21st Century Holding Company Reports Third Quarter Results with Earnings of $0.29 Per Share.

LAUDERDALE LAKES, Fla. -- 21st Century Holding Company (Nasdaq:TCHC) today reported results for the quarter ended September 30, 2005 (see attached tables).

For the three months ended September 30, 2005, the Company reported net income of $1,852,718, or $0.29 per share on 6,384,386 undiluted shares, versus a net loss of $16,946,258 or $2.86 per share on 5,925,952 undiluted shares in the same three-month period last year. On a diluted share basis, the Company reported earnings of $0.28 per share, based on 6,589,257 average diluted shares outstanding for the three month period.

For the nine months ended September 30, 2005, the Company reported net income of $10,696,539, or $1.73 per share on 6,189,040 undiluted shares versus net loss of $10,347,473 or $1.79 per share on 5,786,803 undiluted shares in the same nine month period last year. On a diluted share basis, the Company reported earnings of $1.64 per share, based on 6,533,575 average diluted shares outstanding for the nine month period.

Net premiums earned decreased $6.1 million or 22.6% to $20.7 million for the three months ended September 30, 2005, as compared to $26.8 million for the same three-month period last year. Net premium earned increased $6.2 million or 11.2% to $61.4 million for the nine months ended September 30, 2005, as compared to $55.2 million for the same nine month period last year.

Total revenues decreased $5.4 million or 18.5% to $23.7 million for the three months ended September 30, 2005, as compared to $29.1 million for the same three-month period last year. Total revenues increased $7.7 million or 12.4% to $70.2 million for the nine months ended September 30, 2005, as compared to $62.5 million for the same nine month period last year.

Edward J. (Ted) Lawson, Chairman, CEO, and President, said, "Had the Company not been hit by two major hurricanes in the third quarter, the Company would have earned approximately $1.00 per share for the quarter. The drop in revenues and net premiums earned recorded in the third quarter of this year versus the third quarter of last year will not be repeated in the fourth quarter. Revenues and net premiums earned are both projected to increase substantially during the current fourth quarter and next year. Company guidance of $4.00 per share in calendar year 2006 reflects those increases."

The Company will hold an investor conference call at 4:30 PM (ET) today, November 10, 2005. Mr. Lawson and Mr. J. Gordon Jennings III, CFO, will discuss the financial results and review the outlook for the Company. Messrs. Lawson and Jennings invite interested parties to participate in the conference call. Listeners can access the conference call by dialing toll free 888-460-6235, conference ID 2068660. Please call at least five minutes in advance to ensure that you are connected prior to the presentation. A replay of the conference call will be available for 7 days at 800-642-1687.

About the Company

The Company, through its subsidiaries, underwrites standard and non-standard personal automobile insurance, flood insurance, general liability insurance, mobile home insurance and homeowners' property and casualty insurance in the State of Florida. The Company underwrites general liability coverage as an admitted carrier in the States of Louisiana, Texas and Alabama for more than 300 classes of business, including special events. The Company also operates as an approved (non-admitted) carrier in the States of Georgia and Kentucky offering the same general liability products. In addition, the Company has underwriting authority and processes claims for third party insurance companies. In addition to insurance services, the Company offers premium finance services to its insureds as well as insureds of certain third party insurance companies.

Safe harbor statements under the Private Securities Litigation Reform Act of 1995: Statements in this press release that are not historical fact are forward-looking statements that are subject to certain risks and uncertainties that could cause actual events and results to differ materially from those discussed herein. Without limiting the generality of the foregoing, words such as "may," "will," "expect," "believe," "anticipate," "intend," "could," "would," "estimate," or "continue" or the other negative variations thereof or comparable terminology are intended to identify forward-looking statements. The risks and uncertainties include, without limitation, uncertainties related to estimates, assumptions and projections generally; inflation and other changes in economic conditions (including changes in interest rates and financial markets); pricing competition and other initiatives by competitors; ability to obtain regulatory approval for applications to underwrite in an additional jurisdiction or for requested rate changes, and the timing thereof; legislative and regulatory developments; the outcome of litigation pending against the Company and any settlement thereof; risks related to the nature of the Company's business; dependence on investment income and the composition of the Company's investment portfolio; the adequacy of the Company's liability for loss and loss adjustment expense; insurance agents; claims experience; limited experience in the insurance industry; ratings by industry services; catastrophe losses; reliance on key personnel; weather conditions (including the severity and frequency of storms, hurricanes, tornadoes and hail); changes in driving patterns and loss trends; acts of war and terrorist activities; court decisions and trends in litigation, and health care and auto repair costs; and other matters described from time to time by the Company in releases and publications, and in periodic reports and other documents filed with the United States Securities and Exchange Commission. In addition, investors should be aware that generally accepted accounting principles prescribe when a company may reserve for particular risks, including litigation exposures. Accordingly, results for a given reporting period could be significantly affected if and when a reserve is established for a major contingency. Reported results may therefore appear to be volatile in certain accounting periods.

