Document:

<Page>

                                                                  Exhibit 4.15

DEBENTURE PLEDGE AGREEMENT entered into in Montreal, Quebec, as of this 7th
day of February, 2003

<Table>
<S>                                  <C>
BY:                                  SUN MEDIA CORPORATION, a corporation
                                     continued and existing under the laws of
                                     British Columbia, having its registered
                                     office at 800 Park Place, 666 Burrard
                                     Street, Vancouver, British Columbia, V6C
                                     3P3, herein acting and represented by
                                     Claudine Tremblay, duly authorized as
                                     she so declares,

IN FAVOUR OF:                        BANK OF AMERICA, N.A., a Schedule III
                                     Bank governed by the BANK ACT (Canada),
                                     having an office at 200 Front Street
                                     West, Suite 2700, Toronto, Ontario M5V
                                     3L2, herein acting for its own benefit
                                     as a Lender, and as agent and solidary
                                     creditor for the other Lenders as
                                     defined in the Credit Agreement as
                                     hereinafter defined (the "LENDERS").

</Table>

         WHEREAS Sun Media Corporation (the "GRANTOR") has created and
executed a Debenture dated February 7, 2003 (as amended, restated, renewed,
re-issued, supplemented or modified from time to time, the "DEBENTURE") in
favour of the Agent (as defined below) payable on demand in the principal
amount of $600,000,000 in lawful currency of Canada; and

         WHEREAS the Grantor has agreed to pledge the Debenture to the Agent
(as defined below) as a general and continuing collateral security for the
due and punctual payment, performance and fulfilment of the Obligations (as
defined below).

         NOW THEREFORE THIS AGREEMENT WITNESSETH THAT the parties hereto
agree as follows:

1.       DEFINITIONS AND INTERPRETIVE PROVISIONS

1.1      DEFINITIONS

         Capitalized terms not otherwise defined herein shall have the
         meaning ascribed thereto in the Credit Agreement. The following
         words or expressions whenever used in this debenture pledge
         agreement (the "AGREEMENT") (and in the preamble above which forms
         an integral part of this Agreement) shall have the following
         meanings:

         1.1.1.   "AGENT" means Bank of America, N.A., for its own benefit as
                  a Lender, and as agent and solidary creditor on behalf and
                  for the benefit of the other Lenders, and

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                                     - 2 -

                  includes such other Person, if any, as shall hereafter be
                  appointed as a  successor Agent under and in accordance with
                  the provisions of the Credit Agreement;

         1.1.2.   "CREDIT AGREEMENT" means that certain credit agreement
                  dated as of February 7, 2003 among the Grantor, as
                  Borrower, the financial institutions named on the signature
                  pages thereto, as Lenders, and Bank of America, N.A., as
                  Administrative Agent, as same may subsequently be amended,
                  amended and restated, modified, supplemented or replaced
                  from time to time;

         1.1.3.   "DEBENTURE" has the meaning ascribed to such term in the
                  preamble;

         1.1.4.   "EVENT OF DEFAULT" has the meaning ascribed to such term in
                  the Credit Agreement;

         1.1.5.   "GRANTOR" has the meaning ascribed to such term in the
                  preamble;

         1.1.6.   "OBLIGATIONS" means all obligations of the Grantor owed to
                  the Agent and the Lenders  pursuant to the Credit
                  Agreement, the other Credit Documents and hereunder; and

         1.1.7.   "PERSON" has the meaning ascribed to such term in the
                  Credit Agreement.

1.2      INTERPRETATION

         This Agreement shall be interpreted in accordance with the following:

         1.2.1.   words denoting the singular include the plural and vice
                  versa, and words denoting any gender include all genders;

         1.2.2.   the division of this Agreement into articles and sections
                  and the insertion of headings are for convenience of
                  reference only and shall not affect the construction or
                  interpretation of this Agreement; and

         1.2.3.   the word "including" shall mean "including without
                  limitation", and "includes" shall mean "includes without
                  limitation".

