SETTLEMENT AGREEMENT

Exhibit 10.1

SETTLEMENT AGREEMENT

entered into as of

April 20, 2005,

by and among

THE GREENBRIER COMPANIES, INC.,

a Delaware corporation,

WILLIAM A. FURMAN,

GEORGE L. CHELIUS,

as Executor of the Will and Estate of Alan James and as Trustee,

and

ERIC EPPERSON,

as Executor of the Will and Estate of Alan James and as Trustee

SETTLEMENT AGREEMENT

This Settlement Agreement (the “Agreement”) is entered into as of April 20, 2005, by and among George L. Chelius and Eric Epperson, not in their individual capacities but solely in their capacities as Executors (each a “Representative” and together the “Representatives”) of the will and estate of Alan James pursuant to Letters Testamentary (Case Number 050290219), dated February 17, 2005, issued by the Circuit Court of the State of Oregon for the County of Multnomah (the “Estate”) and, to the extent provided in Section 3.12 of this Agreement, as Trustees of the Trust referred to in Section 3.12, William A. Furman (“Furman”) and The Greenbrier Companies, Inc., a Delaware corporation (“Greenbrier” or the “Company”), (the Representatives, Furman and the Company sometimes referred to collectively as the “Parties” or individually as a “Party”).

WHEREAS, Alan James (“James”), Furman and Greenbrier entered into a Stockholders Agreement, dated as of July 1, 1994, as amended by Amendment No. 1 dated December 23, 1994 (the “Stockholders’ Agreement”), Section 5.02 of which provided that Furman and James would have a right of first refusal (the “Old ROFR”) with respect to transfers of shares of Common Stock par value $.001 per share of Greenbrier (“Shares”) owned by Furman and James, respectively;

WHEREAS, James died on January 28, 2005 and at the time of his death he owned 3,915,000 Shares (excluding 3,000 shares subject to the James Furman Supplemental 1994 Stock Option Plan) which are currently vested in the beneficiaries of the Estate, subject to administration of the Estate by the Representatives (the “Estate Shares”);

WHEREAS, James on or about July 26, 2004 filed a complaint in the Court of Chancery of the State of Delaware in and for New Castle County (the “Court”), entitled Alan James v. William A. Furman, Benjamin R. Whiteley, C. Bruce Ward, Victor G. Atiyeh, A. Daniel O’Neal, Jr., Duane C. McDougall and The Greenbrier Companies, Inc., C.A. No. 597-N, related to, among other matters, the Stockholders’ Agreement and Greenbrier’s adoption of a stockholder rights plan (the “Delaware Litigation”).

WHEREAS, James engaged FTI Consulting Inc. (“FTI”) to conduct certain investigations, studies and inquiries pertaining to Greenbrier and its operations (the “Investigation”);

WHEREAS, FTI has completed its Investigation and delivered a complete report of its Investigation to the Representatives, and the Representatives have delivered a true, correct and complete copy of such report to Greenbrier;

WHEREAS, the Representatives desire to sell some or all the Estate Shares;

WHEREAS, Furman desires to sell some of the Shares held by him (the “Furman Shares”);

WHEREAS, Greenbrier desires to acquire some or all of the Estate Shares and some of the Furman Shares, subject to completion of a public offering of Shares, and subject to the terms and conditions of this Agreement including the Exhibits and Schedules hereto;

WHEREAS, Greenbrier, Furman and the Representatives desire, upon the terms and conditions set forth herein, to waive, amend and terminate certain provisions of the Old ROFR to permit the sale of Shares to the Company and to adopt terms and conditions providing for a revised right of first refusal (the “New ROFR”);

WHEREAS, Greenbrier, its directors, including Furman, and the Representatives desire to dismiss the Delaware Litigation with prejudice and the Parties desire to enter into mutual general releases with respect to certain other claims, whether known or unknown, among them;

