SCHEDULE 14A INFORMATION

                    Proxy Statement Pursuant to Section 14(a)
                     of the Securities Exchange Act of 1934

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

Check the appropriate box:

[X]    Preliminary Proxy Statement
[ ]    Confidential, For Use of the Commission Only
       (as permitted by Rule 14a-6(e)(2))
[ ]    Definitive Proxy Statement
[ ]    Definitive Additional Materials
[ ]    Soliciting Material Pursuant to Rule 14a-11(c) or Rule 14a-12

                          21st CENTURY HOLDING COMPANY
                (Name of Registrant as Specified in Its Charter)

    (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 the table below per Exchange Act Rules 14a-6(i)(1) and 0-11.

      (1) Title of each class of securities to which transaction applies:

      (2) Aggregate number of securities to which transaction applies:

      (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):

      (4) Proposed maximum aggregate value of transaction:

      (5) Total fee paid:

[ ]   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:

      (2)   Form, Schedule or Registration Statement No.:

      (3)   Filing Party:

      (4)   Date Filed:


                          21st CENTURY HOLDING COMPANY


                    NOTICE OF ANNUAL MEETING OF SHAREHOLDERS
                           TO BE HELD ON JULY 19, 2005


To the Shareholders of 21st Century Holding Company:

      NOTICE IS HEREBY  GIVEN  that the  Annual  Meeting  of  Shareholders  (the
"Annual  Meeting") of 21st Century Holding Company,  a Florida  corporation (the
"Company"), will be held at our principal executive offices at 3661 West Oakland
Park Boulevard,  Suite 207,  Lauderdale Lakes,  Florida 33311, at 11:00 A.M., on
July 19, 2005 for the following purposes:

      1.    To elect two directors to serve until 2008;

      2.    To  authorize  the  possible  issuance  of 20% or more of our common
            stock,  $.01 par value (the "Common Stock"),  in connection with our
            2004 private placement of senior  subordinated notes and warrants to
            purchase shares of Common Stock;

      3.    To authorize the issuance of 3,500 shares of our Common Stock to our
            Chief Executive Officer;

      4.    To ratify the  selection  of the firm of DeMeo Young  McGrath as the
            Company's  independent  auditors for the fiscal year ended  December
            31, 2004;

      5.    To approve the  adjournment or postponement of the Annual Meeting to
            a later date if necessary in order to solicit  additional proxies in
            favor  of  any of  the  proposals  to be  considered  at the  Annual
            Meeting; and

      6.    To  transact  such other  business as may  properly  come before the
            Annual Meeting and any adjournments or postponements thereof.

      The Board of Directors  has fixed the close of business on May 20, 2005 as
the record date for determining those shareholders entitled to notice of, and to
vote at, the Annual Meeting and any adjournments or postponements thereof.

      Whether or not you expect to be present,  please sign, date and return the
enclosed proxy card in the  pre-addressed  envelope provided for that purpose as
promptly as possible. No postage is required if mailed in the United States.

                                       By Order of the Board of Directors,


                                       -----------------------------------------
                                       Rebecca L. Campillo, Secretary

Lauderdale Lakes, Florida
June XX, 2005

ALL  SHAREHOLDERS  ARE  INVITED TO ATTEND THE  ANNUAL  MEETING IN PERSON.  THOSE
SHAREHOLDERS  WHO ARE UNABLE TO ATTEND  ARE  RESPECTFULLY  URGED TO EXECUTE  AND
RETURN THE ENCLOSED  PROXY AS PROMPTLY AS POSSIBLE.  SHAREHOLDERS  WHO EXECUTE A
PROXY MAY  NEVERTHELESS  ATTEND THE ANNUAL MEETING,  REVOKE THEIR PROXY AND VOTE
THEIR SHARES IN PERSON.


                          21st CENTURY HOLDING COMPANY

           ANNUAL MEETING OF SHAREHOLDERS TO BE HELD ON JULY 19, 2005

                              ---------------------
                                 PROXY STATEMENT
                              ---------------------

                     TIME, DATE AND PLACE OF ANNUAL MEETING

      This Proxy Statement is furnished in connection  with the  solicitation by
the Board of Directors of 21st Century Holding  Company,  a Florida  corporation
(the "Company"), of proxies from the holders of our common stock, par value $.01
per share (the "Common Stock"), for use at the Annual Meeting of Shareholders to
be held at 11:00 A.M., on July 19, 2005, at our principal  executive  offices at
3661 West Oakland Park Boulevard,  Suite 207, Lauderdale Lakes, FL 33311, and at
any adjournments or postponements  thereof (the "Annual  Meeting"),  pursuant to
the enclosed Notice of Annual Meeting.

      The  approximate  date this Proxy Statement and the enclosed form of proxy
are first  being sent to  shareholders  is June XX,  2005.  Shareholders  should
review the information  provided herein in conjunction with our Annual Report to
Shareholders  that  accompanies this Proxy  Statement.  Our principal  executive
offices are located at 3661 West Oakland Park Boulevard,  Suite 300,  Lauderdale
Lakes, FL 33311, and our telephone number is (954) 581-9993.

                          INFORMATION CONCERNING PROXY

      The enclosed  proxy is solicited on behalf of our Board of Directors.  The
giving of a proxy  does not  preclude  the right to vote in  person  should  any
shareholder giving the proxy so desire. Shareholders have an unconditional right
to revoke  their  proxy at any time  prior to the  exercise  thereof,  either in
person at the Annual  Meeting or by filing with our  Secretary at our  principal
executive  offices  indicated above a written  revocation or duly executed proxy
bearing a later  date;  however,  no such  revocation  will be  effective  until
written  notice of the  revocation  is  received by us at or prior to the Annual
Meeting.

      The cost of preparing,  assembling and mailing this Proxy  Statement,  the
Notice  of  Annual  Meeting  and the  enclosed  proxy is to be  borne by us.  In
addition to the use of mail, our employees may solicit proxies personally and by
telephone.  Our employees will receive no  compensation  for soliciting  proxies
other than their  regular  salaries.  We may  request  banks,  brokers and other
custodians,  nominees and fiduciaries to forward copies of the proxy material to
their principals and to request  authority for the execution of proxies.  We may
reimburse such persons for their expenses in so doing.

                         PURPOSES OF THE ANNUAL MEETING

      At the Annual Meeting,  our  shareholders  will consider and vote upon the
following matters:

      1.    To elect two directors to serve until 2008;

      2.    To  authorize  the  possible  issuance  of 20% or more of our Common
            Stock in  connection  with  our 2004  private  placement  of  senior
            subordinated  notes and  warrants to  purchase  shares of our Common
            Stock;

      3.    To authorize the issuance of 3,500 shares of our Common Stock to our
            Chief Executive Officer;

      4.    To ratify the  selection  of the firm of DeMeo Young  McGrath as the
            Company's  independent auditors for the calendar year ended December
            31, 2004;

      5.    To approve the  adjournment or postponement of the Annual Meeting to
            a later date if necessary in order to solicit  additional proxies in
            favor  of  any of  the  proposals  to be  considered  at the  Annual
            Meeting; and


      6.    To  transact  such other  business as may  properly  come before the
            Annual Meeting and any adjournments or postponements thereof.

      Unless  contrary  instructions  are indicated on the enclosed  proxy,  all
shares  represented by valid proxies received pursuant to this solicitation (and
which have not been revoked in accordance  with the procedures set forth herein)
will be voted (a) for the election of the respective nominees for director named
below and (b) in favor of all other proposals  described in the Notice of Annual
Meeting. In the event a shareholder specifies a different choice by means of the
enclosed proxy,  the  shareholder's  shares will be voted in accordance with the
specification so made.

                  ADJOURNMENT OR POSTPONEMENT OF ANNUAL MEETING

      We are seeking  discretionary  authority to vote, in the discretion of the
persons named as proxy in the  accompanying  form of proxy,  on any proposals to
adjourn  or  postpone  the  Annual  Meeting,  including  if the  reason  for the
adjournment or  postponement  is to provide  additional time to solicit votes to
approve  any of the  proposals  described  in this proxy  statement.  The Annual
Meeting  may  be  adjourned  or  postponed  without  notice  other  than  by  an
announcement  made at the  Annual  Meeting,  if  approved  by the  holders  of a
majority of the shares  represented  and entitled to vote at the Annual Meeting.
No proxies voted against approval of any of the proposals will be voted in favor
of adjournment or postponement for the purpose of soliciting additional proxies.
If we postpone the Annual Meeting, we will issue a press release to announce the
new date, time and location of the Annual Meeting.

                 OUTSTANDING VOTING SECURITIES AND VOTING RIGHTS

      The Board of  Directors  has set the close of  business on May 20, 2005 as
the record date (the "Record  Date") for  determining  shareholders  entitled to
notice of and to vote at the Annual Meeting.  As of the Record Date,  there were
6,343,207  shares of  Common  Stock  issued  and  outstanding,  all of which are
entitled  to be voted at the  Annual  Meeting.  Each  share of  Common  Stock is
entitled to one vote on each matter  submitted to  shareholders  for approval at
the Annual Meeting.

      The attendance, in person or by proxy, of the holders of a majority of the
outstanding  shares of Common  Stock  entitled to vote at the Annual  Meeting is
necessary to  constitute a quorum.  Directors  will be elected by a plurality of
the votes cast by the shares of Common Stock  represented  in person or by proxy
at the Annual  Meeting.  Proposals  Two,  Three and Four will each  require  the
affirmative  vote of a  majority  of the total  votes cast on each  proposal  in
person  or by  proxy at the  Annual  Meeting.  If less  than a  majority  of the
outstanding  shares entitled to vote are  represented at the Annual  Meeting,  a
majority of the shares so represented  may adjourn the Annual Meeting to another
date, time or place, and notice need not be given of the new date, time or place
if the new date, time or place is announced at the meeting before an adjournment
is taken.

      Prior to the Annual  Meeting,  we will  select one or more  inspectors  of
election for the meeting. Such inspector(s) shall determine the number of shares
of Common Stock  represented  at the meeting,  the existence of a quorum and the
validity and effect of proxies,  and shall receive,  count and tabulate  ballots
and votes and determine the results  thereof.  Abstentions will be considered as
shares present and entitled to vote at the Annual Meeting and will be counted as
votes cast at the Annual  Meeting,  but will not be counted as votes cast for or
against any given matter.

