Document:

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                                                                   EXHIBIT 10.38

                             SHAREHOLDERS AGREEMENT

                          dated as of December 21, 1995

                                      among

                        THE FIRST MARBLEHEAD CORPORATION

                                       and

                          THE SHAREHOLDERS NAMED HEREIN

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                                TABLE OF CONTENTS

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1.   Certain Definitions...............................................................1

2.   Representations of Shareholders...................................................2

3.   Riqhts with Respect to Transfers of Shares........................................3

4.   Rights of First Offer.............................................................3

5.   Co-Sale Provisions................................................................5

6.   Rights to Require Sale............................................................6

7.   Agreements with Respect to voting.................................................7

8.   Regarding Business Opportunities; Shareholder Obligations.........................8

9.   Rights to Acquire Additional Securities...........................................8

10.  Registration Rights...............................................................9

11.  Covenants of the Company.........................................................12

12.  Confidentiality..................................................................13

13.  Termination......................................................................13

14.  Notices..........................................................................14

15.  Legends..........................................................................14

16.  Equitable Relief.................................................................14

17.  Third Party Rights...............................................................14

18.  Counterparts.....................................................................15

19.  Governing Law....................................................................15

20.  Benefit and Binding Effect.......................................................15

21.  Amendment and Waiver.............................................................15
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                             SHAREHOLDERS AGREEMENT

     This SHAREHOLDERS AGREEMENT, made as of the 21st day of December, 1995, by
and among each of the persons named on Schedule A hereto and The First
Marblehead Corporation;

                              W I T N E S S E T H:

     WHEREAS, the parties hereto, other than The First Marblehead Corporation,
are the owners of all of the issued and outstanding shares of the common stock,
par value $.10 per share, of The First Marblehead Corporation, a Delaware
corporation, owning the respective numbers of such shares set forth opposite
their names on Schedule A hereto; and

     WHEREAS, the parties hereto wish to make certain agreements with respect to
the ownership and transfer of such shares and certain related matters;

     NOW, THEREFORE, the parties hereto agree as follows:

     1.   CERTAIN DEFINITIONS.

     As used in this Agreement, the following terms shall have the meanings
indicated:

     "AFFILIATE" means, with respect to any Person, (i) any director or officer
of such Person or any Person (a "5% Holder") that owns, of record or
beneficially, at least 5% of the outstanding voting securities, or partnership
or other equity interests, of such Person, (ii) any director, officer, partner
or 5% Holder of any Person referred to in clause (i), (iii) any spouse or
relative of any Person referred to in clause (ii) or (iii) and (iv) any Person
that has the power to direct the management or policies of such Person, directly
or indirectly, whether through the ownership of voting securities, by contract
or otherwise.

     "AGREEMENT" means this Shareholders Agreement, as amended from time to time
in accordance with its terms.

     "BOARD" means the Board of Directors of the Company.

     "COMPANY" means The First Marblehead Corporation, a Delaware corporation.

     "CONTROL SALE" means a sale by any Shareholder or Shareholders to any
Person or group of related Persons, in any transaction or series of related
transactions, of (i) Shares aggregating at least 30% of all Shares then
outstanding or (ii) Shares which, together with all other Shares theretofore
sold to any such Person or group of Persons by Shareholders, would aggregate at
least 30% of all Shares then outstanding. For purposes of this definition,
Shares sold by any Person to whom any Shareholder has transferred Shares
pursuant to Section 3(c) hereof shall be deemed to be Shares sold by such
Shareholder.

     "EXCLUDED OFFERING" means (i) the Company's initial public offering of
equity securities, (ii) the Initial Public Offering (if different from the
offering referred to in clause (i)) and (iii) any offering of securities on Form
S-4 or Form S8, or any successor form, under the Securities Act.

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     "INITIAL PUBLIC OFFERING" means an underwritten public offering and sale of
common stock of the Company pursuant to a registration statement which has
become effective under the Securities Act and pursuant to which the Company
sells shares of common stock representing not less than 20% of the issued and
outstanding shares of common stock after giving effect to such offering and
sale.

     "INTERLAKEN SHAREHOLDER" means Interlaken Investment Partners, L.P., a
Delaware limited partnership, and any Person acquiring Shares from such
Interlaken Shareholder pursuant to Section 3(c) hereof.

     "MAJORITY SHAREHOLDERS" means, with respect to any matter, any Shareholder
or Shareholders whose aggregate ownership of Shares exceeds 50% of all Shares
issued and outstanding and held by all Shareholders or, as the context may
require, any Person in the group that constitutes such Majority Shareholders.

     "NON-SHAREHOLDER," when used with reference to any purchase of Shares,
means a Person, not affiliated with any of the Shareholders, that, immediately
prior to such purchase, did not own any equity securities of the Company.

     "PERSON" means any natural person, limited liability company, corporation,
partnership, firm, trust, joint venture, government or governmental body or
agency.

     "SECURITIES ACT" means the Securities Act of 1933, as amended.

     "SHAREHOLDER" means a Person who has a beneficial interest in Shares and
who is a party to this Agreement.

     "SHAREHOLDER INTEREST," when used with reference to any Shareholder, means
all of the rights and interests of such Shareholder pursuant to this Agreement.

     "SHAREHOLDER PERCENTAGE," when used with reference to any Shareholder,
means the Shares held by such Shareholder as a percentage of all Shares issued
and outstanding and held by all Shareholders.

     "SHARES" means shares of the common stock, par value $.10 per share, of the
Company.

     "SIGNIFICANT HOLDER" means a Shareholder whose Shares represent at least
10% of the number of Shares then issued and outstanding.

     2.   REPRESENTATIONS OF SHAREHOLDERS.

          (a)  Each Shareholder by execution of this Agreement represents and
warrants to each other Shareholder and to the Company that such Shareholder has
such knowledge and experience in financial and business matters as to be capable
of evaluating the merits and risks of its investment in the Shares acquired by
such Shareholder, that it is capable of bearing the economic risks of such
investment and that it is acquiring such Shares for its own account for
investment with no present intention of distributing or selling any of the
Shares or any interest therein. Each Shareholder agrees that if in the future it
should decide to offer or dispose of any

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Shares or interest therein, it will do so only in compliance with the Securities
Act and any other applicable securities laws. Each Shareholder acknowledges that
prior to its acquisition of Shares, it was provided with access to such
information relating to the Company as such Shareholder requested and that such
Shareholder is not relying on the Company with regard to tax or other financial
considerations relating to its investment in the Shares but has, to the extent
that such Shareholder deemed it necessary or appropriate, relied upon advice of
its own advisors.

