SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549


                                   FORM 10-K/A
                                 AMENDMENT NO. 2
                        FOR ANNUAL AND TRANSITION REPORTS
                     PURSUANT TO SECTIONS 13 OR 15(d) OF THE
                         SECURITIES EXCHANGE ACT OF 1934


(MARK ONE)

[X]      ANNUAL REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES ACT OF 1934
         For the fiscal year ended December 31, 2002

                                       or

[ ]      TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE
         ACT OF 1934 For the transition period of _____________to_______________

                        Commission file number 0-2500111

                          21ST CENTURY HOLDING COMPANY
             (Exact name of registrant as specified in its Charter)

             FLORIDA                                   65-0248866
----------------------------------          ------------------------------------
(State or other jurisdiction of             (I.R.S.  Employer Identification No)
incorporation or organization)


                4161 N.W. 5TH STREET, PLANTATION, FLORIDA 33317
                -----------------------------------------------
               (Address of Principal executive offices) (Zip Code)

                                 (954) 581-9993
                                 --------------
               Registrant's telephone number, including area code


    Securities registered pursuant to Section 12(b) of the Exchange Act: None

      Securities registered pursuant to Section 12(g) of the Exchange Act:
                     Common Stock, par value $0.01 per share
                                (Title of Class)

         Indicate by check mark whether the registrant (1) has filed all reports
required to be filed by Section 13 or 15(d) of the Securities Exchange Act of
1934 during the preceding 12 months, and (2) has been subject to such filing
requirements for the past 90 days. Yes [X]   No [ ]

         Indicate by check mark if disclosure of delinquent filers pursuant to
Item 405 of Regulation S-X is not contained herein, and will not be contained,
to the best of registrant's knowledge, in definitive proxy or information
statements incorporated by reference in Part III of this Form 10-K or any
amendment to this Form 10-K. [X]


         Indicate by check mark whether the registrant is an accelerated filer
(as defined in the Exchange Act Rule 12b-2). Yes [ ]  No [X]


         The aggregate market value of the Issuer's common stock held by
non-affiliates (based on the last sale of the common stock as reported by the
Nasdaq National Market) on June 30, 2002 was: $13,298,055.

         As of March 28, 2003, there were 3,012,201 shares of the common stock
outstanding.

                       DOCUMENTS INCORPORATED BY REFERENCE

         The following documents are incorporated by reference: Portions of the
Company's Proxy Statement for the 2003 Annual Meeting - Part III.




         The Company is filing this Amendment No. 2 to its Form 10-K for the
year ended December 31, 2002 solely for the purpose of adding Exhibits 10.24
through 10.27.

                                    PART IV


ITEM 15. EXHIBITS, FINANCIAL STATEMENT SCHEDULES, AND REPORTS ON FORM 8
-------  --------------------------------------------------------------

         (a)      THE FOLLOWING DOCUMENTS ARE FILED AS PART OF THIS REPORT:

                  (1)      Financial Statements

                           The following consolidated financial statements of
                           the Company and the reports of independent auditors
                           thereon are filed with this report:

                           Independent Auditors' Report (De Meo, Young,
                           McGrath).

                           Independent Auditors' Report (McKean, Paul, Chrycy,
                           Fletcher & Co.).

                           Consolidated Balance Sheets as of December 31, 2002
                           and 2001.

                           Consolidated Statements of Operations for the years
                           ended December 31, 2002, 2001 and 2000.

                           Consolidated Statements of Shareholders' Equity and
                           Comprehensive Income (Loss) for the years ended
                           December 31, 2002, 2001 and 2000.

                           Consolidated Statements of Cash Flows for the years
                           ended December 31, 2002, 2001 and 2000.

                           Notes to Consolidated Financial Statements for the
                           years ended December 31, 2002, 2001 and 2000.

                  (2)      Financial Statement Schedules

                           Schedule VI - Supplemental information concerning
                           property-casualty insurance operations


