JACKSON BOULEVARD CAPITAL MANAGEMENT LTD
DEFN14A, 2000-03-30
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                PRELIMINARY PROXY MATERIALS DATED MARCH 30, 2000

         The information included herein is as it is expected to be when the
definitive proxy statement is mailed to stockholders of PS Financial, Inc. This
proxy statement will be revised to reflect actual facts at the time of the
filing of the definitive proxy statement.

                                   MAY 3, 2000

                         ANNUAL MEETING OF STOCKHOLDERS

                                       OF

                               PS FINANCIAL, INC.

                               PROXY STATEMENT OF

                                 PAUL J. DUGGAN

                 AND THE COMMITTEE TO ENHANCE SHAREHOLDER VALUE

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

                 IMPORTANT INFORMATION ABOUT THE ANNUAL MEETING

Why You Were Sent This Proxy Statement

         This Proxy Statement and the enclosed BLUE proxy card are being
furnished to you by Paul J. Duggan and the Committee to Enhance Shareholder
Value (the "Committee") in connection with the solicitation of proxies for the
Annual Meeting of Stockholders of PS Financial, Inc. ("PSFI" or the "Company"),
scheduled to be held on May 3, 2000 at 11:00 a.m. (local time) at the main
office of the Company located at 4800 South Pulaski Road, Chicago, Illinois, and
any adjournment(s) or postponement(s) thereof (the "Annual Meeting").

         This Proxy Statement and accompanying proxy card are first being sent
to stockholders on or about April ___, 2000.

         MR. DUGGAN AND THE COMMITTEE STRONGLY RECOMMEND A VOTE FOR PAUL J.
DUGGAN AS DIRECTOR AND A VOTE "FOR" THE STOCKHOLDER PROPOSAL TO APPOINT AN
INVESTMENT BANKER AND ESTABLISH A COMMITTEE COMPOSED OF INDEPENDENT DIRECTORS TO
EVALUATE PROPOSALS TO SELL OR MERGE THE COMPANY.

         Mr. Duggan is a PSFI stockholder and Manager of Jackson Boulevard
Partners ("Jackson Partners"), an investment consulting firm in Chicago,
Illinois, and President of Jackson Boulevard Capital Management, Ltd., ("Jackson
Capital"), an investment management firm with an emphasis on securities of
savings and loans, banks and other companies in the banking field. The members
of the Committee are Paul J. Duggan, Jackson Partners, Jackson Boulevard
Equities, L.P. ("Equities"), Jackson Boulevard Investments, L.P.
("Investments"), Jackson Capital ("Jackson Capital") and Jackson Offshore Fund,
Ltd. ("Offshore"), which are investment funds of which Mr. Duggan serves as
Manager or President. The member of the Committee has beneficial ownership of a
total of 131,700 shares of Common Stock, par value $.01 per share, of the
Company ("PSFI Common Stock"), representing approximately 7.89% of the issued
and outstanding PSFI Common Stock.

What You Are Voting On

         At the Annual Meeting, among other things, the stockholders of the
Company will be asked to vote to:

o        elect two directors;

o        ratify the appointment of Crowe, Chizek and Company LLP as the
         auditors of the Company for the fiscal year ending December 31,
         2000; and

o approve a stockholder proposal directing the Board of Directors of the Company
to appoint an investment banker to pursue merger or acquisition candidates for
the Company and to establish a committee consisting of all directors who are not
current or former officers or employees or relatives of current or former
officers of the Company in order to consider and recommend to the full Board of
Directors for approval the best available offer to acquire the Company by sale
or merger.

Who Can Vote at the Annual Meeting

         Stockholders who owned shares of PSFI Common Stock at the close of
business on March 15, 2000 (the "Record Date") are entitled to vote at the
Annual Meeting. As of March 15, 2000, according to the Company's Preliminary
Proxy Statement filed by the Company with the U.S. Securities and Exchange
Commission (the "SEC") on March 15, 2000 (the "PSFI Preliminary Proxy
Statement"), there were 1,669,290 issued and outstanding shares of the Company's
Common Stock. Each share of PSFI Common Stock held on the Record Date is
entitled to one (1) vote at the Annual Meeting.

How to Vote by Proxy

         To elect Mr. Duggan to the Board, and to vote in favor of the
stockholder proposal (set forth in this Proxy Statement), promptly complete,
sign, date and mail the enclosed BLUE proxy card in the enclosed postage-paid
envelope. Whether you plan to attend the Annual Meeting or not, we urge you to
complete and return the enclosed BLUE proxy card.

