EXHIBIT 99

                             FOR IMMEDIATE RELEASE


OREGON TRAIL FINANCIAL CORP. REJECTS STILWELL REQUEST

Baker City, OR, Feb 14, 2001 / Stephen R. Whittemore, Chairman of the Board of
Directors of Oregon Trail  Financial  Corp.(Nasdaq:OTFC)  announced today that
the Board of  Directors  had  rejected  Joseph  Stilwell's  request that he be
allowed to name two persons to the Board of Directors.  Mr. Whittemore stated,
"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.  We are
confident that earnings per share will improve over the next fiscal year."

Joseph Stilwell has filed an Amended Schedule 13D advising of the ownership of
284,000 shares (8.5%) with the stated purpose of influencing management of the
Company to pursue specific steps he believes would enhance  shareholder  value
including  the sale of the  Company.  He  recently  filed a  separate  Amended
Schedule 13D reporting that he had requested the Company to increase its board
from 6 to 8 and appoint two persons  selected by him. One of those  identified
was his  attorney  from New  York,  New York.  The  other's  identity  was not
disclosed but was described as a lawyer living in or adjacent to the Company's
market area.

This press  release  includes  forward-looking  statements,  which the Company
believes   are  a  benefit  to   shareholders.   Within  the  meaning  of  the
"Safe-Harbor"  provisions of the Private  Securities  Litigation Reform Act of
1995,  these  statements are  necessarily  subject to risk and uncertainty and
actual results could differ materially due to certain risk factors,  including
without limitation  economic  conditions,  acquisition risk factors and others
set forth from time to time in the  Company's  filings with the SEC.  Specific
risks in this press  release  include but are not limited  to,  interest  rate
trends,  the general  economic  climate in the  Company's  market area and the
country as a whole,  the  success  in  opening  new  branches,  marketing  new
products,   and  implementing  its  cost  reduction  and  revenue  enhancement
strategies,  deposit flows,  demand for mortgages and other loans, real estate
values, competition, loan delinquency rates, changes in accounting principles,
practices,   policies,  or  guidelines,  and  changes  in  federal  and  state
regulations.   These  factors   should  be   considered   in  evaluating   the
forward-looking statements.

CONTACT: Berniel L. Maughan,  President and CEO, Oregon Trail Financial Corp.,
(541) 523-6327.