CUMBERLAND MOUNTAIN BANCSHARES INC
DEF 14A, 2000-09-15
SAVINGS INSTITUTION, FEDERALLY CHARTERED
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                            SCHEDULE 14A INFORMATION
                                 (RULE 14a-101)
                     INFORMATION REQUIRED IN PROXY STATEMENT

                            SCHEDULE 14A INFORMATION
           PROXY STATEMENT PURSUANT TO SECTION 14(A) OF THE SECURITIES
                    EXCHANGE ACT OF 1934 (AMENDMENT NO. ___)

Filed by the Registrant [x]
Filed by a Party other than the Registrant [ ]

Check the appropriate box:
[ ]Preliminary Proxy Statement                 [ ]Confidential, for Use of the
[x]Definitive Proxy Statement                     Commission Only (as permitted
[ ]Definitive Additional Materials                by Rule 14a-6(e)(2))
[ ]Soliciting Material Under Rule 14a-12

                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
--------------------------------------------------------------------------------
                (Name of Registrant as Specified in Its Charger)


--------------------------------------------------------------------------------
    (Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)

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.

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      2. Aggregate number of securities to which transaction applies:

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      3. Per  unit  price  or other  underlying  value  of  transaction
         computed  pursuant  to  Exchange  Act Rule 0-11 (Set forth the
         amount on which the filing fee is calculated  and state how it
         was determined):

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      4. Proposed maximum aggregate value of transaction:

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      5. Total fee paid:

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[ ]   Fee paid previously with preliminary materials:
[ ]   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:

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      2. Form, Schedule or Registration Statement No.:

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      4. Date Filed:

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<PAGE>


              [LETTERHEAD OF CUMBERLAND MOUNTAIN BANCSHARES, INC.]












                               September 15, 2000


Dear Stockholder:

     We invite you to attend the 2000  Annual  Meeting  of the  Stockholders  of
Cumberland Mountain Bancshares,  Inc. to be held at the Fountain City Park Bank,
5320 N.  Broadway,  Fountain City,  Tennessee on Wednesday,  October 18, 2000 at
3:30 p.m., Eastern Time.

     The accompanying notice and proxy statement describe the formal business to
be transacted  Enclosed with this proxy statement are a proxy card and an Annual
Report to Stockholders  for the 2000 fiscal year.  Directors and officers of the
Company,  as well as representatives of Marr, Miller & Myers, PSC, the Company's
independent  auditors,  will be present at the Annual  Meeting to respond to any
questions the stockholders may have.

     You are  cordially  invited  to attend the Annual  Meeting.  REGARDLESS  OF
WHETHER YOU PLAN TO ATTEND,  WE URGE YOU TO SIGN,  DATE AND RETURN THE  ENCLOSED
PROXY CARD AS SOON AS POSSIBLE EVEN IF YOU  CURRENTLY  PLAN TO ATTEND THE ANNUAL
MEETING.  This will not  prevent  you from voting in person but will assure that
your vote is counted if you are unable to attend the meeting.

     To help us with our planning, please check the box on the proxy card if you
plan to attend the meeting in person.

                                Sincerely,


                                /s/ James J. Shoffner


                                James J. Shoffner
                                President

<PAGE>


--------------------------------------------------------------------------------
                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                             1431 CUMBERLAND AVENUE
                           MIDDLESBORO, KENTUCKY 40965
                                 (606) 248-4584


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                    NOTICE OF ANNUAL MEETING OF STOCKHOLDERS
                         TO BE HELD ON OCTOBER 18, 2000
--------------------------------------------------------------------------------

     NOTICE IS HEREBY GIVEN that the Annual Meeting of Stockholders (the "Annual
Meeting") of Cumberland Mountain Bancshares,  Inc. (the "Company"), will be held
at the Fountain City Park Bank,  5320 N. Broadway,  Fountain City,  Tennessee at
3:30 p. m., Eastern Time, on Wednesday, October 18, 2000.

     The Annual Meeting is for the purpose of considering and acting upon:

     1.   The election of one director for a three-year term;

     2.   The  transaction of such other matters as may properly come before the
          Annual Meeting or any adjournments thereof.

     Any action may be taken on any one of the foregoing proposals at the Annual
Meeting  on the date  specified  above or on any  date or  dates  to  which,  by
original or later adjournment, the Annual Meeting may be adjourned. Stockholders
of record at the close of business  on  September  5, 2000 are the  stockholders
entitled  to notice of and to vote at the Annual  Meeting  and any  adjournments
thereof.

     The Company's  Proxy  Statement  for the Annual  Meeting  accompanies  this
Notice and a form of proxy is enclosed  herewith.  You are  requested to fill in
and sign the  enclosed  proxy card which is  solicited by the Board of Directors
and to mail it promptly in the enclosed envelope.  The proxy will not be used if
you attend and vote at the Annual Meeting in person.

