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CUSIP No. 685932105 SCHEDULE 14A Page 1 of 30
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SCHEDULE 14A
(RULE 14A-101)

INFORMATION REQUIRED IN PROXY STATEMENT
SCHEDULE 14A INFORMATION

PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE
SECURITIES EXCHANGE ACT OF 1934
(Amendment No. 3)

Filed by the registrant [ ]

Filed by a party other than the registrant [X]

Check the appropriate box:

[X] Preliminary proxy statement.

[ ] Confidential, for use of the Commission only (as permitted by
Rule 14a-6(e)(2).

[ ] Definitive proxy statement.

[ ] Definitive additional materials.

[ ] Soliciting material under Rule 14a-12.

OREGON TRAIL FINANCIAL CORP.
--------------------------------------------------------------
(Name of Registrant as Specified in its Charter)

THE STILWELL GROUP
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(Name of Person(s) Filing Proxy Statement if Other Than the Registrant)

Payment of filing fee (check the appropriate box):

[X] No fee required.

[ ] Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11.

(1) Title of each class of securities to which transaction applies:

(2) Aggregate number of securities to which transaction applies:

(3) Per unit price or other underlying value of transaction computed
pursuant to Exchange Act Rule 0-11 (set forth the amount on which the
filing fee is calculated and state how it was determined):

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CUSIP No. 685932105 SCHEDULE 14A Page 2 of 30
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(4) Proposed maximum aggregate value of transaction:

(5) Total fee paid:

[ ] Fee paid previously with preliminary materials.

[ ] Check box if any part of the fee is offset as provided by Exchange Act Rule
0-11(a)(2) and identify the filing for which the offsetting fee was paid
previously. Identify the previous filing by registration statement number, or
the form or schedule and the date of its filing.

(1) Amount Previously Paid:

(2) Form, Schedule or Registration Statement No.:

(3) Filing Party:

(4) Date Filed:

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CUSIP No. 685932105 SCHEDULE 14A Page 3 of 30
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Preliminary Copy

OREGON TRAIL FINANCIAL CORP.
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ANNUAL MEETING OF SHAREHOLDERS
_________ ___, 2001
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PROXY STATEMENT OF THE STILWELL GROUP ("THE GROUP")
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IN OPPOSITION TO
THE MANAGEMENT OF OREGON TRAIL FINANCIAL CORP.
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WHY YOU WERE SENT THIS PROXY STATEMENT

This Proxy Statement and accompanying WHITE proxy card are being furnished to
holders (the "Shareholders") of the common stock, par value $.01 per share (the
"Common Stock"), of Oregon Trail Financial Corp., an Oregon corporation (the
"Company"), in connection with the solicitation of proxies (the "Proxy
Solicitation") by The Stilwell Group ("the Group", "we" or "us"). The Annual
Meeting of Stockholders is to be held on __________ __, 2001, at ____ _.m.
Pacific Time, at ______________________, Oregon (the "Annual Meeting").
Shareholders who own the Common Stock on __________ __, 2001, will be entitled
to vote ("Annual Meeting Record Date"). The Company's principal executive
offices are located at 2055 First Street, Baker City, Oregon 97814.

At the Annual Meeting, the Company will be seeking (1) the election of two
directors for a term of three years, or until their successors have been elected
and qualified and (2) the ratification of the appointment of Deloitte & Touche
LLP as independent auditors.

The Stilwell Group, members of which own, as of the date of this Proxy
Statement, an aggregate of 290,800 shares of Common Stock, is the Company's
largest shareholder. We seek to elect one candidate, Mr. Kevin D. Padrick (the
"Group Nominee"), to the Company's Board of Directors (the "Board"). The
Stilwell Group is soliciting the votes of other Shareholders in favor of the
election of the Group Nominee. Our solicitation of votes is in opposition to the
directors nominated for election by management. We believe the election of the
Group Nominee will send a strong message to the Company and to management. We
also believe that if the Group Nominee is elected to the Board of Directors, he
will be able to encourage the Company to take steps to increase shareholder
value and to monitor closely management's progress with respect to enhancing
shareholder value. However, there can be no assurance that the election of the
Group Nominee will result in maximizing shareholder value.

The Stilwell Group consists of Stilwell Value Partners II, L.P., a Delaware
limited partnership ("Stilwell Value Partners II"); Stilwell Associates, L.P., a
Delaware limited partnership ("Stilwell Associates"); Stilwell Value LLC, a
Delaware limited liability company which is the general partner of Stilwell
Value Partners II and Stilwell Associates ("Stilwell Value LLC"); and Joseph
Stilwell, individually and as the managing and sole member of Stilwell Value
LLC. Additional information concerning The Stilwell Group is set forth under the
heading "Certain Information Regarding the Participants". This Proxy Statement
and WHITE proxy card are being first mailed or furnished to Shareholders on or
about __________ __, 2001.

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CUSIP No. 685932105 SCHEDULE 14A Page 4 of 30
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Remember, your last dated proxy is the only one that counts, so return the WHITE
proxy card even if you delivered a prior proxy. We urge you not to return any
proxy card sent to you by the Company.

Your vote is important, no matter how many or how few shares you hold. If your
shares are held in the name of a brokerage firm, bank or nominee, only that
brokerage firm, bank or nominee can vote your shares and then only upon receipt
of your specific instructions. Accordingly, please return the WHITE proxy card
in the envelope provided by your bank or broker or contact the person
responsible for your account and give instructions for your shares to be voted
for the Group Nominee.

If your shares are registered in more than one name, the WHITE proxy card should
be signed by all the registered owners to ensure that all shares are voted for
the Group Nominee.

Please refer to the Company's proxy statement for a full description of
management's proposals, the securities ownership of the Company, the share vote
required to ratify or approve each proposal and to elect the directors, the
background of the Company's nominees for the Board, information about the
Company's officers and directors, including compensation, information about the
ratification of the appointment of Deloitte & Touche LLP as independent
auditors, stock price performance and the date by which Shareholders must submit
proposals for inclusion in the next Annual Meeting.

Holders of record of shares of Common Stock on the Annual Meeting Record Date
are urged to submit a proxy even if your shares have been sold after that date.
The number of shares of Common Stock outstanding as of the Annual Meeting Record
Date is ___________. Each share of Common Stock is entitled to one vote at the
Annual Meeting.

If you have any questions or need assistance in voting your shares, please call:

D.F. King & Co., Inc.
77 Water Street
New York, NY 10005
(Call Toll Free (800) 207-3159)

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CUSIP No. 685932105 SCHEDULE 14A Page 5 of 30
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OUR GOAL IS TO MAXIMIZE THE
VALUE OF THE COMPANY'S STOCK
FOR ALL SHAREHOLDERS.

The Group believes its fellow Shareholders have this same goal. We believe that
the best way to maximize shareholder value is for the Company to be sold. In
order to accomplish a sale of the Company, the Group believes an investment
banking firm should be retained to evaluate the prospects of selling the Company
at a premium to book value by, among other things, providing analyses, opinions
or reports with respect to such sale. The Group has not independently performed
or commissioned any such analyses, opinions or reports. We believe the Company
has a responsibility to its shareholders to do so. We also believe that the
Company should aggressively pursue its share repurchase program to acquire its
stock at prices lower than book value. We believe the only way shareholders can
be assured that the Group's proposals receive appropriate consideration is
through Board representation.

WE BELIEVE A VOTE FOR THE GROUP NOMINEE IS A VOTE TO BEGIN THE
PROCESS TO SELL THE COMPANY. WE BELIEVE SUCH A SALE IS OPPOSED
BY THE CURRENT BOARD AND MANAGEMENT.

We believe management and the current Board of Directors are opposed to a sale
of the Company. Since November 7, 2001, when the Group filed its initial
Schedule 13D, we have expressed our opinion in each of our filings that
management should retain an investment banking firm and explore a sale of the
Company in order to maximize shareholder value. We reiterated this belief at a
meeting held with Messrs. Berniel L. Maughan and Stephen R. Whittemore, the
President and the Chairman of the Board, respectively, on January 25, 2001, at
the Company's headquarters. At this meeting, we requested that the Company add
two of the Group's nominees to the Board. In a Form 8-K filed on February 15,
2001, the Company announced its rejection of our proposal. The Form 8-K quoted
the Chairman of the Board as saying: "Although the Board seeks input and
suggestions from our shareholders, we believe directors should represent all
shareholders and not be obligated to just one shareholder, particularly when Mr.
Stilwell's stated objective is to force the Company to sell. This past summer we
hired a new management team who have since implemented a number of strategic
initiatives to improve the Company's performance. We believe that shareholder
values can be better enhanced by completing the implementation of these
initiatives."

Based on these public statements, we believe that the current Board of Directors
has rejected even seriously exploring a sale alternative. Instead, we believe
the Board is focused solely on its "strategic initiatives."

