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 (Date of earliest event reported): June 28, 2005


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


           Florida                      0-2500111              65-0248866
----------------------------    ------------------------   -------------------
(State or other jurisdiction    (Commission File Number)    (I.R.S. Employer
       of incorporation)                                   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 CFR 240.13e-4(c))
<PAGE>

Item 1.01         Entry into a Material Definitive Agreement.

         Federated National Insurance Company ("Federated  National"),  a wholly
owned  subsidiary of 21st Century  Holding Company (the  "Company"),  has, as of
June 28, 2005, agreed upon its aggregate  catastrophe  reinsurance  coverage for
the 2005-2006 hurricane season.

      Federated National's  reinsurance  arrangements are with reinsurers in the
U.S., London and Bermuda  reinsurance  markets, as well as the Florida Hurricane
Catastrophe Fund, as follows:

         Platinum Underwriters Reinsurance, Inc.
         Alea North America Insurance Company
         American Re-Insurance Company
         DaVinci Reinsurance Ltd.
         Renaissance Reinsurance Ltd.
         Rosemont Reinsurance Ltd.
         PXRE Reinsurance Ltd.
         Ace Tempest Reinsurance  Ltd.
         Amlin Underwriting Limited
         Cathedral Underwriting Limited
         Axa Re

         This  reinsurance   coverage  will  reimburse  Federated  National  for
property losses under its homeowners'  insurance  policies resulting from storms
that cause damage in the State of Florida, the state in which Federated National
is currently writing these types of policies,  through June 30, 2006. Under this
coverage, Federated National is responsible for the first $3 million in property
losses  resulting  from  a  storm  and  Federated   National's   reinsurers  are
responsible  for the next $212  million in  aggregate  property  losses for said
storm.  Our amount of  reinsurance  coverage was  determined by  subjecting  our
property risks to statistical forecasting models that are designed to quantify a
catastrophic  event in terms of the frequency of a storm occurring once in every
"n" years. Our reinsurance coverage  contemplates a catastrophic event occurring
once  every  100  years.   Federated   National  has  also  obtained   automatic
reinstatement   coverage,   meaning  that  the  reinsurance   coverage  will  be
automatically available for a second storm with the same $3 million retention by
Federated National.

         As  compared  to  Federated  National's  reinsurance  coverage  for the
2004-2005  hurricane  season,  the current  season's  coverage  would reduce the
losses retained by Federated National. For example, whereas Federated National's
net  retained  losses  in 2004  from  Hurricanes  Charley  and  Frances  totaled
approximately $20 million,  if the current year's coverage had been in effect in
2004, Federated National's net retained losses would have totaled  approximately
$6 million.

         Federated  National's  premiums  for the  reinsurance  coverage are $19
million payable in quarterly installments beginning July 1, 2005 for the private
reinsurers  and a total  of $7  million  payable  in three  installments  to the
Florida  Hurricane  Catastrophe Fund from August 2005 through December 2005. The
greater  expense  resulting  from  these  premiums  has  been  reflected  in the
Company's previously announced earnings guidance for 2005.

<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:  July 1, 2005                By: /s/ J. Gordon Jennings III
                                       ----------------------------
                                    Name:    J. Gordon Jennings III
                                    Title:   Chief Financial Officer
                                    (Principal Accounting and Financial Officer)
{"company-data": {"conformed-name": "21ST CENTURY HOLDING CO", "cik": "0001069996", "assigned-sic": "6331", "irs-number": "650248866", "state-of-incorporation": "FL", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "8-K", "act": "34", "file-number": "000-25001", "film-number": "05933193"}, "business-address": {"street1": "3661 WEST OAKLAND PARK BLVD", "street2": "SUITE 300", "city": "LAUDERDALE LAKES", "state": "FL", "zip": "33311", "phone": "9545819993"}, "mail-address": {"street1": "3661 WEST OAKLAND PARK BLVD", "street2": "SUITE 300", "city": "LAUDERDALE LAKES", "state": "FL", "zip": "33311"}}
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 (Date of earliest event reported): June 28, 2005

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

           Florida                      0-2500111              65-0248866
----------------------------    ------------------------   -------------------
(State or other jurisdiction    (Commission File Number)    (I.R.S. Employer
       of incorporation)                                   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 CFR 240.13e-4(c))
Item 1.01         Entry into a Material Definitive Agreement.

         Federated National Insurance Company ("Federated  National"),  a wholly
owned  subsidiary of 21st Century  Holding Company (the  "Company"),  has, as of
June 28, 2005, agreed upon its aggregate  catastrophe  reinsurance  coverage for
the 2005-2006 hurricane season.

      Federated National's  reinsurance  arrangements are with reinsurers in the
U.S., London and Bermuda  reinsurance  markets, as well as the Florida Hurricane
Catastrophe Fund, as follows:

         Platinum Underwriters Reinsurance, Inc.
         Alea North America Insurance Company
         American Re-Insurance Company
         DaVinci Reinsurance Ltd.
         Renaissance Reinsurance Ltd.
         Rosemont Reinsurance Ltd.
         PXRE Reinsurance Ltd.
         Ace Tempest Reinsurance  Ltd.
         Amlin Underwriting Limited
         Cathedral Underwriting Limited
         Axa Re

         This  reinsurance   coverage  will  reimburse  Federated  National  for
property losses under its homeowners'  insurance  policies resulting from storms
that cause damage in the State of Florida, the state in which Federated National
is currently writing these types of policies,  through June 30, 2006. Under this
coverage, Federated National is responsible for the first $3 million in property
losses  resulting  from  a  storm  and  Federated   National's   reinsurers  are
responsible  for the next $212  million in  aggregate  property  losses for said
storm.  Our amount of  reinsurance  coverage was  determined by  subjecting  our
property risks to statistical forecasting models that are designed to quantify a
catastrophic  event in terms of the frequency of a storm occurring once in every
"n" years. Our reinsurance coverage  contemplates a catastrophic event occurring
once  every  100  years.   Federated   National  has  also  obtained   automatic
reinstatement   coverage,   meaning  that  the  reinsurance   coverage  will  be
automatically available for a second storm with the same $3 million retention by
Federated National.

         As  compared  to  Federated  National's  reinsurance  coverage  for the
2004-2005  hurricane  season,  the current  season's  coverage  would reduce the
losses retained by Federated National. For example, whereas Federated National's
net  retained  losses  in 2004  from  Hurricanes  Charley  and  Frances  totaled
approximately $20 million,  if the current year's coverage had been in effect in
2004, Federated National's net retained losses would have totaled  approximately
$6 million.

         Federated  National's  premiums  for the  reinsurance  coverage are $19
million payable in quarterly installments beginning July 1, 2005 for the private
reinsurers  and a total  of $7  million  payable  in three  installments  to the
Florida  Hurricane  Catastrophe Fund from August 2005 through December 2005. The
greater  expense  resulting  from  these  premiums  has  been  reflected  in the
Company's previously announced earnings guidance for 2005.
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:  July 1, 2005                By: /s/ J. Gordon Jennings III
                                       ----------------------------
                                    Name:    J. Gordon Jennings III
                                    Title:   Chief Financial Officer
                                    (Principal Accounting and Financial Officer)