         Properly executed proxies will be voted in accordance with the
directions indicated thereon. If you sign the BLUE proxy card but do not make
any specific choices, your proxy will vote your shares as follows:

o        "FOR" the election of Mr. Duggan to the Board of Directors.

o "FOR" the ratification of the appointment of Crowe, Chizek and Company LLP as
the auditors of the Company for the fiscal year ending December 31, 2000.

o "FOR" the stockholder proposal directing the Board of Directors of the Company
to appoint an investment banker to pursue merger or acquisition candidates for
the Company and to establish a committee consisting of all directors who are not
current or former officers or employees or relatives of current or former
officers or employees of the Company in order to consider and recommend to the
full Board of Directors for approval the best available offer to acquire the
Company by sale or merger.

         If any other matter is presented at the Annual Meeting, your proxy will
vote in accordance with his best judgment. At the time this Proxy Statement was
mailed, we knew of no matters which needed to be acted on at the Annual Meeting,
other than those discussed in this Proxy Statement.

         If any of your shares are held in the name of a brokerage firm, bank,
bank nominee or other institution on the Record Date, only that entity can vote
your shares and only upon its receipt of your specific instructions.
Accordingly, please contact the person responsible for your account at such
entity and instruct that person to execute and return the BLUE proxy card on
your behalf. You should also sign, date and mail the voting instruction form
your broker or banker sends you when you receive it. Please do this for each
account you maintain to ensure that all of your shares are voted.

How You Can Revoke a Proxy

         If you have executed the Board of Directors' WHITE proxy card before
receiving Mr. Duggan's Proxy Statement, you have every right to change your vote
by completing, signing, dating and returning the enclosed BLUE proxy card. ONLY
YOUR LATEST DATED PROXY WILL COUNT AT THE ANNUAL MEETING. Any proxy may be
revoked at any time before it is voted by (i) submitting a duly executed proxy
card bearing a later date to the Secretary of the Company or to Mr. Duggan, (ii)
filing with the Secretary of the Company a written revocation, or (iii)
attending and voting at the Annual Meeting in person.

Who You Can Call If You Have Questions

         If you have any questions concerning this Proxy Statement or need
assistance in voting your shares, please call Paul J. Duggan at (888) 522-5332
or Mr. Duggan's proxy solicitor:

                             THE ALTMAN GROUP, INC.
                              60 East 42nd Street,
                                   Suite 1241
                               New York, NY 10165
                                 (800) 206-0007


                            ANNUAL MEETING PROPOSALS

         At the Annual Meeting, the Company's stockholders will be asked to vote
on the following matters: the election of two directors, the ratification of the
appointment of Crowe, Chizek and Company LLP as the auditors of the Company, and
a stockholder proposal directing the Company to appoint an investment banker to
pursue merger or acquisition candidates for the Company and establish a
committee composed of independent directors to evaluate proposals to sell or
merge the Company. As discussed in more detail below, we believe that the
current Board of Directors as a group have not been acting in your best
interests as stockholders of the Company. The election of Mr. Duggan and the
approval of the stockholder proposal is, in our opinion, in your best interest
as stockholders.

                              ELECTION OF DIRECTORS


         PSFI's Board of Directors consists of six directors, who serve
three-year terms. Two of the six directors are being elected at this year's
Annual Meeting. Mr. Duggan and the Committee are proposing one nominee for
election as a director of PSFI, namely Mr. Duggan himself.

         We are asking you to elect Mr. Duggan, the one director nominated by
Mr. Duggan and supported by the Committee, instead of one of the directors
nominated by the Company. We believe it is in your best interest as stockholders
to do so because we believe that the performance of the current Board of
Directors has been inadequate in the areas of increasing stockholder value,
increasing the profitability of the Company and taking advantage of
opportunities available to the Company.

         We believe that Mr. Duggan has superior experience in the management
and supervision of financial institutions and the successful sales of financial
institutions, is more independent and will be more dedicated to enhancing
stockholder value than the Company's nominees and the current membership of the
Company's Board of Directors.

         In addition, Mr. Duggan and the Committee have concluded that PSFI
should seriously explore whether it can be acquired or merged. Mr. Duggan will
recommend that the Board engage an investment banker and aggressively pursue the
acquisition or merger of PSFI as an alternative for increasing the value of PSFI
to stockholders. In this respect, if elected, Mr. Duggan will constitute only
one of six directors and therefore cannot compel the Board to act and can only
advise that PSFI seriously consider proposals of acquisition or merger.

