Exhibit 10.1

EXECUTION COPY

SECURITIES PURCHASE AGREEMENT

SECURITIES PURCHASE AGREEMENT, dated as of July 31, 2006 (this "Agreement"), by
and among (a) Oppenheimer Holdings Inc., a Canadian corporation (the "Parent"),
(b) E. A. Viner International Co., a Delaware corporation and a wholly-owned
subsidiary of the Parent (the "Company"), and (c) Canadian Imperial Bank of
Commerce, a bank under the laws of Canada ("CIBC").  The Parent, the Company and
CIBC are collectively referred to herein as the "Parties" and each individually
as a "Party."

W I T N E S S E T H:

WHEREAS

, the Company issued and sold to CIBC (a) on January 6, 2003, the Variable Rate
Exchangeable Debenture due 2013, in the original principal sum of $69,980,828
(the "First Exchangeable Debenture"), and (b) on May 12, 2003, the Second
Variable Rate Exchangeable Debenture due 2013, in the original principal sum of
$90,841,572 (the "Second Exchangeable Debenture" and, together with the First
Exchangeable Debenture, the "Debentures"), as partial consideration in respect
of the Parent's acquisition from CIBC of the United States Private Client and
Asset Management Divisions of CIBC World Markets Corp. (collectively, the "World
Markets Acquisition");

WHEREAS, upon the terms set forth in this Agreement, on the Initial Closing Date
(as defined below), the Company desires to purchase from CIBC, and CIBC desires
to sell to the Company, all right, title and interest of CIBC in and to (a)
$49,980,828 aggregate principal amount of the First Exchangeable Debenture and
(b) all outstanding aggregate principal amounts under the Second Exchangeable
Debenture (collectively, the "Initial Purchase Debentures"), in each case, plus
accrued and unpaid interest thereon up to and including the Initial Closing
Date;

WHEREAS, upon the terms and subject to the conditions set forth in this
Agreement, on the Subsequent Closing Date (as defined below), the Company
desires to purchase from CIBC, and CIBC desires to sell to the Company, all
right, title and interest of CIBC in and to $20,000,000 aggregate principal
amount of the First Exchangeable Debenture (the "Subsequent Purchase
Debenture"), plus accrued and unpaid interest thereon up to and including the
Subsequent Closing Date; and

WHEREAS, upon the terms and subject to the conditions set forth in this
Agreement, the Parent, the Company and CIBC desire to irrevocably terminate in
all respects as of the Subsequent Closing (as defined below), (a) the
Stakeholders Agreement, dated as of December 9, 2002, by and among the Parent,
CIBC and the Parent Stockholders (as defined below) (the "Stakeholders
Agreement") and (b) the Registration Rights Agreement, dated January 2, 2003, by
and between the Parent and CIBC (the "Registration Rights Agreement"), in each
case, entered into in connection with the World Markets Acquisition.

588275.26-New York Server 6A - MSW

NOW, THEREFORE, in consideration of the foregoing and of the representations,
warranties, covenants, conditions and agreements contained herein, and intending
to be legally bound hereby, the Parties hereby agree as follows:

SECTION 1.

Definitions.  As used herein, the following terms shall have the following
respective meanings:

(a)

"Affiliate" shall mean any Person who or which, directly or indirectly, through
one or more intermediaries, controls or is controlled by, or is under common
control with, any specified Person; provided, that in no event shall CIBC be
deemed an Affiliate of the Company or any of its Affiliates solely by reason of
its ownership of the Debentures.  For the purposes of this definition, "control"
(including, with correlative meanings, the terms "controlling," "controlled by"
and "under common control with") shall mean, with respect to any Person, the
possession, directly or indirectly, of the power to direct or cause the
direction of the management and policies of such Person, whether through the
ownership of debt or equity securities or other debt or equity ownership
interest, by contract or otherwise.

(b)

"Agreement" shall have the meaning ascribed to it in the preamble hereto.

(c)

"CIBC" shall have the meaning ascribed to it in the preamble hereto.

(d)

"Class A Shares" shall mean the Class A non-voting shares of the Parent.

(e)

"Class B Shares" shall mean the Class B voting shares of the Parent.

(f)

"Commitment Letter" shall mean the commitment letter (together with the fee
letter incorporated therein by reference) from Morgan Stanley Senior Funding,
Inc. with respect to the debt financing of the Company for the transactions
contemplated hereby, a copy of which has previously been provided to CIBC in
connection with the Letter of Intent.

(g)

"Company" shall have the meaning ascribed to it in the preamble hereto.

(h)

"Debentures" shall have the meaning ascribed to it in the recitals hereto.

(i)

"FIRPTA Certificate" shall mean a certificate of the Company, in a form
reasonably acceptable to CIBC, issued pursuant to and in compliance with
Treasury Regulation section 1.1445-2(c)(3) and section 1.897-2(h) (including the
making of any required filings with the Internal Revenue Service), certifying
that an interest in

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the Company is not a United States real property interest within the meaning of
Treasury Section 897(c) of the Internal Revenue Code.

(j)

"First Exchangeable Debenture" shall have the meaning ascribed to it in the
recitals hereto.

(k)

"Governmental Entity" shall mean any court, administrative agency or commission,
government, self-regulatory organization, federal, state, provincial, municipal,
local or other governmental entity, authority or instrumentality, whether
domestic or foreign, or any court, tribunal or arbitrator.

(l)

"Initial Closing" shall have the meaning ascribed to it in Section 4(a)(i).

(m)

"Initial Closing Date" shall mean the date upon which the Initial Closing
occurs.

(n)

"Initial Purchase" shall have the meaning ascribed to it in Section 4(a)(i).

(o)

"Initial Purchase Debentures" shall have the meaning ascribed to it in the
recitals hereto.

(p)

"Initial Purchase Price" shall have the meaning ascribed to it in Section
3(a)(i).

(q)

"Letter of Intent" shall mean the letter of intent and accompanying term sheet,
dated as of June 16, 2006, by and between the Parent and CIBC.

(r)

"Lowenthal Group" shall mean the following stockholders of Class B Shares:  (i)
Albert G. Lowenthal, (ii) Phase II Financial L.P., a New York limited
partnership, (iii) Phase II Financial Limited, an Ontario corporation, and (iv)
The Albert G. Lowenthal Foundation.

(s)

"NYSE" shall mean the New York Stock Exchange.

