UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                    FORM 8-K

                                 CURRENT REPORT

                     Pursuant to Section 13 or 15(d) of the
                         Securities Exchange Act of 1934

                        Date of Report: December 29, 2005
                        (Date of earliest event reported)

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

            Florida                    0-2500111             65-0248866
--------------------------------    ----------------   -------------------------
(State or other jurisdiction of     (Commission File      (I.R.S. Employer
         incorporation)                  Number)         Identification No.)

       3661 West Oakland Park Blvd., Suite 300
                Lauderdale Lakes, FL                           33311
------------------------------------------------------   ------------------
      (Address of principal executive offices)              (Zip Code)

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

                                 NOT APPLICABLE
          (Former Name or Former Address, if Changed Since Last Report)

Check the appropriate box below if the Form 8-K filing is intended to
simultaneously satisfy the filing obligation of the registrant under any of the
following provisions (see General Instruction A.2. below):

|_|         Written communications pursuant to Rule 425 under the Securities Act
            (17 CFR 230.425)

|_|         Soliciting  material  pursuant to Rule 14a-12 under the Exchange Act
            (17 CFR 240.14a-12)

|_|         Pre-commencement  communications pursuant to Rule 14d-2(b) under the
            Exchange Act (17 CFR 240.14d-2(b))

|_|         Pre-commencement communications pursuant to Rule 13e-4( c) under the
            Exchange Act (17 CFT 240.13e-4( c))


<PAGE>

Item 5.02. Departure of Directors or Principal Officers;  Election of Directors;
Appointment of Principal Officers

      Mr. Michael H. Braun was  unanimously  appointed to the Board of Directors
of 21st Century  Holding  Company (the  "Company")  effective as of December 29,
2005. Mr. Braun will fill the vacancy  created by the resignation of Mr. Richard
Widdicombe effective as of November 10, 2005. Mr. Braun will serve the remainder
of the class I term through the annual shareholders meeting to be held in 2007.

      Mr. Braun has been with the Company since  December  1998. He is currently
the President of Federated National Insurance Company, a wholly-owned subsidiary
of the Company and receives an annual  salary of $137,000 per year. He currently
owns options to purchase  40,000 shares of the Company's  common stock according
to the following grant  criteria:  1) 15,000 fully vested options at an exercise
price of 9.167  which  expire on June 4, 2008;  2) 5,000  options at an exercise
price of $16.00, vesting at 20% per year and expiring on September 14, 2011; and
3) 20,000 options at an exercise price of $15.79 per share, vesting 20% per year
and expiring on December 5, 2011.  Mr. Braun has been in the insurance  industry
since 1996 and holds a 220  property  and  casualty  insurance  license with the
State of Florida.  He earned his Bachelors degree in Business  Administration at
Suny University in Buffalo, New York.

      The  following  agreements  are currently in force between the Company and
Mr.  Braun:  Non-Compete  Agreement  dated  December  19,  2005,  Annual  Review
Agreement  dated  December  19,  2005  and an  Indemnification  Agreement  dated
December 19, 2005.

Item 9.01 Financial Statements and Exhibits.

      (c) Exhibits.

            10.1  Non-Compete  Agreement  between the Company and Michael  Braun
                  dated December 19, 2005,

            10.2  Annual Review Agreement  between the Company and Michael Braun
                  dated December 19, 2005

            10.3  Indemnification  Agreement  between  the  Company  and Michael
                  Braun dated December 19, 2005


                                       2
<PAGE>

                                   SIGNATURES

Pursuant  to the  requirements  of the  Securities  Exchange  Act of  1934,  the
registrant  has duly  caused  this  report  to be  signed  on its  behalf by the
undersigned hereunto duly authorized.


                                        21ST CENTURY HOLDING COMPANY


Date:  December 30, 2005                By: /s/ JAMES GORDON JENNINGS, III
                                           -------------------------------------
                                        Name:   James Gordon Jennings, III
                                        Title:  Chief Financial Officer
                                                (Principal Accounting and
                                                Financial Officer)


                                       3
<PAGE>

                                  EXHIBIT LIST


            10.1  Non-Compete  Agreement  between the Company and Michael  Braun
                  dated December 19, 2005,

            10.2  Annual Review Agreement  between the Company and Michael Braun
                  dated December 19, 2005

            10.3  Indemnification  Agreement  between  the  Company  and Michael
                  Braun dated December 19, 2005



                                       4
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UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                    FORM 8-K

                                 CURRENT REPORT

                     Pursuant to Section 13 or 15(d) of the
                         Securities Exchange Act of 1934

                        Date of Report: December 29, 2005
                        (Date of earliest event reported)

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

            Florida                    0-2500111             65-0248866
--------------------------------    ----------------   -------------------------
(State or other jurisdiction of     (Commission File      (I.R.S. Employer
         incorporation)                  Number)         Identification No.)