         How We Disagree With Current Directors on Operation of the Company -
Our Objectives

         We believe that the current management and Board of Directors of the
bank have failed to maximize stockholder value and the profitability of the
Company and that this is evident in the performance of the Company's stock price
as compared to the stock prices of other financial institutions.

         Over the three years since PSFI's Common Stock commenced trading on the
NASDAQ National Market System, the return on PSFI's Common Stock has
underperformed each of the NASDAQ Bank Index (an index of U.S. banks stock
traded on NASDAQ published by NASDAQ), the SNL Thrift Index (an index of savings
and loans institutions published by SNL Securities) and the SNL Bank & Thrift
Index (an index of bank and thrift institutions published by SNL Securities). A
table comparing the returns of PSFI's Common Stock to these indices as well as
to the Dow Jones Industrial Average and S&P 500 and NASDAQ is set forth below.



                                      11/27/1996       03/16/2000      % CHANGE
- -------------------------------------------------------------------------------
PS Financial, Inc. Stock Price         $    11.64     $     12.00         3.09%
Dow Jones Industrial Average             6,499.34       10,630.29        63.56%
S&P 500                                    755.00        1,458.47        93.17%
NASDAQ Composite Index                   1,287.32        4,717.36       266.45%
NASDAQ Bank Index                        1,263.71        1,505.01        19.09%
SNL Thrift Index                           484.10          540.80        11.71%

In January 1998, PSFI paid a special dividend. After this dividend was paid, the
stock was priced at $15.25. Since that date the stock has lost 21% of its value,
while the broad market indices have risen.


                                       01/13/1998      03/16/2000      % CHANGE
- -------------------------------------------------------------------------------
PS Financial, Inc. Stock Price         $     15.25    $      12.00      -21.31%
Dow Jones Industrial Average              7,732.13       10,630.29       37.48%
S&P 500                                     952.12        1,458.47       53.18%
NASDAQ Composite Index                    1,541.63        4,717.36      206.00%




<PAGE>


         To maximize shareholder value, Mr. Duggan and the Committee have
concluded that PSFI should seriously explore the feasibility of being acquired
by or merging with another institution. If elected, our nominee will recommend
that the Board engage an investment banker and aggressively pursue the
acquisition of PSFI as an alternative for increasing share value, although this
nominee will be open-minded and will consider all recommendations from other
stockholders or directors. Mr. Duggan and the Committee, therefore, support the
stockholder proposal set forth in the PSFI Board of Directors Proxy Statement
that recommends the appointment of an investment banker. If you share this view,
then you should vote for our nominee. If elected, our nominee would constitute
only one of six directors and could not compel action by the Board. However, by
electing our candidate, we believe you will be sending a message to the
remaining Board members that you wish them to focus on enhancing share values.

         None of the members of the Committee knows of any agreements or
understandings concerning the possible acquisition of PSFI and there can be no
assurance that an acquisition can be effected at prices materially above the
current market value for PSFI Common Stock.

Why the Director Nominated by Paul J. Duggan Will Better Serve Investors Than
Any of PSFI's Nominees

         Mr. Duggan and the other members of the Committee have collectively
invested more than $1,300,000 in shares of PSFI Common Stock, and as of March
15, 2000, Mr. Duggan himself beneficially owned 131,700 shares of PSFI Common
Stock. Mr. Duggan and the Committee believe that this significant investment
entitles Mr. Duggan to representation on the Board of Directors and qualifies
him to represent stockholders who are concerned about enhancing stock values.
All of the shares purchased by Mr. Duggan and the other members of the Committee
have been purchased at market price and not at favorable option prices, as is
the case with many of the shares held by the Directors supported by management.
In our opinion, Mr. Duggan's significant stockholdings in the Company more
closely align his interests with your interests as stockholders as compared to
current members of the Board of Directors.

         Mr. Duggan has over 20 years of experience in investing in securities
of banks and financial institutions. Since 1993, Mr. Duggan has served as
Managing General Partner of Jackson Capital, which was organized as a limited
partnership for the purpose of investing in marketable securities with an
emphasis on securities of savings and loans, banks and other companies in the
banking field. Mr. Duggan is also President of Jackson Capital, a hedge fund
management firm. Jackson Capital offers money management and venture capital
activities in addition to managing hedge funds, which concentrate in investing
in the thrift and small cap bank areas. In this position, Mr. Duggan has
invested in over 150 financial institutions, including over 40 financial
institutions that have been acquired or that have merged with other financial
institutions. Mr. Duggan served on the Board of Directors of Damen Financial
Corporation, a Chicago area bank. Mr. Duggan served on the Damen Board when such
bank was sold in 1999.