If elected, the Group Nominee is committed to acting in the best interest of the
Shareholders and, subject to his fiduciary duties as a director of the Company,
will work diligently toward a sale of the Company. We believe such a sale is
advisable for several reasons. First, we believe there currently exists a
positive climate for small thrifts to be purchased by larger financial
institutions. The Company is one of only two thrifts in Oregon. In addition, the
Company's return on average equity, or ratio of earnings per share to average
book value per share ("ROE"), has been below 5% since the Company became a
public company in 1998. According to the June 18, 2001 edition of Barron's
Market Week, the yield on Barron's index of medium grade corporate bonds was
7.70%. A medium grade corporate bond is issued by a higher rated issuer than the
Company, which is unrated. Therefore, the Company's ROE is below the comparable
rate of return yielded by lower-risk senior securities.

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CUSIP No. 685932105 SCHEDULE 14A Page 6 of 30
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If a sale of the Company is not possible at a premium to book value, the Group
Nominee, although he has not yet formulated specific plans for doing so, will
work to increase the Company's earnings, earnings per share and deposits. In
addition, the Group Nominee will, subject to his fiduciary duties as a director
of the Company, strongly recommend that the Company aggressively pursue its
stock repurchase program at prices below book value. In a sale, the Board would
have to determine a satisfactory price, which could be either all cash or a
combination of cash and stock. Such a sale would also have to be submitted to
the Shareholders for their vote and approval.

Each Shareholder should be aware that in the present election the Group is
seeking to elect one director to the Board. To accomplish the Group's goal, the
Group Nominee, if elected, will need the cooperation of at least three of the
Company's other directors. We believe the Group Nominee's presence on the Board,
and the action of the Shareholders in electing him to the Board, will send a
strong message to the Company and the remaining directors regarding the desire
of the Shareholders to maximize shareholder value. If elected, the Group Nominee
will be able to closely monitor management's progress with respect to enhancing
shareholder value from his position on the Board.

Shareholders should also be aware that this election has nothing to do with the
election of directors to Pioneer Bank, a federal savings bank (the
"Association") and wholly owned banking subsidiary of the Company. The present
directors of the Company, even if the Group Nominee wins this election, will
still be able to appoint the board of directors of the Association, including
the Company's nominees, even if they lose the election.

WE BELIEVE THE CURRENT BOARD OF DIRECTORS
HAS NOT SHOWN AN ABILITY
TO MANAGE THE COMPANY EFFECTIVELY
OR TO TAKE THE AGGRESSIVE STEPS NECESSARY
TO MAXIMIZE SHAREHOLDER VALUE.

The current Board has been in place since the Company became a public company in
1998. During that time, the Company has had three different senior management
teams. During this same period, the Company has produced a return on average
equity below 5% in every year. In fact, ROE has declined in each of the last two
fiscal years. We believe ROE is one of best and most basic standards by which to
measure how profitably shareholder capital is employed by management, and
therefore to judge a thrift's performance. The table below lists the Company's
annual ROE.

---------------------------
Fiscal Year ROE
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1998* 4.46% (1)
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1999 4.90% (1)
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2000 4.60% (1)
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2001 3.09% (2)
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* Annualized for one quarter as a public company
(1) As reported by SNL Securities
(2) As reported in the Company's Form 8-K filed May 17, 2001

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CUSIP No. 685932105 SCHEDULE 14A Page 7 of 30
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On January 19, 2001, just over two months after we filed our initial Schedule
13D encouraging the Board to take action to maximize shareholder value, the
Company announced a restructuring program. However, in announcing this plan,
management projected that, in the best case, earnings for the current fiscal
year would result in less than a 7% ROE. The Group still considers this to be
unacceptably low and believes that more aggressive steps, such as a sale of the
Company and aggressive share repurchases, can produce more value for the
Shareholders.

During the period from April 1, 2000 through March 31, 2001, the market price
per share of the Common Stock ranged from $8.94 to $14.38. This price range was
significantly below the March 31, 2000 book value per share of $16.01 reported
by the Company. We believe that the appropriate response in such a situation is
to engage in substantial share repurchases at prices less than book value. We
believe that share repurchases at discounts to book value improve ROE, book
value, and franchise value. Despite this significant market opportunity and the
Company's announced commitment to "increase earnings per share through stock
repurchases while shares trade at significant discounts to book value," as
reported in the Company's Form 10K filed June 29, 2001, the Company actually
issued 8,751 more shares than it repurchased during the period from April 1,
2000 through March 31, 2001. Since March 31, 2001, as reported in the Company's
Form 10K filed June 29, 2001, the Company's outstanding shares has increased by
another 13,962 shares. We believe that the Company's failure to repurchase, net
of new share issuances, a significant number of shares through its share
repurchase program is another indication that the current Board is unwilling or
unable to take the steps necessary to maximize shareholder value.

If the Company is not able to be sold for greater than book value (which as of
March 31, 2001 was $17.38 per share, as reported in the Company's Form 8-K filed
May 17, 2001), the Group Nominee will, subject to his fiduciary duties as a
director of the Company, support an aggressive repurchase of shares at prices
below book value until a buyer can be found who will pay greater than book value
for the Company. While there is no assurance that a buyer will be located to
purchase the Company at a premium to book value, share repurchases at a discount
to book value, as recommended by the Group, have the effect of increasing
earnings per share and book value for all remaining shares.

THE STILWELL GROUP'S PREVIOUS EXPERIENCE MAXIMIZING SHAREHOLDER VALUE

Members of the Group have made Schedules 13D filings with respect to four other
financial institutions that were sold shortly after the Group's respective
filings. In each Schedule 13D filing, members of the Group actively encouraged
management of each of these companies to take steps to maximize shareholder
value. While there can be no assurance that the Group's Schedule 13D filings
caused the sale of these companies, the Group believes its filings may have been
a factor in or played some role in such sales.

With respect to Security of Pennsylvania Financial Corp. ("Pennsylvania
Financial"), the Group filed its initial Schedule 13D on May 9, 2000.
Thereafter, the Group scheduled a meeting with senior management of the company
in order to discuss maximizing short and long-term value of Pennsylvania
Financial's assets. On June 2, 2000, prior to the scheduled meeting,
Pennsylvania Financial publicly announced its sale to Northeast Pennsylvania
Financial Corp.

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CUSIP No. 685932105 SCHEDULE 14A Page 8 of 30
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With respect to Cameron Financial Corp. ("Cameron"), the Group filed its initial
Schedule 13D on July 7, 2000, approximately one month after another shareholder
filed a Schedule 13D reporting that such shareholder had purchased shares of
Cameron for investment purposes, believed the shares were undervalued and had
asked Cameron's management to repurchase such shares. On August 10, 2000, the
Group met with Cameron's management and demanded that they invite the nominees
of the Group to join the Board. On September 7, 2000, the Group wrote to other
Cameron shareholders to express their dismay with management. On October 6,
2000, approximately three months after the Group's initial Schedule 13D filing,
Cameron publicly announced its sale to Dickinson Financial.

With respect to Community Financial Corp. ("Community Financial'), the Group
filed its initial Schedule 13D on January 4, 2001, reporting that it acquired
shares of Community Financial after the company announced the sale of two of its
four subsidiary banks and its intent to sell one or more of its remaining two
subsidiaries. On January 25, 2001, Community Financial announced the sale of
another subsidiary bank. On January 29, 2001, the Group disclosed its intent to
nominate alternate candidates to the company's board of directors if Community
Financial did not enter into a sale of its remaining subsidiary bank before its
annual meeting of shareholders. On March 8, 2001, the Group confirmed in writing
that it was requesting Community Financial to invite a nominee of the Group to
join the Board. On March 27, 2001, the Group wrote to Community Financial
confirming that the company had agreed to meet with the Group's nominee during
the first week of April. On March 30, 2001, Community Financial publicly
announced the sale of its last remaining subsidiary to First Financial
Corporation.

With respect to Montgomery Financial Corporation ("Montgomery"), the Group filed
its initial Schedule 13D on February 23, 2001. On April 20, 2001, the Group met
with Montgomery's management, suggested to management that it should maximize
shareholder value by selling the institution and notified management that it
would run an alternate slate of directors at the 2001 annual meeting unless
Montgomery entered into a transaction. On June 5, 2001, Montgomery announced
that it had hired an investment banking firm, to "help evaluate available
alternatives to improve financial performance and maximize shareholder value. .
. . [including] a potential acquisition or merger." On June 13, 2001, the Group
noticed its intention to nominate two persons to Montgomery's board at the 2001
annual meeting. On July 24, 2001, Montgomery announced that it signed a
definitive agreement with Union Community Bancorp ("Union") providing for the
merger of Montgomery into Union.

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CUSIP No. 685932105 SCHEDULE 14A Page 9 of 30
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The following table lists the closing price of each company's stock the day
before the Group filed its initial Schedule 13D and the sale price per share as
announced by each company. All sales were for cash.