      A broker or nominee holding shares  registered in its name, or in the name
of its nominee,  which are beneficially owned by another person and for which it
has not received  instructions as to voting from the beneficial  owner, may have
discretion to vote the beneficial owner's shares with respect to the election of
directors and certain other matters  addressed at the Annual  Meeting.  Any such
shares that are not  represented  at the Annual  Meeting  either in person or by
proxy will not be considered to have cast votes on any matters  addressed at the
Annual Meeting.


                                       2


                          BENEFICIAL SECURITY OWNERSHIP

      The following  table sets forth, as of the Record Date,  information  with
respect to the  beneficial  ownership of our Common Stock by (i) each person who
is known by us to beneficially  own 5% or more of our outstanding  Common Stock,
(ii) each of our executive  officers named in the Summary  Compensation Table in
the section "Executive Compenstation," (iii) each of our directors, and (iv) all
directors and executive officers as a group.




                                                                          Number of Shares         Percent of
                                                                            Beneficially             Class
Name and Address of Beneficial Owner (1)                                      Owned (2)           Outstanding
----------------------------------------                                  ----------------        -----------
                                                                                               
Edward J. Lawson (3)..........................................                1,120,962              17.7%
Bruce F. Simberg (4)..........................................                  165,750               2.6
Richard A. Widdicombe (5).....................................                  141,833               2.2
Kent M. Linder (6)............................................                  125,150               1.9
Carl Dorf (7).................................................                   89,648               1.4
Richard W. Wilcox, Jr. (8)....................................                   48,250                 *
J. Gordon Jennings, III (9)...................................                   21,500                 *
Charles B. Hart, Jr. (10).....................................                   15,000                 *
Peter J. Prygelski (11) ......................................                    3,900                 *

All directors and executive officers as a group (9 persons) (12)              1,731,993              25.9%

5% or greater holders:
Michele V. Lawson (13)                                                        1,120,962              17.7%
3661 West Oakland Park Blvd, Suite 300
Lauderdale Lakes, FL 33311

Whitebox Advisors, LLC (14)                                                     905,922              12.5%
3033 Excelsior Blvd., Suite 300
Minneapolis, MN  55416

Leon G. Cooperman (15)                                                          389,000               6.1%
88 Pine Street
Wall Street Plaza - 31st Floor
New York, NY 10005

William D. Witter, Inc. (16)                                                    349,800               5.5%
One Citicorp Center
153 East 53rd Street, 51st Floor
New York, NY 10022



----------------
*        Less than 1%.

(1)   Except as  otherwise  indicated,  the address of each person  named in the
      table  is c/o  21st  Century  Holding  Company,  3661  West  Oakland  Park
      Boulevard, Suite 300, Lauderdale Lakes, FL 33311.

(2)   Except as otherwise  indicated,  the persons named in this table have sole
      voting and  investment  power with  respect to all shares of Common  Stock
      listed,  which  include  shares of Common Stock in which such persons have
      the right to acquire a beneficial interest within 60 days from the date of
      this Proxy Statement.


                                       3



(3)   Represents  435,645  shares of Common  Stock  held of record by Michele V.
      Lawson,  25,425  shares held in an account for a minor,  66,324  shares of
      Common  Stock  issuable  upon the  exercise of stock  options  held by Mr.
      Lawson and 20,676  shares of Common  Stock  issuable  upon the exercise of
      stock options held by Mrs. Lawson.


(4)   Includes 28,500 shares of Common Stock issuable upon the exercise of stock
      options held by Mr. Simberg.

(5)   Includes  3,083 shares of Common Stock held jointly with spouse and 90,000
      shares of Common Stock issuable upon the exercise of stock options held by
      Mr. Widdicombe.

(6)   Includes 75,000 shares of Common Stock issuable upon the exercise of stock
      options held by Mr. Linder.

(7)   Includes  5,764  shares of Common  Stock  held by Dorf  Partners  2001 LP,
      67,384  shares of Common Stock held by Dorf Trust,  1,500 shares of Common
      Stock held in a joint account with Mr. Dorf's spouse, and 15,000 shares of
      Common Stock issuable upon the exercise of stock options held by Mr. Dorf.

(8)   Includes 3,000 shares of Common Stock held in Mr.  Wilcox's IRA and 15,000
      shares of Common Stock issuable upon the exercise of stock options held by
      Mr. Wilcox.

(9)   Includes 21,500 shares of Common Stock issuable upon the exercise of stock
      options held by Mr. Jennings.

(10)  Includes 15,000 shares of Common Stock issuable upon the exercise of stock
      options held by Mr. Hart.

(11)  Includes 300 shares of Common Stock held in Mr.  Prygelski's IRA and 3,000
      shares of Common Stock issuable upon the exercise of stock options held by
      Mr. Prygelski.

(12)  Includes  350,000  shares of Common  Stock  issuable  upon the exercise of
      stock options.


(13)  Represents  572,892  shares  of Common  Stock  held of record by Edward J.
      Lawson,  25,425  shares held in an account for a minor,  20,676  shares of
      Common  Stock  issuable  upon the  exercise of stock  options held by Mrs.
      Lawson and 66,324  shares of Common  Stock  issuable  upon the exercise of
      stock options held by Mr. Lawson.


(14)  Includes  532,244  shares of Common  Stock  issuable  upon the exercise of
      warrants   held   by   Whitebox   Convertible   Arbitrage   Partners,   LP
      ("Convertible"); 143,142 shares of Common Stock issuable upon the exercise
      of warrants held by Whitebox Hedged High Yield Partners, LP; 58,823 shares
      of Common Stock  issuable  upon the exercise of warrants  held by Whitebox
      Intermarket  Partners,  LP  ("Intermarket");  and 149,702 shares of Common
      Stock  issuable  upon the  exercise  of  warrants  held by Pandora  Select
      Partners,  LP  ("Pandora").  Andrew Redleaf is the sole managing member of
      Whitebox Advisors, LLC, the general partner of each of these entities, and
      has sole voting and dispositive  power over these shares.  The Company has
      entered into  agreements  with each of the  Convertible,  Intermarket  and
      Pandora  funds  whereby the  Company has agreed that it will not  exercise
      warrants  held by these funds to the extent  necessary  to ensure that the
      beneficial  ownership  by such fund and its  affiliates  would not  exceed
      9.999% in the aggregate.


(15)  Includes  339,000 shares held by Omega Equity  Investors,  L.P. and 50,000
      shares held by Omega Capital Investors, L.P. Mr. Cooperman is the managing
      member of Omega Associates,  L.L.C., which is the general partner of these
      partnerships.

(16)  Includes  296,620  shares of Common Stock  beneficially  held on behalf of
      various  clients of William D. Witter,  Inc. This  information is based on
      the beneficial owner's filing with the Securities and Exchange  Commission
      under Section 13 and/or Section 16 of the Securities Exchange Act of 1934.



                                       4


                       PROPOSAL ONE: ELECTION OF DIRECTORS

      Under our  Articles of  Incorporation,  our Board of  Directors is divided
into three classes.  Each class of directors  serves a staggered term. Carl Dorf
and Charles B. Hart, Jr. hold office until the 2005 Annual Meeting, and each has
been  nominated  for  reelection  to the Board,  to serve as class III directors
until the Annual  Meeting to be held in 2008 or until their  successors are duly
elected  and  qualified.  Bruce  Simberg,  Richard W.  Wilcox,  Jr. and Peter J.
Prygelski are class II directors and hold office until the 2006 Annual  Meeting.
Edward J. Lawson and Richard A. Widdicombe are class I directors and hold office
until the 2007 Annual Meeting.

      The accompanying  form of proxy when properly executed and returned to us,
will be voted FOR the  election  to our Board of  Directors  of the two  persons
named below, unless the proxy contains contrary instructions.  Proxies cannot be
voted for a greater  number of persons than the number of nominees  named in the
Proxy  Statement.  We have no reason to  believe  that any of the  nominees  are
unable or unwilling to serve if elected.  If any of the nominees  should  become
unable or unwilling to serve as a director, however, the proxy will be voted for
the  election of such person or persons as shall be  designated  by the Board of
Directors,  unless a  shareholder  has withheld  authority or voted  against the
slate proposed in this proxy statement.

Nominees

      The following  persons were  recommended by the Board of Directors and are
nominated as directors as follows:

Name                                      Age        Position with the Company
----                                      ---        -------------------------

Carl Dorf (1)(2)                          64         Director

Charles B. Hart, Jr. (1)(2)(3)            66         Director

      Carl Dorf was  appointed to the Board of  Directors in August 2001.  Since
April 2001, Mr. Dorf has been the principal of Dorf Asset  Management,  LLC, and
is responsible for all investment  decisions made by that company.  From January
1991 to February  2001,  Mr. Dorf served as the Fund Manager of ING Pilgrim Bank
and Thrift Fund. Prior to his experience at Pilgrim, Mr. Dorf was a principal in
Dorf & Associates, an investment management company.

      Charles B. Hart, Jr. has more than 40 years of experience in the insurance
industry.  From 1973 to 1999,  Mr. Hart served as President of Public  Assurance
Group and as General Manager of Operations for Bristol West Insurance  Services.
Since  1999,  Mr.  Hart  has  acted as an  insurance  consultant.  Mr.  Hart was
appointed to the Board of Directors in March 2002.

-----------------
(1) Member of Independent Directors Committee.
(2) Member of Investment Committee.
(3) Member of Audit Committee.

      The Board of Directors unanimously recommends that shareholders vote "FOR"
each of the nominees for election as directors.  Directors  must be elected by a
plurality of the votes cast.

      Set forth below is certain  information  concerning  the directors who are
not currently standing for election:

Name                               Age     Position with the Company
----                               ---     -------------------------

Edward J. Lawson (2)               55      President, Chairman of the Board and
                                           Director

Richard A. Widdicombe              46      Chief Executive Officer and Director


                                       5


Bruce F. Simberg (2)               56      Director

Richard W. Wilcox, Jr. (1)(2)(3)   63      Director

Peter J. Prygelski (1)(2)(3)       36      Director

-------------------
(1) Member of Independent Directors Committee.
(2) Member of Investment Committee.
(3) Member of Audit Committee.