(t)

"NYSE Approvals" shall mean all required approvals, consents and authorizations
of, or notifications to, the NYSE, including approval from the NYSE in
connection with any capital withdrawals from Oppenheimer in connection with the
transactions contemplated hereby.

(u)

"Oppenheimer" shall mean Oppenheimer & Co., Inc., a New York corporation and a
wholly-owned broker-dealer subsidiary of the Parent.

(v)

"Parent" shall have the meaning ascribed to it in the preamble hereto.

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(w)

"Parent Sale" shall mean (i) the consolidation, merger, recapitalization or
similar business combination of the Parent or any other transaction or series of
transactions, including any tender offer or exchange offer, whereby any "person"
or related "group" of "persons" (as such terms are used in Section 13(d) and
14(d)(2) of the Securities Exchange Act of 1934, as amended (the "Exchange
Act")) (other than any of the Parent Stockholders or any of their respective
Related Persons or any of the Parent's wholly-owned subsidiaries), directly or
indirectly acquires beneficial ownership (within the meaning of Rule 13d-3 under
the Exchange Act), of more than fifty percent (50%) of the issued and
outstanding Class A Shares and the Class B Shares, or of securities of the
Parent possessing more than fifty percent (50%) of the total combined voting
power of the Parent's securities outstanding, (ii) the voluntary or involuntary
sale, assignment, transfer, conveyance or other disposition by the Parent,
directly or indirectly, in one or a series of related transactions, of all or
substantially all of the assets of the Parent to any "person" (as defined above)
(other than any of the Parent Stockholders or any of their respective Related
Persons or any of the Parent's wholly-owned subsidiaries), (iii) any transaction
or series of related transactions that constitute a going private "Rule 13e-3
transaction" (within the meaning of Rule 13e-3 under the Exchange Act) by one or
more members of the Lowenthal Group as a result of which the Lowenthal Group or
any Related Person of the Lowenthal Group has beneficial ownership of all or
substantially all of the outstanding equity securities of  the Parent and the
Parent is no longer a reporting company under the Exchange Act or (iv) any
public tender offer or exchange offer pursuant to Rule 13e-4 under the Exchange
Act by the Lowenthal Group or any member or Related Person thereof pursuant to
which the Lowenthal Group acquires all or substantially all of the outstanding
equity securities of  the Parent.

(x)

"Parent Sale Closing" shall have the meaning ascribed to it in Section 8(e).

(y)

"Parent Sale Initiation" shall mean (i) the issuance by, or on behalf of, the
Parent, of a press release announcing a Parent Sale and/or (ii) the execution
and delivery by the Parent or any of its Affiliates of any written agreement in
principle, letter of intent or definitive agreement containing pricing and other
material terms with respect to a Parent Sale.

(z)

"Parent Stockholders" shall mean the following stockholders of Class B Shares
that are party to the Stakeholders Agreement:  (i) Albert G. Lowenthal, (ii)
Phase II Financial L.P., a New York limited partnership, (iii) Phase II
Financial Limited, an Ontario corporation, (iv) The Albert G. Lowenthal
Foundation, (v) Olga Roberts and (vi) Elka Estates Limited, an Ontario
corporation.

(aa)

"Party" and "Parties" shall have the respective meanings ascribed to them in the
preamble hereto.

(bb)

"Per Share Purchase Price" shall mean either (x) in connection with a Parent
Sale of the type described in clause (i), (iii) or (iv) of the definition of

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"Parent Sale," the average price per share paid for each of the then outstanding
Class A Shares and Class B Shares, on a fully-diluted basis, or (y) in
connection with a Parent Sale of the type described in clause (ii) of the
definition of "Parent Sale," an amount equal to the book value per share of the
then outstanding Class A Shares and Class B Shares, on a fully-diluted basis, as
set forth in the books and records of the Parent immediately following such
Parent Sale.

(cc)

"Person" shall mean any individual, corporation, partnership, association,
trust, limited liability company or other entity or organization, including a
government or political subdivision or an agency or instrumentality thereof.

(dd)

"Registration Rights Agreement" shall have the meaning ascribed to it in the
recitals hereto.

(ee)

"Related Person" shall mean, with respect to any Person, (i) any controlling
stockholder or a majority (or more) owned subsidiary of such Person or, in the
case of an individual, any spouse or immediate family member of such Person, any
trust created for the benefit of such individual or such individual's estate,
executor, administrator, committee or beneficiaries or (ii) any trust,
corporation, partnership or other entity, the beneficiaries, stockholders,
partners, owners or Persons beneficially holding a majority (or more)
controlling interest of which consist of such subject Person and/or such other
Persons referred to in clause (i) hereof.

(ff)

"Second Exchangeable Debenture" shall have the meaning ascribed to it in the
recitals hereto.

(gg)

"Stakeholders Agreement" shall have the meaning ascribed to it in the recitals
hereto.

(hh)

"Stock Price" shall mean $27.13, subject to customary adjustments for stock
splits, combinations, extraordinary dividends or distributions,
reclassifications, recapitalizations and similar transactions.

(ii)

"Subsequent Closing" shall have the meaning ascribed to it in Section 4(a)(ii).

(jj)

"Subsequent Closing Date" shall mean the date upon which the Subsequent Closing
occurs.

(kk)

"Subsequent Closing Deadline" shall have the meaning ascribed to it in Section
4(a)(ii).

(ll)

"Subsequent Purchase" shall have the meaning ascribed to it in Section 4(a)(ii).

(mm)

"Subsequent Purchase Debenture" shall have the meaning ascribed to it in the
recitals hereto.

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(nn)

"Subsequent Purchase Price" shall have the meaning ascribed to it in Section
3(a)(ii).

(oo)

"World Markets Acquisition" shall have the meaning ascribed to it in the
recitals hereto.

(pp)

"Zero Coupon Note shall have the meaning ascribed to it in Section 2.

SECTION 2.

Consent to the Financing.  Notwithstanding anything to the contrary in the
Debentures or in the Second Amended and Restated Promissory Note, dated April
30, 2003 (the "Zero Coupon Note"), made by Viner Finance Inc., a wholly-owned
subsidiary of the Company, in connection with the World Markets Acquisition for
the benefit of CIBC World Markets Corp., a subsidiary of CIBC, CIBC, for so long
as any portion of the Debentures (including the Subsequent Purchase Debenture)
is owned by CIBC, agrees and consents that the incurrence of indebtedness
pursuant to the financing of the Company for the transactions contemplated by
the Commitment Letter and the entering into of any agreements or instruments in
connection therewith by the Parent, the Company or any of their respective
Affiliates shall be permitted indebtedness under the Debentures and the Zero
Coupon Note and shall not be deemed to be in violation of the terms of the
Debentures or the Zero Coupon Note in any respect.  