                                       BY ORDER OF THE BOARD OF DIRECTORS

                                       /s/ J. D. Howard

                                       J. D. HOWARD
                                       SECRETARY
Middlesboro, Kentucky
September 15, 2000


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IMPORTANT:  THE PROMPT  RETURN OF PROXIES  WILL SAVE YOUR COMPANY THE EXPENSE OF
FURTHER  REQUESTS  FOR  PROXIES  IN ORDER TO ENSURE A QUORUM.  A  SELF-ADDRESSED
ENVELOPE IS ENCLOSED FOR YOUR  CONVENIENCE.  NO POSTAGE IS REQUIRED IF MAILED IN
THE UNITED STATES.
--------------------------------------------------------------------------------

<PAGE>

                                 PROXY STATEMENT
                                       OF
                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                             1431 CUMBERLAND AVENUE
                           MIDDLESBORO, KENTUCKY 40965

                         ANNUAL MEETING OF STOCKHOLDERS
                                OCTOBER 18, 2000


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                                     GENERAL
--------------------------------------------------------------------------------

         This Proxy Statement is furnished in connection  with the  solicitation
of proxies by the Board of Directors of  Cumberland  Mountain  Bancshares,  Inc.
(hereinafter  called the  "Company")  to be used at the 2000  Annual  Meeting of
Stockholders of the Company  (hereinafter  called the "Annual  Meeting"),  which
will be held at the Fountain City Park Bank,  5320 N.  Broadway,  Fountain City,
Tennessee  on  Wednesday,  October 18, 2000,  at 3:30 p.m.,  Eastern  Time.  The
accompanying Notice of Annual Meeting and form of proxy and this Proxy Statement
are being first mailed to stockholders on or about September 15, 2000.


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                       VOTING AND REVOCABILITY OF PROXIES
--------------------------------------------------------------------------------

         Proxies  solicited  by the Board of  Directors  of the Company  will be
voted in accordance with the directions given therein. WHERE NO INSTRUCTIONS ARE
INDICATED,  PROXIES WILL BE VOTED FOR THE NOMINEE FOR DIRECTOR NAMED BELOW.  The
                                  ---
proxy confers discretionary  authority on the persons named therein to vote with
respect to the election of any person as a director  where the nominee is unable
to serve or for good cause will not serve,  and with respect to matters incident
to the conduct of the Annual Meeting.  If any other business is presented at the
Annual Meeting,  proxies will be voted by those named therein in accordance with
the  determination  of a majority of the Board of Directors.  Proxies  marked as
abstentions  will not be counted as votes  cast.  In  addition,  shares  held in
street  name which have been  designated  by brokers on proxy cards as not voted
will not be counted as votes cast. Proxies marked as abstentions or as broker no
votes,  however,  will be treated as shares  present for purposes of determining
whether a quorum is present.

         Stockholders who execute proxies retain the right to revoke them at any
time.  Unless so revoked,  the shares  represented by properly  executed proxies
will be voted at the Annual Meeting and all adjournments thereof. Proxies may be
revoked by written  notice to the  Secretary of the Company at the address above
or by the  filing  of a later  dated  proxy  prior  to a vote  being  taken on a
particular  proposal  at the  Annual  Meeting.  A proxy  will  not be voted if a
stockholder  attends the Annual  Meeting and votes in person.  The presence of a
stockholder at the Annual Meeting will not revoke such stockholder's proxy.


--------------------------------------------------------------------------------
                 VOTING SECURITIES AND PRINCIPAL HOLDERS THEREOF
--------------------------------------------------------------------------------

         The securities  entitled to vote at the Annual  Meeting  consist of the
Company's  common  stock,  $.01  par  value  per  share  (the  "Common  Stock").
Stockholders  of record as of the close of  business on  September  5, 2000 (the
"Record  Date") are  entitled  to one vote for each  share of Common  Stock then
held.  As of the Record Date,  there were 680,159  shares of Common Stock issued
and outstanding.


<PAGE>

         Persons  and groups  beneficially  owning in excess of 5% of the Common
Stock are  required  to file  certain  reports  with  respect to such  ownership
pursuant  to the  Securities  Exchange  Act of 1934 (the  "Exchange  Act").  The
following table sets forth, as of the Record Date, certain information as to the
Common  Stock  beneficially  owned by all  persons  who have  filed the  reports
required of persons  beneficially owning more than 5% of the Common Stock or who
were known to the Company to  beneficially  own more than 5% of the Common Stock
outstanding at the Record Date and the shares of Common Stock beneficially owned
by all executive officers and directors of the Company as a group.
<TABLE>
<CAPTION>

                                          AMOUNT AND             PERCENT OF
                                          NATURE OF              SHARES OF
NAME AND ADDRESS                          BENEFICIAL            COMMON STOCK
OF BENEFICIAL OWNER                       OWNERSHIP (1)        OUTSTANDING (2)
-------------------                       -------------        ---------------

<S>                                            <C>                   <C>
James J. Shoffner                              66,497 (3)            9.67%
1431 Cumberland Avenue
Middlesboro, Kentucky 40961