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Company Closing Price Per Sale Price Per Share Difference Between
Share on Day Before of Company Closing Price Per Share
Schedule 13D Filed and Sale Price Per
Share (%)
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Security of Pennsylvania Financial Corp. $10.25 $17.50 70.7%
(AMEX: SPN)
(Buyer: Northeast PA Financial Corp.)
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Cameron Financial Corp. (NASDAQ: CMRN) $16.38 $20.75 25.2%
(Buyer: Dickinson Financial)
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Community Financial Corp. (NASDAQ: CFIC) $11.13 $15.00 (1) 34.8% (1)
(Buyer: First Financial Corp.)
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Montgomery Financial Corp. (NASDAQ: MONT) $11.25 $15.00(2) 33.3% (2)
(Buyer: Union Community Bancorp)
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(1) These figures are estimates. CFIC's sale announcement stated $15.00 as
an approximate price per share, subject to adjustments at closing. The
sale is not expected to close until late summer or early fall of 2001.

(2) These figures are estimates. In its Form 425 filed July 24, 2001 MONT
stated that its shareholders would have the option "to elect to receive
either 1.1244 shares of Union common stock (valued at $15.18, based on
Union's July 23, 2001 closing price), or $15.00 in cash for each share
of Montgomery common stock owned by them. However, 50% of the aggregate
consideration must be paid in shares of Union common stock, and there
may be pro rata allocations of cash or stock made to shareholders to
ensure that this requirement is satisfied." There is no guarantee that
the Company can be sold for a premium equal to or greater than the
premium paid for the other commercial banks and thrifts mentioned in
this Proxy Statement. There is also no guarantee that the Company can
be sold at all.

LITIGATION BETWEEN THE GROUP AND THE COMPANY

On January 5, 2001, Stilwell Associates commenced a lawsuit against the
Company in the Circuit Court of the State of Oregon for the County of Baker
requesting that the Court issue an alternative writ of mandamus commanding the
Company to either turn over the record of shareholders previously requested by
Stilwell Associates, or to appear before the Court to show cause why it had not
turned over the documents to Stilwell Associates. The suit also sought, pursuant
to Oregon law, all of Stilwell Associates' attorneys' fees and costs incurred in
seeking the requested documents. On January 8, 2001, Circuit Judge Gregory L.
Baxter issued an order allowing an alternative writ of mandamus, scheduling the
show cause hearing for January 12, 2001. The Company moved to dismiss the
proceeding for improper service of process, claiming it had produced the
requested documents and alleging that it was not required to produce a Cede list
or a NOBO list. The show cause hearing was held on May 5, 2001. On June 30,
2001, Judge Baxter granted the Company's motion to dismiss the proceeding for
improper service and awarded the Company attorney fees. Judge Baxter stated,
however, that because he was dismissing the action he would not rule on the
merits but "is prepared to rule" if the issues are "properly presented before
the court once more", in a new proceeding. Therefore, on July 5, 2001, Stilwell
Associates commenced a new proceeding seeking the Cede list and NOBO list. On
July 27, 2001, Judge Baxter issued an order requiring the Company to turn over
to Stilwell Associates the Company's Cede list and its NOBO list (if the Company
possesses the latter), and finding it "fair and equitable" to award Stilwell
Associates its attorney fees and costs incurred in this case.

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CUSIP No. 685932105 SCHEDULE 14A Page 10 of 30
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On February 16, 2001, Stilwell Associates filed a lawsuit against Charles Henry
Rouse, a director of the Company. This lawsuit seeks a judgment to remove Mr.
Rouse from the Board, alleging Mr. Rouse violated the residency requirement
contained in the Company's bylaws when he moved his primary residence away from
the Company's market area. The lawsuit also seeks the maximum fine against Mr.
Rouse under the Oregon Code for violation of the applicable statute. The
Company's counsel is defending Mr. Rouse. Discovery between the parties is
proceeding. On July 26, 2001, the court denied Mr. Rouse's motion to compel the
production of portions of the Group's attorney's file. On July 31, 2001, Mr.
Rouse indicated that he intends to move for summary judgment to dismiss the
action. Trial of the matter is scheduled to be held in September 2001.

On May 8, 2001, Stilwell Associates sent a letter to the Company demanding that
the Company remove Edward H. Elms from the Board, alleging that he gave false
deposition testimony in the above-mentioned Rouse lawsuit. The demand letter
alleged that during the course of the deposition, Elms intentionally testified
falsely with respect to three material issues in the Rouse lawsuit. The demand
letter further alleged that the intentional giving of false testimony
constitutes a crime under Oregon law, constitutes fraudulent or dishonest
conduct and that the removal of defendant Elms is in the best interests of the
Company. The Company did not comply with the demand within the letter's
deadline. On May 22, 2001, a derivative action was filed by Stilwell Associates
in the U.S. District Court for the District of Oregon seeking to remove Mr.
Elms. In the suit, Stilwell Associates seeks to recover its reasonable
attorneys' fees from Mr. Elms on the grounds that the action is a derivative
suit that will benefit the Company. On May 29, 2001, the Company and Mr. Elms
filed their answer, defenses, affirmative defenses, counterclaims and
third-party complaint against the Group. The Company and Mr. Elms denied the
material allegations of the complaint. Additionally, four counterclaims and
third-party claims were asserted against the Group. Two of the counterclaims and
third-party claims allege that the May 8, 2001 Schedule 13D and demand letter
attached thereto contained defamatory statements against Elms and the Company.
The Company and Mr. Elms maintain that Mr. Elms did not commit perjury and that
the May 8, 2001 Schedule 13D and demand letter attached thereto is false and
misleading. The other two counterclaims and third-party claims charge the Group
with filing an incomplete, inaccurate and misleading Schedule 13D because the
Group's May 8, 2001 Schedule 13D attached the demand letter which the Company
and Mr. Elms claim is defamatory. The prayer for relief seeks unspecified
damages and an order requiring the Group to make a corrective amendment to its
Schedule 13D and enjoining the Group from purchasing additional stock,
exercising voting rights, soliciting proxies, and acting as a group to exercise
control over the Company. The Group believes that the allegations contained in
the counterclaims and third-party claims are without merit.

On June 26, 2001, the Company noticed a motion to dismiss the derivative action
alleging that the complaint fails to state a cause of action. On July 9, 2001,
Stilwell Associates moved to supplement the complaint so as to refer to the fact
that on May 25, 2001, after the original complaint was filed, the Company sent
Stilwell Associates a written rejection of the May 8th demand letter. Also on
July 9, 2001, Stilwell Associates filed its opposition papers to the Company's
motion to dismiss. On July 17, 2001, following a demand by the Group, the
Company's counsel agreed to withdraw from simultaneously representing Elms and
the Company, and new counsel appeared for Elms. On July 30, 2001, Stilwell
Associates filed a motion to dismiss the third-party claims and counterclaims
for defamation and Section 13(d) violations alleging that the statements
concerning Elms are true, absolutely privileged and do not constitute Section
13(d) violations.

The Group Nominee will support the recoupment of legal fees and expenses
advanced by the Company on behalf of any director who is subsequently found to
have engaged in improper conduct. If necessary, the Group Nominee will support
legal action to recover these fees and expenses. The Group intends to continue
its legal actions against Messrs. Rouse and Elms even if the Group Nominee is
elected to the Board.

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CUSIP No. 685932105 SCHEDULE 14A Page 11 of 30
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ELECTION OF THE GROUP NOMINEE

The Board currently consists of six members. Two seats on the Board are up for
election at the Annual Meeting.

At the Annual Meeting, the Group will seek to elect Mr. Kevin D. Padrick, who
has consented to being named in this Proxy Statement and to serving as a
director on the Board if elected, to fill one of the open director seats, in
opposition to one of the Company's nominees. The election of Mr. Padrick
requires the affirmative vote of a plurality of the votes cast. If elected, Mr.
Padrick would be entitled to serve a three-year term. Mr. Padrick, an Oregon
resident, is an attorney and business consultant with experience in the area of
troubled institutions. We believe he would be strong addition to the Board.

When you return the Group's WHITE proxy card you are voting for Mr. Padrick.

KEVIN D. PADRICK
Kevin D. Padrick, an attorney, is a consultant for businesses in need of an
individual with a background in both business and law. He holds a B.S. (with
honors) from the University of Santa Clara, an M.B.A. (with honors) from the
University of Santa Clara Business School and a J.D. (with highest honors) from
the University of Santa Clara Law School. From 1979 through 1994, Mr. Padrick
practiced bankruptcy law, first as an associate and then as a partner, with
Miller Nash LP, one of the largest law firms in Portland, Oregon. He formed the
bankruptcy department in the firm's Portland office. Mr. Padrick left the firm
to start his own business and has since operated, among others, consulting,
construction, and transportation businesses.