SECTION 3.

Purchase of the Debentures.

(a)

Purchase and Sale of the Debentures.  

(i)

At the Initial Closing, upon the terms set forth in this Agreement, the Company
agrees to purchase and acquire from CIBC, and CIBC hereby agrees to sell,
assign, transfer and deliver to the Company, the Initial Purchase Debentures for
the aggregate cash purchase price of $141,307,454.93 (the "Initial Purchase
Price").

(ii)

At the Subsequent Closing, upon the terms and subject to the conditions set
forth in this Agreement, the Company agrees to purchase and acquire from CIBC,
and CIBC hereby agrees to sell, assign, transfer and deliver to the Company, the
Subsequent Purchase Debenture for the aggregate cash purchase price of an amount
equal to $20,000,000, plus accrued and unpaid interest thereon up to and
including the Subsequent Closing Date (the "Subsequent Purchase Price").

(iii)

If the Subsequent Purchase Debenture has not been purchased by the Company from
CIBC as a result of not meeting the conditions of  closing prior to the
Subsequent Closing Deadline, notwithstanding anything to the contrary in the
Subsequent Purchase Debenture, the Parties agree that, from and after the
Subsequent Closing Deadline through January 15, 2007, upon ten (10) days notice
by the Parent to CIBC, the Company shall have the right to purchase and acquire
from CIBC, and CIBC shall sell, assign, transfer and deliver to the Company, the
Subsequent Purchase Debenture.

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(b)

Purchase Price.  

(i)

At the Initial Closing, upon the terms set forth in this Agreement, as
consideration in full for the Initial Purchase Debentures, the Company shall
cause the Initial Purchase Price, net of the applicable tax withholding amount
of $48,505.49, to be paid to CIBC by wire transfer of immediately available
funds to an account designated by CIBC prior to the Initial Closing Date.

(ii)

At the Subsequent Closing, upon the terms and subject to the conditions set
forth in this Agreement, as consideration in full for the Subsequent Purchase
Debenture, the Company shall cause the Subsequent Purchase Price, net of any
applicable tax withholding amounts, to be paid to CIBC by wire transfer of
immediately available funds to an account designated by CIBC prior to the
Subsequent Closing Date.

(c)

Debentures.  

(i)

At the Initial Closing, upon the terms set forth in this Agreement, (A) CIBC
shall deliver to the Company the original certificates evidencing the
Debentures, such certificates endorsed in blank by an effective endorsement,
against payment of the Initial Purchase Price for the Initial Purchase
Debentures and (B) the Company shall issue to CIBC at the Initial Closing an
original certificate evidencing the Subsequent Purchase Debenture.

(ii)

At the Subsequent Closing, upon the terms and subject to the conditions set
forth in this Agreement, CIBC shall deliver to the Company the original
certificate evidencing the Subsequent Purchase Debenture, such certificate
endorsed in blank by an effective endorsement, against payment of the Subsequent
Purchase Price therefor.  

SECTION 4.

The Closing.

(a)

Closing.  

(i)

The initial closing  (the "Initial Closing") with respect to the transactions
contemplated hereby in connection with, among other things, the purchase and
sale of the Initial Purchase Debentures and all transactions related thereto
(collectively, the "Initial Purchase") shall take place at the offices of
Skadden, Arps, Slate, Meagher & Flom LLP, Four Times Square, New York, New York
10036 at 10:00 a.m. on the date hereof, or at such other location as the Parties
shall agree contemporaneous with the execution and delivery of this Agreement.

(ii)

The subsequent closing (the "Subsequent Closing") with respect to the
transactions contemplated hereby in connection with, among other things, the
purchase and sale of the Subsequent Purchase Debenture and all transactions
related thereto (collectively, the "Subsequent Purchase") shall take place, upon
ten (10) days notice by the Parent to CIBC, at the offices of Skadden, Arps,
Slate, Meagher &

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Flom LLP, Four Times Square, New York, New York 10036 at 10:00 a.m. on a date
that is no later than ninety (90) days following the Initial Closing Date (the
"Subsequent Closing Deadline"), or at such other location or date as the Parties
shall agree, following the satisfaction or waiver of each of the conditions set
forth herein.

(b)

Initial Closing Deliveries.

(i)

At or prior to the Initial Closing, the Parent or the Company shall deliver, or
cause one or more of its respective Affiliates to deliver, to CIBC:

(A)

copies of all necessary corporate approvals on the part of the Company and the
Parent in connection with this Agreement and the consummation of the Initial
Purchase; and

(B)

copies or other evidence, if any, of any NYSE Approvals related to the Initial
Purchase.

(ii)

At the Initial Closing, the Parent or the Company shall deliver, or cause one or
more of its respective Affiliates to deliver, to CIBC:

(A)

the Initial Purchase Price as provided in Section 3(b)(i);

(B)

the original certificate evidencing the Subsequent Purchase Debenture, as
provided in Section 3(c)(i)(B); and

(C)

the duly executed FIRPTA Certificate related to the Initial Purchase; and

(D)

such other documents and instruments as counsel for the Parent, the Company and
CIBC mutually agree to be reasonably necessary to consummate the Initial
Purchase.

(iii)

At or prior to the Initial Closing, CIBC shall deliver, or cause one or more of
its Affiliates to deliver, to the Company, copies of all necessary corporate
approvals on the part of CIBC in connection with this Agreement and the
consummation of the Initial Purchase.

(iv)

At the Initial Closing, CIBC shall deliver, or cause one or more of its
Affiliates to deliver, to the Company:

(A)

the original certificates evidencing the Debentures, such certificates endorsed
in blank by an effective endorsement, as provided in Section 3(c)(i)(A); and

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(B)

such other documents and instruments as counsel for the Parent, the Company and
CIBC mutually agree to be reasonably necessary to consummate the Initial
Purchase.

(c)

Subsequent Closing Deliveries.