     3.   RIGHTS WITH RESPECT TO TRANSFERS OF SHARES.

          (a)  Each Shareholder agrees that such Shareholder will not sell,
donate, assign, pledge or otherwise dispose of or transfer any of the Shares of
such Shareholder or any of its Shareholder Interest except pursuant to
applicable provisions of this Section 3 or Section 4, 5 or 6 hereof. Any sale,
gift, assignment, pledge, transfer or other disposition of any Shares by any
Shareholder, whether voluntary or involuntary, made in violation of the
foregoing provisions of this Section 3(a) shall be void and ineffective.

          (b)  Any Shareholder may sell or donate Shares to any other
Shareholder upon such terms as may be agreed to between or among such
Shareholders.

          (c)  Shares of any Shareholder may be transferred to a trust
established for the benefit of such Shareholder or a family member, to the
estate of any individual Shareholder upon his death, to a corporation or other
entity of which such Shareholder is the principal controlling Person or, in the
case of the Interlaken Shareholder, to its partners, provided that such trust,
estate, corporation or other entity or partners, as the case may be, shall take
such Shares subject to all of the terms and provisions of this Agreement and
that such trust, the representative of such estate or such corporation or other
entity or partners shall execute an agreement or agreements and such other
instruments as may be necessary, in the opinion of the Board, to evidence that
such trust, estate, corporation or entity or partners are bound by such terms
and provisions.

          (d)  Upon any transfer of Shares pursuant to subsection (b) or (c) of
the Section 3, Schedule A hereto shall be revised to reflect the changes in the
Shareholder Percentages resulting from such transfer. All Shares acquired by any
Shareholder, pursuant to the provisions of this Agreement or otherwise, shall be
subject to this Agreement.

     4.   RIGHTS OF FIRST OFFER.

          (a)  If at any time any Shareholder desires to sell, for cash (other
than pursuant to Section 3, 5 or 6 hereof), any Shares of such Shareholder (for
purposes of this Section 4, the "Selling Shareholder"), the Selling Shareholder
shall give notice of such proposal to the Company, which shall in turn, within
three days of its receipt of such notice, give copies of such notice to each
other Shareholder (a "Notice of First Offer"), which notice shall state that the
Selling Shareholder desires to sell Shares pursuant to this Section 4, the
number of Shares (the "Offered Shares") that may be sold and the cash purchase
price (the "First Offer Price") which the Selling Shareholder proposes be paid
for the Offered Shares. The date on which the Notice of First Offer is so given
by the Company to such other Shareholders is referred to hereinafter as the
"Notice Date." Each Notice of First Offer shall be deemed an irrevocable offer
to sell, on the terms set forth in such Notice of First Offer and herein, the
Offered Shares, and the Company

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will have the irrevocable and exclusive option, as hereinafter provided, to buy
such Shares on the terms set forth herein and at the First Offer Price. If the
Company does not wish to purchase all of the Offered Shares on such terms, the
other Shareholders will have irrevocable and exclusive options, as hereinafter
provided, to buy all of such Shares on such terms and at the First Offer Price.

          (b)  (i) Within twenty (20) days following the Notice Date, the
Company shall notify the Selling Shareholder and the other Shareholders as to
whether or not the Company elects to purchase all of the Offered Shares (such
notice of election to purchase such Shares being referred to herein as a
"Company Acceptance"). If the Selling Shareholder does not receive the Company
Acceptance within such 20-day period, the Company shall be deemed to have
declined to purchase the offered Shares. A Company Acceptance shall be deemed to
be an irrevocable commitment to purchase the Offered Shares from the Selling
Shareholder on the terms set forth herein and at the First Offer Price.

               (ii)    If the Selling Shareholder does not receive a Company
Acceptance pursuant to paragraph (ii) of this subsection (b), each Shareholder
(other than the Selling Shareholder) shall have the right, within ten (10) days
following the first to occur of (x) the date of any notice from the Company to
all Shareholders stating that the Company will not deliver a Company Acceptance
and (y) the twentieth day after the Notice Date, to notify the Company and the
Selling Shareholder as to the number of Offered Shares which such Shareholder
elects to purchase (a "Shareholder Acceptance"). If the Selling Shareholder does
not receive within such 10-day period Shareholder Acceptances with respect to
all of the Offered Shares, then none of such Shareholders shall have any right
to purchase any of such Shares. Subject to the foregoing, each Shareholder
Acceptance shall be deemed to be an irrevocable commitment to purchase from the
Selling Shareholder the Shares referred to in such Shareholder Acceptance.

               (iii)   For purposes of paragraph (ii) of this subsection (b),
each Shareholder (other than the Selling Shareholder) shall have the right to
purchase Offered Shares PRO RATA in accordance with the number of Shares owned
by such Shareholder on the Notice Date and the number of Shares owned by all
Shareholders (other than the Selling Shareholder) on such date. If any such
Shareholder declines to purchase Offered Shares in the full amount permitted
pursuant to the preceding sentence, the other such Shareholders shall have the
right to purchase such Shares on a PRO RATA basis in accordance with the total
number of Shares owned on the Notice Date by each such Shareholder and the total
number of Shares owned by all Shareholders who are purchasing Offered Shares,
provided that not less than all of the Offered Shares must be purchased in
accordance with this subsection (b).

          (c)  The purchase price for the Offered Shares sold to the Company or
any Shareholder pursuant to this Section 4 shall be the First Offer Price.

          (d)  Upon exercise of their respective options hereunder, the Company,
the accepting Shareholders and the Selling Shareholder shall be respectively
legally obligated (subject to applicable law) to consummate the purchase and
sale contemplated hereby. If the Company and the accepting Shareholders do not
exercise their respective options hereunder with respect to all (but not less
than all) of the Offered Shares within the time specified for such exercise, the
Selling Shareholder shall be free, during a period of three months following the

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expiration of the last time for such exercise, to sell the Offered Shares, but
only to one or more Non-Shareholders (who shall have been identified in a notice
given by the Selling Shareholder to each Significant Holder not later than seven
(7) days prior to the date upon which such sale is to be made) at a price, in
cash, equal to or greater than the First Offer Price and provided that each such
Non-Shareholder enters into an agreement pursuant to which such Non-Shareholder
agrees to be bound by the provisions hereof. If the Selling Shareholder does not
complete such sale within such three-month period, the provisions of this
Section 4 shall again apply, and no sale of Shares by such Shareholder shall be
made otherwise than in accordance with the terms of this Agreement.