In September 1998, Mr. Padrick was hired as a consultant by Southern Pacific
Funding Corporation ("Southern Pacific") to evaluate strategic options available
to the company with respect to its indebtedness. Prior to Southern Pacific's
filing on October 1, 1998 of a Chapter 11 petition under the Federal bankruptcy
laws, Mr. Padrick was hired by the company as an executive officer. As an
Executive Vice President and later as President of Southern Pacific through July
1999, Mr. Padrick worked to maximize the return to creditors of the company,
which had $4 billion in filed claims. He directed the sale of Southern Pacific
to Goldman Sachs, and on July 12, 1999, obtained confirmation by the United
States Bankruptcy Court for the District of Oregon of a plan of reorganization
of the company, which was the largest Chapter 11 case in the history of Oregon
at the time. Southern Pacific's principal business was mortgage financing.

As a consultant, Mr. Padrick's assignments have included being retained by
Goldman Sachs to assist in a residual interest loan purchase involving $5
billion in mortgage loans, structuring the sale of a distributor of pet
products, providing consulting services to a start-up companies, and providing
advisory services to Riverbend Limited Partnership on the Old Mill District
reclamation project. Riverbend Limited Partnership's principal business is real
estate development.

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CUSIP No. 685932105 SCHEDULE 14A Page 12 of 30
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None of the corporations or organizations that have employed Mr. Padrick are a
parent, subsidiary of other affiliate of Oregon Trail Financial Corp.

Mr. Padrick is a member of the Bars of the States of Oregon, Alaska, Colorado
and Washington. He is 45 years old and resides at 12 River Road, Sunriver,
Oregon 97707, which is in a county which qualifies under the Company's residency
requirement. His business address is 12 River Road, Sunriver, OR 97707, and the
name of his business is K2 Enterprises, LLC.

Mr. Padrick, Stilwell Value Partners II and Stilwell Associates are parties to
two agreements under which Mr. Padrick has consented to be nominated to and sit
on the Board, and Stilwell Value Partners II has agreed to grant Mr. Padrick
options on 20,000 shares of Common Stock, at a purchase price of $14.05 per
share, which will vest in two portions of 10,000 each: (i) on the date after the
Annual Meeting, provided that prior to such date either (i) Mr. Padrick's name
has been publicly disclosed by the Group as a nominee or potential nominee for
the Board or (ii) the Group has sent the Company a notice of nomination in
accordance with the provisions of the Company's By-laws and (ii) on the date Mr.
Padrick is seated on the Board. Alternatively, all of Mr. Padrick's options will
vest if he is seated on the Board of Directors by invitation of the Company and
Stilwell Value Partners II consents in writing to such invitation. Upon vesting,
the options will be exercisable in whole or in part at any time within the 18
months following the Annual Meeting, unless, among other things, Mr. Padrick
withdraws from election for or resigns or is removed from the Board. In
addition, Stilwell Value Partners II has agreed to reimburse Mr. Padrick for his
expenses incurred in connection with his nomination to the Board and indemnify
and hold Mr. Padrick harmless for all damages and claims which may arise in
connection with being nominated to the Board. Copies of these agreements are
annexed hereto as Appendix C.

If Mr. Padrick is unable to serve as a director, Joseph Stilwell and Spencer L.
Schneider, named as proxies on the attached WHITE card, will vote for the
election of another nominee as may be proposed by the Group.

Two directors are to be elected at the Annual Meeting. Since the Group is only
proposing one nominee, if the Group Nominee is elected, one of the Company's
nominees will also be elected. We are also soliciting authority to vote for one
of the nominees being sponsored by the Company. Although we are not permitted to
state affirmatively who we intend to vote for, we can tell you that if you grant
us authority to vote for one of the Company's nominees, we will NOT vote for Mr.
John A. Lienkaemper. If you vote on our WHITE proxy card, you have the
opportunity to withhold authority to vote for the Company's remaining nominee by
writing his name on the WHITE proxy card in the space provided. For information
regarding the Company's nominees for election as directors, please refer to the
Company's proxy statement, when it becomes available. There can be no assurance
that the Company's nominee will serve if elected with our nominee.

AUDITORS

The Group supports the ratification of the appointment of Deloitte & Touche LLP,
as independent accountants for the Company for the fiscal year ending March 31,
2002.

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 13 of 30
- --------------------------------------------------------------------------------

CERTAIN INFORMATION REGARDING THE PARTICIPANTS

Except as described herein, neither any Group member nor the Group Nominee is
now, or within the past year has been, a party to any contract, arrangement or
understanding with any person with respect to any securities of the Company
(including, but not limited to, joint ventures, loan or option arrangements,
puts or calls, guarantees against loss or guarantees of profit, division of
losses or profits, or the giving or withholding of proxies). Stilwell Value LLC,
as general partner of Stilwell Value Partners II and Stilwell Associates, is
entitled to an allocation of profits and income.

Except as described herein, there are no material proceedings to which any Group
member, the Group Nominee, or any associate of any Group member or the Group
Nominee is a party adverse to the Company or any of its subsidiaries or has a
material interest adverse to the Company or any of its subsidiaries. Except as
described herein, neither any Group member, the Group Nominee, nor any associate
of any Group member or the Group Nominee has any interest in the matters to be
voted upon at the Annual Meeting, other than an interest, if any, as a
shareholder of the Company, or with respect to the Group Nominee, as a nominee
for director.

Except as described herein, neither any Group member, the Group Nominee nor any
associate of any Group member or the Group Nominee (1) has engaged in or has a
direct or indirect interest in any transaction or series of transactions since
the beginning of the Company's last fiscal year, or in any currently proposed
transaction, to which the Company or any of its subsidiaries is a party where
the amount involved was in excess of $60,000; (2) has been indebted to the
Company or any of its subsidiaries; (3) has borrowed any funds for the purpose
of acquiring or holding any securities of the Company, or is presently, or has
been within the past year, a party to any contract, arrangement or understanding
with any person with respect to any securities of the Company, any future
employment by the Company or its affiliates, or any future transaction to which
the Company or any of its affiliates will or may be a party; or (4) is the
beneficial or record owner of any securities of the Company or any parent or
subsidiary thereof.

Neither any Group member, the Group Nominee nor any associate of any Group
member or the Group Nominee has, during the past 10 years, been convicted in a
criminal proceeding (excluding traffic violations or similar misdemeanors).

Additional information concerning The Stilwell Group and the Group Nominee,
including, but not limited to, beneficial ownership of and transactions in the
Common Stock, is set forth in Appendices A and B hereto. Each of the individuals
listed on Appendix A attached hereto is a citizen of the United States.

OTHER MATTERS

The Group anticipates that the Company's proxy statement, when it becomes
available, will contain information regarding (1) securities ownership of
certain beneficial owners and management; (2) the committees of the Board; (3)
the meetings of the Board and all committees thereof; (4) the background of the
Company's nominees for the Board; (5) the compensation and remuneration paid and
payable to the Company's directors and management; (6) stock price performance;
(7) voting procedures, including the share vote required for approval or
election, at the Annual Meeting and (8) the submission of shareholder proposals
at the Company's 2002 annual meeting of shareholders. The Group has no knowledge
of the accuracy of the Company's disclosures in its proxy materials.

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 14 of 30
- --------------------------------------------------------------------------------

SOLICITATION; EXPENSES

Proxies may be solicited by the Group by mail, advertisement, telephone,
facsimile, telegraph, and personal solicitation. Phone calls will be made to
individual Shareholders by Joseph Stilwell and certain of his administrative
personnel and employees of D.F. King & Co., Inc. Mr. Stilwell will be
principally responsible for soliciting proxies for the Group and certain of his
administrative personnel will perform secretarial work in connection with the
solicitation of proxies, for which no additional compensation will be paid.
Banks, brokerage houses, and other custodians, nominees, and fiduciaries will be
requested to forward the Group's solicitation material to their customers for
whom they hold shares and the Group will reimburse them for their reasonable
out-of-pocket expenses. The Group has retained D.F. King & Co., Inc. to assist
in the solicitation of proxies and for related services. The Group will pay D.F.
King & Co., Inc. a fee of up to $20,000 and has agreed to reimburse it for its
reasonable out-of-pocket expenses. In addition, the Group has agreed to
indemnify D.F. King & Co., Inc. against certain liabilities and expenses,
including liabilities and expenses under the federal securities laws. The
Securities and Exchange Commission deems such an indemnification to be against
public policy. Approximately 20 persons will be used by D.F. King & Co., Inc. in
its solicitation efforts.

The entire expense of preparing, assembling, printing, and mailing this Proxy
Statement and related materials and the cost of soliciting proxies will be borne
by the Group.

