JACKSON BOULEVARD CAPITAL MANAGEMENT LTD
PRRN14A, 2000-04-07
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                 PRELIMINARY PROXY MATERIALS DATED APRIL 6, 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 10, 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

<PAGE>

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.

                                       2
<PAGE>

        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.

                                       3
<PAGE>

        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 experience in the management and
supervision of financial institutions, is independent and will be dedicated to
enhancing stockholder value.

        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 of $4. 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%


                                       4
<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 prices.

        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.

                                       5
<PAGE>

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,
  (Nominee)                      Jackson 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

                                       6
<PAGE>

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.

                                       7
<PAGE>

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

                                       8
<PAGE>

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 10, 2000


                                       9
<PAGE>


                                   SCHEDULE 1

                        PARTICIPANTS IN THE SOLICITATION
                        --------------------------------

     The following table identifies and provides certain information as of April
6, 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).


                                       10
<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.


                                       11
<PAGE>




                                   SCHEDULE 2

Beneficial Ownership of Shares by Participants in the Solicitation

        The following table shows, as of April 6, 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                                  April 6, 2000       Of Class
- ----------------                                  -------------       --------
Paul J. Duggan(1)                                      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%

- --------
     (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.

                                       12
<PAGE>


                                   SCHEDULE 3

        The following table sets forth all shares of PSFI Common Stock purchased
or sold during the two years ended April 6, 2000 by participants in the
solicitations of proxies pursuant to this Proxy Statement.

                           Date                    Shares Purchased /
                                                         (Sold)
      ------------------------------------------------------------------
      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



                                       13
<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,


                                /s/ Paul Duggan

                                Paul Duggan

Cc:  Mr. SJ Ptak, Secretary



                                       14
<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.
- -----------------------------------------------------------------------------


                                       15
<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.


                                       16


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