Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 [x]Filed by the registrant [ ]Filed by a party other than the registrant Check the appropriate box: [ ] Preliminary proxy statement [ ] Definitive proxy statement [ ] Definitive additional materials [x] Soliciting material pursuant to Rule 14a-12 OREGON TRAIL FINANCIAL CORP. - ----------------------------------------------------------------------------- (Name of Registrant as Specified in Its Charter) OREGON TRAIL FINANCIAL CORP - ------------------------------------------------------------------------------ (Name of Person(s) Filing Proxy Statement) 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: N/A - ------------------------------------------------------------------------------ (2) Aggregate number of securities to which transactions applies: N/A - ------------------------------------------------------------------------------ (3) Per unit price or other underlying value of transaction computed pursuant to Exchange Act Rule 0-11: N/A - ------------------------------------------------------------------------------ (4) Proposed maximum aggregate value of transaction: N/A - ------------------------------------------------------------------------------ [ ] 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: N/A - ------------------------------------------------------------------------------ (2) Form, schedule or registration statement no.: N/A - ------------------------------------------------------------------------------ (3) Filing party: N/A - ------------------------------------------------------------------------------ (4) Date filed: N/A - ------------------------------------------------------------------------------ Filed by Oregon Trail Financial Corp. pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended. * * * ANNUAL MEETING TO BE HELD SEPTEMBER 28, 2001 Notice of Annual Shareholder Meeting - ------------------------------------ Oregon Trail Financial Corp. will hold its annual shareholder meeting at 10:00 a.m. PDT on September 28, 2001 at the Best Western Sunridge Inn and Conference Center, One Sunridge Lane, Baker City, Oregon. At this meeting, shareholders will elect two directors, each to serve a three year term, approve the appointment of Deloitte & Touche LLP as the Company's independent auditors and consider any other matters to properly come before the meeting. This meeting date is later than last year's because we needed additional time to prepare materials in light of the opposition candidate(s) being proposed by Joseph Stilwell. Shareholders of record as of August 16, 2001 will be entitled to notice of and to vote at the meeting. Important Matters About Joseph Stilwell and the Stilwell Group - -------------------------------------------------------------- You may have received a letter from Joseph Stilwell and the Stilwell Group in April of this year. Over the last 12 months, Mr. Stilwell and the Stilwell Group have purchased approximately 8.25% of the Company's outstanding shares. They want to force a quick sale of Oregon Trail and its 100-year old community bank. The Stilwell Group has announced that it intends to solicit proxies from the Company's shareholders in support of its nominee(s) for the Board. Those persons, if elected, would replace one or both of the Company's current directors standing for re-election. If the Stilwell Group proceeds with its solicitations, you will soon receive proxy materials from the Stilwell Group, seeking support for its candidate(s). You will also soon receive proxy materials and other important information from the Board of Directors about the annual meeting. Please Wait For And Read Our Proxy Statement and Other Materials Before You - --------------------------------------------------------------------------- Send in Your Proxy - ------------------ This year's annual meeting will be important to all of our shareholders and the many customers and communities we serve. It may well determine our future as an independent financial institution. We will address the questions raised in the proxy materials that you receive from the Stilwell Group. PLEASE DO NOT SEND IN YOUR PROXY UNTIL YOU HAVE READ OUR RESPONSE. Please read your Board's proxy materials and other information carefully before you vote your shares. We believe the Stilwell Group's proxy materials do not tell everything you need to know to make an informed decision about the future of your Company. The Stilwell Group's proxy materials assert that current management is not doing enough to maximize shareholder value, but we believe you should consider these important facts: * Last year, your Board of Directors hired a new President, Berniel L. Maughan, and a new Chief Financial Officer, Jonathan McCreary. During their first few months at Pioneer Bank, together with the existing management team they developed a multi-faceted plan to improve Company performance and enhance shareholder value. They announced those initiatives on January 19, 2001. * For the fiscal quarter following the announcement of these initiatives ending March 31, 2001, OREGON TRAIL'S NET INCOME INCREASED 53% TO $849,000 OR $.26 PER SHARE compared to $557,000 or $.17 per share for the same period the year before. Without the expenses caused by Stilwell and his many lawsuits aimed at gaining control of your Company, your COMPANY'S EARNINGS WOULD HAVE INCREASED 71%. * Earnings continued to improve during the first quarter of fiscal 2002 ending June 30, 2001. EARNINGS INCREASED 78% TO $.32 PER SHARE compared to the first quarter last year AND WOULD HAVE BEEN UP 100% if we did not have to incur further costs in responding to the Stilwell Group. * Excluding the expenses caused by the Stilwell Group, OREGON TRAIL'S RETURN ON EQUITY FOR OUR FIRST QUARTER OF FISCAL 2002 INCREASED 82% TO 8.46%, a record high for your Company. These are just a few examples of the substantial improvements our management team has achieved in the past year. The Board has considered various alternatives including the sale of the Company, BUT HAS CONCLUDED THAT SELLING THE COMPANY AT THIS TIME WILL NOT MAXIMIZE SHAREHOLDER VALUE. If the Stilwell Group proceeds with its proxy solicitation, we will send you additional information within a few days after its mailing. PLEASE WAIT UNTIL YOU RECEIVE OUR INFORMATION BEFORE YOU SUBMIT ANY PROXY. Your vote will be critical to your personal financial interests and the future of the Company. SHAREHOLDERS SHOULD READ THE COMPANY'S DEFINITIVE PROXY STATEMENT WHEN IT BECOMES AVAILABLE BECAUSE IT WILL CONTAIN IMPORTANT INFORMATION. THE PROXY STATEMENT AND OTHER RELEVANT DOCUMENTS WILL BE PROVIDED FREE TO ANY SHAREHOLDER BY CALLING (541) 523-6327 OR WRITING THE COMPANY AT P.O. BOX 846, BAKER CITY, OREGON 97814, ATTENTION PRESIDENT. THE INFORMATION IS ALSO AVAILABLE FREE FROM THE SECURITIES AND EXCHANGE COMMISSION'S WEBSITE AT www.sec.gov. August 21, 2001 Sincerely yours, /s/Stephen R. Whittemore /s/Berniel L. Maughan Stephen R. Whittemore Berniel L. Maughan Chairman of the Board President and CEO