(i)

At or prior to the Subsequent Closing, the Parent or the Company shall deliver,
or cause one or more of its respective Affiliates to deliver, to CIBC:

(A)

copies of all necessary corporate approvals on the part of the Company and the
Parent in connection with this Agreement and the consummation of the Subsequent
Purchase (such copies to be provided only to the extent that the approvals
described in Section 4(b)(i)(A) do not already cover the Subsequent Purchase);
and

(B)

copies or other evidence, if any, of any NYSE Approvals related to the
Subsequent Purchase.

(ii)

At the Subsequent Closing, the Parent or the Company shall deliver, or cause one
or more of its respective Affiliates to deliver, to CIBC:

(A)

the Subsequent Purchase Price as provided in Section 3(b)(ii);

(B)

an amount in cash equal to accrued but unpaid fees required to be paid to CIBC
hereunder pursuant to Section 9, if any;

(C)

the duly executed FIRPTA Certificate related to the Subsequent Purchase; and

(D)

such other documents and instruments as counsel for the Parent, the Company and
CIBC mutually agree to be reasonably necessary to consummate the Subsequent
Purchase.

(iii)

At or prior to the Subsequent Closing, CIBC shall deliver, or cause one or more
of its Affiliates to deliver, to the Company, copies of all necessary corporate
approvals on the part of CIBC in connection with this Agreement and the
consummation of the Subsequent Purchase (such copies to be provided only to the
extent that the approvals described in Section 4(b)(iii) do not already cover
the Subsequent Purchase).

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(iv)

At the Subsequent Closing, CIBC shall deliver, or cause one or more of its
Affiliates to deliver, to the Company:

(A)

the original certificate evidencing the Subsequent Purchase Debenture, such
certificate endorsed in blank by an effective endorsement, as provided in
Section 3(c)(ii); and

(B)

such other documents and instruments as counsel for the Parent, the Company and
CIBC mutually agree to be reasonably necessary to consummate the Subsequent
Purchase.

SECTION 5.

Termination of Certain Agreements.  

(a)

Stakeholders Agreement.  Each of the Parties hereby agrees that effective upon
the consummation of the Subsequent Closing, the Stakeholders Agreement shall
irrevocably terminate in its entirety and that the Stakeholders Agreement shall
have no further force or effect; provided, that the Parent shall cause each of
the Parent Stockholders to execute a separate agreement which provides for the
termination of the Stakeholders Agreement as of the Subsequent Closing Date by
each Parent Stockholder.

(b)

Registration Rights Agreement.  Each of the Parent and CIBC hereby agrees that
effective upon the consummation of the Subsequent Closing, the Registration
Rights Agreement shall irrevocably terminate in its entirety and that the
Registration Rights Agreement shall have no further force or effect.  

(c)

Letter of Intent.  Each of the Parent and CIBC hereby agrees that effective upon
the consummation of the Initial Closing, the Letter of Intent shall irrevocably
terminate in its entirety and that the Letter of Intent shall have no further
force or effect.

(d)

Other Agreements.  Except as set forth in Section 5(a), Section 5(b) and Section
8(a), the Parties hereby agree that neither this Agreement nor the consummation
of the transactions contemplated hereby shall be deemed to terminate or modify
in any respect any agreement, obligation or commitment or commercial arrangement
between the Parent, the Company and their respective Affiliates, on the one
hand, and CIBC and its respective Affiliates, on the other hand.  The execution
of this Agreement and the consummation of the transactions contemplated hereby
shall not constitute a waiver, release or discharge by any of the Parties or any
of their respective present or former Affiliates of any past, pending or future
losses, claims, liabilities, controversies, demands, actions, complaints, suits
or causes of action of any kind whatsoever, in law or in equity, arising out of
or relating to any agreement, obligation or commitment between the Parent, the
Company and their respective Affiliates, on the one hand, and CIBC and its
respective Affiliates, on the other hand (other than the

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Stakeholders Agreement, Registration Rights Agreement and Letter of Intent,
which are terminated hereunder).

SECTION 6.

Representations and Warranties of the Company and the Parent.  The Company and
the Parent, jointly and severally, hereby represent and warrant to CIBC as of
the date of this Agreement, as of the Initial Closing Date and as of the
Subsequent Closing Date, as follows:

(a)

Organization; Authority; Enforceability.  

(i)

The Company is a corporation duly organized and validly subsisting under the
laws of the State of Delaware and has all requisite corporate power and
authority to enter into this Agreement and to consummate the transactions
contemplated hereby.  The Parent is a corporation duly organized and validly
subsisting under the laws of Ontario, Canada and has all requisite corporate
power and authority to enter into this Agreement and to consummate the
transactions contemplated hereby.  The execution, delivery and performance of
this Agreement and the consummation of the transactions contemplated hereby have
been duly authorized by all necessary corporate action, including any required
stockholder approval, if any, on the part of each of the Company and the Parent.
 This Agreement has been duly executed and delivered by each of the Company and
the Parent and constitutes a valid and binding obligation of each of the Company
and the Parent, enforceable against each of the Company and the Parent in
accordance with its terms, except that such enforcement may be subject to
bankruptcy, insolvency, reorganization, moratorium or other similar laws now or
hereafter in effect relating to creditors' rights.

(ii)

The execution and delivery of the Subsequent Purchase Debenture have been duly
authorized by all necessary corporate action on the part of each of the Company
and the Parent.  The Subsequent Purchase Debenture has been duly executed and
delivered by each of the Company and the Parent and constitutes a valid and
binding obligation of each of the Company and the Parent, enforceable against
each of the Company and the Parent in accordance with its terms, except that
such enforcement may be subject to bankruptcy, insolvency, reorganization,
moratorium or other similar laws now or hereafter in effect relating to
creditors' rights.

(b)

No Violation; Consents and Approvals.  The execution and delivery of this
Agreement and the Subsequent Purchase Agreement do not, and the consummation of
the transactions contemplated hereby and compliance with the terms hereof and
thereof shall not, conflict with, or result in any violation of or default
under, (i) any provision of the articles of incorporation or by-laws (or similar
organizational documents) of either the Company or the Parent, (ii) any
judgment, order or decree, or material statute, law, ordinance, rule or
regulation applicable to either the Company or the Parent or the property or
assets of either the Company or the Parent or (iii) any note, bond, mortgage,
indenture, license, agreement, lease or other instrument or obligation to which
either the Company or the Parent is a party or by which either the Company or
the Parent may be bound or affected or to which any of its respective assets may
be subject.  Except for the NYSE Approvals, no consent, approval, order or
authorization of, or

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registration, declaration or filing with, or notification to, any Governmental
Entity or any third party is required to be obtained or made by or with respect
to the Company, the Parent or any of their respective Affiliates in connection
with the execution and delivery of this Agreement or the consummation by either
the Company or the Parent of the transactions contemplated hereby.