Cumberland Mountain Bancshares, Inc.           87,856               12.92%
Employee Stock Ownership Plan
1431 Cumberland Avenue
Middlesboro, Kentucky  40961

Jeffrey L. Gendell                             67,116                9.87%
Tontine Management, L.L.C.
Tontine Financial Partners, L.P.
Tontine Overseas Associates, L.L.C.
200 Park Avenue, Suite 3900
New York, New York 10166

Sandler O'Neill Asset Management, LLC          65,000                9.56%
Malta Partners, L.P.
Malta Hedge Fund, L.P.
Malta Partners II, L.P.
Malta Hedge Fund II, L.P.
SOAM Holdings, LLC
Terry Maltese
712 Fifth Avenue
22nd Floor
New York, New York  10019

All Executive Officers and                    128,101 (4)           18.15%
Directors as a group (8 persons)
<FN>
______
(1)  For purposes of this table, a person is deemed to be the  beneficial  owner
     of any  shares  of  Common  Stock  if he or she  has or  shares  voting  or
     investment  power  with  respect  to such  Common  Stock  or has a right to
     acquire  beneficial  ownership  at any time  within 60 days from the Record
     Date.  As used  herein,  "voting  power" is the power to vote or direct the
     voting of shares and  "investment  power" is the power to dispose or direct
     the disposition of shares. Except as otherwise noted,  ownership is direct,
     and the named persons  exercise sole voting and  investment  power over the
     shares of the Common Stock.
(2)  In calculating  percentage  ownership for a named  individual or group, the
     number of shares  outstanding  is deemed to include  shares which the named
     individual  or group has the right to acquire  pursuant to the  exercise of
     options exercisable within 60 days of the Record Date.
(3)  Includes 7,852 shares which Mr. Shoffner has the right to acquire  pursuant
     to the exercise of options.
(4)  Includes  25,552  shares which  directors  and  officers  have the right to
     acquire pursuant to the exercise of options.
</FN>
</TABLE>

                                       2
<PAGE>
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                       PROPOSAL I -- ELECTION OF DIRECTORS
--------------------------------------------------------------------------------

         The Company's Board of Directors is currently composed of five members.
Under the  Company's  Charter,  directors  are  divided  into three  classes and
elected for terms of three years each and until their successors are elected and
qualified.  At the  Annual  Meeting  one  director  will be  elected  for a term
expiring  at the  Annual  Meeting  to be held in the  year  2003.  The  Board of
Directors  has nominated J. Roy  Shoffner,  to serve for an  additional  term of
three years and until his successor is elected and  qualified.  Under  Tennessee
law,  directors  are  elected by a plurality  of the votes  present in person or
represented  by proxy at the Annual Meeting and entitled to vote in the election
of directors.

         Unless contrary  instruction is given, the persons named in the proxies
solicited by the Board of  Directors  will vote each such proxy for the election
of the named nominee.  If the nominee is unable to serve, the shares represented
by all properly  executed  proxies which have not been revoked will be voted for
the election of such substitute as the Board of Directors may recommend. At this
time,  the Board  knows of no reason why the  nominee  might be  unavailable  to
serve.

         The  following  table sets forth,  for the nominee and each  continuing
director,  his  name,  age as of the  Record  Date,  the year he first  became a
director of the Bank,  the  expiration  of his current term as a director of the
Company and the number and  percentage  of shares of Common  Stock  beneficially
owned.  All of the  Company's  current  directors  were  initially  appointed as
directors in 1996 in connection with the  incorporation  and organization of the
Company,  except for Barry Litton who was appointed to the Board of Directors in
November  1997.  Each  director of the Company  also is a member of the Board of
Directors of the Bank. There are no arrangements or  understandings  between the
Company  and any  director  or nominee  pursuant  to which such  person has been
selected as a director or nominee for director of the Company,  and,  except for
J. Roy  Shoffner  and James J.  Shoffner  who are father and son,  no  director,
nominee  or  executive  officer is  related  to any other  director,  nominee or
executive officer by blood, marriage or adoption.

         THE BOARD OF  DIRECTORS  RECOMMENDS  A VOTE  "FOR" THE  NOMINEE  LISTED
BELOW.
<TABLE>
<CAPTION>

                                                                              SHARES OF
                                            YEAR FIRST                      COMMON STOCK
                                            ELECTED AS         CURRENT      BENEFICIALLY
                         AGE AS OF THE       DIRECTOR           TERM       OWNED AS OF THE       PERCENT
NAME                      RECORD DATE       OF THE BANK       TO EXPIRE    RECORD DATE (1)      OF CLASS
----                      -----------       -----------       ---------    ---------------      --------

                                           BOARD NOMINEE FOR TERMS TO EXPIRE
                                              AT THE 2003 ANNUAL MEETING

<S>                           <C>              <C>              <C>           <C>                <C>
J. Roy Shoffner (2)           72               1961             2000          13,161   (3)       1.92%