         Information with respect to this nominee is set forth under the caption
"Paul J. Duggan's Nominee".

         The Director nominees proposed by the PSFI Board of Directors in the
PSFI Preliminary Proxy Statement include Jeanine M. McInerney, a clinical nurse
consultant with Healthpoint Medical who has been employed as a nurse for
approximately fifteen years, and Rocco DiIorio, a retired sewer contractor.

         The biographies for Mr. DiIorio and Ms. McInerney contained in the PSFI
Preliminary Proxy Statement do not describe the existence of any experience with
any other financial institution other than PSFI or Preferred Savings Bank, a
wholly owned subsidiary and predecessor to the Company.

Paul J. Duggan's Nominee

         The table set forth below identifies our nominee for election as a new
director of PSFI and provides information concerning this nominee.

- ------------------------------------------------------------------------------
Name of Nominee     Age  Business Experience During Past Five Years
- ------------------------------------------------------------------------------
Paul J. Duggan      49   Manager/Owner, Duggan & Associates; Manager, Jackson
  (Nominee)              Partners; President, Jackson Capital
- ------------------------------------------------------------------------------

Further biographical information about Paul J. Duggan's nominee is set forth
below:

         Paul J. Duggan, a life-long resident of Chicago, is a licensed CPA in
the State of Illinois. Mr. Duggan owns and has managed a consulting firm, Duggan
and Associates, which specializes in litigation consulting, since 1976, and has
managed Jackson Partners, an investment consulting firm in Chicago, since 1991.
Mr. Duggan has served as an expert witness in commercial litigation issues, in
damages analysis areas and has testified in federal and state courts on issues
concerning business valuation, intellectual property, unjust enrichment, and
various damages areas. Mr. Duggan is also President of Jackson Capital, a hedge
fund management firm since 1993. Jackson Capital offers money management and
venture capital activities in addition to managing hedge funds which concentrate
in investing in the thrift and small cap bank areas. Mr. Duggan currently
manages portfolios with investments in thrifts in excess of $70 million as well
as over $50 million in venture capital and private real estate partnerships. Mr.
Duggan serves on the Boards of Directors of Marinette Marine Corporation in
Marinette, Wisconsin (a manufacturer of ocean going vessels for the U.S. Coast
Guard, U.S. Navy, and commercial customers), Marigold Services of Chicago,
Illinois (a dry and liquid sugar storage terminal) and Napleton St. Louis Honda
in St. Peters, Missouri (a retail Honda dealer). Mr. Duggan received his B.B.A.
in business administration from Loyola University of Chicago in 1974 and his CPA
in the State of Illinois in 1975. Mr. Duggan served on the Board of Directors of
Damen Financial Corporation, a Chicago area bank, from May 1999 until the
company was sold that year.

         There are no arrangements or understandings between Mr. Duggan and any
other person pursuant to which he was selected as nominee, except that Mr.
Duggan has consented to serve as a director if elected. Mr. Duggan and the
Committee do not expect that Mr. Duggan will be unable to stand for election;
but, in the event that Mr. Duggan should be unable to stand for election, the
Common Stock represented by the enclosed BLUE proxy card will be voted for a
substitute candidate selected by Mr. Duggan.

Compensation of Director Nominees

         Mr. Duggan is not now and has never been a director or officer of the
Company nor has he ever received any compensation from the Company. No
discussions have been held and, except as indicated in this Proxy Statement,
there are no understandings with respect to any proposed remuneration from any
source for this nominee in connection with serving as a director of PSFI if
elected. However, if our nominee is elected as a director of PSFI, it is
anticipated he will receive the same compensation as other directors. According
to the PSFI Preliminary Proxy Statement, each member of the Board of Directors
of the Company is paid a fee of $300 per month.

              STOCKHOLDER PROPOSAL TO APPOINT AN INVESTMENT BANKER

         At the Annual Meeting, the stockholders will be asked to vote to
approve or disapprove a stockholder proposal directing the Company's Board of
Directors to appoint an investment banker to pursue merger or acquisition
candidates for the Company, and establish a committee consisting of all
directors who are not current or former officers or employees or relatives of
current or former officers or employees of the Company in order to consider and
recommend to the full Board of Directors for approval the best available offer
to acquire the Company by sale or merger. The specific resolution reads as
follows:

                           RESOLVED, that the stockholders of the Company,
                  believing that the value of their investment in the Company
                  can best be maximized through a sale or merger of the Company,
                  hereby request that the Board of Directors promptly proceed to
                  effect such a sale or merger by (i) retaining a leading
                  qualified investment banking firm for the specific purpose of
                  soliciting offers to acquire the Company by sale or merger and
                  (ii) establishing a committee of the Board of Directors
                  consisting of all directors, who are not current or former
                  officers or employees of the Company or related by blood or
                  marriage to a current or former officer or employee of the
                  Company, to consider and recommend to the full Board of
                  Directors for approval the best available offer to acquire the
                  Company by sale or merger.