          (e)  Notwithstanding any of the foregoing provisions of this Section 4
to the contrary, no sale of Shares to any Non-Shareholder shall be made pursuant
to this Section 4 without the prior written consent of each Significant Holder,
such consent not to be unreasonably withheld or delayed and any determination so
to withhold consent to be based upon reasonable views as to possible detriment
to the business or reputation of the Company or to the value of the Shares held
by such Holder, including, in any such case, as a result of adverse tax
consequences.

          (f)  The closing of purchases of Offered Shares by the Company and/or
the accepting Shareholders pursuant to this Section 4 shall take place within 30
days after the expiration of the applicable option period provided for in
subsection (b) above at 11:00 a.m. at the principal office of the Company or at
such other time or place as the parties may agree. At such closing, the Selling
Shareholder shall sell to each purchaser full right, title and interest in and
to the Shares so purchased, free and clear of all liens, security interests or
adverse claims of any kind and nature, provided that any subsequent transfer of
such Shares shall be subject to compliance with the requirements of this
Agreement, and shall deliver to each purchaser a certificate or certificates
evidencing the Shares sold, in each case duly endorsed for transfer or
accompanied by appropriate stock transfer powers or appropriate instruments of
assignment duly endorsed, together with all necessary transfer tax stamps
affixed thereto at the expense of the Selling Shareholder; and each purchaser
shall deliver to the Selling Shareholder, in full payment of the purchase price
of the Shares purchased, a certified or bank check payable to the order of the
Selling Shareholder in the amount of the purchase price.

     5.   CO-SALE PROVISIONS.

          (a)  If at any time or from time to time a Shareholder or Shareholders
(for purposes of this Section 5, the "Selling Shareholders") propose to effect a
Control Sale, the Selling Shareholders shall by notice in writing to the other
Shareholders designate a representative (the "Representative") for purposes of
this Section 5, and the Representative shall give notice of such proposal (the
"Notice of Sale") to each of the other Shareholders (for purposes of this
Section 5, the "Other Shareholders"), which notice shall identify the proposed
transferee or transferees and the proposed purchase price, terms of payment and
other material terms and conditions of the proposed sale. Upon receipt of the
Notice of Sale, each Other Shareholder shall have until the tenth day after such
receipt to deliver to the Representative a written notice (the "Co-Sale
Acceptance") of its intention to sell in such proposed sale, in replacement of
some of the Shares of the Selling Shareholders, such number of Shares specified
in the Co-Sale Acceptance which shall not exceed the number of Shares proposed
to be sold by the Selling Shareholders times a fraction, the numerator of which
shall be the number of Shares

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then held by such Other Shareholder and the denominator of which shall be the
aggregate number of Shares then held by the Selling Shareholders and all Other
Shareholders (provided that if such sale is a Control Sale of a kind referred to
in clause (ii) of the definition of such term contained in Section 1 hereof,
such calculation shall be based upon the number of Shares then to be sold by the
Selling Shareholders plus the number of Shares theretofore sold to the Person or
group of related Persons referred to in such clause as contemplated thereby, to
the extent not theretofore included in any calculation made pursuant to this
sentence). The Co-Sale Acceptance shall be deemed to be an irrevocable
commitment by each of the selling Other Shareholders to sell the number of
Shares determined as provided above at the price and on the terms and conditions
contained in the Notice of Sale and herein. The transfer of Shares to the
prospective transferee or transferees by the Selling Shareholders and the
selling Other Shareholders shall be consummated simultaneously and on the same
terms. If the prospective transferee or transferees decline to purchase some of
the Shares offered by the Selling Shareholders and the selling Other
Shareholders, then the number of Shares to be sold by the Selling Shareholders
and the selling Other Shareholders shall be proportionately reduced, based upon
the respective numbers of Shares originally proposed to be sold by the Selling
Shareholders and the selling Other Shareholders.

          (b)  If the Representative does not receive a Co-Sale Acceptance from
an Other Shareholder within the time period specified in subsection (a) above,
such Other Shareholder shall be deemed to have declined to exercise its right to
sell any of its Shares in such transaction pursuant to this Section 5. In such
event, the Selling Shareholders and one or more of the other Shareholders may
sell their Shares pursuant to this Section 5 at the price and on substantially
the terms and conditions set forth in the Notice of Sale. If the Selling
Shareholders and such Other Shareholders do not effect the sale at such price
and substantially upon such terms and conditions, the provisions of this
Agreement shall again apply to successive transactions.

          (c)  The foregoing provisions of this Section 5 shall not, apply to
any transfer of Shares pursuant to Section 3(b) or 3(c) hereof.

          (d)  Notwithstanding any provision of this Section 5 to the contrary,
Selling Shareholders may at any time prior to their sale of Shares pursuant to
this Section 5 elect not to proceed with such sale, and in such event no Other
Shareholder shall be required to sell its Shares in such sale and neither the
Selling Shareholders nor any of the Other Shareholders shall have any liability
to any other Shareholder in respect of any such election.

     6.   RIGHTS TO REQUIRE SALE.

     If at any time one or more Shareholders owning at least 51% of all of the
Shares issued and outstanding propose to sell, in any transaction or series of
related. transactions, all of the Shares owned by such Shareholder or
Shareholders (for purposes of this Section 6, the "Selling Shareholders"), the
Selling Shareholders may require all other Shareholders other than any
Significant Holder (all such other Shareholders other than Significant Holders
being referred to in this Section 6 as the "Other Shareholders") to, and by
their execution of this Agreement each Other Shareholder hereby agrees that it
shall, sell all of its Shares to the same Person or Persons (the "Transferee"),
for the same price and upon the same other terms, as are applicable to such