(c)

No Litigation.  There is no action, suit, investigation, arbitration or
proceeding, including any regulatory proceeding, pending or, to the knowledge of
the Company or the Parent, currently threatened against the Company or the
Parent that questions the validity of this Agreement or the right of the Company
or the Parent to enter into this Agreement or to consummate the transactions
contemplated hereby.

(d)

Solvency.  Following the Initial Closing and the Subsequent Closing, after
giving effect to the transactions contemplated by this Agreement, each of the
Parent and the Company and their respective subsidiaries shall (i) have assets,
both at a fair valuation and a present fair salable value, that exceeds its
liabilities, including contingent, subordinated, unmatured, unliquidated and
disputed liabilities, (ii) have sufficient capital with which to conduct its
business and (iii) not have incurred debts beyond its ability to pay such debts
as they mature.  For purposes of this representation, "debt" shall mean any
liability on a claim, and "claim" shall mean (i) a right to payment, whether or
not such right is reduced to judgment, liquidated, unliquidated, fixed,
contingent, matured, unmatured, disputed, undisputed, legal, equitable, secured
or unsecured or (ii) a right to an equitable remedy for breach of performance to
the extent such breach gives rise to a payment, whether or not such right to an
equitable remedy is reduced to judgment, fixed, contingent, matured, unmatured,
disputed, undisputed, secured or unsecured.  With respect to any such contingent
liabilities, such liabilities shall be computed at the amount which, in light of
all of the facts and circumstances existing at the time, represents the amount
which can reasonably be expected to become an actual or matured liability.

(e)

NYSE Approvals.  Each of Parent and the Company has obtained all required NYSE
Approvals.

(f)

No Parent Sale Initiation.  Since the date of the Letter of Intent, no Parent
Sale Initiation has occurred as of the Initial Closing Date.

(g)

Brokers.  Except in connection with the financing of the Company for the
transactions contemplated hereby, neither the Company, the Parent nor any of
their respective Affiliates has any liability or obligation to pay any fees or
commissions to any investment banker, broker, finder or placement agent with
respect to the transactions contemplated by this Agreement.

SECTION 7.

Representations and Warranties of CIBC.  CIBC hereby represents and warrants to
each of the Parent and the Company as of the date of this Agreement, as of the
Initial Closing Date and as of the Subsequent Closing Date, as follows:

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(a)

Organization; Authority; Enforceability.  CIBC is a bank duly organized and
validly existing under the laws of Canada and has all requisite corporate or
other power and authority to enter into this Agreement and to consummate the
transactions contemplated hereby.  The execution, delivery and performance of
this Agreement and the consummation of the transactions contemplated hereby have
been duly authorized by all necessary corporate action, including any required
stockholder approval, if any, on the part of CIBC.  This Agreement has been duly
executed and delivered by CIBC and constitutes a valid and binding obligation of
CIBC, enforceable against CIBC in accordance with its terms, except that such
enforcement may be subject to bankruptcy, insolvency, reorganization, moratorium
or other similar laws now or hereafter in effect relating to creditors' rights.

(b)

No Violation; Consents and Approvals.  The execution and delivery of this
Agreement  do not, and the consummation of the transactions contemplated hereby
and compliance with the terms hereof shall not, conflict with, or result in any
violation of or default under, (a) any provision of the articles of
incorporation or by-laws (or similar organizational documents) of CIBC, (b) any
judgment, order or decree, or material statute, law, ordinance, rule or
regulation applicable to CIBC or the property or assets of CIBC or (c) any note,
bond, mortgage, indenture, license, agreement, lease or other instrument or
obligation to which CIBC is a party or by which CIBC may be bound or affected or
to which any of its respective assets may be subject.  No consent, approval,
order or authorization of, or registration, declaration or filing with, or
notification to, any Governmental Entity or any third party is required to be
obtained or made by or with respect to CIBC or any of its Affiliates in
connection with the execution and delivery of this Agreement or the consummation
by CIBC of the transactions contemplated hereby.

(c)

No Litigation.  There is no action, suit, investigation, arbitration or
proceeding, including any regulatory proceeding, pending or, to the knowledge of
CIBC, currently threatened against CIBC that questions the validity of this
Agreement or the right of CIBC to enter into this Agreement or to consummate the
transactions contemplated hereby.

(d)

Title to the Debentures.  

(i)

CIBC now is and, at the time of delivery of the Initial Purchase Debentures and
the Subsequent Purchase Debenture, as applicable, shall be the lawful owner of
the Initial Purchase Debentures and the Subsequent Purchase Debenture, as
applicable, to be sold by CIBC pursuant to this Agreement free and clear of any
claim, lien, encumbrance, security interest, community property right,
restriction on transfer, other than any restrictions on transfer imposed under
applicable securities laws or pursuant to the terms of the Initial Purchase
Debentures and the Subsequent Purchase Debenture, as applicable, or other defect
in title.

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(ii)

Assuming that the Company has no notice of any adverse claims with respect to
the certificates evidencing the Debentures and the Subsequent Purchase
Debenture, as applicable, then, upon delivery to the Company of such
certificates indorsed in blank by an effective endorsement, the Company shall
acquire such certificates (and the Debentures and the Subsequent Purchase
Debenture, as applicable, represented thereby) free of any adverse claims under
Section 8-303 of the Uniform Commercial Code as in effect on the date hereof in
the State of New York, other than any restrictions or transfer imposed under
applicable securities laws.

(e)

Investment Purpose.  CIBC is acquiring the Subsequent Purchase Debenture for its
own account for the purpose of investment and not with a view to or for sale in
connection with any distribution thereof.

(f)

Brokers.  Neither CIBC nor any of its Affiliates has any liability or obligation
to pay any fees or commissions to any investment banker, broker, finder or
placement agent with respect to the transactions contemplated by this Agreement.

SECTION 8.

Covenants of the Parties.  