WHEREAS, the Representatives, Furman, the Company and Bear Stearns & Co. Inc. (“Bear Stearns”) have entered into a letter agreement, dated as of the date hereof (the “Bear Agreement”), pursuant to which among other matters, (i) Bear Stearns has agreed not to seek to collect any additional fees from Furman or the Representatives or beneficiaries of the Estate under its engagement letter, dated October 14, 2002, with respect to the purchase and sale of Estate Shares and Furman Shares by the Company pursuant to this Agreement, and (ii) the Representatives have agreed to acknowledge that they are bound, as successor to James, by such engagement letter,

WHEREAS Greenbrier shall provide Relational Advisors LLC (“Relational”) with certain rights to monitor the Offering (as defined below), and Greenbrier shall pay Relational the fee specified in the Stock Purchase Agreement (as defined below) as a reimbursement to the Representatives for a portion of the fee the Representatives are obligated to pay to Relational and Greenbrier shall reduce the amount the amount of underwriting discount paid to the Underwriters (as defined below) by an equal amount; and

WHEREAS, the Parties desire to enter into the other agreements described in this Agreement and in the Exhibits hereto;

NOW, THEREFORE, for good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the Parties adopt the foregoing recitals and agree as follows:

ARTICLE I.  – TERMS

1.1           Dismissal of Delaware Litigation .  Contemporaneously with the execution of this Agreement, the Parties shall cause their attorneys to execute the stipulation approving the dismissal with prejudice of the Delaware Litigation, in the form attached hereto as Exhibit A (the “Stipulated Order”).  The Stipulated Order together with such correspondence as shall be agreed by counsel to the parties in the Delaware Litigation shall be filed with the Court as soon as possible, but in no event later than April 21, 2005.

1.2           Stock Purchase Agreement .  Contemporaneously with the execution of this Agreement, Greenbrier, Furman, and the Representatives shall execute the Stock Purchase

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Agreement in the form attached hereto as Exhibit B (the “Stock Purchase Agreement”).  The Stock Purchase Agreement provides for the purchase by the Company of Estate Shares and Furman Shares, subject to the terms and conditions described therein including the completion of a public offering of Company Shares.

1.3           Offering .  Contemporaneously with the execution of this Agreement, Greenbrier shall file a prospectus supplement (the “Supplement”) with the Securities and Exchange Commission (the “Commission”), to its existing shelf registration statement on Form S-3, Registration Number 333-121181, for a primary public offering of  4,500,000 of the Company’s Shares plus the shares issuable upon exercise of the underwriters’ overallotment option (the “Offering”).  The Supplement shall be substantially in the form of the draft dated April 19, 2005 delivered to the Representatives.  The Supplement may be amended to reflect such changes as the Company and the Underwriters deem reasonably necessary or appropriate including, without limitation, to reflect an upsizing or downsizing of the Offering.

1.3.1        Underwriting Agreement .  The Offering shall be made pursuant to an Underwriting Agreement by and among the underwriters named therein (the “Underwriters”) and Greenbrier, substantially similar to the draft dated April 15, 2005 delivered to the Representatives (the “Underwriting Agreement”).

1.3.2        Monitoring of Offering .  As provided in the Stock Purchase Agreement, Greenbrier shall permit Relational, as financial advisor for the Representatives, to observe and receive periodic information about the Offering, including (i) causing Bear Stearns to provide Relational with daily updates on the progress of the Offering, including the status of the book-building process, (ii) providing Relational with an opportunity to review the road show presentation, and (iii) permitting Relational to listen in on the pricing call.  In no event shall Relational have any power or authority to alter or amend any terms of the Offering or to delay, accelerate, terminate or suspend the Offering.

1.3.3        Cooperation .  The Representatives and Furman shall cooperate with Greenbrier and the Underwriters in connection with the Offering to the extent reasonably requested by Greenbrier, provided that the Representatives shall not be required to take action that will cause them to incur any unreimbursed out-of-pocket expenses and shall not be required to enter into any agreement with Greenbrier, the Underwriters or any other party other than the agreement necessary to effect the 90-day lockup described in Section 1.3.4 below.