                                            DIRECTORS CONTINUING IN OFFICE

Reecie Stagnolia, Jr.         64               1993             2001          16,616   (4)       2.44%
Raymond C. Walker             70               1985             2001          14,935   (5)       2.19%
Barry Litton                  49               1997             2002           2,932   (6)       0.43%
James J. Shoffner (2)         39               1988             2002          66,497   (7)       9.67%
<FN>
________________
(1)  In calculating  percentage  ownership for a named  individual or group, the
     number of shares  outstanding  is deemed to include  shares which the named
     individual  or group has the right to acquire  pursuant to the  exercise of
     options.
(2)  On  February  24,  1999,  without  admitting  or denying  any of the claims
     therein, J. Roy Shoffner and James J. Shoffner consented to the issuance by
     the Office of Thrift Supervision of a Cease and Desist Order for an alleged
     violation  of the  Change  in Bank  Control  Act.  The Order  required  the
     Shoffners to pay restitution to the Company in the amount of


                                       3
<PAGE>
     $51,612. James J. Shoffner was also required to pay to the Office of Thrift
     Supervision a civil money penalty in the amount of $10,000.

(3)  Includes  4,291 shares of Common Stock which Mr.  Shoffner has the right to
     acquire pursuant to the exercise of options  exercisable  within 60 days of
     the Record Date. Does not include 66,497 shares  beneficially  owned by Mr.
     Shoffner's adult children as to which he disclaims beneficial ownership.
(4)  Includes 9,154 shares held jointly with Mr.  Stagnolia's wife, 2,266 shares
     held in Mr.  Stagnolia's  IRA and  3,065  shares  held in his  wife's  IRA.
     Includes 2,131 shares which Mr. Stagnolia has the right to acquire pursuant
     to the exercise of options.
(5)  Includes 10,664 shares held jointly with Mr. Walker's wife.  Includes 2,465
     shares which Mr.  Walker has the right to acquire  pursuant to the exercise
     of options exercisable within 60 days of the Record Date.
(6)  Includes 1,465 shares which Mr. Litton has the right to acquire pursuant to
     the exercise of options exercisable within 60 days of the Record Date.
(7)  Includes 7,852 shares which Mr. Shoffner has the right to acquire  pursuant
     to the exercise of options  exercisable  within 60 days of the Record Date.
     Mr.  Shoffner  disclaims  beneficial  ownership  of any shares  held by his
     father.
</FN>
</TABLE>


     Presented below is certain information concerning the nominee and directors
continuing  office.  Unless otherwise stated, all directors and the nominee have
held the positions indicated for at least the past five years.

     J. ROY  SHOFFNER is  currently  Chairman  of the Board and Chief  Executive
Officer of the Company and of Middlesboro  Federal, a position he has held since
1994. He is a graduate of Lincoln  Memorial  University and a veteran USAF pilot
of four years.  Mr. Shoffner owns and operates  Shoffner  Realty,  a real estate
development  company and also owns JRS Restaurant  Corporation.  Mr. Shoffner is
the past owner of a local  plastic pipe  manufacturing  company and is active in
real  estate and  business  properties.  Mr.  Shoffner is the father of James J.
Shoffner.

     REECIE  STAGNOLIA,  JR. is currently  Vice President and the Branch Manager
and Loan Officer at the  Cumberland  Branch  (Tri-City  Office),  of the Bank, a
position  he has held since 1989.  He  previously  worked for the Harlan  County
Board of Education as a teacher,  Assistant  Principal and Principal,  Assistant
Superintendent and Superintendent  from 1962 to 1988. Mr. Stagnolia is currently
a member of the Board of Directors of the Center for Rural  Development,  Harlan
County  Airport,  Kentucky  Coal Mine  Museum,  Tri-City  Chamber  of  Commerce,
Cumberland  Lions Club,  Sleepy  Hollow  Country  Club,  Inc.,  and  Chairman of
Cumberland Tourism Board.

     RAYMOND C.  WALKER  served as  president  of the Mutual  Holding  Company's
subsidiary,  Home Loan Mortgage Corporation from October, 1991 to October, 1996.
He worked for the Middlesboro  Daily News as Advertising  Director for 24 years,
worked at National  Bank as Business  Development  Director  for seven years and
served  five  years as manager of 120 units of the  Section 8  Federally  Funded
Housing.  Mr.  Walker served as mayor of the city of  Middlesboro  and served as
Vice President and Treasurer of the Bank.

     BARRY LITTON is currently  Vice Chairman of the Board.  Mr. Litton owns and
manages Litton's Market, a restaurant located in Knoxville, Tennessee.

