

     “Hollinger International” means Hollinger International Inc., a corporation incorporated under the laws of Delaware and a Guarantor of the Indenture Obligations, until a successor Person shall have become such pursuant to Article VIII of this Indenture and thereafter “Hollinger International” shall mean such successor Person.

     “Incur” means create, issue, assume, guarantee or otherwise in any manner become directly or indirectly liable for or with respect to or otherwise incur.

     “Indebtedness” means, with respect to any Person, without duplication, (i) all indebtedness of such Person for borrowed money or for the deferred purchase price of property or services (or other obligations to former owners of acquired businesses), excluding any trade payables and other accrued current liabilities arising in the ordinary course of business, but including, without limitation, all obligations, contingent or otherwise, of such Person in connection with any letters of credit issued under letter of credit facilities, acceptance facilities or other similar facilities and in connection with any agreement to purchase, redeem, exchange, convert or otherwise acquire for value any Capital Stock of such Person, or any warrants, rights or options to acquire such Capital Stock, now or hereafter outstanding, (ii) all obligations of such Person evidenced by bonds, notes, debentures or other similar instruments, (iii) all indebtedness created or arising under any conditional sale or other title retention agreement with respect to property acquired by such Person (even if the rights and remedies of the seller or lender under such agreement in the event of default are limited to repossession or sale of such property), but excluding trade payables arising in the ordinary course of business, (iv) all obligations under Interest Rate Agreements and Currency Agreements of such Person related to the settlement or termination of those agreements as of the date of determination, (v) all Capital Lease Obligations of such Person, (vi) all Indebtedness referred to in clauses (i) through (v) above of other Persons and all dividends of other Persons, the payment of which is secured by (or for which the holder of such Indebtedness has an existing right, contingent or otherwise, to be secured by) any Lien, upon or with respect to property (including, without limitation, accounts and contract rights) owned by such Person, even though such Person has not assumed or become liable for the payment of such Indebtedness, (vii) all Guaranteed Debt of such Person, (viii) all Redeemable Capital Stock and (without duplication) all Preferred Stock of Restricted Subsidiaries other than Preferred Stock held by Restricted Subsidiaries or Publishing, valued at the greater of its voluntary or involuntary maximum fixed repurchase price plus accrued and unpaid dividends and (ix) any amendment, supplement, modification, deferral, renewal, extension, refunding or refinancing of any Indebtedness of the types referred to in clauses (i) through (viii) above. For purposes hereof, the “maximum fixed repurchase price” of any Redeemable Capital Stock or Preferred Stock which does not have a fixed repurchase price shall be calculated in accordance with the terms of such Redeemable Capital Stock or Preferred Stock as if such Redeemable Capital Stock or Preferred Stock were purchased on any date on which Indebtedness shall be required to be determined pursuant to this Indenture, and if such price is based upon, or measured by, the fair market value of such Redeemable Capital Stock or Preferred Stock, such fair market value to be determined in good faith by the Board of Directors of such Person.

     “Indenture” means this instrument as originally executed (including all exhibits and schedules thereto) and as it may from time to time be supplemented or amended by one or

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more indentures supplemental hereto entered into pursuant to the applicable provisions hereof and shall include the terms of the Notes established as contemplated by Section 2.01.

     “Indenture Obligations” means the obligations of Publishing under this Indenture or under the Notes to pay principal of, premium, if any, and interest when due and payable, and all other amounts due or to become due under or in connection with this Indenture and the Notes, and the performance of all other obligations to the Trustee, the Paying Agent and the holders under this Indenture and the Notes, according to the terms thereof.

     “Independent Committee” means a committee of the board of directors of Publishing whose membership meets the requirements of the New York Stock Exchange applicable to audit committees as in effect on the date of original issuance of the Notes or a committee of the board of directors of Publishing whose membership satisfies any more restrictive requirements of independence of any securities exchange or market on which Publishing’s or Hollinger International’s equity securities are traded or listed.

     “Independent Director” means a member of the board of directors of a Person that is not an officer, employee or former officer or employee of such Person or one of its Affiliates and, with respect to any transaction or series of related transactions, a member of the board of directors who does not have any material direct or indirect financial interest in or with respect to such transaction or series of related transactions (including for such purpose the interest of any other Person with respect to whom such director is also a director, officer or employee).

     “Interest Payment Date” means the Stated Maturity of a regular installment of interest on the Notes or the Special Payment Date with respect to Defaulted Interest.

     “Interest Rate Agreements” means one or more of the following agreements which shall be entered into from time to time with one or more financial institutions: interest rate protection agreements (including, without limitation, interest rate swaps, caps, floors, collars and similar agreements) and/or other types of interest rate hedging agreements.

     “Investment” means, with respect to any Person, directly or indirectly, any advance, loan (including guarantees), or other extension of credit or capital contribution to (by means of any transfer of cash or other property to others or any payment for property or services for the account or use of others), or any purchase, acquisition or ownership by such Person of any Capital Stock, bonds, notes, debentures or other securities issued or owned by, any other Person and all other items that are or would be classified as investments on a balance sheet prepared in accordance with GAAP.