      Edward J. Lawson  co-founded  the Company and has served as our  President
and Chairman of the Board since the Company's  inception in 1991. Mr. Lawson has
more than 18 years'  experience in the insurance  industry,  commencing with the
founding of the Company's initial agency in 1983.

      Richard A. Widdicombe was appointed as our Chief Executive Officer in June
2003.  Mr.  Widdicombe  joined the  Company in  November  1999 as  President  of
Federated  National  Insurance  Company  ("Federated  National")  and  Assurance
Managing General Agents, Inc. ("Assurance MGA"). In August 2001 he was appointed
as the President of American Vehicle Insurance Company ("American Vehicle"). Mr.
Widdicombe holds his adjuster's license and CPCU designation.  Mr. Widdicombe is
a member of the Florida  Department of Financial  Services  (previously  Florida
Department of Insurance)  Initial Disaster  Assessment team. Mr.  Widdicombe was
appointed to the Board of Directors in August 2001.

      Bruce F.  Simberg has served as a director of the  Company  since  January
1998.  Mr.  Simberg has been a practicing  attorney for the last 23 years,  most
recently as managing partner of Conroy,  Simberg, Ganon, Krevans & Abel, P.A., a
law firm in Ft.  Lauderdale,  Florida,  since  October  1979.  Mr.  Simberg  was
appointed to the Board of Directors in January 1998.

      Richard W. Wilcox,  Jr. has been in the  insurance  industry for almost 40
years. In 1963, Mr. Wilcox began an insurance  agency that eventually  developed
into a business  generating $10 million in annual  revenue.  In 1991, Mr. Wilcox
sold his agency to Hilb,  Rogal and Hamilton Company ("HRH") of Fort Lauderdale,
for which he retained the position of President  through 1998.  In 1998,  HRH of
Fort  Lauderdale  merged with Poe and Brown of Fort  Lauderdale,  and Mr. Wilcox
served  as the  Vice  President.  Mr.  Wilcox  retired  in 1999 and  joined  the
Company's Board of Directors in January 2003.

      Peter J.  Prygelski  was appointed as a director of the Company in January
2004.  Since April 2004, Mr.  Prygelski has been Senior  Manager,  Business Risk
Services  Consulting  with  Ernst  &  Young  in Fort  Lauderdale,  Florida.  Mr.
Prygelski is a Certified  Internal  Auditor.  Prior to his employment at Ernst &
Young, Mr. Prygelski was a consultant in Sarbanes-Oxley  compliance and internal
audit matters from  September  2003 to April 2004.  From November 1991 to August
2003, Mr.  Prygelski was employed in the internal  audit  department of American
Express,  where he was most recently the  Director/Assistant  General Auditor of
American Express  Centurion Bank. As such, Mr.  Prygelski  managed the company's
audit  activities  and managed a staff of 12 audit  professionals  and an annual
department budget of $2.5 million. His  responsibilities  included preparing and
implementing  the company's  annual audit plan;  supporting the company's  audit
committee by  communicating  issues  related to planning,  audit  results,  plan
status,  and integrated audit coverage;  managing the relationships  with senior
management,  the external auditors, and regulatory  authorities;  and addressing
risks and control gaps to ensure that the company maintained an adequate control
system.

Compliance with Section 16(a) of the Securities Exchange Act of 1934

      Section  16(a) of the  Securities  Exchange  Act of 1934,  as amended (the
"Exchange Act"), requires executive officers, directors and holders of more than
10% of our Common Stock to file  reports of  ownership  and changes in ownership
with the  Securities  and Exchange  Commission  ("SEC") and The Nasdaq  National
Market  ("Nasdaq").  Such  persons are required to furnish us with copies of all
Section 16(a) forms they file.


                                       6


      Based solely on its review of the copies of such forms  received by it, or
oral or written representations from certain reporting persons, we believe that,
with respect to the fiscal year ended December 31, 2004, all filing requirements
applicable to our executive  officers,  directors and 10% beneficial owners were
complied with, except as follows:  Edward J. Lawson and Michele Lawson each made
one late filing disclosing two separate gifts of shares. Carl Dorf made one late
filing  disclosing  three  purchases  of  shares  by him  and two  sales  by his
estranged  spouse.  Richard W. Wilcox,  Jr. made one late filing disclosing four
purchases of shares on the same day.

Corporate Governance

      We have adopted a Code of Business Conduct for all employees and a Code of
Ethics for the Chief Executive Officer,  President and senior financial officers
including the Chief Financial  Officer.  Copies of our Code of Business  Conduct
and Code of Ethics are available on our web site at www.21stcenturyholding.com.

Meetings and Committees of the Board of Directors

      During  2004,  the Board of Directors  held four formal  meetings and took
actions by written  consent on 16 occasions.  During 2004, no director  attended
fewer than 75% of board and  committee  meetings  held  during  the period  such
director  served  on the  Board.  We do not have a  policy  with  regard  to the
attendance  of directors at the annual  meeting.  All  directors  attended  last
year's annual meeting.

      The Board has  determined  that the following  directors  are  independent
pursuant to NASD Rule 4200 and the  Exchange  Act:  Carl Dorf,  Charles B. Hart,
Jr., Peter J. Prygelski, and Richard W. Wilcox, Jr.

      The standing committees of the Board of Directors are the Audit Committee,
the Independent Directors Committee and the Investment Committee.

      Independent Directors Committee

      The Company's Independent Directors Committee is currently composed of Mr.
Dorf, Mr. Hart, Mr. Prygelski, and Mr. Wilcox. This committee meets in executive
session  biannually  and its duties and  responsibilities  include,  but are not
limited to, the following:

      o     Function  as the  Company's  Compensation  Committee  and review and
            approve the compensation of our executive officers and directors

      o     Administer  the  Company's  1998 Stock Option Plan,  2001  Franchise
            Stock Option Plan and 2002 Stock Option Plan

      o     Function as the Company's Nominating Committee.

      The  committee  held two formal  meetings  and acted five times by written
consent.  The committee  reviewed and approved the compensation of the Company's
executive officers.

      This year's Board of Director  nominees were  recommended and approved for
reelection by the full Board of Directors,  including the Independent  Directors
Committee.

      Audit Committee

      The Audit Committee is currently composed of Charles B. Hart, Jr., Richard
W. Wilcox, Jr. and Peter J. Prygelski.  Mr. Prygelski is a "financial expert" as
that term is defined in the  applicable  rules and  regulations  of the Exchange
Act. The Audit Committee met on five occasions in 2004.

      Pursuant to its written charter,  the duties and  responsibilities  of the
Audit  Committee  include,  but are not limited to, (a) the  appointment  of the
independent certified public accountants and any termination of engagement,  (b)
reviewing the plan and scope of independent  audits,  (c) reviewing  significant
accounting  and reporting  policies and operating  controls,  (d) having general
responsibility for all related auditing and financial statement matters, and (e)
reporting its recommendations  and findings to the full Board of Directors.  The
Audit  Committee  pre-approves  all auditing  services and  permitted  non-audit
services  (including  the  fees  and  terms  thereof)  to be  performed  by  the
independent  accountants,  subject to the de minimus  exceptions  for  non-audit
services described in Section 10A(i)(1)(B) of the Exchange Act that are approved
by the Audit Committee prior to the completion of the audit.


                                       7


      The Audit Committee has adopted guidelines regarding the engagement of our
independent  auditor to perform  services for us. For audit services  (including
statutory  audit  engagements  as required  under state laws),  the  independent
auditor will provide the Audit  Committee  with an engagement  letter during the
fourth quarter of each year  outlining the scope of the audit services  proposed
to be  performed  during the fiscal year.  If agreed to by the Audit  Committee,
this  engagement  letter will be formally  accepted  by the Audit  Committee  at
either its December or March Audit Committee  meeting.  The independent  auditor
will submit to the Audit  Committee for approval an audit  services fee proposal
after acceptance of the engagement letter.

      For non-audit services,  management will submit to the Audit Committee for
approval  (during  December or June of each fiscal  year) the list of  non-audit
services that it  recommends  the Committee  engage the  independent  auditor to
provide for the fiscal year.  Our management  and the  independent  auditor will
each confirm to the Audit  Committee that each non-audit  service on the list is
permissible under all applicable legal requirements.  In addition to the list of
planned non-audit services,  a budget estimating  non-audit service spending for
the fiscal year will be provided. The Audit Committee will approve both the list
of permissible  non-audit  services and the budget for such services.  The Audit
Committee  will be informed  routinely  as to the  non-audit  services  actually
provided by the independent auditor pursuant to this pre-approval process.

      To ensure  prompt  handling of  unexpected  matters,  the Audit  Committee
delegates  to the Chair the  authority  to amend or modify the list of  approved
permissible  non-audit  services and fees. The Chair will report action taken to
the Audit Committee at the next committee meeting.

      The independent  auditor must ensure that all audit and non-audit services
have been  approved  by the Audit  Committee.  The Chief  Financial  Officer  is
responsible  for  tracking all  independent  auditor fees against the budget for
such services and report at least annually to the Audit Committee.

      Investment Committee

      The  Investment  Committee  is  currently  composed  of Edward J.  Lawson,
Charles B. Hart, Jr., Richard W. Wilcox, Jr., Peter J. Prygelski, Bruce Simberg,
and Carl Dorf. The Investment  Committee manages our investment  portfolio.  The
Investment  Committee met informally via  teleconference on several occasions in
2004.

Report of the Audit Committee

      The following  report of the Audit Committee is made pursuant to the rules
of the SEC.  This report  shall not be deemed  incorporated  by  reference  by a
general  statement  incorporating  by reference  this Proxy  statement  into any
filing under the Securities Act of 1933 (the  "Securities  Act") or the Exchange
Act, except to the extent that we specifically  incorporate  this information by
reference, and shall not otherwise be deemed filed under such acts.