2.       PLEDGE AND AGENT'S RIGHTS

         2.1      As a general and continuing collateral security for the due
                  and punctual payment, performance and fulfillment of the
                  Obligations, the Grantor hereby hypothecates and pledges
                  the Debenture to the Agent subject to and in accordance
                  with the terms hereof. The hypothec hereby granted is in
                  the amount of $600,000,000, the whole with interest from
                  the date of this Agreement at the rate of twenty-five
                  percent (25%) per annum, calculated semi-annually and not
                  in advance with interest on overdue interest calculated at
                  the same rate and in the same manner.

<Page>
                                     - 3 -

2.2      Notwithstanding that the Debenture is payable on demand, the Agent
         may, forthwith and from time to time but only upon the occurrence
         and continuance of an Event of Default, exercise and enforce all the
         rights and remedies available to it under the Debenture (subject to
         Section 4.4 hereof). The rights of the Agent herein stipulated with
         respect to the Debenture shall be in addition to and not exclusive
         of all other rights and remedies which the Agent has or may
         otherwise enforce or exercise.

2.3      The Agent may charge on its own behalf and pay to others reasonable
         sums for services rendered (expressly including legal advice and
         services) in connection with realizing, collecting, selling,
         transferring, delivering and/or obtaining payment for the Debenture
         and may deduct the amount of such charges and payments from the
         proceeds thereof. The balance of such proceeds may be held by the
         Agent in lieu of the Debenture and may, as and when the Agent sees
         fit, be applied on account of such part of the Grantor's Obligations
         as the Agent deems best, without prejudice to the claims of the
         Agent or the Lenders upon the Grantor for any deficiency.

3.       COVENANTS

         The Grantor hereby covenants and agrees as follows:

         3.1      ADDITIONAL SECURITY

         It shall perform all acts and execute all deeds and documents
         (including notices of renewal) necessary to give full effect to the
         security constituted by this Agreement and to ensure that such
         security is at all times fully enforceable against third persons.

         3.2      DELIVERY

         It shall deliver to the Agent any instrument of indebtedness that is
         supplemental to, or in replacement of, the Debenture immediately
         upon issuing same or coming into possession thereof, together with
         any power of attorney, document and confirmation that the Agent may
         reasonably request in order to effect the transfer of such
         instrument, if necessary, into the name of the Agent.

4.       ADDITIONAL PROVISIONS

4.1      If any material provision of this Agreement is, or becomes, illegal,
         invalid or unenforceable, such provision shall be severed from this
         Agreement and be ineffective to the extent only of such illegality,
         invalidity or unenforceability. The remaining provisions hereof
         shall be unaffected by such deletion and shall continue to be valid
         and enforceable.

4.2      The parties acknowledge that the Grantor has agreed to grant to the
         Agent, as FONDE DE POUVOIR for the Lenders, a deed of hypothec in
         the Province of Quebec charging all the movable and immovable
         property of the Grantor located in the Province of Quebec and
         securing the payment of the Debenture.

<Page>
                                     - 4 -

4.3      The Agent shall not be obliged to exhaust its recourses against the
         Grantor, any other parties or against any other security any of them
         may hold in respect of the Obligations before realizing upon or
         otherwise dealing with the Debenture in such manner as it may
         consider appropriate.

4.4      Notwithstanding that the Debenture is stated to be payable on
         demand, the Agent agrees that it shall not demand payment under the
         Debenture unless an Event of Default has occurred and is continuing.
         The Agent also agrees that it shall only have the right to demand
         payment from the Grantor under the Debenture of an aggregate amount
         which may not in any manner whatsoever be in excess of the aggregate
         amount of the outstanding Obligations in principal, interest and
         costs.

4.5      The Agent may grant extensions or other indulgences, take and give
         up securities, accept compositions, grant releases and discharges
         and otherwise deal with the Grantor and with other parties, sureties
         or securities as it may deem fit, without prejudice to the
         Obligations or the rights of the Lenders or the Agent in respect of
         the Debenture. The Agent shall not (a) be liable or accountable for
         any failure to collect, realize or obtain payment in respect of the
         Debenture; (b) be bound to institute proceedings for the purpose of
         collecting, enforcing, realizing or obtaining payment of the
         Debenture or for the purpose of preserving any rights of the Lenders
         or any of them or of the Grantor in respect thereof; (c) be
         responsible for any loss occasioned by any sale or other dealing
         with the Debenture or by the retention thereof or failure to sell
         same or otherwise deal therewith; or (d) be bound to protect the
         Debenture from depreciating in value or becoming worthless.