     JAMES J. SHOFFNER joined Middlesboro  Federal in 1994 as Vice President and
Chief Operating Officer and became President and Chief Managing Officer in March
1996.  He also  serves  as  President  of the  Company.  He also has  served  as
President of Home Mortgage  Loan  Corporation  since 1996.  Prior to joining the
Bank as a full-time  officer,  Mr.  Shoffner is the President of JRS  Restaurant
Corporation.  He  graduated  from  Middlesboro  High  School  and  attended  the
University  of  Kentucky.  He  is a  Deacon  in  the  First  Baptist  Church  of
Middlesboro.  Mr.  Shoffner is a member of the  Middlesboro  Kiwanis  Club and a
member of the Bell County Industrial  Commission.  He has served on the Board of
Directors of Middlesboro  Federal since June 6, 1988. Mr. Shoffner is the son of
J. Roy Shoffner.


                                       4
<PAGE>
EXECUTIVE OFFICERS WHO ARE NOT DIRECTORS

     The following sets forth information  including their ages as of the Record
Date with respect to  executive  officers of the Company who do not serve on the
Board of Directors.  Executive  officers are appointed  annually by the Board of
Directors.

     J. D. HOWARD,  age 39,  joined the Bank in July 1996 as Vice  President and
was  appointed  Chief  Financial  Officer in October  1996 and named Senior Vice
President in July 1999. He also serves as  Secretary/Treasurer  for the Company.
Prior to joining the Bank,  Mr.  Howard was an internal  auditor and  compliance
officer at Home Federal of Middlesboro for two years. Prior to that he was Chief
Financial  Officer of First  Federal  Savings Bank,  Pineville,  Kentucky for 11
years.

     DIANA J. MIRACLE, age 38, joined the Bank as a compliance officer in August
1995, was named Vice President and Chief  Operating  Officer in October 1996 and
was named  Senior  Vice  President  in July 1999.  Prior to that  time,  she was
employed at Security First Network Bank in Pineville, Kentucky for 11 years. Ms.
Miracle  currently  serves a three-year  term as a director of the Young Bankers
Division of the Kentucky Bankers Association.

     BETTY  HALSEY,  age 50, has been Senior Vice  President  and Chief  Lending
Officer of the Bank since July 1999,  Prior to joining the Bank,  Ms. Halsey was
Chief  Executive  Officer and  President at Community  Trust Bank's  Middlesboro
office since June 1995. Prior to 1995, Ms. Halsey was Chief Executive Officer of
Commercial Bank, Middlesboro, since 1994. Prior to that she was Senior Lender at
Commercial  Bank.  Ms.  Halsey is a member of the  Middlesboro  Kiwanis Club and
Financial Women International.


--------------------------------------------------------------------------------
                MEETINGS AND COMMITTEES OF THE BOARD OF DIRECTORS
--------------------------------------------------------------------------------

     The business of the Company is conducted at regular and special meetings of
the full Board and its standing  committees.  The standing committees consist of
the Audit, Compensation, Finance, Insurance, Investment and Loan Committees.

     During fiscal year 2000,  the Board of Directors  held 12 regular  meetings
and one  special  meeting  called in  accordance  with the  bylaws.  No director
attended less than 75% of said meetings and the meetings held by all  committees
of the Board of Directors on which he served.

     The Audit  Committee  consists  of  Directors  Barry  Litton and Raymond C.
Walker.  This committee  regularly  meets on a quarterly basis with the internal
auditor to review audit  programs and the results of audits of specific areas as
well as other regulatory  compliance  issues.  In addition,  the Audit Committee
meets with the independent certified public accountants to review the results of
the annual audit and other  related  matters.  The Audit  Committee met 13 times
during the fiscal year ended June 30, 2000.

     The Compensation Committee is comprised of any three non-employee directors
and one senior officer who does not participate in  deliberations  regarding his
compensation.  The Compensation  Committee  annually reviews the compensation of
the officers of the Bank and makes  recommendations  to the Board of  Directors.
The  Committee  reports to the full Board of Directors at the regular  meetings.
The Compensation Committee met three during the fiscal year ended June 30, 2000.

     The Loan Committee is made up of any one director and two senior  officers.
The committee meets weekly to review and ratify  management's  approval of loans
made  within the scope of its  authority  since the last  committee  meeting and
approve all loans up to  $250,000.  The Loan  Committee  met 79 times during the
fiscal year ended June 30, 2000.


                                       5
<PAGE>

     Under the Company's  Bylaws,  the Board of Directors serves as a nominating
committee for selecting  management's nominees for election as directors.  While
the Board of Directors will consider  nominees  recommended by stockholders,  it
has not established any procedures for this purpose.  The Board of Directors met
six times in its  capacity as the  nominating  committee  during the fiscal year
ended June 30, 2000.

--------------------------------------------------------------------------------
                              DIRECTOR COMPENSATION
--------------------------------------------------------------------------------

     DIRECTOR  FEES.  The members of the Board of Directors  receive  $1,100 for
regular  monthly Board meetings and committee  meetings  attended.  The Chairman
receives  $1,500  monthly for regularly  scheduled  Board meetings and committee
meetings.  The Vice Chairman  receives $1,200 for regular monthly board meetings
attended.