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sale by the Selling Shareholders. The Selling Shareholders (or a representative
thereof) shall give each Significant Holder and each of the Other Shareholders
notice of the proposal of the Selling Shareholders to effect such sale, stating
the identity of the Transferee, the proposed sale price and other principal
terms of the sale and the approximate date or dates on which such sale is to be
made. Within twenty (20) days after receipt of such notice (the "Drag-along
Notice"), each Significant Holder shall advise the Selling Shareholders (or a
representative thereof) in writing as to whether such Significant Holder will
sell its Shares in such transaction pursuant to this Section 6. Within five (5)
days after the expiration of such 20day period, the Selling Shareholders will
give notice to each Shareholder (other than the Selling Shareholders)
identifying the Significant Holders who have elected to sell their Shares in
such transaction. Thereupon, unless the proposed sale is abandoned by the
Selling Shareholders, each Shareholder, other than any Significant Holder or
Holders who have elected not to sell their Shares in such transaction, will sell
all of its Shares to the Transferee on the date specified in such notice (which
shall be not earlier than fifteen (15) days from the date of such notice) on the
terms and for the price set forth in the Drag-along Notice. To effect each such
sale, each such Shareholder shall sell to the Transferee full right, title and
interest in and to the Shares so sold, free and clear of all liens, security
interests or adverse claims of any kind and nature, and shall deliver to the
Transferee the certificate or certificates evidencing the Shares sold, in
each-case duly endorsed for transfer or accompanied by appropriate stock
transfer powers or appropriate instruments of assignment duly endorsed, together
with all necessary transfer tax stamps affixed thereto at the expense of such
Shareholder.

     7.   AGREEMENTS WITH RESPECT TO VOTING.

     From and after the date of this Agreement, each Shareholder shall vote all
of its Shares and shall take all other necessary or desirable actions within its
control (including, without limitation, attendance at meetings in person or by
proxy for purposes of obtaining a quorum and execution of written consents in
lieu of meetings), and the Company shall take all necessary and desirable
actions within its control (including, without limitation, calling special board
and shareholder meetings), so that:

               (i)     the authorized number of directors shall be established
at seven directors;

               (ii)    the following persons shall be elected to the Board:

                       (A)  three representatives designated by Stephen
               Anbinder, Daniel M. Meyers and Catamaran Holdings, Ltd.;

                       (B)  two representatives designated by the Interlaken
               Shareholder;

                       (C)  one representative designated by Leslie Alexander;
               and

                       (D)  Dort A. Cameron, III, unless he shall advise the
               Company that he does not wish to serve as a director; from and
               after delivery of such notice, the Shareholders shall be entitled
               to vote their Shares for such directorship without restriction
               under this Section 7;

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               (iii)   the composition of the board of directors of each of the
Company's subsidiaries (if any) (a "Sub Board") shall be the same as that of the
Board;

               (iv)    any committees of the Board or a Sub Board shall be
created only upon the approval of five members of the Board and the composition
of each such committee shall be proportionately equivalent to that of the Board;

               (v)     the removal from the Board or a Sub Board of any
representative designated hereunder by a Person pursuant to clause (ii) above
shall be only at the written request of such Person and under no other
circumstances, except that any director may be removed for Cause by a unanimous
vote of all of the directors who were not designated by the same Person who
designated the director whose removal is being considered or, in the case of a
director provided for in clause (ii)(D) above, by a vote of not less than five
directors; and

               (vi)    in the event that any representative designated hereunder
for any reason (including a removal for Cause) ceases to serve as a member of
the Board or a Sub Board during his term of office, the resulting vacancy on the
Board or the Sub Board shall be filled by a representative designated by the
Person entitled to designate such representative pursuant to clause (ii) above.

     As used in this Section 8, the term "Cause" means misconduct involving
moral turpitude or conduct materially detrimental to the business or reputation
of the Company.

     8.   REGARDING BUSINESS OPPORTUNITIES; SHAREHOLDER OBLIGATIONS.

          (a)  Each Shareholder acknowledges that the other Shareholders and
their Affiliates engage and will engage in and have interests in other business
activities, independently or with others, and agrees that such activities shall
not be limited in any way whatsoever by reason of the Shareholder Interest of
any Shareholder or by reason of its ownership of Shares or this Agreement.
Without limiting the generality of the foregoing, such activities may include
investments in and the acquisition, disposition and financing of securities or
other assets of any kind. No Shareholder or any of its Affiliates shall have any
obligation to make any investment for the account of the Company or the
Shareholders generally, or any of them, rather than for its own account or for
the account of any other Person or Persons. The provisions of this Section 8
are, however, in the case of any Shareholder, subject to the provisions of any
other agreement to which the Company and such Shareholder are parties, and the
provisions of this Section 8 shall not be deemed to affect the obligations of
any Shareholder, or any director or officer of the Company, under applicable
law.

          (b)  No Shareholder shall have any liability in respect of the
obligations of any other Shareholder.

     9.   RIGHTS TO ACQUIRE ADDITIONAL SECURITIES.

          (a)  In the event that the Company proposes to issue, at any time
after the date hereof, additional Shares or equity securities, or warrants,
options, convertible securities or other securities exercisable for or
convertible into Shares or other equity securities (Shares and other equity
securities and such warrants, options, convertible securities or other such
securities being

                                       -8-
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referred to herein as "Equity Securities"), the Company shall give each
Shareholder notice of such proposal, describing the Equity Securities in
question and the proposed terms of their issuance. In such event, each
Shareholder shall have the right, exercisable by notice given to the Company
within 15 days after its receipt of the said notice from the Company, to
purchase such Equity Securities in an amount which, after giving effect to such
Shareholder's purchase and the issuance of such Equity Securities to others in
such transaction, will result in such Shareholder's maintaining its percentage
equity interest in the Company (on a fully diluted basis) (referred to herein as
"Shareholder's Percentage Interest") at the same level as obtained immediately
prior to such transaction. Each Shareholder's purchase of such Equity Securities
shall be for the same price, and upon the same terms, as nearly as may be
practicable, upon which such Equity Securities are being issued to others in
such transaction. Any Shareholder may assign, in whole or in part, to any
Affiliate of such Shareholder such Shareholder's right to acquire Equity
Securities pursuant to this Section 9, provided that upon any such purchase by
any such Affiliate, such Affiliate shall become a party to this Agreement.