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       (3)      Exhibits



                  EXHIBIT        DESCRIPTION
                  -------        -----------
                           
                  3.1            Amended and Restated Articles of Incorporation (1)
                  3.2            Form of Registrant's Amended and Restated Bylaws (1)
                  4.1            Specimen of Common Stock Certificate (1)
                  4.2            Revised Representative's Warrant Agreement including form of Representative's Warrant (2)
                  10.1           Stock Option Plan, as amended (3)*
                  10.2           Employment Agreement between the Registrant and Edward J. Lawson (1)*
                  10.3           Employment Agreement between the Registrant and Michele V. Lawson (1)*
                  10.4           Form of Indemnification Agreement between the Registrant and its directors and executive
                                 officers (1)*
                  10.5           Revolving Credit and Term Loan Agreement between FlatIron Funding Company, LLC and FPF,
                                 Inc., as amended (1)
                  10.9           Employment Agreement between Registrant and Richard A. Widdicombe (4)*
                  10.12          Third Modification Agreement to Revolving Credit and Term Loan Agreement between FlatIron
                                 Funding Company, LLC and FPF, Inc., and Sale and Assignment Agreement between Federated
                                 Premium and FPF, Inc. (5)
                  10.13          Fourth Modification Agreement to Revolving Credit and Term Loan Agreement between Federated
                                 Premium Finance, Inc., FlatIron Funding Company, LLC, FlatIron Funding Company and FlatIron
                                 Credit Company, Inc. (6)
                  10.14          Sale and Assignment Agreement between Federated Premium Finance, Inc. and FPF, Inc.
                  10.15          Premium Receivable Servicing Agreement between Federated Premium Finance, Inc. and FPF,
                                 Inc. (6)
                  10.21          First Modification Agreement between Federated Premium Finance, Inc. and FPF, Inc. (7)
                  10.22          General Agency Agreement dated August 1, 1998 between Federated National Insurance Company
                                 and Assurance Managing General Agents, Inc. (8)
                  10.23          Managing General Agency Agreement dated September 4, 2001 between American Vehicle
                                 Insurance Company and Assurance Managing General Agents, Inc. (8)
                  10.24          Commercial and Private Passenger Automobile Quota Share Treaty dated July 18, 2003 between
                                 Federated National Insurance Company and TransAtlantic Reinsurance Company (9)
                  10.25          Addendum No. 1 dated August 22, 2002 to Commercial and Private Passenger Automobile Quota
                                 Share Treaty between Federated National Insurance Company and TransAtlantic Reinsurance
                                 Company (9)
                  10.26          Private Passenger Automobile Quota Share Treaty dated April 29, 2002 between American
                                 Vehicle Insurance Company and TransAtlantic Reinsurance Company (9)
                  10.27          Addendum No. 1 dated August 8, 2002 to Private Passenger Automobile Quota Share Treaty
                                 between American Vehicle Insurance Company and TransAtlantic Reinsurance COmpany (9)
                  16.1           Letter from McKean, Paul, Chrycy, Fletcher & Co. (10)
                  21.1           Subsidiaries of the Registrant (6)
                  23.1           Consent of McKean, Paul, Chrycy, Fletcher & Co., Independent Certified Public Accountants
                                 (8)
                  23.2           Consent of De Meo, Young, McGrath, Independent Certified Public Accountants (8)
                  31.1           Certification of Chief Executive Officer pursuant to Section 302 of the Sarbanes-Oxley Act
                                 (9)
                  31.2           Certification of Chief Financial Officer pursuant to Section 302 of the Sarbanes-Oxley Act
                                 (9)
                  32.1           Certification of Chief Executive Officer pursuant to Section 906 of the Sarbanes-Oxley Act
                                 (9)
                  32.2           Certification of Chief Financial Officer pursuant to Section 906 of the Sarbanes-Oxley Act
                                 (9)
                  99.1           Form S-8 filed January 14, 2003 to register 1998 Stock Option Plan as amended, 2001
                                 Franchise Program Stock Option Plan, 2002 Stock Option Plan, Warrant to Purchase 12,500
                                 Shares of Common Stock, and Warrant to Purchase 50,000 Shares of Common Stock and
                                 incorporated herein by reference. (11)


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*        MANAGEMENT COMPENSATION PLAN OR ARRANGEMENT
(1)      Previously filed as an exhibit of the same number to the Registrant's
         Registration Statement on Form SB-2 (File No. 333-63623) and
         incorporated herein by reference.
(2)      Previously filed as an exhibit of the same number of the 1998 Annual
         Report on Form 10-KSB.
(3)      Previously filed as an exhibit to the Company's 2000 Annual Meeting
         Proxy Statement.
(4)      Previously filed as an exhibit of the same number of the 1999 Annual
         Report on Form 10-KSB.
(5)      Previously filed as an exhibit of the same number of the 2000 Annual
         Report on Form 10-KSB.
(6)      Previously filed as an exhibit of the same number of the 2001 Annual
         Report on Form 10-K.
(7)      Previously filed as an exhibit of the same number of the 2002 Annual
         Report on Form 10-K as originally filed.
(8)      Previously filed as an exhibit of the same number of Amendment No. 1 to
         the 2002 Annual Report on Form 10K.
(9)      Filed herewith.
(10)     Previously filed as an exhibit of the same number of Form 8-K
         dated December 4, 2002.
(11)     Previously filed as an exhibit of the same number of Form S-8,
         filed on January 16, 2003.


         (b)      REPORTS ON FORM 8-K

         On December 3, 2002, the Company's Board of Directors recommended and
approved the replacement of its principal accountants, McKean, Paul, Chrycy,
Fletcher and Co. Also on December 3, 2002 the Board of Directors recommended and
approved the replacement firm of De Meo, Young, McGrath as its independent
auditors, effective December 5, 2002.


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                                   SIGNATURES


         Pursuant to the requirements of Section 13 or 15(d) of the Exchange
Act of 1934, the registrant has duly caused this Form 10K/A (Amendment No. 2) to
be signed on its behalf by the undersigned, thereto duly authorized.


                                21ST CENTURY HOLDING COMPANY


                                By: /s/ Richard A. Widdicombe
                                   --------------------------------------
                                Richard A. Widdicombe, Chief Executive Officer


                                By: /s/ James G. Jennings, III
                                   --------------------------------------
                                James G.  Jennings, III, Chief Financial Officer
                                (Principal Financial and Accounting Officer)

Dated:  October 23, 2003

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