The Audit Committee hereby reports as follows:

      1. The Audit  Committee has reviewed and  discussed the audited  financial
statements with our management.

      2.  The  Audit  Committee  has  discussed  with  De  Meo,  Young,  McGrath
("DeMeo"),  independent accountants, the matters required to be discussed by SAS
61 (Communication with Audit Committees).


                                       8


      3. The Audit Committee has received the written disclosures and the letter
from DeMeo  required  by the  Independence  Standards  Board No. 1  (Independent
Discussions  with  Audit  Committees),   and  has  discussed  with  DeMeo  their
independence.

      4.  Based on the review  and  discussion  referred  to in  paragraphs  (1)
through (3) above, the Audit Committee  recommended to the Board of the Company,
and the Board has approved, that the audited financial statements be included in
the Company's  Annual Report on Form 10-K for the fiscal year ended December 31,
2004, for filing with the SEC.

      /s/ Peter J. Prygelski, Chairman
      /s/ Charles B. Hart, Jr.
      /s/ Richard W. Wilcox, Jr.

      Director Nomination Process

      Shareholders  may  communicate  generally with our Board by contacting our
Secretary.  In particular,  shareholders may recommend  nominees to the Board by
notifying  the  Secretary,  in  writing,  of the  identity  of the  nominee  and
enclosing a resume,  curriculum vitae or other relevant  information  describing
the nominee's qualifications. The Secretary will then forward these materials to
the Independent  Directors Committee,  functioning as our Nominating  Committee,
who will consider the candidate at the next meeting scheduled for the purpose of
considering nominees to the Board.

      Shareholders may also nominate  directors,  along with the presentation of
other business, at our annual meeting, pursuant to Article II, Section 10 of our
Bylaws and SEC regulations.  For business to be brought before an annual meeting
by a shareholder,  notice thereof must be delivered to or mailed and received at
our principal executive offices, not less than 120 calendar days before the date
of the proxy statement  released to shareholders in connection with the previous
year's  annual  meeting.  The  Bylaws  require  a  shareholder's  notice  to the
Secretary  to set forth as to each  matter  the  shareholder  proposes  to bring
before the annual meeting (i) a brief  description of the business desired to be
brought before the annual  meeting and the reasons for conducting  such business
at the  annual  meeting,  (ii) the name and record  address  of the  shareholder
proposing  such  business,  (iii)  the class  and  number  of  shares  which are
beneficially  owned by the  shareholder,  and (iv) any material  interest of the
shareholder in such business.

      With regard to the  nomination of  directors,  such notice shall set forth
(a) as to each person whom the shareholder  proposes to nominate for election or
re-election as a director,  (i) the name,  age,  business  address and residence
address of the  person,  (ii) the  principal  occupation  or  employment  of the
person,  (iii) the  class and  number  of  shares  of  capital  stock  which are
beneficially owned by the person, (iv) the consent of each nominee to serve as a
director if so  elected,  and (v) any other  information  relating to the person
that is required to be disclosed in  solicitations  for proxies for the election
of directors  pursuant to Rule 14a-3 under the  Exchange  Act; and (b) as to the
shareholder giving notice,  (i) the name and record address of shareholder,  and
(ii) the class and  number of shares of  capital  stock  which are  beneficially
owned by the  shareholder.  We may require any proposed  nominee to furnish such
other  information as may reasonably be required to determine the eligibility of
such proposed nominee to serve as a director.

                             EXECUTIVE COMPENSATION

Summary Compensation Table

      The following  table  summarizes  compensation  earned for the years ended
December 31, 2004, 2003, and 2002, by our Chief Executive  Officer and the three
other most highly compensated  executive  officers whose  compensation  exceeded
$100,000  during  2004 and is required  to be  reported  (the  "named  executive
officers").


                                       9




                                                                                          Long-Term
                                          Annual Compensation (1)                       Compensation
                                    --------------------------------------      --------------------------------
                                                                                Securities
                                                                                Underlying          All Other
Name and Principal Position         Year          Salary($)       Bonus($)      Options(#)       Compensation($)
---------------------------         ----          ---------       --------      ----------       ---------------
                                                                                    
Richard A. Widdicombe               2004          $143,100           0              --             $18,207 (1)
Chief Executive Officer             2003           126,250           0              --                  -- (2)
                                    2002           122,200           0              --                  -- (2)

Edward J. Lawson                    2004          $154,500           0              --             $16,160 (3)
President and Chairman              2003           156,000           0              --                  -- (2)
                                    2002           156,000           0              --                 --  (2)

J. Gordon Jennings, III             2004          $129,577           0              --             $11,036 (4)
Chief Financial Officer             2003           104,000           0              --                  -- (2)
                                    2002            89,800           0              --                  -- (2)

Kent M. Linder                      2004          $118,800           0              --             $16,157 (5)
Chief Operating Officer             2003           107,000           0              --                  -- (2)
                                    2002           104,000           0              --                  -- (2)


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

(1)   Includes  $7,200  car  allowance,   $851  cellular  phone,  $8,667  health
      insurance premiums,  $300 for events attended by officer and/or family and
      $1,189 airfare and hotel for management trip including family.

(2)   Perquisites and other personal  benefits totaling less than the applicable
      reporting threshold for 2002 and 2003 have been excluded.

(3)   Includes $9,044 car allowance,  $1,064  cellular phone,  $4,924 health and
      dental  insurance  premiums,  $100 for events  attended by officer  and/or
      family and $1,028 airfare and hotel for management trip including family.

(4)   Includes $10,536 health insurance premiums and $500 for events attended by
      officer and/or family.

(5)   Includes  $12,935 health and dental  insurance  premiums,  $1,404 cellular
      phone,  $400 for  events  attended  by  officer  and/or  family and $1,418
      airfare and hotel for management trip including family.

Option Grants in Last Fiscal Year

      The following table sets forth information concerning individual grants of
stock  options  made  during  2004 to the  CFO.  We  have  never  granted  stock
appreciation rights.



                                                     % of Total
                           Number of Securities      Options/SAR Granted    Exercise or
                           Underlying Options        to Employees in        Base Price
Name                       Granted (#)(1)            Fiscal Year            ($/share)      Expiration Date
-----------                --------------            -----------            ---------      ---------------
                                                                                  
J. Gordon Jennings, III         30,000                  16.8%                20.00            May 6, 2010



                                       10


Stock Option Exercises and Holdings

      The following table sets forth certain  information  with respect to stock
options  and/or  warrants  exercised  during  calendar  year  2004 by the  named
executive  officers and  unexercised  stock options  and/or  warrants held as of
December 31, 2004 by such executive officers.



                                                                    Number of Securities               Value of Unexercised
                                 Shares                           Underlying Unexercised               In-the-Money Options
                               Underlying                       Options at Fiscal Year-End              At Fiscal Year-End
                                Options          Value        ------------------------------    -----------------------------------
Name                           Exercised      Realized(1)     Exercisable      Unexercisable    Exercisable(2)     Unexercisable(2)
----------------               ---------      -----------     -----------      -------------    --------------     ----------------
                                                                                                    
Richard A. Widdicombe                --             --            90,000             --           $526,020                  --
Edward J. Lawson                     --             --            66,324             --           $384,220                  --
J. Gordon Jennings, III          16,000        $99,328             5,000         59,000           $ 23,665            $151,092
Kent M. Linder                       --             --            75,000             --           $392,475                  --


-----------------
(1) All values are shown pretax and are rounded to the nearest whole dollar.
(2) Based on a fair market value of $13.90 per share at December 31, 2004.

Independent Directors Committee Report on Executive Compensation

      Under rules  established  by the SEC, we are  required to provide a report
explaining the rationale and considerations that led to fundamental compensation
decisions  affecting  the  executive  officers  (including  the named  executive
officers)  during the past fiscal year. The report of our Independent  Directors
Committee for 2004 is set forth below.

      Compensation Philosophy

      The three principal components of executive compensation are salary, bonus
and stock options.  These  components are designed to facilitate  fulfillment of
the Board's compensation objectives,  which include (i) attracting and retaining
competent  management,  (ii) recognizing  individual initiative and achievement,
(iii)  rewarding  management for short and long term  accomplishments,  and (iv)
aligning  management  compensation  with the  achievement  of company  goals and
performance.

      Base salaries for new  management  employees are  determined  initially by
evaluating the  responsibilities  of the position held and the experience of the
individual,  and by  reference to the  competitive  marketplace  for  managerial
talent,  including a comparison  of base  salaries for  comparable  positions at
similar  companies of comparable sales and  capitalization.  Unless specified in
the executive's  employment agreement,  annual salary adjustments are determined
by evaluating the competitive marketplace,  Company performance, the performance
of the executive, and the responsibilities assumed by the executive.

      The  Independent  Directors  Committee  endorses the position  that equity
ownership by management is beneficial in aligning management's and shareholders'
interests  in the  enhancement  of  shareholder  value.  The  Board has used the
selective  grant of stock options and shares of Common Stock to accomplish  this
goal.

      In  2005,  the  Independent   Directors  Committee  will  review  existing
management  compensation programs on an ongoing basis and will (i) meet with the
Chief  Executive  Officer to consider  and set  mutually  agreeable  performance
standards  and goals for members of senior  management,  as  appropriate,  or as
otherwise required pursuant to any such officer's  employment agreement and (ii)
consider and, as appropriate, approve modifications to such programs to ensure a
proper fit with the philosophy of the  Independent  Directors  Committee and the
agreed-upon standards and goals.


                                       11


      Chief Executive Officer Compensation

      The increase in the salary and bonus for Richard A. Widdicombe,  our Chief
Executive Officer, pursuant to his employment agreement, included an analysis of
Mr.  Widdicombe's   contribution  to  the  Company.  The  Independent  Directors
Committee also considered the fiscal 2004 earnings,  expectations for the fiscal
year ending December 31, 2005 and other performance  measures in determining Mr.
Widdicombe's compensation,  but there was no specific relationship or formula by
which such compensation was tied to company performance.