          (b)  The provisions of subsection (a) above shall not apply, however,
to the following: (i) the issuance by the Company to its directors, officers,
employees or consultants (other than any who are Shareholders), pursuant to a
plan or arrangement adopted or otherwise approved by the Board, of Shares or
stock options, stock appreciation rights or other kinds of Equity Securities
customarily offered to employees, (ii) the issuance by the Company of Equity
Securities upon exercise or conversion of other Equity Securities in respect of
which notice was given to the Shareholders, at the time of their issuance,
pursuant to subsection (a) above or (iii) the issuance by the Company of Equity
Securities in order to acquire the assets or equity of one or more businesses
not owned or controlled by Shareholders or their Affiliates, provided that any
issuance of Shares, stock options, stock appreciation rights or other Equity
Securities as provided in clause (i), or any issuance of Equity Securities as
provided in clause (iii), that would result in dilution of any Shareholder's
Percentage Interest shall have been approved by not less than five members of
the Board. The Company shall have the right to make appropriate adjustments,
pursuant to and consistent with the intent of this Section 9, to reflect
repurchases or other acquisitions by the Company of Equity Securities, or the
termination or expiration of any warrant, option or convertible security, to
which the provisions of this Section 9 were applicable upon the issuance
thereof.

          (c)  Except as expressly provided in this Agreement, no Shareholder
shall have, by virtue of this Agreement, any right to acquire shares of capital
stock or other securities of the Company from the Company or from any other
Shareholder, whether upon issuance of stock or securities by the Company, upon
any transfer of stock or securities by any Shareholder or otherwise.

     10.  REGISTRATION RIGHTS.

          (a)  In the event that the Company proposes to file a registration
statement under the Securities Act for an offering of its common stock (other
than an Excluded Offering), the Company shall give each Shareholder not less
than 10 days prior notice of such filing, and, if requested by Shareholders
owning Shares representing not less than 10% of all outstanding Shares, by
notice given to the Company within five days of the date of such notice from the
Company (the "Registration Notice"), will use its reasonable best efforts to
include all or a

                                       -9-
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portion, as requested by such Shareholders, of the Shares held by such
Shareholders) (but in no event less than 5% of the total number of Shares then
held by all Shareholders) in the common stock to be registered pursuant to such
registration statement; provided that the Company shall have no obligation to
register any Shares transferable by any Shareholder pursuant to Rule 144 or any
successor rule promulgated under the Securities Act (provided that the Company
is then in compliance with the current public information and any other
provisions of such Rule applicable to the Company so as to allow such
Shareholder to transfer Shares in reliance upon such Rule) and provided further
that Shareholders shall be entitled to have Shares included in such a
registration statement pursuant to this Section 10 only twice, unless (x) the
total number of Shares requested by Shareholders is not included in any such
registration statement (including any non-inclusion resulting from an
underwriter's limitation), (y) such registration statement is not declared
effective by the Securities and Exchange Commission or is withdrawn by the
Company or (z) a stop order suspending the effectiveness of the registration
statement shall prevent the sale of such Shares. If an event specified in clause
(x), (y) or (z) should occur, the provisions of this Section 10 shall continue
in effect until such time as Shares of Shareholders shall have been included,
pursuant to this Section 10, in registration statements filed by the Company in
respect of which no event so specified shall have occurred.

          (b)  Notwithstanding any other provision of this Section 10, if an
underwriter's limitation is imposed with respect to a registration statement
filed by the Company for an offering of its common stock that may include Shares
held by Shareholders, the amount of such Shares that the Company shall be
obligated to include in such registration statement shall be reduced in
accordance with the underwriter's limitation. In such event, the number of
Shares of each Shareholder so to be included (each Shareholder having Shares so
to be included being referred to in this subsection (b) as a "Registering
Shareholder") shall be that number that bears the same ratio to all Shares owned
by such Shareholder and designated in the Registration Notice as the total
number of Shares of all Registering Shareholders to be included in such
registration statement bears to the total number of Shares of all Registering
Shareholders designated in the Registration Notice. Notwithstanding the
foregoing provisions, (i) if the Company files a registration statement as a
result of the exercise of "demand" registration rights hereafter granted to any
Person or Persons, the Shares held by such Person or Persons which are to be
included in such registration statement shall have priority over any Shares held
by any Registering Shareholder that would otherwise be entitled to be included
therein and (ii) if the Company files a registration statement as to which any
Person or Persons ("Other Holders") have so-called "piggyback" registration
rights, the number of Shares held by Registering Shareholders that shall be
entitled to be included therein shall not exceed that number which bears the
same proportion to the number of Shares to be included therein on behalf of
Other Holders as the total number of Shares held by Registering Shareholders
bears to the total number of Shares held by the Other Holders whose Shares are
being included therein. The parties hereto acknowledge that it is their
intention that, for any registration to which the provisions of this Section 10
are applicable, the Company will provide pro rata treatment to all Shareholders,
to the extent of the numbers of Shares requested by each Shareholder for
inclusion in such registration.

          (c)  In the event that the Company files a registration statement for
an offering of its common stock that includes Shares held by Shareholders (for
purposes of this Section 10, "Selling Shareholders"), the Company will use its
best efforts to register or qualify such Shares covered by the registration
statement under the state securities or blue sky laws (to the extent

                                      -10-
<Page>

applicable) of such jurisdictions within the United States as the holders of not
less than 51% of the Shares of the Selling Shareholders being included therein
shall reasonably request; provided that the Company shall not be required to
register or qualify as a foreign corporation or to take any action that would
subject it to service of process in suits, other than as to matters and
transactions relating to the offer and sale of such Shares.

          (d)  In connection with any registration pursuant to this Section 10,
the Company shall pay the fees and expenses of counsel and accountants for the
Company and all other costs and expenses of the Company incident to the
preparation, printing and filing under the Securities Act of the registration
statement (and all amendments and supplements thereto), and the costs and
expenses incurred by the Company in connection with the qualification of the
Shares under state securities or blue sky laws. The Company shall not be
obligated to pay, or reimburse any Selling Shareholder for, selling commissions
or similar payments attributable to Shares of any Selling Shareholder or other
expenses of any Selling Shareholder (including the fees and expenses of any
counsel retained by any Selling Shareholder) in connection with such
registration or qualification.

          (e)  Each Selling Shareholder shall furnish to the Company such
information concerning such Shareholder or any proposed sale or other
disposition by such Shareholder of any Shares as may be required by law or
reasonably requested by the Company, shall execute such documents as are
customarily executed by Selling Shareholders in like transactions and shall
cooperate with the Company and any underwriter in connection with any action
taken pursuant to this Section 10.