Although no precise estimate can be made at the present time, the Group
currently estimates that the total expenditures relating to the Proxy
Solicitation incurred by the Group will be approximately $75,000, of which
approximately $10,000 has been incurred to date. The Group intends to seek
reimbursement from the Company for those expenses incurred by the Group in
connection with this Proxy Solicitation, as well as all expenses incurred by the
Group since the filing of its initial Schedule 13D in relation to the Company
(including legal expenses associated with the aforementioned litigation), if the
Group Nominee is elected, but does not intend to submit the question of such
reimbursement to a vote of the Shareholders. The total of such costs is
estimated to be between $200,000-$300,000, of which approximately $100,000 has
been incurred to date.

VOTING AND REVOCATION OF PROXIES

For the proxy solicited hereby to be voted, the enclosed WHITE proxy card must
be signed, dated, and returned to the Group, c/o D.F. King & Co., Inc. in the
enclosed envelope in time to be voted at the Annual Meeting. If you wish to vote
for the Group Nominee, you must submit the enclosed WHITE proxy card and must
NOT submit the Company's proxy card. If you have already returned the Company's
proxy card, you have the right to revoke it as to all matters covered thereby
and may do so by subsequently signing, dating, and mailing the enclosed WHITE
proxy card. If you later vote on the Company's proxy card (even if it is to
withhold authority to vote for the Company's nominees ), you will revoke your
previous vote for the Group Nominee. ONLY YOUR LATEST DATED PROXY WILL COUNT AT
THE ANNUAL MEETING.

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 15 of 30
- --------------------------------------------------------------------------------

Execution of a WHITE proxy card will not affect your right to attend the Annual
Meeting and to vote in person. Any proxy may be revoked as to all matters
covered thereby at any time prior to the time a vote is taken by (i) filing with
the Secretary of the Company a later dated written revocation; (ii) submitting a
duly executed proxy bearing a later date to the Group; or (iii) attending and
voting at the Annual Meeting in person. Attendance at the Annual Meeting will
not in and of itself constitute a revocation.

Although a revocation will be effective if delivered only to the Company, the
Group requests that either the original or a copy of all revocations be mailed
to The Stilwell Group c/o D.F. King & Co., Inc. at the address set forth on the
back page of this Proxy Statement, so that the Group will be aware of all
revocations and can more accurately determine if and when the requisite proxies
for the election of the Group Nominee as a director have been received. The
Group may contact shareholders who have revoked their proxies.

Shares of Common Stock represented by a valid, unrevoked WHITE proxy card will
be voted as specified. You may vote for the Group Nominee or withhold authority
to vote for the Group Nominee by marking the proper box on the WHITE proxy card.
Shares represented by a WHITE proxy card where no specification has been made
will be voted for the Group Nominee and for Deloitte & Touche LLP, as auditors.

Except as set forth in this Proxy Statement, the Group is not aware of any other
matter to be considered at the Annual Meeting. The persons named as proxies on
the enclosed WHITE proxy card will, however, have discretionary voting authority
as such proxies regarding any other business that may properly come before the
Annual Meeting. The proxies may exercise discretionary authority only as to
matters unknown to the Group a reasonable time before this Proxy Solicitation.

If your shares are held in the name of a brokerage firm, bank or nominee, only
such brokerage firm, bank or nominee can vote such shares and only upon receipt
of your specific instructions. Accordingly, please promptly contact the person
responsible for your account at such institution and instruct that person to
execute and return the WHITE proxy card on your behalf. You should also promptly
sign, date and mail the voting instruction form (or WHITE proxy card) that your
broker or banker sends you. Please do this for each account you maintain to
ensure that all of your shares are voted. If any of your shares were held in the
name of a brokerage firm, bank or nominee on the Annual Meeting Record Date, to
revoke your proxy you will need to give appropriate instructions to such
institution. IF YOU DO NOT GIVE INSTRUCTIONS TO YOUR BROKER OR OTHER NOMINEE,
YOUR SHARES WILL NOT BE VOTED.

Only holders of record of Common Stock on the Annual Meeting Record Date will be
entitled to vote at the Annual Meeting. If you are a Shareholder of record on
the Annual Meeting Record Date, you will retain the voting rights in connection
with the Annual Meeting even if you sell such shares after the Annual Meeting
Record Date. Accordingly, it is important that you vote the shares of Common
Stock held by you on the Annual Meeting Record Date, or grant a proxy to vote
such shares on the WHITE proxy card, even if you sell such shares after such
date.

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 16 of 30
- --------------------------------------------------------------------------------

The Group believes that it is in your best interest to elect the Group Nominee
as a director at the Annual Meeting. THE GROUP STRONGLY RECOMMENDS A VOTE FOR
THE GROUP NOMINEE AS WELL AS A VOTE FOR THE PROPOSED AUDITORS.

THE STILWELL GROUP

I M P O R T A N T !!!

If your shares are held in "Street Name" only your bank or broker can vote your
shares and only upon receipt of your specific instructions. Accordingly, please
promptly contact the person responsible for your account at such institution and
instruct that person to execute and return the WHITE proxy card on your behalf.
You should also promptly sign, date and mail the voting instruction form (or
WHITE proxy card) that your broker or banker sends you. Please do this for each
account you maintain to ensure that all of your shares are voted.

If you have any questions, or need further assistance, please call Joseph
Stilwell at 212-269-5800, or our proxy solicitor: D.F. King & Co., Inc., 77
Water Street, New York, NY 10005, at 800-207-3159.

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 17 of 30
- --------------------------------------------------------------------------------

APPENDIX A

THE STILWELL GROUP AND ITS NOMINEE

The participants who comprise the Group own in the aggregate 290,800 shares of
Common Stock, representing approximately 8.7% of the shares outstanding, and are
as follows:

Stilwell Value LLC ("Stilwell Value LLC") is a Delaware limited liability
company organized to invest in securities, whose principal and executive offices
are located at 26 Broadway, New York, New York 10004. Joseph Stilwell is the
managing and sole member of Stilwell Value LLC and has sole discretion and
voting authority with respect to its investment in securities.

Stilwell Value Partners II, L.P. ("Stilwell Value Partners II") is a Delaware
limited partnership organized to invest in securities, whose principal and
executive offices are located at 26 Broadway, New York, New York 10004. Stilwell
Value LLC is the general partner of Stilwell Value Partners II, and Joseph
Stilwell has sole discretion and voting authority with respect to its investment
in securities.

Stilwell Associates, L.P. ("Stilwell Associates") is a Delaware limited
partnership organized to invest in securities, whose principal and executive
offices are located at 26 Broadway, New York, New York 10004. Stilwell Value LLC
is the general partner of Stilwell Associates, and Joseph Stilwell has sole
discretion and voting authority with respect to its investment in securities.

Joseph Stilwell is an investment manager and is the sole managing member of
Stilwell Value LLC. His business offices are located at 26 Broadway, New York,
New York 10004.

Kevin D. Padrick is a business consultant and member of the Bar in Oregon and
Colorado. His business address is located at 12 River Road, Sunriver, OR 97707.

Spencer L. Schneider is an attorney engaged in private practice. His business
offices are located at 145 Hudson Street, New York, New York 10013.

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 18 of 30
- --------------------------------------------------------------------------------

The following table sets forth information regarding holdings of Common Stock by
members of the Group (who together constitute a "group" as that term is used in
Section 13(d)(3) of the Securities Exchange Act of 1934):

- -------------------------------------------------------------------------------------------------------------------
Participant and Address Shares Held Percent of Class Shares Held By Non-
Beneficially Participant Associates
- -------------------------------------------------------------------------------------------------------------------

Stilwell Value LLC 295,000 8.8% None
26 Broadway
New York, New York 10004
- -------------------------------------------------------------------------------------------------------------------
Stilwell Value Partners II, L.P 295,000 8.8% None
26 Broadway
New York, New York 10004
- -------------------------------------------------------------------------------------------------------------------
Stilwell Associates, L.P
26 Broadway
New York, New York 10004 295,000 8.8% None
- -------------------------------------------------------------------------------------------------------------------
Joseph Stilwell 295,000 8.8% None
26 Broadway
New York, New York 10004
- -------------------------------------------------------------------------------------------------------------------

Mr. Padrick does not beneficially own any shares of the Common Stock. As
described in this proxy statement, Stilwell Value Partners II has granted Mr.
Padrick options to purchase up to 20,000 shares, which options are not yet
vested or exercisable.

Mr. Schneider does not beneficially own any shares of the Common Stock.

No member of the Group owns any shares of the Common Stock of record but not
beneficially.