     Pursuant to the  Cumberland  Mountain  Bancshares,  Inc.  Stock  Option and
Incentive  Plan (the  "Option  Plan"),  non-employee  directors  of the  Company
received  automatic  grants of stock options in fiscal year 1999.  Each director
who was not an  employee  on the  effective  date of the  Option  Plan  received
options to purchase  2,198 shares of Common Stock at an exercise  price equal to
the fair market  value of the Common  Stock on the date of grant  ($16.00).  All
such options will expire on October 21, 2008.  Directors who are also  employees
are  eligible  for awards  under the Option  Plan as well.  During  fiscal  1999
Director  James J.  Shoffner  received  a grant  of  10,993  options  also at an
exercise of $16.00 and subject to a three year vesting schedule.

     DIRECTOR  RETIREMENT  PLAN.  The Bank has adopted the  Middlesboro  Federal
Bank, Federal Savings Bank Retirement Plan for Directors (the "Directors' Plan")
pursuant  to  which  directors  of  the  Bank  are  entitled  to  receive,  upon
retirement, 60 monthly payments in the amount of 75% of the average monthly fees
that the  respective  director  received  for  service  on the Board  during the
12-month period preceding  termination of service on the Board,  subject to a 20
year vesting  schedule.  In connection with the adoption of the Directors' Plan,
the Bank incurred an expense of $169,061 which was recognized  during the fiscal
year 1997.

     In fiscal year 1997, the Bank's Board  converted the Directors' Plan from a
defined  benefit  type  of  plan  to a  defined  contribution  type.  Under  the
Directors' Plan, as amended, a bookkeeping account in each participants' name is
credited,  on an annual  basis  with an amount  equal to the sum of the  accrual
attributable to the participant  equal to the investment return which would have
resulted if such  deferred  amounts had been  invested in either Common Stock or
the Bank's highest annual rate of interest on  certificates  of deposit having a
one-year term.

     Each  participant's  account has been  credited with an amount equal to the
present  value of the  benefits  in which  the  participant  has a fully  vested
interest  before  its  amendment.  This  amount  was  determined  based  on  the
participant's  years of service and 75% of average fees paid to directors in the
year prior to the participant's retirement. In addition, beginning July 1, 1996,
each  participant's  account is  credited  with  $1,516 for each year of service
until a maximum of 20 years worth of credits is reached,  including past service
credits.  Benefits are payable from the Bank's general assets, although the Bank
may establish a grantor trust that will purchase  Common Stock that will be held
to help the Bank meet its liabilities associated with the Directors' Plan.

     Upon a "Change in Control" the present value of each participant's benefits
will become payable in one lump-sum payment within ten days. "Change in Control"
generally  refers to (a) any "person" (as the term is used in Sections 13(d) and
14(d) of the Exchange Act) is or becomes the  "beneficial  owner" (as defined in
Rule 13d-3  promulgated  under the Exchange  Act),  directly or  indirectly,  of
securities of the Bank or the Company  representing twenty percent (20%) or more
of the  combined  voting  power  of the  Bank's  or  the  Company's  outstanding
securities  except  for any  securities  of the  Bank  purchased  by the  Bank's
employee stock  ownership plan and trust;  or (b) individuals who constitute the
Board of the Bank or the board of  directors  of the  Company on the date hereof
("Incumbent  Board")  cease for any  reason to  constitute  at least a  majority
thereof;  provided  that any person  becoming a director  subsequent to the date
          --------
hereof whose election was approved by a vote of at least  three-quarters  of the
directors  comprising the Incumbent  Board, or whose  nomination for election by
the Company's stockholders was approved by the same nominating committee serving
under an Incumbent Board, shall be, for purposes of this


                                       6
<PAGE>

clause (b), considered as though he were a member of the Incumbent Board; or (c)
the occurrence of a plan of reorganization,  merger, consolidation,  sale of all
or  substantially  all  the  assets  of the  Bank  or  the  Company  or  similar
transaction  in which the Bank or the  Company is not the  resulting  entity.  A
Change in Control will not occur as the result of  acquisitions  of Common Stock
by Messrs. J. Roy Shoffner and James J. Shoffner.


--------------------------------------------------------------------------------
                    EXECUTIVE COMPENSATION AND OTHER BENEFITS
--------------------------------------------------------------------------------

     SUMMARY  COMPENSATION  TABLE.  The following  table sets forth the cash and
noncash  compensation  for each of the last  three  fiscal  years  awarded to or
earned by the Chief Executive Officer. No other executive officer of the Company
earned a salary  and bonus  during  fiscal  year  2000  exceeding  $100,000  for
services rendered in all capacities to the Bank.
<TABLE>
<CAPTION>
                                                                                      LONG-TERM COMPENSATION
                                                                                     --------------------------
                                                                                               AWARDS
                                                     ANNUAL COMPENSATION             --------------------------
                                            -------------------------------------    RESTRICTED     SECURITIES
                                 FISCAL                              OTHER ANNUAL       STOCK        UNDERLYING      ALL OTHER
NAME                             YEAR       SALARY       BONUS       COMPENSATION     AWARD(S)        OPTIONS     COMPENSATION(1)
----                             ----       ------       -----       ------------     --------       ----------   ---------------
<S>                              <C>       <C>         <C>             <C>            <C>            <C>
James J. Shoffner
President and Chief Executive    2000      $100,000    $  1,500        $      --      $       --     $      --       $13,200
Officer                          1999       100,000       1,500               --          35,351  (2)   10,993        13,200
                                 1998        87,500       4,369               --              --            --        26,016
<FN>
___________
(1)  Consists  of  director's  fees  and  the  value  of  stock  awarded  to Mr.
     Shoffner's account in the ESOP.
(2)  As of June 30, 2000,  Mr.  Shoffner held 4,221 shares of restricted  Common
     Stock awarded under the MRP. Such shares had an aggregate  value of $25,326
     based on the last known sale price of $6.00 per share.
</FN>
</TABLE>