          (f)  In the event the Company files a registration statement under the
Securities Act for an offering of its common stock that includes Shares held by
any Selling Shareholder, (i) the Company shall, to the extent permitted by law,
indemnify each such Selling Shareholder against any liability, loss or expense
arising out of any untrue statement or alleged untrue statement of a material
fact contained in such registration statement or any prospectus included
therein, or any amendment or supplement thereto, or out of any omission or
alleged omission to state therein a material fact required to be stated therein
or necessary to make the statements therein not misleading (except insofar as
arising out of information furnished to the Company in writing by any Selling
Shareholder expressly for use therein), and (ii) each such Selling Shareholder
shall, to the extent permitted by law, indemnify the Company, the other Selling
Shareholders and any underwriter of such common stock against any such
liability, loss or expense but only to the extent that it arises out of any
information so furnished to the Company by such indemnifying Selling
Shareholder.

          (g)  If the Company or any underwriter of securities to be issued by
the Company or sold by any selling shareholder so requests, each Shareholder
shall sign an agreement not to sell or otherwise transfer or dispose of any
equity securities of the Company held by such Shareholder during such period
following the effective date of the registration statement registering such
securities as the Company or such underwriter shall specify. Such agreement
shall be in writing in a form satisfactory to the Company and such underwriter.
The Company may impose stop transfer instructions with respect to the securities
subject to the foregoing restrictions until the end of the period of
restriction. The provisions of this subsection

                                      -11-
<Page>

(g) shall be applicable in the case of any registration statement filed by the
Company, whether or not Shares of any Shareholders may be eligible for inclusion
therein pursuant to this Section 10.

          (h)  The Company agrees that it will not grant to any Person any right
to require the Company to register securities under the Securities Act, or to
participate as a selling security holder in any such registration (other than
the rights set forth in this Section 10), without the prior written consent of
Majority Shareholders and each Significant Holder.

     11.  COVENANTS OF THE COMPANY.

     The Company hereby covenants and agrees as follows:

          (a)  MAINTENANCE OF CORPORATE RIGHTS. The Company will maintain and
preserve its corporate existence and all rights, franchises and other authority
adequate for the conduct of its business.

          (b)  BOOKS AND RECORDS; AUDITORS. The Company will keep books and
records in which full, true and correct entries are made of all of its dealings,
business and affairs, in accordance with generally accepted accounting
principles consistently applied; the Company will employ certified public
accountants who are "independent" within the meaning of the rules of the
American Institute of Certified Public Accountants and are selected by the
Board; and the Company will have an annual audit made by certified public
accountants who are "independent" as aforesaid, are selected by the Board and
are one of the so-called "Big Six" national accounting firms.

          (c)  TRANSACTIONS WITH AFFILIATES. The Company will not, directly or
indirectly, purchase or sell any properties, assets or rights (or any interest
therein) from or to, contract for services to be provided by or to, or enter
into any other transaction with, any Affiliate of the Company, except (i) on
terms and conditions no less favorable to the Company than could be obtained
from a third party in a comparable arm's-length transaction and (ii) with the
specific approval of at least five members of the Board if such transaction
would involve an amount or benefit (to the Company or such Affiliate) in excess
of $50,000 in any fiscal year.

          (d)  INFORMATION. The Company shall deliver to each Shareholder:

               (i)     as soon as available and in any event within 120 days
          after the end of each fiscal year, a balance sheet of the Company as
          of the end of such year and the related statements of income,
          stockholders' equity and cash flow for the year then ended, setting
          forth in each case, in comparative form the figures for the preceding
          year, prepared in accordance with generally accepted accounting
          principles and reported on by the Company's independent accountants;

               (ii)    as soon as available and in any event within 60 days
          after the end of each of the first three fiscal quarters of each
          fiscal year, a balance sheet of the Company as of the end of such
          quarter and the related statements of income, stockholders' equity and
          cash flow for such quarter and for the portion of the fiscal year then
          ended, setting forth in each case in comparative form the figures for
          the corresponding quarter and portion of the previous fiscal year, all
          prepared

                                      -12-
<Page>

          in accordance with generally accepted accounting principles and
          certified (subject to normal year-end adjustments) as to fairness of
          presentation, generally accepted accounting principles and consistency
          by the chief financial officer of the Company; and

               (iii)   as soon as practicable, such other information relating
          to the business, assets, financial condition, results of operations or
          prospects of the Company as any Shareholder may from time to time
          reasonably request.

          (e)  INSPECTION. The Company will give each Shareholder and its
representatives access to the premises, properties and other assets of the
Company and the rights to examine (and make copies of) its books and records,
including financial and operating data and other information, and to discuss its
businesses, assets, financial condition, results of operations or prospects with
its officers, all at such reasonable times and as often as such Shareholder may
reasonably request.

          (f)  NATURE OF BUSINESS. The Company will not engage in any business
other than the business engaged in as of the date hereof and business reasonably
related thereto (it being acknowledged that such business permitted hereunder
includes the performance for fees of administrative and other services
reasonably related to the basic business of the Company and dealing in residual
interests as described in the Company's business plan).

          (g)  COMPENSATION. The Company shall not pay compensation (including
benefits) to any of its three most highly compensated employees at levels
greater (including benefits more favorable) than those set forth in the Company'
business plan unless such compensation has been approved by not less than five
members of the Board.

     12.  CONFIDENTIALITY.

     Each Shareholder, for itself and its officers, partners, agents and
employees, agrees to maintain in confidence all financial statements and other
documents and business and operating information (including technical concepts
and financial models developed by the Company) (collectively, the "Proprietary
Information") provided to such Shareholder with respect to the Company and its
business (except to the extent that any thereof has been made publicly available
by the Company) and to use such Proprietary Information only for the business of
the Company and in connection with such Shareholder's rights as a shareholder of
the Company and not in any separate enterprise or undertaking which may be
engaged in by the Shareholder or its officers, partners, agents or employees.

     13.  TERMINATION.

     This Agreement shall terminate upon the earliest to occur of the following:

          (a)  the Majority Shareholders and each Significant Holder vote in
favor of termination;

          (b)  December 31, 2025; and

                                      -13-
<Page>

          (c)  except for the provisions of Section 10 hereof, immediately prior
to the effectiveness of the Initial Public Offering.

     The provisions of Sections 4, 5, 6 and 9 hereof shall not be applicable to
Shares to be issued or sold as part of the Initial Public Offering.