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 19 of 30
- --------------------------------------------------------------------------------

APPENDIX B

Transactions in the Common Stock

The following transactions are the only transactions during the past two years
with regard to any Group member:

Stilwell Value Partners II, L.P.
- --------------------------------

- ---------------------------------------------------------------------------------------------
Date Number of Shares Price Per Share ($) Total Cost ($)
- ---------------------------------------------------------------------------------------------

08/15/00 8,000 10.7500 86,000.00
- ---------------------------------------------------------------------------------------------
08/15/00 10,000 10.8125 108,125.00
- ---------------------------------------------------------------------------------------------
08/17/00 2,500 10.7500 26,875.00
- ---------------------------------------------------------------------------------------------
08/22/00 4,000 11.0625 44,250.00
- ---------------------------------------------------------------------------------------------
08/23/00 6,000 11.1875 67,125.00
- ---------------------------------------------------------------------------------------------
08/23/00 4,300 11.1250 47,837.50
- ---------------------------------------------------------------------------------------------
08/28/00 2,000 11.1250 22,250.00
- ---------------------------------------------------------------------------------------------
08/30/00 3,000 11.0625 33,187.50
- ---------------------------------------------------------------------------------------------
09/05/00 10,200 11.0625 112,837.50
- ---------------------------------------------------------------------------------------------
09/06/00 3,000 11.0000 33,000.00
- ---------------------------------------------------------------------------------------------
09/08/00 6,000 11.1250 66,750.00
- ---------------------------------------------------------------------------------------------
09/14/00 4,600 11.5720 53,231.20
- ---------------------------------------------------------------------------------------------
09/19/00 1,300 11.6250 15,112.50
- ---------------------------------------------------------------------------------------------
09/20/00 4,000 12.0625 48,250.00
- ---------------------------------------------------------------------------------------------
09/22/00 2,300 12.0000 27,600.00
- ---------------------------------------------------------------------------------------------
09/25/00 6,000 11.9479 71,687.40
- ---------------------------------------------------------------------------------------------
09/26/00 4,500 11.8819 53.468.55
- ---------------------------------------------------------------------------------------------
09/28/00 6,500 11.7500 76,375.00
- ---------------------------------------------------------------------------------------------
10/02/00 3,000 11.7500 35,250.00
- ---------------------------------------------------------------------------------------------
10/04/00 3,800 11.6875 44,412.50
- ---------------------------------------------------------------------------------------------
10/16/00 4,000 11.5000 46,000.00
- ---------------------------------------------------------------------------------------------
10/19/00 2,500 11.3750 28,437.50
- ---------------------------------------------------------------------------------------------
10/27/00 3,000 11.6875 35,062.50
- ---------------------------------------------------------------------------------------------
10/31/00 13,000 12.2067 158,687.10
- ---------------------------------------------------------------------------------------------
11/03/00 4,500 12.1875 54,843.75
- ---------------------------------------------------------------------------------------------
11/07/00 20,000 12.0000 240,000.00
- ---------------------------------------------------------------------------------------------
11/10/00 5,000 12.4375 62,187.50
- ---------------------------------------------------------------------------------------------
11/13/00 1,900 12,0000 22,800.00
- ---------------------------------------------------------------------------------------------
11/14/00 6,000 12.3688 74,212.80
- ---------------------------------------------------------------------------------------------
11/15/00 13,800 12.5747 173,530.86
- ---------------------------------------------------------------------------------------------
11/16/00 8,800 12,8538 113,113.44
- ---------------------------------------------------------------------------------------------
11/16/00 2,500 13.2500 33,125.00
- ---------------------------------------------------------------------------------------------
12/13/00 9,000 13.6250 122,625.00
- ---------------------------------------------------------------------------------------------
04/11/01 900 14.0666 12,659.94
- ---------------------------------------------------------------------------------------------
04/26/01 700 14.1500 9,905.00
- ---------------------------------------------------------------------------------------------
04/27/01 1,600 14.3093 22,894.88
- ---------------------------------------------------------------------------------------------
04/30/01 2,000 14.2075 28,415.00
- ---------------------------------------------------------------------------------------------

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 20 of 30
- --------------------------------------------------------------------------------

Stilwell Associates, L.P.
- -------------------------

07/13/00 3,000 11.0000 33,000.00
- ---------------------------------------------------------------------------------------------
07/25/00 800 10.6250 8,500.00
- ---------------------------------------------------------------------------------------------
08/01/00 1,000 10.8125 10,812.50
- ---------------------------------------------------------------------------------------------
08/02/00 1,000 10.8125 10,812.50
- ---------------------------------------------------------------------------------------------
08/08/00 1,200 10.8750 13,050.00
- ---------------------------------------------------------------------------------------------
08/14/00 1,000 10.8125 10,812.50
- ---------------------------------------------------------------------------------------------
09/08/00 1,000 11.1250 11,125.00
- ---------------------------------------------------------------------------------------------
09/08/00 2,000 11.1250 22,250.00
- ---------------------------------------------------------------------------------------------
09/12/00 300 11.3750 3,412.50
- ---------------------------------------------------------------------------------------------
10/03/00 1,500 11.7500 17,625.00
- ---------------------------------------------------------------------------------------------
10/10/00 2,000 11.6875 23,375.00
- ---------------------------------------------------------------------------------------------
10/13/00 3,500 11.6250 40,687.50
- ---------------------------------------------------------------------------------------------
10/18/00 2,000 11,4375 22,875.00
- ---------------------------------------------------------------------------------------------
10/23/00 1,000 11.3125 11,312.50
- ---------------------------------------------------------------------------------------------
10/23/00 2,500 11.3750 28,437.50
- ---------------------------------------------------------------------------------------------
10/31/00 10,000 12.2319 122,319.00
- ---------------------------------------------------------------------------------------------
11/08/00 6,300 12.3125 77,568.75
- ---------------------------------------------------------------------------------------------
11/16/00 9,900 13.2500 131,175.00
- ---------------------------------------------------------------------------------------------
04/05/01 1,000 14.0650 14,065.00
- ---------------------------------------------------------------------------------------------
04/16/01 600 14.0750 8,445.00
- ---------------------------------------------------------------------------------------------

Joseph Stilwell
- ---------------

11/16/00 20,000 13.2500 265,000.00
- ---------------------------------------------------------------------------------------------
11/22/00 25,000 13.2500 331.250.00
- ---------------------------------------------------------------------------------------------
7/3-/01 4,200 15.1321 63,555.00
- ---------------------------------------------------------------------------------------------

The total number of shares of Common Stock held by the Group is 295,000,
approximately 8.8% of the Company's total shares outstanding.

The amount of funds expended to date by Stilwell Value Partners II, L.P. to
acquire the 194,200 shares of Common Stock it holds in its name is
$2,312,124.92. Such funds were provided from its available capital and from time
to time, by margin account loans from subsidiaries of The Bear Stearns
Companies, Inc. extended in the ordinary course of business to Stilwell Value
Partners II.

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 21 of 30
- --------------------------------------------------------------------------------

The amount of funds expended to date by Stilwell Associates, L.P. to acquire the
51,600 shares of Common Stock it holds in its name is $621,660.25. Such funds
were provided from its available capital and from time to time, by margin
account loans from subsidiaries of The Bear Stearns Companies, Inc. extended in
the ordinary course of business to Stilwell Associates.

The amount of funds expended to date by Joseph Stilwell to acquire the
49,200shares of Common Stock he holds in his name is $659,805. Such funds were
provided from his personal funds and from time to time, by margin account loans
from subsidiaries of The Bear Stearns Companies, Inc. extended in the ordinary
course of business to Mr. Stilwell.

All purchases of Common Stock made by members of the Group using funds borrowed
from subsidiaries of The Bear Stearns Companies, Inc., if any, were made in
margin transactions on those firms' usual terms and conditions. As of May 30,
2001, the total amount of the Group's indebtedness under such borrowings was
$1,256,777. All or part of the shares of Common Stock owned by members of the
Group may from time to time be pledged with one or more banking institutions or
brokerage firms as collateral for loans made by such entities to members of the
Group. Such loans generally bear interest at a rate based upon the broker's call
rate from time to time in effect. Such indebtedness, if any, may be refinanced
with other banks or broker-dealers.

Neither Mr. Stilwell, Mr. Padrick nor Mr. Schneider is required to file a report
under Section 16(a) of the Securities Exchange Act of 1934, as amended, with
respect to the Common Stock.

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 22 of 30
- --------------------------------------------------------------------------------

APPENDIX C

Agreements with Mr. Padrick

NOMINEE AGREEMENT

This Nominee Agreement is made this 18th day of April, 2001 among
Stilwell Value Partners II, L.P. and Stilwell Associates, L.P. (collectively
referred to as "Stilwell Group"), having their offices at 26 Broadway, 23rd
Floor, New York, New York 10014, and Kevin D. Padrick, residing at 15 Quelah,
Sunriver, Oregon 97707 ("Nominee").