     “Issue Date” means the first date of issuance of Notes under this Indenture.

     “Issue Date Notes” means the $300,000,000 aggregate principal amount of Notes originally issued on the Issue Date, and any replacement Notes, Private Exchange Notes and Exchange Notes, issued therefor in accordance with this Indenture.

     “Issue Date Registration Rights Agreement” means the Registration Rights Agreement dated December 16, 2002 by and among Publishing, Hollinger International and Wachovia Securities, Inc., as initial purchaser.

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     “Lien” means any mortgage, charge, pledge, lien (statutory or otherwise), security interest, hypothecation or other encumbrance upon or with respect to any property of any kind, real or personal, movable or immovable, now owned or hereafter acquired.

     “Lord Black” means Lord Black of Crossharbour, PC(C), OC, KCSG.

     “Marketable Security” means any common stock, debt security or other security of a Person which is (or will, upon distribution thereof, be) listed on the NYSE, the American Stock Exchange or any national securities exchange registered under Section 6 of the Securities Exchange Act of 1934, as amended, or approved for quotation in the Nasdaq National Market or any similar system of automated dissemination of quotations of securities prices in the United States or for which there is a recognized market maker or trading market.

     “Material Restricted Subsidiary” means each Restricted Subsidiary of Publishing which (i) for the most recent fiscal year of Publishing accounted for more than 5% of the Consolidated revenues of Publishing and its Restricted Subsidiaries or (ii) at the end of such fiscal year was the owner (beneficial or otherwise) of more than 5% of the Consolidated Assets of Publishing and its Restricted Subsidiaries, all as shown on Publishing’s Consolidated financial statements for such fiscal year.

     “Maturity” when used with respect to any Note means the date on which the principal of such Note becomes due and payable as therein provided or as provided in this Indenture, whether at Stated Maturity, the Purchase Date or the Redemption Date and whether by declaration of acceleration, Offer in respect of Excess Proceeds, Change of Control, call for redemption or otherwise.

     “Media Business” means the business of the broadcast of radio or television broadcasting, cable and satellite programs (including national, regional or local radio, television, cable and satellite programs).

     “Net Cash Proceeds” means (a) with respect to any Asset Sale by any Person, the proceeds thereof in the form of cash or Cash Equivalents including payments of principal and interest in respect of deferred payment obligations when received in the form of, or stock or other assets when disposed of for, cash or Cash Equivalents (except to the extent that such obligations are financed or sold with recourse to Publishing or any Restricted Subsidiary) net of (i) brokerage commissions and other reasonable fees and expenses (including fees and expenses of counsel and investment bankers) related to such Asset Sale, (ii) provisions for all taxes payable as a result of such Asset Sale, (iii) payments made to retire indebtedness where payment of such indebtedness is secured by the assets or properties the subject of such Asset Sale, (iv) amounts required to be paid to any Person (other than Publishing or any Restricted Subsidiary) owning a beneficial interest in the assets subject to the Asset Sale and (v) appropriate amounts to be provided by Publishing or any Restricted Subsidiary, as the case may be, as a reserve, in accordance with GAAP, against any liabilities associated with such Asset Sale and retained by Publishing or any Restricted Subsidiary, as the case may be, after such Asset Sale, including, without limitation, pension and other post-employment benefit liabilities, liabilities related to environmental matters and liabilities under any indemnification obligations associated with such Asset Sale, all as determined and reflected in an Officers’ Certificate delivered to the Trustee and

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(b) with respect to any issuance or sale of Capital Stock or options, warrants or rights to purchase Capital Stock, or debt securities or Capital Stock that have been converted into or exchanged for Capital Stock, as referred to in Section 10.09, the proceeds of such issuance or sale in the form of Cash Equivalents, including payments in respect of deferred payment obligations when received in the form of, or stock or other assets when disposed of for, Cash Equivalents (except to the extent that such obligations are financed or sold with recourse to Publishing or any Restricted Subsidiary), net of attorneys’ fees, accountants’ fees and brokerage, consultation, underwriting and other fees and expenses actually incurred in connection with such issuance or sale and net of taxes paid or payable as a result thereof.

     “Newspaper Business” means the business of publishing, printing and/or distributing (including distributing by electronic means) newspapers, magazines and other paid or free publications having national, regional, local or targeted markets, including publications having limited or no news or editorial content such as shoppers or other “total market coverage” publications and similar publications.

     “Note Custodian” means the custodian with respect to any Global Note appointed by DTC, or any successor Person thereto, and shall initially be the Trustee.

     “Notes” means any of Publishing’s 9% Senior Notes due 2010 issued and authenticated pursuant to this Indenture.

     “9 1/4% Notes due 2006” means the 9 1/4% Senior Subordinated Notes due 2006 of Publishing governed by the indenture dated as of February 1, 1996 among Publishing, Hollinger International, as guarantor, and Fleet National Bank, as trustee.

     “9 1