     14.  NOTICES.

     All notices, requests, demands and other communications hereunder to any
Shareholder or to the Company shall be in writing and shall be deemed to have
been duly given (i) on the date of service if served personally on the party to
whom notice is to be given, (ii) on the day of transmission if sent via
facsimile transmission to the applicable facsimile number given on Schedule A
hereto, provided that telephonic confirmation of receipt is obtained promptly
after completion of transmission, (iii) on the day after delivery to any
recognized overnight courier service or the Express Mail service maintained by
the United States Postal Service or (iv) on the fifth day after mailing, if
mailed to the party to whom notice is to be given, by first class mail,
registered, with return receipt requested, addressed, in the case of any
Shareholder, to such Shareholder at its address set forth on Schedule A hereto
and, in the case of the Company, to the Company at 7 Tuckers Wharf, Marblehead,
Massachusetts 01945, Attention: Daniel M. Meyers, Telecopy No: 617-639-4583 or
to such other address as such Shareholder or the Company shall have previously
provided in writing to the other Shareholders or to the Company, as the case may
be.

     15.  LEGENDS.

          (a)  Each certificate representing Shares shall contain a legend in
substantially the following form:

          "The securities represented by this certificate are subject to a
     Shareholders Agreement dated as of December 20, 1995, a copy of which is on
     file at the principal office of the Company. Such Shareholders Agreement
     provides, among other things, for certain restrictions on the sale,
     transfer, pledge or other disposition, and the voting, of the securities
     represented by this certificate."

          (b)  Each certificate representing Shares shall also contain a legend
in substantially the following form:

          "The securities represented by this certificate have not been
     registered under the Securities Act of 1933, as amended, and may be
     transferred, sold or offered for sale only if registered under said Act or
     if an exemption from such registration is available."

     16.  EQUITABLE RELIEF.

     The parties hereto agree and declare that legal remedies may be inadequate
to enforce the provisions of this Agreement and that equitable relief, including
specific performance and injunctive relief, may be sought to enforce the
provisions of this Agreement.

     17.  THIRD PARTY RIGHTS.

                                      -14-
<Page>

     Except as otherwise provided herein, nothing herein expressed or implied is
intended or shall be construed to confer upon or give to any Person (other than
the parties hereto) any rights or remedies under or by reason of this Agreement.

     18.  COUNTERPARTS.

     This Agreement may be executed in two or more counterparts, each of which
shall be deemed to be an original, but all of which together shall constitute
one and the same instrument.

     19.  GOVERNING LAW.

     This Agreement shall be governed by and construed in accordance with the
laws of the State of Delaware, without giving effect to any principles of
conflicts of laws.

     20.  BENEFIT AND BINDING EFFECT.

     This Agreement shall be binding-upon and shall inure to the benefit of the
Company and its successors and assigns and, subject to the provisions hereof,
each of the other parties hereto and their respective executors, administrators,
personal representatives, heirs and successors. In the event that any part of
this Agreement shall be held to be invalid or unenforceable, the remaining parts
thereof shall nevertheless continue to be valid and enforceable as though the
invalid portions were not a part hereof.

     21.  AMENDMENT AND WAIVER.

          (a)  No failure on the part of any of the parties hereto to exercise,
and no delay in exercising, any right hereunder shall operate as a waiver
thereof, nor shall any single or partial exercise of any such right preclude any
other or further exercise thereof or the exercise of any other right.

          (b)  This Agreement may be amended, and any obligation of a party
hereto may be waived, with the written consent of the Company, Majority
Shareholders and each Significant Holder, provided that this Agreement may not
be amended so as to reduce the Shareholder Interest of any Shareholder without
the written consent of such Shareholder. This Agreement shall be amended to add
signatories hereto and to amend Schedule A hereto as provided in this Agreement.
Except as expressly provided herein, the Company shall not be required to
provide the benefits of this Agreement to, or to allow to become a party hereto,
any Person other than those listed on Schedule A hereto.

                                      -15-
<Page>

     IN WITNESS WHEREOF, this Agreement has been signed on behalf of each of the
parties hereto as of the date first above written.

                                 INTERLAKEN INVESTMENT PARTNERS, L.P.

                                 INTERLAKEN MANAGEMENT
                                 PARTNERS, L.P.
                                 General Partner

                                 LAKE MANAGEMENT, INC.
                                 General Partner

                                 By: /s/ William R. Berkley
                                     -------------------------------------------
                                 Name:  William R. Berkley, Jr.
                                 Title: Chairman

                                 /s/ William R. Berkley, Jr.
                                 -----------------------------------------------
                                 William R. Berkley, J
                                 Doopy L.P.

                                 By: /s/ Andrew M. Bursky
                                     -------------------------------------------
                                 Andrew M. Bursky, General Partner

                                 /s/ Catherin B. James
                                 -----------------------------------------------
                                 Catherine B. James

                                 /s/ William L. Mahone
                                 -----------------------------------------------
                                 William L. Mahone

                                 /s/ Charles J. Martin
                                 -----------------------------------------------
                                 Charles J. Martin

                                 /s/ Martin B. O'Connell
                                 -----------------------------------------------
                                 Martin B. O'Connell

                                 /s/ Joshua A. Polan
                                 -----------------------------------------------
                                 Joshua A. Polan

                                 THE FIRST MARBLEHEAD CORPORATION

                                 By:/s/ Stephen Anbinder
                                    -------------------------------------------

                                      -16-
<Page>

                                 /s/ Leslie Alexander
                                 -----------------------------------------------
                                 Leslie Alexander

                                 /s/ Stephen Anbinder
                                 -----------------------------------------------
                                 Stephen Anbinder

                                 /s/ Dort A. Camberon, III
                                 -----------------------------------------------
                                 Dort A. Cameron, III

                                 /s/ Joseph L. Fraites
                                 -----------------------------------------------
                                 Joseph L. Fraites

                                 Estate of Michael Malloy

                                 By: /s/ Lucille Ross Molloy
                                     -------------------------------------------
                                     Lucille Molloy, Executrix

                                 /s/ Daniel M. Meyers
                                 -----------------------------------------------
                                 Daniel M. Meyers

                                 /s/ Victor M. Samra, Jr.
                                 -----------------------------------------------
                                 Victor M. Samra, Jr.

                                 /s/ James W. Walker, II
                                 -----------------------------------------------
                                 James W. Walker, II

                                      -17-
<Page>

                                 CATAMARAN HOLDINGS, LTD.