WHEREAS, the Stilwell Group is the beneficial owner of 284,000 shares
of common stock of Oregon Trail Financial Corp. ("OTFC") and may solicit proxies
in order to nominate as many directors as permitted under the law to OTFC's
Board of Directors at the 2001 annual shareholders meeting, such nomination
being in opposition to OTFC's management's slate of nominees;

WHEREAS, the bylaws of OTFC provide in pertinent part that, "To be
eligible for nomination and election to the Board of Directors or for continued
service on the Board of Directors, a nominee's or member's primary residence
shall be located in a county in which Pioneer Bank, a Federal Savings Bank,
occupies a branch office or other office, or in a county contiguous thereto.
Should a director fail to satisfy the continuing service requirement, the
director shall be deemed to have submitted his or her resignation which shall
become effective upon adoption of a resolution acknowledging such ineligibility
by the Board of Directors.";

WHEREAS Nominee's primary residence is located in a county in which the
Savings Bank occupies a branch office or other office, or a county contiguous
thereto ("Qualified County") and Nominee agrees to be nominated for and sit on
the Board of Directors of OTFC if elected at the 2001 annual shareholder's
meeting for a term to last three years;

NOW THEREFORE, in consideration of the premises and other good and
valuable consideration, the receipt and sufficiency of which is hereby
acknowledged, the parties agree as follows:

1. Nominee hereby agrees to have his name placed in nomination by the
Stilwell Group to sit as a director of OTFC, and for that purpose, understands
and agrees that the Stilwell Group may solicit proxies from shareholders to
enable the Stilwell Group to nominate Nominee. Simultaneous with the execution
of this Agreement, Nominee shall deliver his written consent to be named in a
Stilwell Group proxy statement and to serve as a director of OTFC if elected, a
copy of which is attached hereto as Exhibit A.

2. Nominee shall not move his primary residence from a Qualified County
nor commit any act which would otherwise make him ineligible to sit as a
director, but in case of a breach of this provision in no case shall Nominee be
liable for damages beyond the loss of options granted hereunder. Nominee has
executed and delivered to the Stilwell Group a Director Questionnaire and hereby
certifies that the contents thereof are true.

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 23 of 30
- --------------------------------------------------------------------------------

3. In consideration thereof, Stilwell Value Partners I, L.P. hereby
grants Nominee an option to purchase up to twenty thousand (20,000) shares of
OTFC common stock on the terms set forth in the option annexed hereto as Exhibit
B. The exercise price shall equal the closing price on the day this Agreement is
executed.

4. The Stilwell Group shall reimburse all of Nominee's actual expenses
incurred in connection with nomination process, including telephone, postage,
and travel, however, it being understood that should Nominee be elected as a
director, he shall request that OTFC reimburse his expenses for attending
meetings.

5. The Stilwell Group hereby indemnifies and holds the Nominee harmless
for all damages and expenses incurred in connection with agreeing to have his
name placed in nomination and to have proxies solicited in order to elect him to
the Board of Directors of OTFC. Nominee shall give the Stilwell Group notice of
the occurrence of an event requiring indemnification no later than 20 days after
nominee has knowledge of such an event. The Stilwell Group retains the sole
right to select and retain counsel for Nominee. This indemnification shall not
apply to any claims or damages arising out of Nominee being a member of the
Board of Directors of OTFC.

6. Nominee understands that this Agreement may be publicly disclosed by
the Stilwell Group.

/S/
-----------------------------------------------
Joseph Stilwell on behalf of the Stilwell Group

/S/
-----------------------------------------------
Kevin D. Padrick

- --------------------------------------------------------------------------------
CUSIP No. 685932105 SCHEDULE 14A Page 24 of 30
- --------------------------------------------------------------------------------

EXHIBIT A TO NOMINEE AGREEMENT

CONSENT OF PROPOSED NOMINEE

I, Kevin D. Padrick, hereby consent to be named in the proxy statement
of Stilwell Associates, L.P. or Stilwell Value Group II, L.P. to be used in
connection with its solicitation of proxies from the shareholders of Oregon
Trail Financial Corporation for use in voting at the 2001 Annual Meeting of
Shareholders of Oregon Trail Financial Corporation, and I hereby consent and
agree to serve a director of Oregon Trail Financial Corporation if elected at
such Annual Meeting.

/S/
-----------------------------------------------
Kevin D. Padrick
Dated: April 18, 2001

EXHIBIT B TO NOMINEE AGREEMENT

STOCK OPTION AGREEMENT

THIS STOCK OPTION AGREEMENT (the "Agreement") is made and entered into
as of April 18, 2001, by and between Stilwell Value Partners II, L.P., a
Delaware limited partnership with offices at 26 Broadway, 23rd floor, New York,
New York 10004 ("SVP"), and Kevin D. Padrick, residing at 15 Quelah, Sunriver,
Oregon 97707 (the "Optionee").

WHEREAS, SVP owns approximately 189,000 shares of the Common Stock, par
value $.01 per share (the "Common Stock"), of Oregon Trail Financial
Corporation, an Oregon corporation ("OTFC"); and

WHEREAS, SVP and certain other parties, acting as a group (the
"Stilwell Group"), have filed with the Securities and Exchange Commission a
Schedule 13D, and amendments thereto, reporting that it intends to solicit
proxies for a person or persons nominated by SVP and its affiliates for election
to the Board of Directors of OTFC (the "Board"); and

WHEREAS, Optionee has consented to his nomination by the Stilwell Group
to the Board and has concurrently with the execution of this Stock Option
Agreement entered into a Nominee Agreement with the Stilwell Group (the "Nominee
Agreement"); and

WHEREAS, in consideration of the agreements of Optionee in the Nominee
Agreement to stand for election to the Board and to serve if elected, SVP
considers it desirable and in its best interests that the Optionee be granted
the option to purchase up to an aggregate of Twenty Thousand (20,000) shares of
the Common Stock owned by SVP (the "Option Shares"), upon the terms and
conditions set forth in this Agreement.

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CUSIP No. 685932105 SCHEDULE 14A Page 25 of 30
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NOW, THEREFORE, for good and valuable consideration, the adequacy of
which is hereby acknowledged, and the mutual covenants hereinafter set forth,
the parties hereto hereby agree as follows:

1. Grant of Option. SVP hereby grants to the Optionee the right and
option (the "Option") to purchase all or any part of the Option Shares on the
terms and conditions set forth herein. The Option shall vest and become
exercisable as set forth in Section 4.

2. Purchase Price. The purchase price per share of the Option Shares
covered by the Option shall be equal to $14.05 per Option Share (subject to
adjustment as provided in Section 6 below) (the "Purchase Price").

3. Certain Defined Terms. As used in this Option Agreement, the
following terms shall have the following meanings:

(a) Closing Sale Price shall mean on any particular date the
closing sale price per share of Common Stock on such date on the NASDAQ
National Market, or if there is no such price on such date, then the
closing sale price on the NASDAQ National Market on the date nearest
preceding such date.

(b) Expiration Date shall mean the date which is eighteen
months after the First Vesting Date, or such earlier date on which this
Option may terminate in accordance with Section 4 or Section 6, or such
other date as the parties mutually agree in writing.

(d) Second Vesting Date shall mean the date on which the
Optionee is seated on the Board.

(e) Threshold Event shall mean either of the following: (i)
Optionee's name has been publicly disclosed by the Stilwell Group as a
nominee or potential nominee for the Board or (ii) the Stilwell Group
has sent to OTFC a notice in accordance with the advance notice
provisions of the OTFC By-laws advising OTFC of the Stilwell Group's
intention to place Optionee's name in nomination.

4. Vesting and Exercisability of the Option. The Option shall vest and
become exercisable as follows:

(a) the Option shall vest and become exercisable with respect
to Ten Thousand (10,000) Option Shares (the "First Option") at the
First Vesting Date, provided that prior to the First Vesting Date one
or both of the Threshold Events shall have occurred, and thereafter
shall be exercisable at any time or from time to time in whole or in
part on or prior to the Expiration Date. If a Threshold Event does not
occur prior to the First Vesting Date, then the First Option shall be
terminated and shall not become exercisable.

(b) the Option shall vest and become exercisable with respect
to the remaining Ten Thousand (10,000) Option Shares (the "Second
Option") on the Second Vesting Date, and thereafter shall be
exercisable at any time or from time to time in whole or in part prior
to the Expiration Date.

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CUSIP No. 685932105 SCHEDULE 14A Page 26 of 30
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Alternatively, the First Option and the Second Option shall vest if:
(a) the Optionee is seated on the Board by invitation of OTFC, and (b)
SVP consents in writing to Optionee being invited to sit on the Board.

5. Method of Exercising Option.

(a) The Optionee may exercise the Option in whole or in part
(to the extent that it is exercisable in accordance with its terms) by
giving written notice to SVP, specifying therein the number of Option
Shares which the Optionee then elects to purchase or with respect to
which the Option is being exercised, accompanied by payment of the full
Purchase Price for the Option Shares being purchased. The notice of
exercise, accompanied by such payment, shall be delivered to SVP at its
principal business office. The date on which the notice is given to SVP
is hereinafter referred to as the "Date of Exercise." In no event may
the Option granted hereunder be exercised for a fraction of an Option
Share.

(b) The Optionee may pay the Purchase Price in one of the
following manners:

(i) Cash Exercise. The Optionee shall deliver the Purchase
Price to SVP in cash or by certified check or bank check or
wire transfer of immediately available funds.