(a)

Conduct of Business.  Notwithstanding any agreements, arrangements or
understanding between the Parties, the Parties acknowledge and agree that
following the Initial Closing, (i) the Parent, the Parent Stockholders, the
Company and their respective Affiliates shall not be restricted by any agreement
with CIBC or any of its Affiliates in any manner from engaging in or conducting,
directly or indirectly, any broker-dealer business in Canada, and (ii) CIBC and
its Affiliates shall not be restricted by any agreement with the Parent, the
Parent Stockholders, the Company or any of their respective Affiliates in any
manner from engaging in or conducting, directly or indirectly, any broker-dealer
business in the United States, in each case, subject to any applicable law, rule
or regulation.

(b)

Public Disclosure.  The Parties shall not issue any report, statement or press
release or otherwise make any public statement with respect to this Agreement or
the transactions contemplated hereby, without prior consultation with and
approval of the other Parties, except as may be required by law or stock
exchange rule or may otherwise be necessary in order to discharge its disclosure
obligations, in which case such Party nevertheless shall advise the other
Parties and discuss the contents of the disclosure before issuing any such
report, statement or press release.  

(c)

Expenses.  Whether or not the transactions contemplated hereby are consummated
pursuant hereto, CIBC, on the one hand, and the Company and the Parent, on the
other hand, shall each pay all of their own fees and expenses in connection with
or in anticipation of this Agreement and the consummation of the transactions
contemplated hereby.

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(d)

Confidentiality.  The existence and terms of this Agreement and the Letter of
Intent and the transactions contemplated hereby and thereby and any and all
information obtained by the Parties pursuant to this Agreement, the Letter of
Intent or otherwise in connection with the transactions contemplated hereby or
by the Letter of Intent, including the Commitment Letter, shall be treated as
confidential and shall not be disclosed, directly or indirectly, to any other
Person, except that nothing herein shall prevent any of the Parties from
disclosing any such information (i) pursuant to the order of any court or
administrative agency or in any pending legal or administrative proceeding, or
otherwise as required by applicable law (in which case such Party shall inform
the other Parties, to the extent permitted by law, promptly thereof), (ii) upon
the request or demand of any regulatory authority having jurisdiction over any
Party (in which case such Party shall inform the other Parties promptly
thereof), (iii) to the extent that such information becomes publicly available
other than by reason of disclosure by any Party in violation of this Section
8(d) or (iv) to the each of the Parties' respective Affiliates and to each of
the Parties' and the Parties' Affiliates' respective officers, directors,
employees, attorneys, accountants, advisors and financing sources on a
confidential and need-to-know basis.

(e)

Parent Sale.  If any Parent Sale Initiation occurs at any time during the period
from and after the Initial Closing Date and on or prior to December 31, 2007 in
connection with a Parent Sale for a Per Share Purchase Price greater than the
Stock Price, then the Company shall pay to CIBC upon the date on which such
Parent Sale has formally closed (the "Parent Sale Closing"), so long as such
Parent Sale Closing occurs prior to the later of (i) twelve (12) months
following such Parent Sale Initiation or (ii) December 31, 2007, an amount equal
to the product of the number of Class A Shares that would have been issuable
upon an exchange of the Debentures that have been purchased from CIBC by the
Company as of such Parent Sale Closing pursuant to Section 5 of each the
Debentures at the exchange price of $23.20 and:

(i)

If the Parent Sale Initiation occurs six (6) months or less after the Initial
Closing Date, 80% of the amount representing the difference between the Per
Share Purchase Price and the Stock Price;

(ii)

If the Parent Sale Initiation occurs more than six (6) months but not more than
twelve (12) months after the Initial Closing Date, an amount equal to 60% of the
amount representing the difference between the Per Share Purchase Price and the
Stock Price; and

(iii)

If the Parent Sale Initiation occurs more than twelve (12) months after the
Initial Closing Date, an amount equal to 40% of the amount representing the
difference between the Per Share Purchase Price and the Stock Price;

provided, that the Parent and the Company hereby agree that in no event shall
any Parent Sale Closing occur prior to the Subsequent Closing Deadline unless
the Subsequent

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Closing has already been consummated prior to such Parent Sale Closing or is
consummated contemporaneously with such Parent Sale Closing.

Any payments described in this Section 8(e) shall be made by the Company as
promptly as practicable following the Parent Sale Closing, but in no event later
than five (5) business days following such Parent Sale Closing, to CIBC by wire
transfer of immediately available funds to an account designated by CIBC prior
to such payment.  For the avoidance of doubt, any discussions, negotiations or
due diligence investigation in connection with any proposed Parent Sale that
precede a Parent Sale shall not constitute a Parent Sale Initiation and shall
not by itself trigger the provisions of this Section 8(e).

(f)

NYSE Approvals.  The Parent and the Company shall use their respective best
efforts to obtain all required NYSE Approvals.

(g)

Subsequent Purchase.  The Company shall use its best efforts to cause the
Subsequent Purchase to occur on or before the Subsequent Closing Deadline or as
soon as practicable thereafter.

SECTION 9.

Fees.  

(a)

Fees. As consideration for CIBC agreeing to sell the Subsequent Purchase
Debenture to the Company on the Subsequent Closing Date, the Company and/or the
Parent hereby agrees to pay, or cause to be paid, to CIBC, in addition to any
interest payments due and payable by the Company to CIBC pursuant to Section 1
of the Subsequent Purchase Debenture, the following fees:

(i)

An amount equal to 2 ½% per annum on the aggregate principal amount of the
Subsequent Purchase Debenture from and after the Initial Closing Date until the
earlier of (x) the Subsequent Closing or (y) the Subsequent Closing Deadline;

(ii)

If the Subsequent Closing has not occurred on or before the Subsequent Closing
Deadline, an amount equal to 4% per annum on the aggregate principal amount of
the Subsequent Purchase Debenture from and after the Subsequent Closing Deadline
until the earlier of (x) the date on which the Subsequent Purchase Debenture is
repurchased by the Company from CIBC pursuant to Section 3(a)(iii) or (y)
December 31, 2006; and

(iii)

If the Subsequent Purchase Debenture is not repurchased by the Company from CIBC
pursuant to Section 3(a)(iii) on or prior to December 31, 2006, an amount equal
to 3% per annum on the aggregate principal amount of the Subsequent Purchase
Debenture from and after December 31, 2006 until the earlier of (x) the date on
which the Subsequent Purchase Debenture is repurchased by the Company from CIBC
pursuant to Section 3(a)(iii) or (y) January 2, 2013.