      Other Executive Officers' Compensation

      Fiscal 2004 base salary and bonuses for our other executive  officers were
determined by the Independent  Directors Committee.  This determination was made
after a  review  and  consideration  of a  number  of  factors,  including  each
executive's level of responsibility  and commitment,  level of performance (with
respect to specific areas of responsibility  and on an overall basis),  past and
present  contribution to and achievement of Company goals and performance during
fiscal  2004,  and  our  historical   compensation   levels.   Although  Company
performance was one of the factors  considered,  the approval of the Independent
Directors  Committee was based upon an overall  review of the relevant  factors,
and there was no specific relationship or formula by which compensation was tied
to company performance.

      Stock Options

      We maintain  stock option plans,  which are designed to attract and retain
directors,  executive  officers  and  other  employees  and to  reward  them for
delivering  long-term value to the Company and its subsidiaries.  In determining
the  amount  and  timing of stock  option  grants,  we review  the  individual's
existing share and option holdings, as well as performance-related factors.

      /s/, Carl Dorf, Chairman
      /s/ Charles B. Hart
      /s/ Richard W. Wilcox, Jr.
      /s/ Peter J. Prygelski

Compensation of Directors

      Non-employee directors receive cash fees of $1,500 per meeting attended of
the full Board of Directors,  $750 per meeting  attended of the Audit Committee,
and $500 per meeting  attended of the  Independent  Directors  Committee and the
Investment  Committee.  Directors  who are also  officers  do not  receive  this
compensation.  All directors are reimbursed  for travel and lodging  expenses in
connection with their attendance at meetings.

      In January 2004,  Peter J. Prygelski was granted 10,000  six-year  options
under the 2002 plan in connection with his joining the Board.

Indemnification Agreements

      We  have  entered  into  an  indemnification  agreement  with  each of our
directors and executive officers.  Each indemnification  agreement provides that
we  will   indemnify  such  person  against   certain   liabilities   (including
settlements)  and  expenses  actually and  reasonably  incurred by him or her in
connection   with  any  threatened  or  pending  legal  action,   proceeding  or
investigation  (other than actions brought by us or in our right) to which he or
she is, or is threatened to be, made a party by reason of his or her status as a
director,  officer or agent,  provided that such  director or executive  officer
acted in good faith and in a manner he or she  reasonably  believed  to be in or
not opposed to our best interests and, with respect to any criminal proceedings,
had no reasonable cause to believe his or her conduct was unlawful. With respect
to any action  brought by us or in our right,  a director or  executive  officer
will also be  indemnified,  to the  extent not  prohibited  by  applicable  law,
against expenses and amounts paid in settlement,  and certain  liabilities if so
determined  by a  court  of  competent  jurisdiction,  actually  and  reasonably
incurred by him or her in connection with such action if he or she acted in good
faith and in a manner he or she  reasonably  believed to be in or not opposed to
our best interests.


                                       12


Employment Agreements

      Effective September 1, 1998, we entered into an employment  agreement with
Edward J. Lawson, the Company's  President.  Effective June 10, 2003, we entered
into an employment  agreement with Richard A.  Widdicombe,  the Company's  Chief
Executive Officer.  Each employment  agreement has a "rolling" two-year term, so
that at all times the remaining term of the agreement is two years.

      Mr.  Lawson's  agreement was amended in December 2004 to reduce his annual
salary from $156,000 to $117,000 and to increase his monthly car allowance  from
$300 to $1,125.  Contemporaneously with this amendment, the employment agreement
of Michele  Lawson,  Mr.  Lawson's  spouse and an employee of the  Company,  was
amended to increase her annual  salary to $117,000  from $78,000 and to increase
her car allowance to $1,125 per month from $300 per month.

      Mr.  Widdicombe's  employment  agreement  currently provides for an annual
salary of $137,800 and a monthly car allowance of $600.

      Each  employment  agreement  provides  that  the  executive  officer  will
continue to receive  his salary for a period of two years after the  termination
of employment,  if his or her employment is terminated for any reason other than
death,  disability or Cause (as defined in the employment  agreement),  or for a
period of two years after termination of the agreement as a result of his or her
disability  and a bonus equal to twice the amount paid to the executive  officer
during the 12 months  preceding the  termination,  and the  executive  officer's
estate will receive a lump sum payment  equal to two year's  salary plus a bonus
equal to twice the amount  paid to the  executive  officer  during the 12 months
preceding the termination by reason of his death. Each employment agreement also
prohibits the executive  officer from directly or indirectly  competing  with us
for one year after  termination  for any  reason  except a  termination  without
Cause. If a Change of Control (as defined in the employment  agreement)  occurs,
the employment  agreement provides for the continued employment of the executive
officer for a period of two years following the Change of Control.  In addition,
following  the Change of  Control,  if the  executive  officer's  employment  is
terminated  by the  Company  other  than for  Cause or by reason of his death or
disability, or by the executive officer for certain specified reasons (such as a
reduction of compensation  or a diminution of duties),  he or she will receive a
lump sum cash payment equal to 299% of the cash compensation  received by him or
her during the 12 calendar months prior to such termination.

      Effective  May 6, 2004 we entered  into an  employment  agreement  with J.
Gordon  Jennings,  III, the Company's  Chief Financial  Officer.  The employment
agreement is effective through May 6, 2008 and provides for an annual salary set
at $137,000  and such  bonuses and  increases  as may be awarded by the Board of
Directors.

Independent Directors Committee Interlocks and Insider Participation

      During 2004,  the  Independent  Directors  Committee  consisted of Messrs.
Dorf, Hart,  Prygelski,  and Wilcox.  None is a current or former officer of the
Company  or  any  of  its  subsidiaries.  No  committee  interlocks  with  other
companies, within the meaning of the SEC's proxy rules, existed in 2004.

                             STOCK PERFORMANCE GRAPH

      Set  forth  below is a line  graph  comparing  the  dollar  change  in the
cumulative total shareholder return on the Company's Common Stock for the period
beginning  on December  31, 1999 and ending on December  31, 2004 as compared to
the cumulative  total return of the Nasdaq Stock Market Index and the cumulative
total return of the SNL Property & Casualty  Insurance  Index. The graph depicts
the  value  based on the  assumption  of a $100  investment  with all  dividends
reinvested.


                                       13


                  COMPARISON OF 5-YEAR CUMULATIVE TOTAL RETURN



                                                                                 Period Ending
                                                       ---------------------------------------------------------------------
Index                                                    12/31/99    12/31/00   12/31/01    12/31/02   12/31/03    12/31/04
----------------------------------------------------------------------------------------------------------------------------
                                                                                                   
21st Century Holding Company                               100.00       73.14      79.06      347.53     587.52      585.44
NASDAQ Composite                                           100.00       60.82      48.16       33.11      49.93       54.49
SNL Property & Casualty Insurance Index                    100.00      143.42     143.11      134.23     166.08      182.04


[MOUNTAIN GRAPH OMITTED]

Note: The stock price  performance  shown on the graph above is not  necessarily
indicative of future price performance.

Graph and index values provided by: SNL Financial LC, Charlottesville, VA
(434) 977-1600
(C)2005. Used with permission. All rights reserved.

                              CERTAIN TRANSACTIONS

      Bruce Simberg,  a director,  is a partner of the Fort Lauderdale,  Florida
law firm of Conroy,  Simberg,  Ganon,  Krevans & Abel, P.A., which renders legal
services  to the  Company.  In 2004,  the  Company  paid  legal  fees to Conroy,
Simberg,  Ganon,  Krevans & Abel,  P.A. for  services  rendered in the amount of
approximately  $327,000.  We  believe  that the  services  provided  by  Conroy,
Simberg, Ganon, Krevans & Abel, P.A. are on terms at least as favorable as those
that we could secure from a non-affiliated third party.

      The employment  agreement of Michele  Lawson,  Mr.  Lawson's spouse and an
employee of the Company,  was amended to increase her annual  salary to $117,000
from $78,000 and increase her car allowance to $1,125 from $300 per month.  Mrs.
Lawson's duties include  overseeing the Company's  accounts payable,  claims and
commission payment processes.


                                       14


      During 2004, Mr. Lawson's daughter received  compensation totaling $70,200
for  her  services  as a  vice  president  of one  of  the  Company's  insurance
subsidiaries  and  as  human  resources  director;  Mr.  Lawson's  sister-in-law
received  compensation  totaling  $62,701 for her services as an underwriter for
one of the Company's  insurance  subsidiaries;  and Mr. Lawson's nephew received
compensation totaling $72,800 for his services as the president of the Company's
premium finance subsidiary.  We believe that the compensation  provided to these
individuals  is comparable  to that paid by other  companies in our industry and
market for similar positions.

      We have  adopted a policy  that any  transactions  between the Company and
executive officers,  directors,  principal shareholders or their affiliates take
place on an  arms-length  basis and  require  the  approval of a majority of our
independent directors.

      PROPOSAL TWO: APPROVAL OF THE POSSIBLE ISSUANCE OF 20% OR MORE OF OUR
          COMMON STOCK IN CONNECTION WITH THE SECURITIES ISSUED IN OUR
                             2004 PRIVATE PLACEMENT


      Pursuant to the Nasdaq  rules and the terms of the 6% Senior  Subordinated
Notes due September 30, 2007 that we sold in 2004 (the "Notes"), we are required
to submit for approval by our shareholders the potential issuance of 20% or more
of our Common Stock outstanding immediately before the transaction.


Terms of Our 2004 Notes and Warrants


      On  September  30, 2004,  we  completed a private  placement of our Notes,
which were offered and sold to accredited  investors as units  consisting of one
Note with a principal  amount of $1,000 and  warrants to purchase  shares of our
Common Stock (the  "Warrants").  We sold an aggregate of $12.5  million Notes in
this  placement,  which  resulted in proceeds  (net of  placement  agent fees of
$700,000 and offering expenses of $32,500) to us of approximately $11.8 million.
We contributed the net proceeds from this private placement to our two insurance
subsidiaries  to increase  their  equity  surplus as follows:  $4.3  million was
contributed  to  American  Vehicle   Insurance  Company  and  $7.5  million  was
contributed to Federated National Insurance Company.