         Mr. Duggan and the Committee have concluded that PSFI should seriously
explore whether it can be acquired or merged to take advantage of opportunities
current existing in the banking industry. Accordingly, Mr. Duggan has requested
that the Company consider appointing an investment banking firm for the purposes
of evaluating and soliciting offers to acquire the Company. See letter of Mr.
Duggan dated November 18, 1999, which is attached hereto as Schedule 4.

         None of the members of the Committee have any agreement or
understanding concerning the possible acquisition of PSFI and there can be no
assurance that an acquisition can be effected at prices materially above the
current market value of PSFI Common Stock. We are not aware of any proposals for
acquisition of PSFI.

Required Votes and Other Matters

         By signing and returning the enclosed BLUE proxy card, you can vote to
elect Paul J. Duggan as a director of PSFI and vote for the stockholder proposal
included in the Board of Directors' Proxy Statement.

         Directors shall be elected by a plurality of the votes present in
person or represented by proxy at the Annual Meeting and entitled to vote on the
election of Directors. Since Mr. Duggan and the Committee is only proposing one
nominee for the Board of Directors, if such nominee is elected, one of the
Company's nominees with the highest number of shares voted in their favor will
also be elected. There is no assurance that any of the Company nominees will
serve as Directors if the Committee's nominee is elected. The ratification of
the appointment of Crowe, Chizek and Company LLP as auditors and approval of the
stockholder proposal each require the affirmative vote of a majority of the
votes cast on the matter. Proxies marked to abstain with respect to a proposal
have the same effect as votes against the proposal. Votes withheld (for election
of directors) and broker non-votes will have no effect on the vote. One-third of
the shares of the Common Stock, present in person or represented by proxy, shall
constitute a quorum for purposes of the Annual Meeting. Abstentions and broker
non-votes are counted for purposes of determining a quorum.

                                OTHER INFORMATION

How Proxies Will be Solicited

         We may solicit proxies for the Annual Meeting by mail, advertisement,
telephone, telecopier or in person. The persons identified on Schedule 1 to this
Proxy Statement also may make solicitations. None of these persons will receive
additional compensation for participating in the solicitation. We have requested
banks, brokerage houses and other custodians, nominees and fiduciaries to
forward all of our solicitation materials to the beneficial owners of the PSFI
Common Stock they hold.

Important Instructions For "Street Name" Stockholders

         If any of your shares are held in the name of a brokerage firm, bank,
bank nominee or other institution on the record date, only that entity can vote
your shares and only upon its receipt of your specific instructions.
Accordingly, please contact the person responsible for your account at such
entity and instruct that person to execute and return the BLUE proxy card on
your behalf. You should also sign, date and mail the voting instruction form
your broker or banker sends you when you receive it. Please do this for each
account you maintain to ensure that all of your shares are voted.

Information About the Proxy Solicitor

         Mr. Duggan and the Committee have retained The Altman Group, Inc.
("Altman") to assist in the solicitation of proxies. Mr. Duggan and the
Committee have agreed to pay Altman a fee of $10,000 and to reimburse it for its
reasonable out-of-pocket expenses. Approximately 5 persons will be used by
Altman in its solicitation efforts.

Costs of Soliciting Proxies

         The entire expense of preparing, assembling, printing and mailing this
Proxy Statement and related materials and the cost of soliciting proxies
pursuant to this Proxy Statement will be borne by Mr. Duggan, Jackson Capital
and certain other members of the Committee. Mr. Duggan and the Committee
estimate that the total expenditures relating to the solicitation of proxies
will be approximately $32,000. To date, approximately $2,000 of expenses have
been incurred. Mr. Duggan, Jackson Capital and certain other members of the
Committee will pay the costs of soliciting proxies. Mr. Duggan and the Committee
intend to seek approval from the Board of Directors for the reimbursement of the
Committee's cost of soliciting policies.