(b)

Payment of Fees.  Any accrued but unpaid fees due to CIBC pursuant to this
Section 9 shall be payable to CIBC on the earlier of (i) the Subsequent

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Closing Date or (ii) the last business day of each June and December following
the initiation of such fee payment and shall be computed and paid in the same
manner as interest is paid on the Subsequent Purchase Debenture pursuant to
Section 1 thereof.

SECTION 10.

Conditions to Obligations of the Parties.  The respective obligations of each of
the Parties to consummate the Subsequent Purchase are subject to the fulfillment
at or prior to the Subsequent Closing of each of the following conditions (any
or all of which may be waived in whole or in part by the Parties):

(a)

No Violation of Orders, Injunction or Regulatory Actions.  No preliminary or
permanent injunction or other order issued by any Governmental Entity, no
statute, rule or regulation, promulgated or enacted by any Governmental Entity,
and no judgment, order, injunction or decree issued by a court of competent
jurisdiction that prevents, restrains or prohibits the consummation of the
transactions contemplated by this Agreement shall be in effect.

(b)

Receipt of NYSE Approvals.  All required NYSE Approvals shall have been received
or made by the Parent and the Company.

SECTION 11.

Further Assurances.  Each of the Parties shall take or cause to be taken such
further actions, execute, acknowledge, seal and deliver or cause to be executed,
acknowledged, sealed and delivered such further instruments and documents and
use such Party's reasonable best efforts to obtain such requisite consents as
any other Party may from time to time reasonably request, at the expense of the
Party so requesting, in order to consummate more effectively the transactions
contemplated hereby.

SECTION 12.

Amendment, Modification and Waiver.  This Agreement may be amended, modified or
supplemented at any time by written agreement of the Parties.  Any failure of
any Party to comply with any term or provision of this Agreement may be waived
by the other Parties at any time by an instrument in writing signed by or on
behalf of such other Parties, but such waiver or failure to insist upon strict
compliance with such term or provision shall not operate as a waiver of, or
estoppel with respect to, any subsequent or other failure to comply.

SECTION 13.

Notices.  All notices, requests, demands, waivers and other communications
required or permitted to be given under this Agreement shall be in writing and
shall be deemed to have been duly given if delivered personally, by mail
(certified or registered mail, return receipt requested) or by facsimile
transmission (receipt of which is confirmed):

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(a)

If to the Parent or the Company, to:

c/o Oppenheimer Holdings Inc.
P.O. Box 2015, Suite 1110
20 Eglinton Avenue West
Toronto, Ontario M4R 1K8
CANADA
Attention:  Albert G. Lowenthal
Facsimile:  (212) 668-8081

with a copy (which shall not constitute notice), to:

Skadden, Arps, Slate, Meagher & Flom LLP
Four Times Square
New York, NY  10036
Attention:  Patricia Moran, Esq.
Facsimile:  (212) 735-2000

(b)

If to CIBC, to:

Canadian Imperial Bank of Commerce

Commerce Court West

Toronto, Ontario M5L 1A2
CANADA
Attention:   Richard E. Venn

Facsimile:   (416) 956-6828

with a copy (which shall not constitute notice), to:

Canadian Imperial Bank of Commerce
425 Lexington Avenue, 3rd Floor

New York New York 10017-3903
Attention:  Antonio Molestina, Esq.
Facsimile:  (212) 667-8366

and

Mayer, Brown, Rowe & Maw
1675 Broadway
New York, NY 10019-5820
Attention:  James B. Carlson, Esq.
Facsimile:  (212) 849-5515

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(c)

or to such other Person or address as any Party shall specify by notice in
writing to the other Parties.  All such notices, requests, demands, waivers and
communications shall be deemed to have been received on the date on which so
hand-delivered, on the third business day following the date on which so mailed
and on the date on which faxed and confirmed, except for a notice of change of
address, which shall be effective only upon receipt thereof.

SECTION 14.

Entire Agreement.  This Agreement constitutes the entire agreement among the
undersigned with respect to the subject matter contained herein and therein and
supersedes any and all prior agreements or understandings, oral or written,
among any or all of the undersigned relating to such subject matter, including
the Letter of Intent.  The Parties hereby agree that the Letter of Intent shall
terminate in all respects upon the consummation of the Initial Closing.

SECTION 15.

Severability.  Should any provision of this Agreement for any reason be declared
invalid or unenforceable, such decision shall not affect the validity or
enforceability of any of the other provisions of this Agreement, which other
provisions shall remain in full force and effect and the application of such
invalid or unenforceable provision to Persons or circumstances other than those
as to which it is held invalid or unenforceable shall be valid and be enforced
to the fullest extent permitted by law.

SECTION 16.

Binding Effect; Assignment.  This Agreement and all of the provisions hereof
shall be binding upon and inure to the benefit of the Parties and their
respective heirs, executors, successors and permitted assigns.  Neither this
Agreement nor any of the rights, interests or obligations hereunder shall be
assigned, directly or indirectly, by any of the Parties without the prior
written consent of the other Parties; provided, that each of the Company and the
Parent may, without the prior written consent of CIBC, assign any or all of its
respective rights and/or delegate any or all of its respective obligations
hereunder to (a) to any Affiliate of the Company or the Parent, (ii) to any
subsequent purchaser of the Company or the Parent or substantially all of the
assets of the Company or the Parent (whether such sale is structured as a sale
of stock, a sale of assets, a merger or otherwise) and (iii) any Person
providing the financing of the Company for the transactions contemplated hereby
(or any refinancing of such financing) and any such Person may exercise all of
the rights and remedies of the Company or the Parent, as applicable, hereunder;
provided, however, that no such assignment shall relieve the Company or the
Parent, as applicable, of its respective obligations under this Agreement.  Any
purported assignment or delegation in violation of this Section 16 shall be null
and void.

SECTION 17.

No Third-Party Beneficiaries.  This Agreement is not intended and shall not be
deemed to confer upon or give any Person except the Parties and their respective
successors and permitted assigns any remedy, claim, liability, reimbursement,
cause of action or other right under or by reason of this Agreement.

SECTION 18.

Counterparts.  This Agreement may be executed in counterparts (including by
means of facsimile), each of which shall be deemed an original, but all of which
together shall constitute one and the same instrument.  Delivery of an executed

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counterpart of a signature page to this Agreement by facsimile shall be
effective as delivery of a manually executed counterpart of this Agreement.

SECTION 19.