      The Notes pay  interest  at the  annual  rate of 6%, are  subordinated  to
senior debt, and mature on September 30, 2007.  Quarterly  payments of principal
and interest  due on the Notes may be made in cash or, at our option,  in shares
of our Common Stock. If paid in shares of Common Stock,  the number of shares to
be  issued  is   determined   by  dividing   the  payment  due  by  95%  of  the
weighted-average  volume  price for the Common  Stock on Nasdaq as  reported  by
Bloomberg  Financial  Markets for the 20 consecutive  trading days preceding the
payment  date (the  "Calculation  Price").  We paid the January  2005  quarterly
principal  and interest  payment on the Notes by issuing  103,870  shares of our
Common  Stock to the  holders  of the Notes.  We paid the April  2005  quarterly
payment due in cash.  In April 2005,  we announced  the  Company's  intention to
continue to pay in cash the principal and interest due on the Notes,  as well as
the principal and interest due on our 6% Senior  Subordinated Notes due July 31,
2006 that we issued in 2003 (the "2003 Notes").

      We issued  980,392  Warrants  to the  purchasers  of the Notes and  39,216
Warrants to the placement agent in the offering,  J. Giordano  Securities,  LLC,
for a total of 1,109,608 Warrants.  Each Warrant entitles the holder to purchase
one share of our Common Stock at an exercise price of $12.75 per share.


      The terms of the Warrants provide for  "anti-dilution  adjustments" to the
exercise price and the number of shares issuable  thereunder upon the occurrence
of certain events typical for private offerings of this type.  Pursuant to these
anti-dilution  adjustments,  if the Company issues  additional Common Stock at a
price per share less than the exercise price of the Warrants,  then the terms of
the outstanding  Warrants would be  automatically  adjusted to take into account
the effect of the additional shares of Common Stock issued.  The effect of these
adjustments would be to increase  proportionately the number of shares of Common
Stock for which each Warrant is  exercisable  and decrease  proportionately  the
exercise price per share.  The  anti-dilution  adjustments  are not triggered by
certain issuances of Common Stock, such as issuances  pursuant to an existing or
future employee benefit plans or pursuant to a business acquisition or strategic
transaction,  or by issuances of Common Stock in a private  offering  unless the
purchase price per share is less than 80% of the exercise price of the Warrants.


                                       15



      The Warrants will be  exercisable  until  September 30, 2007. The Warrants
may be redeemed,  in whole or in part,  at any time or from time to time, at our
sole option,  beginning  September  30, 2005 at a redemption  price of $0.01 per
share  underlying  the Warrants to be redeemed.  Before a call for redemption of
the  Warrants  may occur,  however,  the  weighted-average  volume price for our
Common Stock quoted on Nasdaq must have been,  for 20  consecutive  trading days
ending not more than 10 days prior to the notice of  redemption,  more than 150%
of the exercise  price, as the exercise price may be adjusted from time to time.
Redemption of the Warrants may only occur upon 30 days' prior written  notice to
the holders.  This notice must include certification of the trading price of our
Common Stock on Nasdaq as reported by Bloomberg.


Registration Rights Granted to Holders of Notes and Warrants

      We agreed to  provide  the  holders  of the  Notes and the  Warrants  with
"registration rights." Pursuant to these contractual rights, we are obligated to
file with the SEC a registration  statement covering the right of the holders to
resell the shares of Common Stock paid to them as principal  and interest on the
Notes. These  registration  statements must be filed within two business days of
the quarterly payment date. We may be required to make a penalty cash payment to
our Note holders if:

      o     A registration statement filed pursuant to these registration rights
            is declared  effective  by the SEC more than 10 business  days after
            the quarterly payment date; and

      o     The  average  trading  price  of our  Common  Stock as  reported  by
            Bloomberg  for  the  three  business  days up to and  including  the
            effectiveness  date is less than the  Calculation  Price, as defined
            above.

The amount of the cash payment payable to each Note holder would be equal to the
difference  between the Calculation  Price and the average trading price for the
three business days up to and including the  effectiveness  date,  multiplied by
the number of shares of Common Stock issued to each Note holder.

      We have already  registered  our holders' right to resell the Common Stock
issuable upon exercise of the Warrants.

      The  availability of these  registration  rights may adversely  affect our
shareholders because our Note and Warrant holders would have the right to resell
their shares of Common  Stock in any  quantity and at any time.  These sales may
have the effect of depressing the trading prices of our Common Stock.

Possible Future Issuances of Common Stock Pursuant to Our Notes and Warrants

      Under the terms of the Notes, the number of shares that would be issued to
pay the quarterly  principal and interest due is determined  based on the market
prices of our Common Stock prior to each  quarterly  payment date, and therefore
it is not possible to determine  precisely the number of shares that  ultimately
may be issued by us. In addition, the anti-dilution  adjustments to the Warrants
may require us to issue an indeterminate  number of additional  shares of Common
Stock.


      For illustrative purposes, we are providing the table below to demonstrate
the possible  number of shares that may be issued by us in the future in payment
of the  principal  and  interest  due on the  Notes  and  upon  exercise  of the
Warrants.  In this table,  we have  reflected a range of possible  future market
prices of our common stock. This table reflects:

      o     The  shares  that  would be issued by us if we were to pay in shares
            the principal  and interest due through  maturity on our 2003 Notes.
            The terms of the 2003 Notes, which we sold in a private placement in
            2003,   are  very  similar  to  the  Notes  we  sold  in  2004.  Our
            shareholders  approved at our 2004 annual  meeting the Common  Stock
            that may be issued in the future pursuant to the 2003 Notes.



                                       16


      o     The  shares  that would be issued by us if the  warrants  (the "2003
            Warrants")  we also sold to the  purchasers  of our 2003  Notes were
            exercised.  Our shareholders approved at our 2004 annual meeting the
            Common  Stock that may be issued in the future  pursuant to the 2003
            Warrants.

      o     The shares that would be issued by us if currently outstanding stock
            options were exercised.


      o     The  shares  that we would have to issue if we were to decide to pay
            all of the  remaining  payments of principal and interest due on the
            Notes  sold in 2004 in shares of Common  Stock,  with the  number of
            shares  issuable  reflecting  various  market  prices of our  Common
            Stock.



                                         -----------------------                -----------------------                -------
                                         2003 Private Placement                 2004 Private Placement                  Total
                                         -----------------------                -----------------------                -------
                                                        Shares                                Shares
                                                       issuable                              issuable
                                                        to pay                                to pay       Total
                              Shares                   principal  Total shares               principal     shares
                             issuable                    and        issuable                   and        issuable
                             pursuant     Shares       interest    other than     Shares     interest      as a
                                to       issuable      on 2003     as a result   issuable    on 2004      result
                             employee    pursuant       Notes        of 2004     pursuant     Notes       of 2004
                               stock      to 2003      through       private      to 2004    through      private
                              options    Warrants      maturity     placement    Warrants    maturity    placement
                             ---------   ---------    ----------  ------------  ----------  ----------   ----------  
                                                                                             
Asumption A
-----------
20-day weighted
average stock price   $6.00

95% of 20-day
weighted average
stock price           $5.70

Stock option plans             944,409                                 944,409                                   --    944,409
Note holders                        --          --       573,158       573,158          --   1,978,172    1,978,172  1,978,172
J. Giordano Securities              --          --            --            --          --          --           --         --
                             ---------   ---------    ----------  ------------  ----------  ----------   ----------  ---------
Total                          944,409          --       573,158     1,517,567          --   1,978,172    1,978,172  2,922,581
---------------------        ---------   ---------    ----------  ------------  ----------  ----------   ----------  ---------

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

Asumption B
-----------
20-day weighted
average stock price   $8.00

95% of 20-day
weighted average
stock price           $7.60

Stock option plans             944,409                                 944,409                                   --    944,409
Note holders                        --          --       429,868       429,868          --   1,483,629    1,483,629  1,483,629
J. Giordano Securities              --          --            --            --          --          --           --         --
                             ---------   ---------    ----------    ----------  ----------  ----------   ----------  ---------
Total                          944,409          --       429,868     1,374,277          --   1,483,629    1,483,629  2,428,038
---------------------        ---------   ---------    ----------    ----------  ----------  ----------   ----------  ---------



                                       17





                                         -----------------------                -----------------------                -------
                                         2003 Private Placement                 2004 Private Placement                  Total
                                         -----------------------                -----------------------                -------
                                                        Shares                                Shares
                                                       issuable                              issuable
                                                        to pay                                to pay       Total
                              Shares                   principal  Total shares               principal     shares
                             issuable                    and        issuable                   and        issuable
                             pursuant     Shares       interest    other than     Shares     interest      as a
                                to       issuable      on 2003     as a result   issuable    on 2004      result
                             employee    pursuant       Notes        of 2004     pursuant     Notes       of 2004
                               stock      to 2003      through       private      to 2004    through      private
                              options    Warrants      maturity     placement    Warrants    maturity    placement
                             ---------   ---------    ----------  ------------  ----------  ----------   ----------  
                                                                                             
Asumption C
-----------

20-day weighted
average stock price  $10.00

95% of 20-day
weighted average
stock price           $9.50

Stock option plans             944,409                                 944,409                                   --    944,409
Note holders                        --          --       343,895       343,895          --   1,186,903    1,186,903  1,186,903
J. Giordano Securities              --          --            --            --          --          --           --         --
                             ---------   ---------    ----------  ------------  ----------  ----------   ----------  ---------
Total                          944,409          --       343,895     1,288,304          --   1,186,903    1,186,903  2,131,312
---------------------        ---------   ---------    ----------    ----------  ----------  ----------   ----------  ---------

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

Asumption D
-----------

20-day weighted
average stock price  $12.50

95% of 20-day
weighted average
stock price          $11.88

Stock option plans             944,409                                 944,409                                   --    944,409
Note holders                        --          --       275,000       275,000          --     949,123      949,123  1,224,123
J. Giordano Securities              --          --            --            --          --          --           --         --
                             ---------   ---------    ----------    ----------  ----------  ----------   ----------  ---------
Total                          944,409          --       275,000     1,219,409          --     949,123      949,123  2,168,532
---------------------        ---------   ---------    ----------    ----------  ----------  ----------   ----------  ---------