4.6      If Bank of America, N.A. shall at any time resign as Agent, and
         another Person be appointed as a successor to Bank of America, N.A.
         as Agent under and in accordance with the provisions of the Credit
         Agreement, the Agent shall assign the Debenture to its successor,
         and such successor shall become vested with all rights, powers,
         privileges, obligations and duties of the Agent hereunder, and Bank
         of America, N.A. shall be discharged from its duties and obligations
         hereunder except as may be otherwise set forth in the Credit
         Agreement. This provision shall apply, MUTATIS MUTANDIS, to and be
         binding upon each and every successor Agent.

4.7      This  Agreement  shall be binding  upon and inure to the benefit of
         the parties hereto and their respective successors and assigns.

4.8      This Agreement shall be governed by, and interpreted in accordance
         with, the laws of the Province of Quebec and the laws of Canada
         applicable therein, without giving effect to any conflicts of law
         rules thereof. The Grantor hereby irrevocably attorns and submits to
         the non-exclusive jurisdiction of the courts of the Province of
         Quebec with respect to any matter arising under or relating to this
         Agreement, the whole without prejudice to the rights of the Agent or
         the Lenders to bring proceedings against the Grantor in any other
         jurisdiction.

4.9      In the event of any contradiction or inconsistency between the
         provisions of this Agreement and those of the Credit Agreement, the
         provisions of the latter shall prevail to the extent of such
         contradiction or inconsistency.

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                                     - 5 -

IN WITNESS WHEREOF the parties hereto have duly executed this Agreement as of
the date first written above.

                                            SUN MEDIA CORPORATION

                                            Per:  /s/ CLAUDINE TREMBLAY
                                                  ---------------------
                                                  Name: Claudine Tremblay
                                                  Title: Corporate Secretary

                         BANK OF AMERICA, N.A., in its aforementioned
                         capacities

                                            Per:  /s/ ROBERT CAMPBELL
                                                  -------------------
                                                  Name: Robert Campbell
                                                  Title:    Mandatary<PAGE>

                                                                    Exhibit 4.16

DEBENTURE PLEDGE AGREEMENT entered into in Montreal, Quebec, as of this 7th
day of February, 2003

<TABLE>

<S>                               <C>
BY:                               3351611 CANADA INC., a corporation existing
                                  under the laws of Canada, having its
                                  registered office at 300 Viger Avenue,
                                  Montreal, Quebec, H2X 2W4, herein acting
                                  and represented by Claudine Tremblay, duly
                                  authorized as she so declares,

IN FAVOUR OF:                     BANK OF AMERICA, N.A., a Schedule III Bank governed by the
                                  BANK ACT (Canada), having an office at 200 Front Street
                                  West, Suite 2700, Toronto, Ontario M5V 3L2, herein acting
                                  for its own  benefit as a Lender, and as agent and solidary
                                  creditor for the other Lenders as defined in the Credit
                                  Agreement as hereinafter defined (the "LENDERS").

</TABLE>

         WHEREAS 3351611 Canada Inc. (the "GRANTOR") has created and executed
a Debenture dated February 7, 2003 (as amended, restated, renewed, re-issued,
supplemented or modified from time to time, the "DEBENTURE") in favour of the
Agent (as defined below) payable on demand in the principal amount of
$600,000,000 in lawful currency of Canada; and

         WHEREAS the Grantor has agreed to pledge the Debenture to the Agent
(as defined below) as a general and continuing collateral security for the
due and punctual payment, performance and fulfilment of the Obligations (as
defined below).