Other Matters

         The PSFI Preliminary Proxy Statement contains information regarding (1)
securities ownership of 5% or more beneficial ownership and management; (2) the
committees of the Company's Board of Directors; (3) the meetings of the
Company's Board of Directors and all committees thereof; (4) the background of
the nominees of the Company's Board of Directors; (5) the compensation and
remuneration paid and payable to the Company's directors and management; (6)
stock price performance; and (7) the submission of stockholder proposals at the
company's 2001 annual meeting of stockholders. The Committee has no knowledge of
the accuracy of the Company's disclosures in its proxy materials.

Information About Paul J. Duggan and the Committee to Enhance Shareholder Value

         Certain information about persons who may participate in the
solicitation of proxies is set forth in Schedule 1 to this Proxy Statement.
Schedule 2 to this Proxy Statement sets forth certain information relating to
beneficial ownership of shares of PSFI Common Stock by such persons (including
our nominee and persons involved in this solicitation known to us to
beneficially own more than five percent of PSFI Common Stock), and Schedule 3
lists all transactions in PSFI Common Stock effected by such persons in the two
years prior to the date of this proxy statement.

         MR. DUGGAN AND THE COMMITTEE STRONGLY RECOMMEND A VOTE FOR PAUL J.
DUGGAN AS DIRECTOR AND A VOTE "FOR" THE STOCKHOLDER PROPOSAL TO APPOINT AN
INVESTMENT BANKER AND APPOINT A COMMITTEE COMPOSED OF INDEPENDENT DIRECTORS TO
EVALUATE PROPOSALS TO SELL OR MERGE THE COMPANY.

        IT IS IMPORTANT THAT YOU RETURN YOUR PROXY PROMPTLY. PLEASE SIGN AND
DATE YOUR BLUE PROXY CARD PROMPTLY AND RETURN IT IN THE ENCLOSED ENVELOPE TO
AVOID UNNECESSARY EXPENSE AND DELAY. NO POSTAGE IS NECESSARY.

                                   Sincerely,

                                   /s/ Paul J. Duggan

                                   Paul J. Duggan
                                   Chairman, Committee to Enhance
                                   Shareholder Value



April ___, 2000



<PAGE>


                                   SCHEDULE 1

                        PARTICIPANTS IN THE SOLICITATION

         The following table identifies and provides certain information as of
March 20, 2000 about individuals and entities that might be deemed participants
in this proxy solicitation within the meaning of Rule 14a-11(b) promulgated
under the Securities Exchange Act of 1934, as amended:

1.       Paul J. Duggan
         53 West Jackson Boulevard, Suite 400
         Chicago, IL  60604

         Mr. Duggan is an individual who is Manager/Owner of Duggan &
         Associates, a consulting firm specializing in consulting,
         since 1976, and has managed Jackson Partners, an investment
         consulting firm in Chicago, since 1991. Mr. Duggan is
         also President of Jackson Capital, a hedge fund management firm.

         Mr. Duggan, together with reporting group members Jackson Capital,
         Equities, Investments, Offshore and Jackson Partners, has filed a
         Schedule 13D and will make amendments as required by law with respect
         to beneficial ownership of Common Stock.

2.       Jackson Boulevard Capital Management, Ltd.
         53 West Jackson Boulevard, Suite 400
         Chicago, IL  60604

         Jackson Capital is an Illinois corporation and a hedge fund management
         firm. Jackson Capital offers money management and venture capital
         activities, in addition to managing hedge funds which concentrate in
         investing in the thrift and small cap bank areas. Jackson Capital is
         the sole General Partner of Equities and Investments.

3.       Jackson Boulevard Equities, L.P.
         53 West Jackson Boulevard, Suite 400
         Chicago, IL  60604

         Equities is an Illinois limited partnership. Equities invests in
         marketable securities with an emphasis on securities of savings &
         loans, banks and of other companies in the banking industry.

4.       Jackson Boulevard Investments, L.P.
         53 West Jackson Boulevard, Suite 400
         Chicago, IL  60604

         Investments is an Illinois limited partnership. Investments specializes
         in buying and selling securities for investments, particularly
         securities related to the banking industry (including banks and
         thrifts).



<PAGE>


5.       Jackson Offshore Fund
         31 Kildare Street
         Dublin 2
         IRELAND

         Offshore is an Illinois corporation and a Tortolla, British Virgin
         Island corporation. Offshore specializes in buying and selling
         securities for investments, particularly securities related to the
         financial industry (including banks and thrifts).

6.       Jackson Boulevard Partners
         53 West Jackson Boulevard, Suite 400
         Chicago, IL  60604

         Jackson Partners is an Illinois general partnership and Jackson
         Partners is an investment consulting firm.