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

Asumption E
-----------

20-day weighted
average stock price  $13.00

95% of 20-day
weighted average
stock price          $12.35

Stock option plans             944,409                                 944,409                                   --    944,409
Note holders                        --     570,880       264,423       835,303     980,392     912,618    1,893,010  2,728,313
J. Giordano Securities              --      23,541            --        23,541      39,216          --       39,216     62,757
                             ---------   ---------    ----------    ----------  ----------  ----------   ----------  ---------
Total                          944,409     594,421       264,423     1,803,253   1,019,608     912,618    1,932,226  3,735,479
---------------------        ---------   ---------    ----------    ----------  ----------  ----------   ----------  ---------



                                       18





                                         -----------------------                -----------------------                -------
                                         2003 Private Placement                 2004 Private Placement                  Total
                                         -----------------------                -----------------------                -------
                                                        Shares                                Shares
                                                       issuable                              issuable
                                                        to pay                                to pay       Total
                              Shares                   principal  Total shares               principal     shares
                             issuable                    and        issuable                   and        issuable
                             pursuant     Shares       interest    other than     Shares     interest      as a
                                to       issuable      on 2003     as a result   issuable    on 2004      result
                             employee    pursuant       Notes        of 2004     pursuant     Notes       of 2004
                               stock      to 2003      through       private      to 2004    through      private
                              options    Warrants      maturity     placement    Warrants    maturity    placement
                             ---------   ---------    ----------  ------------  ----------  ----------   ----------  
                                                                                             
Asumption F
-----------

20-day weighted
average stock price  $13.50

95% of 20-day
weighted average
stock price          $12.83

Stock option plans             944,409                                 944,409                                   --    944,409
Note holders                        --     570,880       254,630       805,510     980,392     878,817    1,859,209  2,684,719
J. Giordano Securities              --      23,541            --        23,541      39,216          --       39,216     62,757
                             ---------   ---------    ----------    ----------  ----------  ----------   ----------  ---------
Total                          944,409     594,421       254,630     1,793,460   1,019,608     878,817    1,898,425  3,691,885
---------------------        ---------   ---------    ----------    ----------  ----------  ----------   ----------  ---------


      Our 2003 Warrants are each  exercisable for 3/4 of a share of Common Stock
at an exercise  price of $12.74 per whole  share.  The 2003  Warrants  currently
outstanding  are  issuable  for a total of 594,421  shares of our Common  Stock,
including 23,541 shares that would be issued to J. Giordano Securities, LLC, who
was also the placement agent in our 2003 private  placement.  Our 2004 Warrants,
of which we issued a total of 1,109,608,  are each  exercisable for one share of
Common Stock at an exercise price of $12.75 per whole share. The following table
illustrates  the  percentage  ownership  of our Note  holders  depending  on the
exercise of the 2003 Warrants and 2004 Warrants.  This table reflects the shares
of Common Stock  currently  beneficially  owned by our Note holders based on the
most recent information  provided to us by these holders.  We have not reflected
in the table,  however, any adjustments to the warrant exercise prices under the
anti-dilution provisions.



                                                             Percentage of Total Shares Outstanding (A)
                                                      ---------------------------------------------------
                                                      If all 2003        If all 2004
                                   Common Stock       Warrants           Warrants           If all Warrants
                                   Owned (B)          are exercised      are exercised      are exercised
                                   ---------          -------------      -------------      -------------
                                                                                     
J. Giordano Securities, LLC            --                  *                  *                  *

Whitebox Advisors, LLC (C)           14,011              5.3%               7.1%               11.2%

All other Note holders               35,723              3.6%               6.1%               8.8%



----------------------
*Less than 1%


(A)   Based on  6,343,207  shares of Common Stock  outstanding  as of the Record
      Date.


(B)   Reflects  Common  Stock  issued under the terms of the 2003 Notes and 2004
      Notes through the date of this proxy statement.


                                       19


(C)   Includes  warrants  held  by the  following  funds:  Whitebox  Convertible
      Arbitrage Partners,  LP, Whitebox Hedged High Yield Partners, LP, Whitebox
      Intermarket Partners, LP, and Pandora Select Partners, LP.


Description of Nasdaq Rule

      The  terms of the Notes and the  Warrants  provide  that we will not issue
shares  to pay  principal  and  interest  on the  Notes  or  make  anti-dilution
adjustments  to the Warrants in violation of the Nasdaq rule that is  applicable
to the  proposed  issuance  of shares  described  in this  proposal.  That rule,
Section  4350(i)(1)(D)(ii)  of the Marketplace  Rules of The Nasdaq Stock Market
(the "Nasdaq Rules"),  prohibits the sale, issuance or potential issuance of the
Company's  Common  Stock at a price less than the book value or the market value
of the Common Stock,  whichever is greater, if the shares issued would equal 20%
or more of the Common Stock outstanding before the issuance. This section of the
Nasdaq Rules applies because:

      o     Under the terms of the Notes, the Calculation  Price for purposes of
            determining  the number of shares to be issued if the  principal and
            interest is paid in shares equals 95% of the 20-day weighted-average
            volume price of our Common Stock; and

      o     Under  the  terms of the Notes  and  Warrants,  the total  number of
            shares of Common Stock issuable could exceed 20% of our Common Stock
            outstanding before our 2004 private placement.

      Immediately prior to our 2004 private  placement,  we had 5,946,275 shares
of Common Stock  outstanding.  We have issued  103,870 shares of Common Stock to
the holders of our Notes in payment of the principal and interest due in January
2005.  The April 2005 payment was made in cash.  To date,  no Warrants have been
exercised.


Effect of Failure to Obtain Shareholder Approval for this Proposal


      The  Board  of  Directors  recommends  that  shareholders   authorize  the
potential  issuance of 20% or more of our Common  Stock in  connection  with our
2004 private  placement.  Although the Company  currently intends to pay in cash
the  principal  and  interest  due on the Notes,  as we announced in April 2005,
unforeseen  events  may  occur  in the  future  that may  make it  desirable  or
necessary to make these payments in shares. We may also have to issue additional
securities  in the future at a price below the exercise  price of the  Warrants,
which would trigger the anti-dilution provisions of the Warrants.

      If the  shareholders do not approve this proposal,  under the terms of the
Notes the  Company  will be  required  to pay in cash the future  principal  and
interest due on the Notes.  If we are not able to pay the principal and interest
in cash,  we would be in default under the Notes.  Note  holders'  remedies with
respect to an event of default include acceleration of the outstanding principal
amount of the Notes due,  which as of the date of this Proxy  Statement  totaled
approximately  $10.1 million,  and such other legal or equitable relief to which
the Note holders may prove themselves to be entitled.

      Under the terms of the  Warrants,  if  shareholders  do not  approve  this
proposal and the anti-dilution  adjustments of the Warrants are triggered by the
Company's issuance of additional securities,  the exercise price of the Warrants
would be reduced to equal the issuance  price of the  securities  that triggered
the anti-dilution adjustment.


      The Board of Directors unanimously recommends that shareholders vote "FOR"
this proposal.  The approval of this proposal requires the affirmative vote of a
majority of the total votes cast on the proposal in person or by proxy.


                                       20


           PROPOSAL THREE: APPROVAL OF THE ISSUANCE OF 3,500 SHARES OF
                 OUR COMMON STOCK TO OUR CHIEF EXECUTIVE OFFICER


      Pursuant to Section  4350(i)(1)(A)  of the Nasdaq Rules, we are submitting
to our shareholders,  for their approval,  the proposed issuance of 3,500 shares
of our Common Stock to our Chief Executive Officer, Richard A. Widdicombe. These
shares  were  granted by the Board of  Directors  on March 3,  2005,  subject to
shareholder approval, in recognition of Mr. Widdicombe's service to the Company.


      Although stock grants have the effect of diluting our other  shareholders,
the Board of Directors  believes  that stock  grants play an  important  role in
providing   designated  members  of  our  management  team  with  incentives  to
contribute  to  the  growth  and  development  of  the  Company  because  of the
opportunity to acquire an equity interest in the Company.  In our proposed stock
issuance to Mr.  Widdicombe,  he will receive the opportunity to profit from any
rise in the market value of our Common Stock.

      These  shares  will be issued in  reliance  on the  exemption  provided by
Section  4(2) of the  Securities  Act as a  transaction  not  involving a public
offering.

      The Board of Directors unanimously recommends that shareholders vote "FOR"
this proposal.  The approval of this proposal requires the affirmative vote of a
majority of the total votes cast on the proposal in person or by proxy.

              PROPOSAL FOUR: RATIFICATION OF SELECTION OF AUDITORS

      The selection of DeMeo Young McGrath ("DeMeo") to serve as the independent
auditors of the Company for the fiscal year ended  December  31,  2004,  will be
submitted  to  the  shareholders  of the  Corporation  for  ratification  at the
Meeting.  Representatives of DeMeo will be present at the Meeting, will have the
opportunity  to make a  statement  if they so desire  and will be  available  to
answer appropriate questions.

      DeMeo has served as the  Company's  independent  auditors  for each fiscal
year  since  2002.  McKean,  Paul,  Chrycy,  Fletcher & Co.  ("McKean")  was the
Company's independent auditors prior to 2002.

      DeMeo has advised the Company that neither it, nor any of its members, has
any direct financial interest in the Company as a promoter,  underwriter, voting
trustee,  director,  officer or employee.  All professional services rendered by
DeMeo during the fiscal year ended December 31, 2004 were furnished at customary
rates.

      For the fiscal year ended December 31, 2004, fees for services provided by
DeMeo and McKean were as follows:

                                                      DeMeo              McKean 
                                                     --------           --------
      Audit Fees(1)                                  $290,302           $ 16,713
      
      Audit-Related Fees(2)                          $ 22,743           $      0
      
      Tax Fees(3)                                    $ 56,748           $      0
                                                     --------           --------
      
      Total                                          $369,793           $ 16,713

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

      (1)   Audit fees consisted of audit work  performed in the  preparation of
            financial statements, as well as work generally only the independent
            auditor can  reasonably  be expected to provide,  such as  statutory
            audits.
      
      (2)   Audit-related fees consisted primarily of audits of employee benefit
            plans and special procedures related to regulatory filings in 2004.

      (3)   Tax fees consisted  primarily of assistance  with tax compliance and
            reporting.