1.3.4        Offering Period; No Solicitation .  Greenbrier shall have 60 days from the date the Supplement is first filed with the Commission to complete the Offering (plus any extensions thereof which may be agreed by the Parties, the “Offering Period”).    During the Offering Period the Representatives shall not sell or otherwise transfer any interest in Shares, directly or indirectly, or offer or solicit the offer to purchase Shares (other than, in each case, in connection with the Loan described in Section 1.8 below) and shall discontinue any negotiations with respect to the sale of Shares (except in connection with the Loan) as more particularly described in Section 6.2 of the Stock Purchase Agreement.  Contemporaneously with the execution of this Agreement, the Representatives and Furman shall each enter into an agreement with the Underwriters in the form attached hereto as Exhibit C (the “Lock-up Agreement”).  The Lock-up Agreement shall not prohibit the pledge or transfer of Pledged Shares in connection with the Loan.

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Following the earlier to occur of (i) the end of the Offering Period, (ii) the “Closing” under the Stock Purchase Agreement, or (iii) the termination of the Stock Purchase Agreement, and subject to the Lock-up Agreement, the Representatives may sell or otherwise transfer any remaining Estate Shares provided it complies with Section 1.5 or Section 1.6 of this Agreement, whichever is applicable.

1.3.5        Rejection of Offering Price .  Either the Representatives, Furman, or both, may reject the price offered by the Underwriters to purchase Shares from the Company (the “Offering Price”) as inadequate, which Offering Price affects the price the Company is obligated to pay to the Representatives and Furman for its purchase of Estate Shares and Furman Shares pursuant to the Stock Purchase Agreement.  Such rejection of the Offering Price must be made on the pricing call with the Underwriters within one hour after such Offering Price is proposed by the Underwriters to the Company, Furman and the Representatives.  If the Representatives or Furman reject the Offering Price it or he shall not be obligated to sell, and the Company shall not be obligated to purchase, any Estate Shares or Furman Shares, as applicable, pursuant to the Stock Purchase Agreement and the sale or other transfer of Estate Shares shall be subject to the restrictions and covenants contained in Section 1.5 or Section 1.6, whichever is applicable.  The consequences of the rejection of the Offering Price by the Representatives or Furman and the effects on the Company’s obligations to purchase Estate Shares and Furman Shares are described in more detail in the Stock Purchase Agreement.  Notwithstanding any rejection of the Offering Price by the Representatives or Furman, the other covenants and agreements contained in this Settlement Agreement, including Exhibits and Schedules, other than the purchase and sale of Estate Shares and Furman Shares, as applicable, pursuant to the Stock Purchase Agreement, shall remain in full force and effect.

1.4           Termination of Stockholders’ Agreement and Old ROFR .  The Stockholders’ Agreement and the Old ROFR shall terminate and shall be of no force and effect upon the earliest of (i) the end of the Offering Period, (ii) the first Closing under the Stock Purchase Agreement, or (iii) the termination of the Stock Purchase Agreement.

1.4.1        Waiver and Consent under Old ROFR .  Each of Furman, the Representatives and the Company waives any and all rights it may have with respect to restrictions on transfer contained in the Stockholders’ Agreement and under the Old ROFR with respect to, and each Party consents to, the sale of Estate Shares and Furman Shares to the Company pursuant to the Stock Purchase Agreement.

1.4.2        No Notice Under Old ROFR .  Neither Furman nor the Representatives shall deliver an “Offer Notice” as described in Section 5.02 of the Stockholders’ Agreement.