       3661 West Oakland Park Blvd., Suite 300
                Lauderdale Lakes, FL                           33311
------------------------------------------------------   ------------------
      (Address of principal executive offices)              (Zip Code)

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

                                 NOT APPLICABLE
          (Former Name or Former Address, if Changed Since Last Report)

Check the appropriate box below if the Form 8-K filing is intended to
simultaneously satisfy the filing obligation of the registrant under any of the
following provisions (see General Instruction A.2. below):

|_|         Written communications pursuant to Rule 425 under the Securities Act
            (17 CFR 230.425)

|_|         Soliciting  material  pursuant to Rule 14a-12 under the Exchange Act
            (17 CFR 240.14a-12)

|_|         Pre-commencement  communications pursuant to Rule 14d-2(b) under the
            Exchange Act (17 CFR 240.14d-2(b))

|_|         Pre-commencement communications pursuant to Rule 13e-4( c) under the
            Exchange Act (17 CFT 240.13e-4( c))
Item 5.02. Departure of Directors or Principal Officers;  Election of Directors;
Appointment of Principal Officers

      Mr. Michael H. Braun was  unanimously  appointed to the Board of Directors
of 21st Century  Holding  Company (the  "Company")  effective as of December 29,
2005. Mr. Braun will fill the vacancy  created by the resignation of Mr. Richard
Widdicombe effective as of November 10, 2005. Mr. Braun will serve the remainder
of the class I term through the annual shareholders meeting to be held in 2007.

      Mr. Braun has been with the Company since  December  1998. He is currently
the President of Federated National Insurance Company, a wholly-owned subsidiary
of the Company and receives an annual  salary of $137,000 per year. He currently
owns options to purchase  40,000 shares of the Company's  common stock according
to the following grant  criteria:  1) 15,000 fully vested options at an exercise
price of 9.167  which  expire on June 4, 2008;  2) 5,000  options at an exercise
price of $16.00, vesting at 20% per year and expiring on September 14, 2011; and
3) 20,000 options at an exercise price of $15.79 per share, vesting 20% per year
and expiring on December 5, 2011.  Mr. Braun has been in the insurance  industry
since 1996 and holds a 220  property  and  casualty  insurance  license with the
State of Florida.  He earned his Bachelors degree in Business  Administration at
Suny University in Buffalo, New York.

      The  following  agreements  are currently in force between the Company and
Mr.  Braun:  Non-Compete  Agreement  dated  December  19,  2005,  Annual  Review
Agreement  dated  December  19,  2005  and an  Indemnification  Agreement  dated
December 19, 2005.

Item 9.01 Financial Statements and Exhibits.

      (c) Exhibits.

            10.1  Non-Compete  Agreement  between the Company and Michael  Braun
                  dated December 19, 2005,

            10.2  Annual Review Agreement  between the Company and Michael Braun
                  dated December 19, 2005

            10.3  Indemnification  Agreement  between  the  Company  and Michael
                  Braun dated December 19, 2005

                                       2
SIGNATURES

Pursuant  to the  requirements  of the  Securities  Exchange  Act of  1934,  the
registrant  has duly  caused  this  report  to be  signed  on its  behalf by the
undersigned hereunto duly authorized.

                                        21ST CENTURY HOLDING COMPANY

Date:  December 30, 2005                By: /s/ JAMES GORDON JENNINGS, III
                                           -------------------------------------
                                        Name:   James Gordon Jennings, III
                                        Title:  Chief Financial Officer
                                                (Principal Accounting and
                                                Financial Officer)

                                       3
EXHIBIT LIST

            10.1  Non-Compete  Agreement  between the Company and Michael  Braun
                  dated December 19, 2005,

            10.2  Annual Review Agreement  between the Company and Michael Braun
                  dated December 19, 2005

            10.3  Indemnification  Agreement  between  the  Company  and Michael
                  Braun dated December 19, 2005

                                       4