                                       21


      The Board of Directors unanimously recommends that shareholders vote "FOR"
this proposal.  The approval of this proposal requires the affirmative vote of a
majority of the total votes cast on the proposal in person or by proxy.

                   SUBMISSION OF FUTURE SHAREHOLDER PROPOSALS

Shareholder Proposals for Inclusion in Next Year's Proxy Statement

      Pursuant to Rule 14a-8 of the SEC's proxy rules,  a shareholder  intending
to present a proposal to be included in the proxy  statement for our 2006 Annual
Meeting of  Shareholders  must  deliver a proposal  in writing to our  principal
executive  offices no later than the close of business on January ____, 2006 (or
a reasonable  time before we begin to print and mail the proxy materials for the
2006 annual meeting,  if we change the date of the 2006 annual meeting more than
30 days  from the date of this  year's  Annual  Meeting).  Proposals  should  be
addressed to:  Secretary,  21st Century Holding Company,  3661 West Oakland Park
Boulevard, Suite 300, Lauderdale Lakes, Florida 33311. Proposals of shareholders
must also comply with the SEC's rules  regarding  the  inclusion of  shareholder
proposals  in  proxy  materials,  and we may omit any  proposal  from our  proxy
materials that does not comply with the SEC's rules.

Other Shareholder Proposals for Presentation at Next Year's Annual Meeting


      Shareholder proposals intended to be presented at, but not included in the
proxy materials for, our 2006 annual  meeting,  must be timely received by us in
writing at our principal  executive  offices,  addressed to the Secretary of the
Company  as  indicated  above.  Under the  Company's  bylaws,  to be  timely,  a
shareholder's  notice  must  be  delivered  to or  mailed  and  received  at the
Company's  principal  executive  offices not less than 60 days, nor more than 90
days, prior to the meeting. If we give less than 70 days' notice or prior public
disclosure of the meeting date, however,  notice by a shareholder will be timely
given if  received  by the  Company  not later than the close of business on the
tenth day following either the date we publicly  announce the date of our annual
meeting or the date of mailing of the notice of the  meeting,  whichever  occurs
first. A shareholder's  notice to the Secretary must set forth as to each matter
the shareholder proposes to bring before the annual meeting:


      o     A brief description of the business desired to be brought before the
            annual meeting and the reasons for  conducting  such business at the
            annual meeting,

      o     The  name and  record  address  of the  shareholder  proposing  such
            business,

      o     The  class  and   number  of  shares   beneficially   owned  by  the
            shareholder, and

      o     Any material interest of the shareholder in such business.

      The SEC's  rules  permit  our  management  to vote  proxies  on a proposal
presented by a shareholder as described  above, in the discretion of the persons
named as proxy, if:

      o     We receive timely notice of the proposal and advise our shareholders
            in the 2006  proxy  materials  of the  nature of the  matter and how
            management intends to vote on the matter; or

      o     We do not receive  timely notice of the proposal in compliance  with
            our bylaws.


                                       22


                                 OTHER BUSINESS

      The Board  knows of no other  business  to be  brought  before  the Annual
Meeting.  If, however, any other business should properly come before the Annual
Meeting,  the persons named in the accompanying proxy will vote proxies in their
discretion as they may deem appropriate,  unless they are directed by a proxy to
do otherwise.

                   HOUSEHOLDING OF ANNUAL DISCLOSURE DOCUMENTS

      As permitted by the Exchange Act, only one copy of this Proxy Statement is
being  delivered  to  shareholders  residing  at the same  address,  unless such
shareholders  have notified us of their desire to receive multiple copies of the
Proxy Statement.

      We will promptly deliver, upon oral or written request, a separate copy of
the Proxy Statement to any shareholder  residing at an address to which only one
copy was mailed.  Requests for additional copies should be directed to our Chief
Financial  Officer by phone at (954) 581-9993 or by mail to the Chief  Financial
Officer, 3661 West Oakland Park Boulevard,  Suite 300, Lauderdale Lakes, Florida
33311.

      Shareholders residing at the same address and currently receiving only one
copy of the Proxy Statement may contact our Chief Financial  Officer by phone at
(954) 581-9993 or by mail to the Chief Financial Officer, 3661 West Oakland Park
Boulevard, Suite 300, Lauderdale Lakes, Florida 33311 to request multiple copies
of the Proxy Statement in the future.


                INCORPORATION OF CERTAIN INFORMATION BY REFERENCE

      The SEC allows us to  "incorporate  by  reference"  information  into this
Proxy Statement. This means that we can disclose important information to you by
referring you to another document filed separately with the SEC. The information
incorporated  by reference is considered  to be a part of this Proxy  Statement,
except for any  information  that is superseded by information  that is included
directly in this Proxy Statement.

      This Proxy Statement  incorporates by reference the following  sections of
our Annual  Report on Form 10-K for the year ended  December 31, 2004,  as filed
previously  with the SEC and as amended  and  restated  in its  entirety by Form
10-K/As filed on April 29, 2005 and May 17, 2005:

      o     Item 6, Selected Financial Data;

      o     Item 7, Management's  Discussion and Analysis of Financial Condition
            and Results of Operations;

      o     Item 7A,  Quantitative  and Qualitative  Disclosure About Management
            Risk; and

      o     Item 8, Financial Statements and Supplementary Data.

      This Proxy Statement also incorporates by reference the following sections
of our  Quarterly  Report on Form 10-Q for the quarter  ended March 31, 2005, as
filed previously with the SEC on May 16, 2005:

      o     Item 1, Financial Statements;

      o     Item 2, Management's  Discussion and Analysis of Financial Condition
            and Results of Operations; and

      o     Item 3,  Quantitative  and Qualitative  Disclosure  About Management
            Risk.

      Copies of each of these reports are being mailed to shareholders with this
Proxy Statement. In addition, we will provide, without charge, to each person to
whom this Proxy  Statement  is  delivered,  upon written or oral request of such
person and by first class mail or other equally prompt means within one business
day of  receipt  of  such  request,  a copy of the  information  that  has  been
incorporated  by  reference.  You may obtain a copy of these  documents  and any
amendments  thereto by writing to the Secretary at our executive offices at 3661
West Oakland Park Boulevard,  Suite 300, Lauderdale Lakes,  Florida 33311. These
documents  are  also  included  in  our  SEC  filings,   which  you  can  access
electronically at the SEC's website at http://www.sec.gov.


                                        By Order of the Board of Directors

                                        REBECCA L. CAMPILLO, Secretary

Lauderdale Lakes, Florida
June XX, 2005


                                       23


                          21st CENTURY HOLDING COMPANY
                 ANNUAL MEETING OF SHAREHOLDERS - JULY 19, 2005

           THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF DIRECTORS

      The   undersigned   hereby  appoints  Edward  J.  Lawson  and  Richard  A.
Widdicombe,  as  Proxies,  each with full  power to  appoint  a  substitute,  to
represent  and to vote,  with  all the  powers  the  undersigned  would  have if
personally  present,  all the shares of common  stock,  $.01 par value per share
(the "Common  Stock"),  of 21st Century  Holding Company (the "Company") held of
record by the  undersigned on May 20, 2005 at the Annual Meeting of Shareholders
to be held on July 19, 2005 or any adjournments or postponements thereof.

Proposal 1. ELECTION OF DIRECTORS

[ ]   FOR ALL THE NOMINEES LISTED BELOW
[ ]   WITHHOLD  AUTHORITY  (except as marked to the contrary  below) TO VOTE FOR
      ALL NOMINEES LISTED BELOW.

         Carl Dorf                          Charles B. Hart, Jr.

(INSTRUCTION:  To withhold  authority for any  individual  nominees,  write that
nominee's name in the space below.)

--------------------------------------------------------------------------------
Proposal 2.  APPROVAL OF THE POSSIBLE  ISSUANCE OF 20% OR MORE OF THE  COMPANY'S
COMMON STOCK IN CONNECTION WITH SECURITIES  ISSUED IN THE COMPANY'S 2004 PRIVATE
PLACEMENT

[  ] For      [  ] Against      [  ] Abstain

--------------------------------------------------------------------------------
Proposal 3.  APPROVAL OF THE  ISSUANCE OF 3,500 SHARES OF THE  COMPANY'S  COMMON
STOCK TO THE COMPANY'S CHIEF EXECUTIVE OFFICER

[  ] For      [  ] Against      [  ] Abstain

--------------------------------------------------------------------------------
Proposal 4.  RATIFICATION  OF SELECTION OF DEMEO YOUNG  MCGRATH AS THE COMPANY'S
INDEPDENDENT AUDITORS FOR THE FISCAL YEAR ENDED DECEMBER 31, 2004

[  ] For      [  ] Against      [  ] Abstain

--------------------------------------------------------------------------------
Proposal 5. APPROVAL OF THE ADJOURNMENT OR POSTPONEMENT OF THE ANNUAL MEETING TO
A LATER DATE IF NECESSARY IN ORDER TO SOLICIT ADDITIONAL PROXIES IN FAVOR OF ANY
OF THE PROPOSALS TO BE CONSIDERED AT THE ANNUAL MEETING

[  ] For      [  ] Against      [  ] Abstain

      This proxy, when properly  executed,  will be voted in the manner directed
herein by the undersigned  shareholder.  If no direction is made, the Proxy will
be voted FOR  Proposals  1, 2, 3 and 4. In their  discretion,  the  Proxies  are
authorized  to vote upon such other  business  as may  properly  come before the
meeting or any adjournments or postponements thereof.

                                       Dated:
                                             -----------------------------, 2005


-----------------------------------    -----------------------------------------
(Signature)                            (Signature)

                                PLEASE SIGN HERE

Please date this proxy and sign your name exactly as it appears hereon.

Where there is more than one owner,  each should sign. When signing as an agent,
attorney,  administrator,  executor, guardian, or trustee, please add your title
as such.  If executed  by a  corporation,  the proxy  should be signed by a duly
authorized officer who should indicate his office.

PLEASE DATE, SIGN, AND MAIL THIS PROXY CARD IN THE ENCLOSED ENVELOPE. NO POSTAGE
                  IS REQUIRED IF MAILED IN THE UNITED STATES.