         Except as described in this Proxy Statement, none of the above-listed
participants in the solicitation is now, or was within the last two years, a
party to any contract, arrangement or understanding with any person with respect
to any securities of PSFI, future employment by PSFI or future transactions
involving PSFI.



<PAGE>




                                   SCHEDULE 2

Beneficial Ownership of Shares by Participants in the Solicitation

         The following table shows, as of March 30, 2000 (except as otherwise
noted), the shares of PSFI Common Stock beneficially owned by the participants
in the solicitation of proxies pursuant to this Proxy Statement. Unless
otherwise indicated, each participant has sole voting and investment power over
the shares beneficially owned.

                                              Shares Beneficially
                                                   Owned at        Percent
Beneficial Owner                                March 20, 2000     Of Class

Paul J. Duggan1                                       131,700        7.89%

Jackson Boulevard Capital Management, Ltd. 2            75,700      4.53%

Jackson Boulevard Equities, L.P.                        37,814       2.27%

Jackson Boulevard Investment, L.P.                      19,261       1.15%

Jackson Offshore Funds                                  18,625       1.12%

Jackson Boulevard Partners                              55,500       3.32%


<PAGE>


                                   SCHEDULE 3

         The following table sets forth all shares of PSFI Common Stock
purchased or sold during the two years ended March 30, 2000 by participants in
the solicitations of proxies pursuant to this Proxy Statement.
<TABLE>
<CAPTION>
                                 Date                              Shares Purchased / (Sold)
       -----------------------------------------------------------------------------------------
<S>    <C>                                                                    <C>
       JACKSON BOULEVARD EQUITIES, L.P.
       5/05/99                                                                6,000

       JACKSON BOULEVARD INVESTMENTS, L.P.
       5/05/99                                                                2,000
       8/30/99                                                               17,261

       JACKSON OFFSHORE FUND, LTD.
       8/11/88                                                               18,265

       JACKSON BOULEVARD PARTNERS, L.P.                                            0

       PAUL J. DUGGAN                                                              0
</TABLE>



<PAGE>


                                   SCHEDULE 4

                                                             November 18, 1999
VIA FEDERAL EXPRESS
AND MESSEGER

Ms. Kimberly P. Rooney
President, CEO
PS Financial, Inc.
4800 South Pulaski Road
Chicago, IL  60632

         Re:      Stockholders Proposal

Dear Ms. Rooney:


         I am the record owner of 500 shares and the beneficial owner of 131,200
shares of the common stock, par value $.01 per share (the "Common Stock") of PS
Financial, Inc. (the "Company"). My address of record, as it appears on the
Company's books, is 53 West Jackson Boulevard, Chicago, Illinois 60604. As shown
by the attached Schedule 13D (including amendments), I have continuously held at
least $2,000 in market value of the Common Stock for more than one year, as of
the date of this letter. I intend to continue ownership of at least $2,000 in
market value of the Common Stock through the date of the Company's 2000 annual
meeting of stockholders.

         I hereby give notice of my intent to introduce the attached
stockholders resolution (the "Proposal") at the 2000 annual meeting of
stockholders of the Company pursuant to the Company's By-laws and the
stockholders proposals section of the Company's Definitive Proxy Statement filed
March 31, 1999. I have no material interest in the Proposal aside from my
interest as a stockholder in the Company. I request, pursuant to Rule 14a-8
promulgated under the Securities Exchange Act of 1934, as amended, that the
Proposal and the accompanying Supporting Statement be included in the Company's
proxy materials and identified in the Company's form of proxy for the 2000
annual meeting of stockholders.

         Please do not hesitate to call should you have any questions.

                                                     Very truly yours,



                                                     Paul Duggan

Cc:  Mr. SJ Ptak, Secretary



<PAGE>


                              [Face of Proxy Card]

                                      PROXY

                      This proxy is solicited on behalf of
          Paul J. Duggan and the Committee to Enhance Shareholder Value
                               With Respect to the
                              PSFI Financial, Inc.
                         Annual Meeting of Stockholders
                            To be held on May 3, 2000

         The undersigned appoints Paul J. Duggan with full power of
substitution, as proxy for the undersigned, to represent and vote, as designated
below, all shares of Common Stock of PS Financial, Inc. (the "Company") which
the undersigned is entitled to vote at the Annual Meeting of Stockholders of the
Company to be held as scheduled on May 3, 2000 at 11:00 a.m. (local time) at the
main office of the Company located at 4800 South Pulaski Road, Chicago,
Illinois.