Headings.  The article and section headings contained in this Agreement are
solely for the purpose of reference, are not part of the agreement of the
Parties and shall not in any way affect the meaning or interpretation of this
Agreement.

SECTION 20.

Governing Law.  This Agreement shall be construed, performed and enforced in
accordance with, and governed by, the laws of the State of New York, without
giving effect to the principles of conflicts of laws thereof.

SECTION 21.

Jurisdiction.  Each Party irrevocably submits to the exclusive jurisdiction of
(a) the Supreme Court of the State of New York, New York County, and (b) the
United States District Court for the Southern District of New York, for the
purposes of any suit, action or other proceeding arising out of this Agreement
or any transaction contemplated hereby.  Each Party agrees to commence any
action, suit or proceeding relating hereto either in the United States District
Court for the Southern District of New York or if such suit, action or other
proceeding may not be brought in such court for reasons of subject matter
jurisdiction, in the Supreme Court of the State of New York, New York County.
 Each Party irrevocably and unconditionally waives any objection to the laying
of venue of any action, suit or proceeding arising out of this Agreement or the
transactions contemplated hereby in (a) the Supreme Court of the State of New
York, New York County, or (b) the United Sates District Court for the Southern
District of New York, and hereby further irrevocably and unconditionally waives
and agrees not to plead or claim in any such court that any such action, suit or
proceeding brought in any such court has been brought in an inconvenient forum.

SECTION 22.

WAIVER OF JURY TRIAL.  EACH PARTY HEREBY WAIVES ITS RESPECTIVE RIGHTS TO A JURY
TRIAL OF ANY CLAIM OR CAUSE OF ACTION BASED UPON OR ARISING OUT OF THIS
AGREEMENT OR ANY DEALINGS BETWEEN THE PARTIES RELATING TO THE SUBJECT MATTER OF
THIS AGREEMENT AND THE RELATIONSHIP THAT IS BEING ESTABLISHED.  THE SCOPE OF
THIS WAIVER IS INTENDED TO BE ALL-ENCOMPASSING OF ANY AND ALL DISPUTES THAT MAY
BE FILED IN ANY COURT AND THAT RELATE TO THE SUBJECT MATTER OF THIS AGREEMENT,
INCLUDING CONTRACT CLAIMS, TORT CLAIMS, BREACH OF DUTY CLAIMS, AND ALL OTHER
COMMON LAW AND STATUTORY CLAIMS.  THE PARTIES ACKNOWLEDGE THAT THIS WAIVER IS A
MATERIAL INDUCEMENT TO ENTER INTO A BUSINESS RELATIONSHIP, THAT EACH PARTY HAS
ALREADY RELIED ON THE WAIVER IN ENTERING INTO THIS AGREEMENT AND THAT EACH PARTY
SHALL CONTINUE TO RELY ON THE WAIVER IN THEIR RELATED FUTURE DEALINGS.  EACH
PARTY FURTHER WARRANTS AND REPRESENTS IT HAS REVIEWED THIS WAIVER WITH ITS LEGAL
COUNSEL, AND THAT EACH KNOWINGLY AND VOLUNTARILY WAIVES ITS JURY TRIAL RIGHTS
FOLLOWING CONSULTATION WITH LEGAL COUNSEL.  THIS WAIVER IS IRREVOCABLE, MEANING
THAT IT MAY NOT BE MODIFIED EITHER ORALLY OR IN WRITING, AND THE WAIVER SHALL
APPLY TO ANY SUBSEQUENT AMENDMENTS, RENEWALS, SUPPLEMENTS OR MODIFICATIONS TO
THIS AGREEMENT OR TO ANY OTHER DOCUMENTS OR AGREEMENTS RELATING TO

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THE TRANSACTIONS CONTEMPLATED HEREBY.  IN THE EVENT OF LITIGATION, THIS SECTION
22 MAY BE FILED AS A WRITTEN CONSENT TO A TRIAL BY THE COURT.

SECTION 23.

Specific Performance.  Each of the Parties acknowledges and agrees that in the
event of any breach of this Agreement, each non-breaching Party would be
irreparably and immediately harmed and could not be made whole by monetary
damages.  It is accordingly agreed that the Parties (a) shall waive, in any
action for specific performance, the defense of adequacy of a remedy at law and
(b) shall be entitled, in addition to any other remedy to which they may be
entitled at law or in equity, to compel specific performance of this Agreement
in any action instituted hereunder.

SECTION 24.

Interpretation.  In this Agreement, unless the context clearly indicates
otherwise:

(a)

words used in the singular include the plural and words in the plural include
the singular;

(b)

reference to any Person includes such Person's successors and assigns, but only
if such successors and assigns are permitted by this Agreement;

(c)

reference to any gender includes the other gender;

(d)

the word "including" (and with correlative meaning "include") shall mean
"including but not limited to" or "including without limitation;"

(e)

reference to any Section shall mean such Section of this Agreement, and
reference in any Section or definition to any clause shall mean such clause of
such Section or definition;

(f)

the words "herein," "hereunder," "hereof," "hereto" and words of similar import
shall be deemed references to this Agreement as a whole and not to any
particular Section or other provision hereof;

(g)

reference to any agreement, instrument or other document shall mean such
agreement, instrument or other document as amended, supplemented and modified
from time to time to the extent permitted by the provisions thereof and by this
Agreement;

(h)

reference to any law (including statutes and ordinances) shall mean such law
(including all rules and regulations promulgated thereunder) as amended,
modified, codified or reenacted, in whole or in part, and in effect at the time
of determining compliance or applicability;

(i)

relative to the determination of any period of time, "from" shall mean "from and
including," "to" shall mean "to but excluding" and "through" shall mean "through
and including;" and

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(j)

all references to "dollars" or "$" shall mean United States Dollars unless
otherwise specifically indicated.

[Remainder of page left blank intentionally]

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IN WITNESS WHEREOF, the parties hereto have executed this Agreement on the date
first above written.

OPPENHEIMER HOLDINGS INC.

By: _______________________

Name:  Albert G. Lowenthal

Title:  Chief Executive Officer

E. A. VINER INTERNATIONAL CO.

By: _______________________

Name:  Dennis P. McNamara

Title:  Secretary

CANADIAN IMPERIAL BANK OF COMMERCE

By: ____________________________

Name:

Richard E. Venn

Title:

Senior Executive Vice-President,

Corporate Development

[Signature Page to the Securities Purchase Agreement]

588275.26-New York Server 6A - MSW