                                 By:/s/ Stephen Anbinder
                                    --------------------------------------------
                                 Stephen Anbinder,
                                 Vice President

                                      -18-
<Page>

                                   SCHEDULE A

<Table>
<Caption>
                                                                    Number of
Name and Address of Shareholder                                      Shares
-------------------------------                                     ---------
<S>                                                                   <C>
Leslie Alexander                                                      333,000
1220 North Federal Highway
Suite 307
Boca Raton, Florida 33432
Telecopy No.: 407-368-4143

Stephen Anbinder                                                      129,836*
c/o The First Marblehead Corporation
Park Avenue Atrium
237 Park Avenue
New York, New York 10017
Telecopy No.: 212-551-1781

Dort A. Cameron, II                                                    17,951
c/o Philip F. Strassler, C.P.A.
Marcum & Kliegman, LLP
485 Underhill Blvd.
Syosset, New York  11791
Telecopy No.: 516-921-6006

Joseph Fraites                                                         52,192
41 Hemlock Ridge
Weston, Connecticut 06883
Telecopy No.: 203-454-2280

Daniel M. Meyers                                                      197,916*
c/o The First Marblehead Corporation
7 Tuckers Wharf
Marblehead, Massachusetts 01945
Telecopy No.: 617-639-4563

Estate of Michael Molloy                                                5,000
Lucille Molloy, Executrix of the Estate of Michael Molloy
c/o Joseph M. Cassin, Esq.
Cassin Cassin & Joseph
300 East 42nd Street
New York, New York 10017
Telecopy No.: 212-557-2952
</Table>

                                      -19-
<Page>

<Table>
<S>                                                                    <C>
Victor M. Samra, Jr.                                                   27,696
c/o The First Marblehead Corporation
Park Avenue Atrium
237 Park Avenue
New York, New York 10017
Telecopy No.: 212-551-1781 27,696

James W. Walker, Jr.                                                    7,957
10 Sunny Brae Place
Bronxville, New York

Catamaran Holdings, Ltd.                                               20,000*
7 Tuckers Wharf
Marblehead, Massachusetts 01945
Telecopy No.: 617-639-4563
</Table>

----------
*    Upon the merger of Catamaran Holdings, Ltd. ("Catamaran") with the Company,
     the Shares held by Catamaran will be cancelled, and this Schedule will be
     deemed revised to add to the Shares held by Messrs. Anbinder and Meyers'
     and specified above 10,000 Shares to be issued to each of them in such
     merger.

                                      -20-
<Page>

<Table>
<S>                                                                   <C>
Interlaken Investment Partners, L.P.                                  196,987
165 Mason Street
Greenwich, Connecticut 06830
Attention:  William L. Mahone, Esq.
Telecopy No.: 203-629-8554

William R. Berkley, Jr.                                                 3,891
Doopy L.P.                                                              1,946
Catherine B. James                                                      2,919
William L. Mahone                                                         305
Charles J. Martin                                                         153
Martin B. O'Connell                                                       305
Joshua A. Polan                                                         1,946
</Table>

Address and telecopy number for the seven
Shareholders listed immediately above:

165 Mason Street
Greenwich, Connecticut  06830
Attention: William L. Mahone, Esq.
Telecopy No.: 203-629-8554

                                      -21-<Page>

                                                                   EXHIBIT 10.39

FIRST MARBLEHEAD                                FIRST MARBLEHEAD CORPORATION
                                                30 Little Harbor
                                                Marblehead, MA 01945
                                                Tel 781-639-2000 or 800-895-4283
                                                Fax 781-639-4583

                                                230 Park Avenue, 10th Floor
                                                New York, NY  10169
                                                Tel 212-808-7225
                                                Fax 212-808-7226

February 24, 2003

Mr. John Hupalo
13 Sunnybrae Place
Bronxville, NY 10708

Dear John:

First Marblehead is pleased to offer you the position of Executive Vice
President, Group Head of Capital Markets. Your primary responsibilities will be
to manage the day to day activities of Capital Markets personnel, to shape and
staff the Group so it is in a position to provide needed information and
services on a timely basis to both internal and external clients, and to
contribute to the overall strategic direction of FMC through active
participation as a member of Management Committee. I understand you can start
these duties as soon as you are able to relinquish your current responsibilities
with UBS Paine Webber.

Your compensation will include direct annual cash compensation of $400,000, paid
on a twice-monthly basis. You will also receive annual cash incentive
compensation in the amount of not less than $200,000, to be paid on each
anniversary date of your employment if you continue to be employed by FMC on
that date. In addition to these two forms of cash compensation, upon acceptance
of this offer of employment, we will issue you a grant of Incentive Stock
Options to purchase 75,000 shares of First Marblehead common stock at a strike
price of $28. The vesting schedule, which will be detailed in the formal grant
document, is over four years, with 20% vesting immediately and 20% vesting at
each of the 1st, 2nd, 3rd and 4th anniversary dates. As with all FMC employees,
your performance and contributions to the firm will be reviewed at regular
annual intervals.

Please note that this letter does not constitute an employment contract or a
contract for a specific term of employment and that the employment relationship
is at will. This letter will certify, however, that should there be change of
control event within the first 18 months of your employment and as a result of
that event your exercised options do not yield you $1,000,000 of pretax profit,
then FMC will make up the difference between the pretax profit you do actually
yield and the $1,000,000 goal as a form of "guaranteed severance".

Ms. Jo-Ann Burnham, our HR Administration Manager, is available to discuss the
details of our benefits program. In a nutshell, you will be immediately eligible
to enroll in our Group Medical Insurance, our Group Dental Plan, our Group Life
Plan (two times salary up to a maximum of

<Page>

FIRST MARBLEHEAD

$500,000), and our Long Term Disability Plan. For each of these, all costs are
borne by the firm and you are eligible for coverage on the first day of
employment. Ms. Burnham can also fill you in on other benefits, such as our
non-contributory 401K Plan, which has proven to be an outstanding method of
saving for the future. We offer accrual of vacation up to fifteen days and eight
paid holidays per year.

As a condition of hire, First Marblehead requires that all employees sign a
Non-Disclosure letter. Due to the nature of our business, this offer is
contingent on satisfactory results of a credit check the company runs on
prospective employees to make sure they are not in default on any student loans.

On behalf of everyone at First Marblehead, especially my Management Committee
colleagues, I want you to know how pleased we are at the prospect of having you
join us to help build First Marblehead into a national powerhouse. Welcome
aboard.

Sincerely,

Ralph M. James
President

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