         NOW THEREFORE THIS AGREEMENT WITNESSETH THAT the parties hereto
agree as follows:

1.       DEFINITIONS AND INTERPRETIVE PROVISIONS

1.1      DEFINITIONS

         Capitalized terms not otherwise defined herein shall have the
         meaning ascribed thereto in the Credit Agreement. The following
         words or expressions whenever used in this debenture pledge
         agreement (the "AGREEMENT") (and in the preamble above which forms
         an integral part of this Agreement) shall have the following
         meanings:

         1.1.1.   "AGENT" means Bank of America, N.A., for its own benefit as
                  a Lender, and as agent and solidary creditor on behalf and
                  for the benefit of the other Lenders, and

<PAGE>
                                      - 2 -

                  includes such other Person, if any, as shall hereafter be
                  appointed as a successor Agent under and in accordance with
                  the provisions of the Credit Agreement;

         1.1.2.   "CREDIT AGREEMENT" means that certain credit agreement
                  dated as of February 7, 2003 among Sun Media Corporation,
                  as Borrower, the financial institutions named on the
                  signature pages thereto, as Lenders, and Bank of America,
                  N.A., as Administrative Agent, as same may subsequently be
                  amended, amended and restated, modified, supplemented or
                  replaced from time to time;

         1.1.3.   "DEBENTURE" has the meaning ascribed to such term in the
                  preamble;

         1.1.4.   "EVENT OF DEFAULT" has the meaning ascribed to such term in
                  the Credit Agreement;

         1.1.5.   "GRANTOR" has the meaning ascribed to such term in the
                  preamble;

         1.1.6.   "OBLIGATIONS" means all obligations of the Grantor owed to
                  the Agent and the Lenders pursuant to the Credit Documents
                  to which it is a party, including without limitation its
                  obligations hereunder; and

         1.1.7.   "PERSON" has the meaning ascribed to such term in the
                  Credit Agreement.

1.2      INTERPRETATION

         This Agreement shall be interpreted in accordance with the following:

         1.2.1.   words denoting the singular include the plural and vice
                  versa, and words denoting any gender include all genders;

         1.2.2.   the division of this Agreement into articles and sections
                  and the insertion of headings are for convenience of
                  reference only and shall not affect the construction or
                  interpretation of this Agreement; and

         1.2.3.   the word "including" shall mean "including without
                  limitation", and "includes" shall mean "includes without
                  limitation".

2.       PLEDGE AND AGENT'S RIGHTS

2.1      As a general and continuing collateral security for the due and
         punctual payment, performance and fulfillment of the Obligations,
         the Grantor hereby hypothecates and pledges the Debenture to the
         Agent subject to and in accordance with the terms hereof. The
         hypothec hereby granted is in the amount of $600,000,000, the whole
         with interest from the date of this Agreement at the rate of
         twenty-five percent (25%) per annum, calculated semi-annually and
         not in advance with interest on overdue interest calculated at the
         same rate and in the same manner.

<PAGE>
                                      - 3 -

2.2      Notwithstanding that the Debenture is payable on demand, the Agent
         may, forthwith and from time to time but only upon the occurrence
         and continuance of an Event of Default, exercise and enforce all the
         rights and remedies available to it under the Debenture (subject to
         Section 4.4 hereof). The rights of the Agent herein stipulated with
         respect to the Debenture shall be in addition to and not exclusive
         of all other rights and remedies which the Agent has or may
         otherwise enforce or exercise.

2.3      The Agent may charge on its own behalf and pay to others reasonable
         sums for services rendered (expressly including legal advice and
         services) in connection with realizing, collecting, selling,
         transferring, delivering and/or obtaining payment for the Debenture
         and may deduct the amount of such charges and payments from the
         proceeds thereof. The balance of such proceeds may be held by the
         Agent in lieu of the Debenture and may, as and when the Agent sees
         fit, be applied on account of such part of the Grantor's Obligations
         as the Agent deems best, without prejudice to the claims of the
         Agent or the Lenders upon the Grantor for any deficiency.

3.       COVENANTS

         The Grantor hereby covenants and agrees as follows:

         3.1      ADDITIONAL SECURITY

         It shall perform all acts and execute all deeds and documents
         (including notices of renewal) necessary to give full effect to the
         security constituted by this Agreement and to ensure that such
         security is at all times fully enforceable against third persons.

         3.2      DELIVERY

         It shall deliver to the Agent any instrument of indebtedness that is
         supplemental to, or in replacement of, the Debenture immediately
         upon issuing same or coming into possession thereof, together with
         any power of attorney, document and confirmation that the Agent may
         reasonably request in order to effect the transfer of such
         instrument, if necessary, into the name of the Agent.