         This proxy, when properly executed, will be voted in the manner
directed by the undersigned stockholder. If no direction is made, this proxy
will be voted FOR the election of Paul J. Duggan as a director of the Company,
FOR the ratification of the appointment of Crowe, Chizek and Company LLP as the
auditors of the Company for the fiscal year ending December 31, 2000, and FOR
the stockholder proposal directing the Board of Directors to appoint an
investment banker to pursue merger or acquisition candidates for the Company and
to establish a committee consisting of all directors who are not current or
former officers or employees or relatives of such persons in order to recommend
to the Board of Directors the best available offer to acquire the Company.

     This proxy is solicited on behalf of Paul J. Duggan and the Committee to
Enhance Shareholder Value.


- --------------------------------------------------------------------------------
   PLEASE SIGN, DATE AND RETURN THIS PROXY PROMPTLY IN THE ENCLOSED ENVELOPE.
- --------------------------------------------------------------------------------


<PAGE>


                             [Reverse of Proxy Card]

         The Committee to Enhance Shareholder Value recommends that you vote FOR
the election of Paul J. Duggan as a director of the Company, FOR the
ratification of the appointment of Crowe, Chizek and Company LLP as the auditors
of the Company for the fiscal year ending December 31, 2000, and FOR the
stockholder proposal directing the Board of Directors to appoint an investment
banker to pursue merger or acquisition candidates for the Company and to
establish a committee consisting of all directors who are not current or former
officers or employees or relatives of such persons in order to recommend to the
Board of Directors the best available offer to acquire the Company.

1.       To elect Paul J. Duggan as a Director of the Company.

         [ ]        FOR                 [ ]        WITHHOLD

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

         The Committee intends to use this proxy to vote for persons who have
been nominated by the Company to serve as Directors, other than the Company
nominee listed below. You may withhold authority to vote for one or more
additional Company nominees, by writing the name of the nominee(s) below. You
should refer to the proxy statement and form of proxy distributed by the Company
for the names, background, qualifications, and other information concerning the
Company's nominees.

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


         There is no assurance that any of the Company's nominees will serve as
Directors if the Committee nominee is elected to the Board.

         The Committee is NOT seeking authority to vote for and will NOT
exercise any such authority for the following Company nominee: Rocco DiIorio

2.       To ratify the appointment of Crowe, Chizek and Company LLP as the
auditors of the Company for the fiscal year ending December 31, 2000.

                         [ ] FOR [ ] AGAINST [ ] ABSTAIN

3. To approve the stockholder proposal directing the Board of Directors to
appoint an investment banker to pursue merger or acquisition candidates for the
Company and to establish a committee consisting of all directors who are not
current or former officers or employees or relatives of such persons in order to
recommend to the Board of Directors the best available offer to acquire the
Company.

                         [ ] FOR [ ] AGAINST [ ] ABSTAIN


                                            Please sign your name exactly as it
                                            appears on this card. If you are a
                                            joint owner, each /owner should
                                            sign. When signing as executor,
                                            administrator, attorney, trustee, or
                                            guardian, or as custodian for a
                                            minor, please give your full title
                                            as such. If you are signing for a
                                            corporation, please sign the full
                                            corporate name and indicate the
                                            signer's office. If you are a
                                            partner, sign in the partnership
                                            name.



                                            Shareholder sign here       Date



                                            Co-owner sign here          Date



If you need assistance in voting your shares, please call Paul J. Duggan at
(888) 522-5322 or The Altman Group, Inc., which is assisting the Committee in
its solicitation of your proxy for the Annual Meeting, at (212) 681-9600.

- --------

     1 Includes 500 shares held directly by Mr. Duggan, 55,500 shares held by
Jackson Partners, 75,700 shares held by Jackson Capital, 37,814 shares held by
Equities and 19,261 shares held by Investments, 18,625 shares held by Offshore.
Mr. Duggan is one of two general partners of Jackson Partners and shares voting
and investment power concerning the shares held by Jackson Partners with Deborah
Duggan, Mr. Duggan's spouse. Mr. Duggan is the sole stockholder and a director
and officer of Jackson Capital, which is the sole general partner of Equities
and Investments. Mr. Duggan, Jackson Capital, Equities, and Investments have
shared voting and investment power with regard to the 57,075 shares held by
Equities and Investments.

     2 57,075 shares are beneficially owned as sole General Partner of Equities
and Investments. 18,625 shares are beneficially owned as investment manager of
Offshore.



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