1.4.3        New ROFR .  The New ROFR shall only be effective, and shall always be effective unless terminated as provided in this Section 1.4.3, upon termination of the Old ROFR pursuant to Section 1.4 above.  Under the New ROFR:

(a)           If the Representatives desire to transfer any Shares or any interest therein, other than (i) to a Trust or a beneficiary of the Estate, or (ii) subject to the limitations contained in Section 1.5 or 1.6, in the open market in “brokers’ transactions” as defined in Rule

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144(g) under the Securities Act of 1933 (the “Securities Act”), the Representatives shall give written notice (the “New ROFR Notice”) to the Company and Furman specifying that the New ROFR Notice is being given pursuant to Section 1.4.3 of this Agreement, and further specifying (I) the number of Shares the Representatives desire to transfer (the “Offered Shares”), (II) except as described in Section 1.4.3(d) below, the identity of the person to whom the transfer is proposed to be made (the “Proposed Transferee”), (III) except as described in Section 1.4.3(d) and 1.4.3(e) below, the purchase price offered by the Proposed Transferee, and (IV) the other material terms and conditions of the offer including payment terms together with copies of any proposed agreements or other documents related to the offer.

(b)           Except as described in Section 1.4.3(d) below, for the period of seven (7) days after Furman has received the New ROFR Notice, he shall have the exclusive option to purchase (except as otherwise provided in Section 1.4.3(e) below) all, but not less than all, of the Offered Shares on the same terms and conditions, including payment terms (except to the extent otherwise provided in Section 1.4.3(c) below) (collectively, the “Offered Terms”) as described in the New ROFR Notice.  Furman may assign all or, except with respect to a Financing Transaction (as defined in Section 1.4.3(e) below), part of his right to purchase Offered Shares under this Section 1.4.3(b) to the Company, provided that in the case of any such partial assignment, the Company and Furman, collectively, shall upon exercise of the option, be permitted to purchase all, but not less than all, of the Offered Shares on the Offered Terms.

(c)           Subject to Section 1.4.3(e) below, if Furman or the Company elects to exercise the option granted above to purchase the Offered Shares on the Offered Terms, then Furman or the Company shall so notify the Representatives in writing and shall close the purchase and sale of Offered Shares on the later of (i) the seventh (7 ^th ) day after receipt of the New ROFR Notice, or (ii) upon the expiration of a longer period of time, if any, provided the Proposed Transferee as described in the Offered Terms.  Payment for purchase of the Offered Shares, must be made in cash unless the Offered Terms provide for another form of payment and the credit worthiness of Furman or the Company, as the case may be, is comparable, in the reasonable judgment of the Representatives to that of the Proposed Transferee, in which case payment, at the option of Furman or the Company, as the case may be, may be made in accordance with the Offered Terms or in cash.  In the event Furman or the Company, or both, elect to exercise the option to purchase the Offered Shares on the Offered Terms or, with respect to a Financing Transaction, elect to match the material terms and conditions of the Financing Transaction as provided in Section 1.4.3(e), but fails, or fail, where such failure constitutes a breach of his or its obligations hereunder, to close the purchase and sale of Offered Shares, or the matching of the material terms and conditions of the Financing Transaction, as the case may be, on or prior to the seventh (7th) day after receipt of the New ROFR Notice or such later date as provided in the Offered Terms, then (i) Furman or the Company or both, as the case may be, shall be liable to the Representatives for breach of their respective covenants to close the purchase and sale or the matching of material terms and conditions on or prior to that day, and (ii) the New ROFR shall terminate in full at 12:01 a.m., West Coast time, on the eighth (8th) day after receipt of the ROFR Notice, or the day after such later date as provided in the Offered Terms, and shall be of no further force and effect.

(d)           Notwithstanding Section 1.4.3(a) and 1.4.3(c) above if the Representatives propose to transfer Estate Shares in a block trade or sale through a broker, placement agent, investment bank or other transaction intermediary (a “Block Sale”), then (i) the