4.       ADDITIONAL PROVISIONS

4.1      If any material provision of this Agreement is, or becomes, illegal,
         invalid or unenforceable, such provision shall be severed from this
         Agreement and be ineffective to the extent only of such illegality,
         invalidity or unenforceability. The remaining provisions hereof
         shall be unaffected by such deletion and shall continue to be valid
         and enforceable.

4.2      The parties acknowledge that the Grantor has agreed to grant to the
         Agent, as FONDE DE POUVOIR for the Lenders, a deed of hypothec in
         the Province of Quebec charging all the movable property of the
         Grantor located in the Province of Quebec and securing the payment
         of the Debenture.

<PAGE>
                                      - 4 -

4.3      The Agent shall not be obliged to exhaust its recourses against the
         Grantor, any other parties or against any other security any of them
         may hold in respect of the Obligations before realizing upon or
         otherwise dealing with the Debenture in such manner as it may
         consider appropriate.

4.4      Notwithstanding that the Debenture is stated to be payable on
         demand, the Agent agrees that it shall not demand payment under the
         Debenture unless an Event of Default has occurred and is continuing.
         The Agent also agrees that it shall only have the right to demand
         payment from the Grantor under the Debenture of an aggregate amount
         which may not in any manner whatsoever be in excess of the aggregate
         amount of the outstanding Obligations in principal, interest and
         costs.

4.5      The Agent may grant extensions or other indulgences, take and give
         up securities, accept compositions, grant releases and discharges
         and otherwise deal with the Grantor and with other parties, sureties
         or securities as it may deem fit, without prejudice to the
         Obligations or the rights of the Lenders or the Agent in respect of
         the Debenture. The Agent shall not (a) be liable or accountable for
         any failure to collect, realize or obtain payment in respect of the
         Debenture; (b) be bound to institute proceedings for the purpose of
         collecting, enforcing, realizing or obtaining payment of the
         Debenture or for the purpose of preserving any rights of the Lenders
         or any of them or of the Grantor in respect thereof; (c) be
         responsible for any loss occasioned by any sale or other dealing
         with the Debenture or by the retention thereof or failure to sell
         same or otherwise deal therewith; or (d) be bound to protect the
         Debenture from depreciating in value or becoming worthless.

4.6      If Bank of America, N.A. shall at any time resign as Agent, and
         another Person be appointed as a successor to Bank of America, N.A.
         as Agent under and in accordance with the provisions of the Credit
         Agreement, the Agent shall assign the Debenture to its successor,
         and such successor shall become vested with all rights, powers,
         privileges, obligations and duties of the Agent hereunder, and Bank
         of America, N.A. shall be discharged from its duties and obligations
         hereunder except as may be otherwise set forth in the Credit
         Agreement. This provision shall apply, MUTATIS MUTANDIS, to and be
         binding upon each and every successor Agent.

4.7      This Agreement shall be binding upon and inure to the benefit of the
         parties hereto and their respective successors and assigns.

4.8      This Agreement shall be governed by, and interpreted in accordance
         with, the laws of the Province of Quebec and the laws of Canada
         applicable therein, without giving effect to any conflicts of law
         rules thereof. The Grantor hereby irrevocably attorns and submits to
         the non-exclusive jurisdiction of the courts of the Province of
         Quebec with respect to any matter arising under or relating to this
         Agreement, the whole without prejudice to the rights of the Agent or
         the Lenders to bring proceedings against the Grantor in any other
         jurisdiction.

4.9      In the event of any contradiction or inconsistency between the
         provisions of this Agreement and those of the Credit Agreement, the
         provisions of the latter shall prevail to the extent of such
         contradiction or inconsistency.

<PAGE>
                                      - 5 -

IN WITNESS WHEREOF the parties hereto have duly executed this Agreement as of
the date first written above.

                                            3351611 CANADA INC.

                                             Per: /s/ CLAUDINE TREMBLAY
                                                  ---------------------
                                                  Name: Claudine Tremblay
                                                  Title: Assistant Secretary

                         BANK OF AMERICA, N.A., in its aforementioned capacities

                                         Per: /s/ ROBERT CAMPBELL
                                              -------------------
                                               Name: Robert Campbell
                                               Title: Mandatary

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