CHESTER BANCORP INC
S-8, EX-5.1, 2000-09-01
SAVINGS INSTITUTION, FEDERALLY CHARTERED
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                                                                     Exhibit 5.1

                                 BRYAN CAVE LLP
                             ONE METROPOLITAN SQUARE
                           211 N. BROADWAY, SUITE 3600
                         ST. LOUIS, MISSOURI 63102-2750
                                 (314) 259-2000
                            FACSIMILE: (314) 259-2020

                                 August 31, 2000

Board of Directors
Chester Bancorp, Inc.
1112 State Street
Chester, Illinois  62233

Ladies and Gentlemen:

         We are  acting  as  counsel  for  Chester  Bancorp,  Inc.,  a  Delaware
corporation (the "Company"),  in connection with the preparation and filing of a
Registration  Statement  on Form S-8  (the  "Registration  Statement")  with the
Securities and Exchange Commission under the Securities Act of 1933, as amended.
The  Registration  Statement  relates to 268,212 shares of the Company's  common
stock, $0.01 par value per share,  issuable under the Chester Bancorp, Inc. 1997
Stock  Option  Plan  and the  Chester  Bancorp,  Inc.  2000  Stock  Option  Plan
(collectively, the "Plans").

         In connection herewith, we have examined and relied without independent
investigation as to matters of fact upon such  certificates of public officials,
such  statements  and  certificates  of officers of the Company and originals or
copies  certified  to  our  satisfaction  of  the  Registration  Statement,  the
Certificate  of  Incorporation  and Bylaws of the  Company as amended and now in
effect,  proceedings  of the Board of  Directors  of the  Company and such other
corporate  records,  documents,  certificates  and instruments as we have deemed
necessary  or  appropriate  in order to  enable us to render  this  opinion.  In
rendering this opinion, we have assumed the genuineness of all signatures on all
documents  examined  by us,  the  due  authority  of the  parties  signing  such
documents,  the  authenticity of all documents  submitted to us as originals and
the conformity to the originals of all documents submitted to us as copies.

         Based upon and subject to the  foregoing,  it is our  opinion  that the
268,212  shares of  common  stock of the  Company  covered  by the  Registration
Statement, have been duly authorized by all necessary action and, when issued on
exercise of options granted pursuant to the Plans, will be legally issued, fully
paid and non-assessable shares of common stock of the Company.

         This  opinion is not  rendered  with respect to any laws other than the
laws of the  State of  Missouri,  the  General  Corporation  Law of the State of
Delaware,  and the Federal law of the United  States.  We hereby  consent to the
filing of this opinion as Exhibit 5.1 to the Registration Statement.

                                                     Very truly yours,

                                                     /s/ Bryan Cave LLP



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