     OPTION  YEAR-END VALUE TABLE.  The following  table sets forth  information
concerning the value of options held by the Chief Executive  Officer at June 30,
2000.
<TABLE>
<CAPTION>

                           NUMBER OF SECURITIES           VALUE OF UNEXERCISED
                         UNDERLYING UNEXERCISED            IN-THE-MONEY OPTIONS
                        OPTIONS AT FISCAL YEAR-END         AT FISCAL YEAR-END (1)
                        ----------------------------    ---------------------------
NAME                    EXERCISABLE    UNEXERCISABLE    EXERCISABLE   UNEXERCISABLE
----                    -----------    -------------    -----------   -------------

<S>                       <C>            <C>             <C>           <C>
James J. Shoffner         7,852          3,664           $    --        $    --
<FN>
___________
(1)      Based on  aggregate  fair  market  value of the shares of Common  Stock
         underlying the options at June 30, 2000 less aggregate  exercise price.
         For purposes of this  calculation,  the fair market value of the Common
         Stock at June 30,  2000 is  assumed  to be equal to the last known sale
         price of $6.00 per share.  Of the11,516  options held by Mr.  Shoffner,
         523 options  were  granted at an adjusted  exercise  price of $7.50 per
         share, and 10,993 options were granted at an exercise price of $16.00.
</FN>
</TABLE>


                                       7
<PAGE>
--------------------------------------------------------------------------------
                              CERTAIN TRANSACTIONS
--------------------------------------------------------------------------------

         During the fiscal year ended June 30, 2000,  certain  loans made by the
Bank were  outstanding in an amount exceeding  $60,000 to certain  directors and
executive  officers and associates of directors and executive  officers.  All of
such  loans  were  made  in the  ordinary  course  of  business,  were  made  on
substantially the same terms, including interest rates and collateral,  as those
prevailing at the time for comparable  transactions with other persons,  and did
not  involve  more than the  normal  risk of  collectibility  or  present  other
unfavorable features.


--------------------------------------------------------------------------------
                                  OTHER MATTERS
--------------------------------------------------------------------------------

         The Board of  Directors is not aware of any business to come before the
Annual Meeting other than those matters  described above in this Proxy Statement
and matters incident to the conduct of the Annual Meeting.  If any other matters
should properly come before the Annual  Meeting,  it is intended that proxies in
the  accompanying  form will be voted in respect  thereof in accordance with the
determination of a majority of the Board of Directors.


--------------------------------------------------------------------------------
             SECTION 16(A) BENEFICIAL OWNERSHIP REPORTING COMPLIANCE
--------------------------------------------------------------------------------

         Pursuant  to  regulations  promulgated  under  the  Exchange  Act,  the
Company's  officers,  directors and persons who own more than ten percent of the
outstanding  Common Stock are required to file reports detailing their ownership
and changes of ownership in such Common  Stock,  and to furnish the Company with
copies of all such reports.  Based on the Company's review of such reports which
the Company  received  during the last fiscal year,  or written  representations
from such persons that no annual  report of change in  beneficial  ownership was
required,  the Company  believes that,  during the last fiscal year, all persons
subject  to  such  reporting  requirements  have  complied  with  the  reporting
requirements.


--------------------------------------------------------------------------------
                                  MISCELLANEOUS
--------------------------------------------------------------------------------

         The  cost of  soliciting  proxies  will be borne  by the  Company.  The
Company  will  reimburse  brokerage  firms and other  custodians,  nominees  and
fiduciaries for reasonable  expenses incurred by them in sending proxy materials
to the beneficial  owners of Common Stock. In addition to solicitations by mail,
directors,  officers and regular  employees  of the Company may solicit  proxies
personally or by telegraph or telephone without additional compensation.

         The Company's 2000 Annual Report to Stockholders,  including  financial
statements,  has been  mailed to all  stockholders  of record as of the close of
business on the Record Date. Any stockholder who has not received a copy of such
Annual Report may obtain a copy by writing to the Secretary of the Company. Such
Annual Report is not to be treated as a part of the proxy solicitation  material
or as having been incorporated herein by reference.