(ii) Cashless Exercise. The Optionee shall surrender this
Option to SVP together with a notice of cashless exercise, in
which event SVP shall issue to the Optionee the number of
Option Shares determined as follows:

X = (Y* (A-B))/A

where:

X = the number of Option Shares to be issued to the Optionee;

Y = the number of Option Shares with respect to which this
Option is being exercised;

A = the average of the Closing Sale Prices of the Common Stock
for the five (5) trading days immediately prior to (but not
including) the Date of Exercise.

B = the Purchase Price (as adjusted to the date of such
calculation).

(c) As soon as practicable after receipt by SVP of a notice of
exercise and of payment in full of the Purchase Price of all the Option
Shares with respect to which the Option has been exercised, SVP shall
transfer the Option Shares being purchased to the Optionee.

6. Termination of Option. Except as otherwise stated herein, the
Option, to the extent not theretofore exercised, shall terminate on the
Expiration Date or, if earlier, upon the first of the occurrence of any of the
following events, unless SVP otherwise elects in writing:

(a) In the event of Optionee's withdrawal from the election
for the Board;

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CUSIP No. 685932105 SCHEDULE 14A Page 27 of 30
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(b) In the event of Optionee becoming ineligible to be elected
to the Board for any reason, including, but not limited to, his moving
his residence out of a Qualified County, as that term is defined in the
Nominee Agreement; or

7. Adjustments. If prior to the exercise of any portion of the Option
OTFC shall have effected one or more stock splits, reverse stock splits, stock
dividends, stock combinations, reclassifications, recapitalizations or similar
events, the number of Option Shares subject to this Option and the Purchase
Price shall be equitably adjusted as determined by SVP in good faith. SVP shall
give notice of each adjustment or readjustment of the Purchase Price or the
number of Option Shares to the Optionee.

8. Restrictions. The holder of this Option, by acceptance hereof,
represents, warrants and covenants that this Option and the right to purchase
the Option Shares is personal to the holder and shall not be transferred to any
other person, other than by will or the laws of descent and distribution.
Notwithstanding the foregoing, the Optionee may, at any time and from time to
time, transfer all or any part of his rights under this Option and the right to
purchase the Option Shares in accordance with the terms of this Option Agreement
to his spouse or children, or to a trust created by the Optionee for the benefit
of the Optionee or his immediate family or to a corporation or other entity
controlled by the Optionee and in which the Optionee or members of his immediate
family beneficially own all of the economic interests.

9. No Rights as Optionee. Nothing contained herein shall be construed
to confer upon the Optionee any right to be nominated by the Stilwell Group to
the Board or, if elected, to continue to serve on the Board.

10. Withholding. In the event that the Optionee elects to exercise this
Option or any part thereof, and if SVP shall be required to withhold any amounts
by reason of any federal, state or local tax laws, rules or regulations in
respect of the issuance of Option Shares to the Optionee pursuant to the Option,
SVP shall be entitled to deduct and withhold such amounts from any payments to
be made to the Optionee. In any event, the Optionee shall make available to SVP
promptly when requested by SVP sufficient funds to meet the requirements of such
withholding; and SVP shall be entitled to take and authorize such steps as it
may deem advisable in order to have such funds available to SVP out of any funds
or property due or to become due to the Optionee. Notwithstanding the foregoing,
the Optionee may request SVP not to withhold any or all of the amounts otherwise
required to be withheld; provided that the Optionee provides SVP with sufficient
documentation as may be required by federal, state or local tax laws, rules or
regulations supporting his request that such amount is not required to be
withheld, in which case SVP may, in its reasonable discretion, reduce such
withholding amounts to the extent permitted by applicable laws, rules and
regulations.

11. Validity and Construction. This Option shall be governed by and
construed and enforced in accordance with the laws of the State of New York.

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CUSIP No. 685932105 SCHEDULE 14A Page 28 of 30
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12. Amendment: This Agreement may be amended only in a writing signed
on behalf of SVP and the Optionee.

13. Notices. Any notice which either party hereto may be required or
permitted to give to the other shall be in writing, and may be delivered
personally or by mail, postage prepaid, or overnight courier, addressed as
follows: if to SVP, at its office address set forth at the beginning of this
Agreement, Attention: Mr. Joseph Stilwell, or at such other address as SVP by
notice to the Optionee may designate in writing from time to time; and if to the
Optionee, at his address set forth at the beginning of this Agreement, or at
such other address as the Optionee by notice to SVP may designate in writing
from time to time. Notices shall be effective upon receipt.

14. Successors and Assigns. This Agreement shall inure to the benefit
of and be binding upon the parties hereto and to the extent not prohibited
herein, their respective heirs, successor, assigns and representatives. Nothing
in this Agreement, expressed or implied, is intended to confer on any person
other than the parties hereto and as provided above, their respective heirs,
successors, assigns and representatives any rights, remedies, obligations or
liabilities.

15. Reservation and Ownership of Option Shares. At all times during the
period the Option is exercisable SVP shall own and make available for transfer
on exercise of the Option a number of shares of Common Stock necessary to
satisfy its obligations under the terms of this Option Agreement.

IN WITNESS WHEREOF, the parties hereto have executed this Stock Option
Agreement as of the date set forth above.

STILWELL VALUE PARTNERS I, L.P.

By: Stilwell Value LLC

By: /S/ /
-------------------------------
Joseph Stilwell
Managing Member

ACCEPTED:

/S/ /
- -------------------------------
Kevin D. Padrick

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CUSIP No. 685932105 SCHEDULE 14A Page 29 of 30
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Preliminary Copy

P R O X Y

THIS PROXY IS SOLICITED BY THE STILWELL GROUP IN OPPOSITION TO
THE BOARD OF DIRECTORS OF OREGON TRAIL FINANCIAL CORP.

OREGON TRAIL FINANCIAL CORP.
2001 ANNUAL MEETING OF SHAREHOLDERS

The undersigned hereby appoints Joseph Stilwell and Spencer L. Schneider, or
either of them, as proxies with full power of substitution, to vote in the name
of and as proxies for the undersigned at the Annual Meeting of Oregon Trail
Financial Corp. (the "Company"), to be held on __________ __, 2001, at ___ _m.
(local time), and at any adjournment(s) or postponement(s) thereof, according to
the number of votes that the undersigned would be entitled to cast if personally
present on the following matters:

1. ELECTION OF DIRECTORS - To elect KEVIN D. PADRICK as a director of the
Company

-- FOR -- WITHHOLD

To withhold authority to vote for the election of Kevin D. Padrick, place an X
next to Withhold or strike out Mr. Padrick's name above.

The Stilwell Group intends to use this Proxy to vote for one person nominated by
the Company other than the Company nominee listed below. To withhold authority
to vote for the other Company nominee, write the name of the nominee below.
Refer to the Proxy Statement and Proxy distributed by the Company for the names
and other information concerning such nominees. There is no assurance that any
of the Company's nominees will serve as directors if the Stilwell Group's
nominees are elected to the Board of Directors. The Stilwell Group is NOT
seeking authority to vote for and will NOT exercise any such authority for Mr.
John A. Lienkaemper.

Write in below the name of the Company nominee for which authority to vote is
withheld.

-------------------------

2. APPOINTMENT OF DELOITTE & TOUCHE LLP AS INDEPENDENT ACCOUNTANTS FOR THE
FISCAL YEAR ENDING MARCH 31, 2002:

For ___ Against ___ Abstain __

IMPORTANT: PLEASE SIGN AND DATE ON THE REVERSE SIDE.

This proxy, when properly executed, will be voted in the manner directed herein
by the undersigned Shareholder. Unless otherwise specified, this proxy will be
voted "FOR" the election of the Group Nominee as Director and "FOR" the
appointment of Deloitte & Touche LLP the independent accountants. This proxy
revokes all prior proxies given by the undersigned.

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CUSIP No. 685932105 SCHEDULE 14A Page 30 of 30
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In their discretion, the proxies are authorized to vote upon such other business
as may properly come before the meeting, or any adjournments or postponements
thereof, as provided in the proxy statement provided herewith. The proxies may
exercise discretionary authority only as to matters unknown to the Group a
reasonable time before their proxy solicitation.

Please sign exactly as your name appears hereon or on your proxy cards
previously sent to you. When shares are held by joint tenants, both should sign.
When signing as an attorney, executor, administrator, trustee, or guardian,
please give full title as such. If a corporation, please sign in full
corporation name by the President or other duly authorized officer. If a
partnership, please sign in partnership name by authorized person. This proxy
card votes all shares held in all capacities.

Dated:
----------------------------------

----------------------------------------
(Signature)

----------------------------------------
(Signature, if jointly held)

Title:
----------------------------------

PLEASE SIGN, DATE, AND MAIL THIS PROXY CARD TODAY.