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New ROFR Notice need not specify the name of the Proposed Transferee, if such name is not known, (ii) the purchase price per Offered Share as specified in the New ROFR Notice may be a formula price based on the market price of Shares at the time of sale, (iii) Furman or the Company or both, as applicable, shall have two business days from the date of receipt of the New ROFR Notice to exercise the option to purchase the Offered Shares on the Offered Terms, and (iv) if Furman or the Company or both so exercise the option to purchase the Offered Shares, Furman or the Company or both, as the case may be, shall close the purchase of the Offered Shares on the Offered Terms not later than the seventh (7 ^th ) day following receipt of the New ROFR Notice.  In the event Furman or the Company, or both, elect to exercise the foregoing option to purchase the Offered Shares on the Offered Terms but fails, or fail, where such failure constitutes a breach of his or its obligations hereunder, to close the purchase and sale of Offered Shares on the Offered Terms on or prior to the seventh (7 ^th ) day after receipt of the New ROFR Notice, then (i) Furman or the Company or both, as the case may be, shall be liable to the Representatives for breach of their respective covenants to close the purchase and sale on or prior to that day, and (ii) the New ROFR shall terminate in full at 12:01 a.m., West Coast time, on the eighth (8 ^th ) day after receipt of the ROFR Notice and shall be of no further force and effect.

(e)           Notwithstanding Section 1.4.3(a) if the Representatives propose to enter into (x) a sale, transfer of interest in or lending of Shares in connection with a hedging transaction with a nationally recognized brokerage firm, investment bank, insurance company, commercial bank or other lending institution, or (y) a pledge of Estate Shares to an investment bank, insurance company, commercial bank or other lending institution to secure a loan or other extension of credit ((x) and (y) collectively, a “Financing Transaction”), then (i) the Offered Terms in the New ROFR Notice must contain the name of such entity facilitating the Financing Transaction, the number of Shares subject to the Financing Transaction, the other material terms and conditions of such Financing Transaction together with copies of any proposed agreements or other documents related to such Financing Transaction, (ii) Furman or the Company, as applicable, may exercise the New ROFR as described in Section 1.4.3(b) above by matching the material terms and conditions of such Financing Transaction, and (iii) if Furman or the Company, as applicable, do not elect to exercise the New ROFR with respect to such Financing Transaction, then any subsequent foreclosure or closing out of a hedge position related to such Financing Transaction shall not be subject to the New ROFR.

(f)            If Furman or the Company, as applicable, do not exercise the option granted above to purchase all of the Offered Shares or to match the material terms and conditions of a Financing Transaction within the respective time periods described in Section 1.4.3(b), (c) or (d), then the Representatives shall thereafter (i) with respect to Block Sales be free, for a period of 21 days following expiration of the two business day notice period to close transfer of Offered Shares pursuant to such Block Sale in accordance with Offered Terms, and (ii) with respect to all other sales or transfers of Estate Shares including Financing Transactions subject to the New ROFR, the Representatives shall be free, for a period of 30 days following expiration of the seven (7) day notice period, to close the sale or other transfer of such Estate Shares pursuant to the Offered Terms.

(g)           Any transfer, or purported transfer, of Estate Shares including, without limitation, any attachment, judgment, creditor execution, foreclosure of security interest, bankruptcy, sale or property settlement or award, which is not in accordance with this Section 1.4.3

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shall be null and void and shall have no force or effect and need not be recognized or acknowledged by the Company or any of its stockholders.

(h)           Notwithstanding the foregoing or anything else contained in this Settlement Agreement and the Exhibits or Schedules hereto, or elsewhere, Greenbrier shall have no obligation to waive or otherwise modify its rights pursuant to that Stockholder Rights Agreement, dated as of July 13, 2004, as the same may be amended from time to time.

(i)            the Parties shall cause certificates representing shares held by the Representatives to bear a legend prominently referring to the New ROFR.

1.5           Sale of Estate Shares Not Purchased by the Company .  Except as described in Section 1.6 below, the sale or transfer of Estate Shares not purchased by the Company pursuant to the Stock Purchase Agreement shall be governed by this Section 1.5.

1.5.1        Registration Rights .  Subject to Section 1.6 and Section 3.12, so long as the Representatives hold subject to administration in the Estate at least 500,000 Shares and the Company has advised the Representatives that it believes the Representatives are “affiliates” as defined in Securities Act Rule 144(a)(1), then the Represen