--------------------------------------------------------------------------------
                              STOCKHOLDER PROPOSALS
--------------------------------------------------------------------------------

         In order to be eligible for inclusion in the Company's  proxy materials
for next year's Annual Meeting of Stockholders, any stockholder proposal to take
action at such meeting  must be received at the  Company's  executive  office at
1431 Cumberland Avenue, Middlesboro,  Kentucky 40961 no later than May 18, 2001.
Any such  proposals  shall be subject  to the  requirements  of the proxy  rules
adopted by the Securities and Exchange Commission under the Exchange Act.


                                       8
<PAGE>

         Stockholder  proposals,  other than  those  submitted  pursuant  to the
Exchange Act,  must be submitted in writing,  delivered or mailed by first class
United States mail,  postage prepaid,  to the secretary of the Company not fewer
than 30 days nor more than 60 days prior to any such meeting; provided, however,
that if notice or public  disclosure  of the meeting is given fewer than 40 days
before the  meeting,  such  written  notice  shall be delivered or mailed to the
secretary of the Company not later than the close of the 10th day  following the
day on which notice of the meeting was mailed to shareholders.

                                  BY ORDER OF THE BOARD OF DIRECTORS

                                  /s/ J. D. Howard

                                  J. D. HOWARD
                                  SECRETARY

Middlesboro, Kentucky
September 15, 2000


--------------------------------------------------------------------------------
                                   FORM 10-KSB
--------------------------------------------------------------------------------

         A COPY OF THE COMPANY'S  FORM 10-KSB FOR THE FISCAL YEAR ENDED JUNE 30,
2000 AS FILED WITH THE  SECURITIES  AND  EXCHANGE  COMMISSION  WILL BE FURNISHED
WITHOUT CHARGE TO STOCKHOLDERS AS OF THE RECORD DATE UPON WRITTEN REQUEST TO THE
STOCKHOLDER  RELATIONS,  CUMBERLAND MOUNTAIN  BANCSHARES,  INC., 1431 CUMBERLAND
AVENUE, MIDDLESBORO, KENTUCKY 40961.
--------------------------------------------------------------------------------


                                       9
<PAGE>


                      CUMBERLAND MOUNTAIN BANCSHARES, INC.
                             1431 CUMBERLAND AVENUE
                           MIDDLESBORO, KENTUCKY 40965
           THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF DIRECTORS

The undersigned hereby appoints Reecie Stagnolia,  Jr., Barry Litton and Raymond
C. Walker, with full powers of substitution, to act as attorneys and proxies for
the  undersigned,  to vote all  shares of Common  Stock of  Cumberland  Mountain
Bancshares,  Inc. (the  "Company")  which the undersigned is entitled to vote at
the Annual Meeting of  Stockholders  (the "Annual  Meeting"),  to be held at the
Fountain  City  Park  Bank,  5320  N.  Broadway,  Fountain  City,  Tennessee  on
Wednesday,  October 18, 2000,  at 3:30 p.m.,  Eastern  Time,  and at any and all
adjournments   thereof,   as  indicated   below  and  in  accordance   with  the
determination  of a majority  of the Board of  Directors  with  respect to other
matters which come before the Annual Meeting.

A VOTE "FOR" THE NOMINEE IS RECOMMENDED BY THE BOARD OF DIRECTORS

1.       Election of director
         [    ]  FOR the nominee listed below (except as marked to the contrary)
         [    ]  WITHHOLD AUTHORITY to vote for the nominee

                  J. Roy Shoffner

Instructions:  To withhold authority to vote for any individual nominees,  write
the nominee's name in the space provided.

THIS PROXY WILL BE VOTED AS DIRECTED, BUT IF NO INSTRUCTIONS ARE SPECIFIED, THIS
PROXY WILL BE VOTED FOR THE  NOMINEE  LISTED  ABOVE.  IF ANY OTHER  BUSINESS  IS
PRESENTED AT THE ANNUAL MEETING, THIS PROXY WILL BE VOTED BY THOSE NAMED IN THIS
PROXY IN  ACCORDANCE  WITH  THE  DETERMINATION  OF A  MAJORITY  OF THE  BOARD OF
DIRECTORS.  THIS PROXY CONFERS DISCRETIONARY AUTHORITY ON THE HOLDERS THEREOF TO
VOTE WITH RESPECT TO THE ELECTION OF ANY PERSON AS DIRECTOR WHERE THE NOMINEE IS
UNABLE TO SERVE OR FOR GOOD CAUSE  WILL NOT SERVE AND  MATTERS  INCIDENT  TO THE
CONDUCT OF THE ANNUAL MEETING.

___________________________________, 2000


___________________________________
Signature


___________________________________
Signature if Held Jointly




Please sign exactly as your name appears above. For joint accounts,  both owners
should  sign.  When  signing as executor,  administrator,  attorney,  trustee or
guardian,  etc.,  please give your full title. If a corporation,  please sign in
full corporate name by President or other authorized  officer. If a partnership,
please sign in partnership name by authorized person.



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