21st CENTURY HOLDING COMPANY
                 Consolidated Statements of Operations
                              (Unaudited)

                      Three Months Ended        Nine Months Ended
                           Sept 30,                  Sept 30,
Revenue:               2005         2004         2005         2004
                   ------------ ------------ ------------ ------------
  Gross premiums
   written        $ 25,355,235 $ 24,301,800 $ 86,815,187 $ 73,929,571
  Gross premiums
   ceded            (7,188,343)   1,535,612  (12,142,786)     975,429
                   ------------ ------------ ------------ ------------

    Net premiums
     written        18,166,892   25,837,412   74,672,401   74,905,000
                   ------------ ------------ ------------ ------------

  Increase
   (Decrease)
   in prepaid
   reinsurance
   premiums             72,745      760,823   (5,437,633)  (5,334,921)
  Decrease
   (Increase)
   in unearned
   premiums          2,462,575      156,954   (7,808,508) (14,342,263)
                   ------------ ------------ ------------ ------------
    Net change in
     prepaid
     reinsurance
     premiums and
     unearned
     premiums        2,535,320      917,777  (13,246,141) (19,677,184)
                   ------------ ------------ ------------ ------------

    Net premiums
     earned         20,702,212   26,755,189   61,426,260   55,227,816
  Finance revenue      807,778      784,584    2,849,989    2,824,568
  Managing general
   agent fees          558,883      501,225    1,811,576    1,488,405
  Net investment
   income              972,302      839,641    2,776,098    2,141,686
  Net realized
   investment
   gains                    --       80,959      285,033      261,386
  Other income         673,643      148,595    1,078,024      539,300
                   ------------ ------------ ------------ ------------

    Total revenue   23,714,818   29,110,193   70,226,980   62,483,161
                   ------------ ------------ ------------ ------------

Expenses:
  Loss and loss
   adjustment
   expenses         13,806,490   42,292,556   33,025,262   56,385,548
  Operating and
   underwriting
   expenses          1,136,199    8,424,750    4,925,011   12,341,613
  Salaries and
   wages             1,600,716    1,623,134    4,759,417    4,391,306
  Interest expense     313,962      186,902    1,123,893      631,824
  Policy
   acquisition
   costs, net of
   amortization      3,920,679    2,521,738   10,968,721    4,645,906
                   ------------ ------------ ------------ ------------

    Total expenses  20,778,046   55,049,080   54,802,304   78,396,197

Income (loss) from
 cont'd ops before
 provision
 (benefit) for inc
 tax exp             2,936,772  (25,938,887)  15,424,676  (15,913,036)
Provision
 (benefit) for
 income tax
 expense             1,084,054   (9,337,258)   5,762,741   (5,677,392)
                   ------------ ------------ ------------ ------------
    Net income
     (loss) from
     continuing
     operations      1,852,718  (16,601,629)   9,661,935  (10,235,644)
Discontinued
 operations:
    Income (loss)
     from
     discontinued
     operations
     (including
     gain on
     disposal of
     $1,630,000
     and $0,
     respectively)          --     (540,496)   1,630,000     (173,857)
Provision
 (benefit) for
 income tax
 expense                    --     (195,867)     595,396      (62,028)
                   ------------ ------------ ------------ ------------
    Income (loss)
     from
     discontinued
     operations             --     (344,629)   1,034,604     (111,829)
                   ------------ ------------ ------------ ------------
    Net income
     (loss)       $  1,852,718 $(16,946,258)$ 10,696,539 $(10,347,473)
                   ============ ============ ============ ============
Basic net income
 (loss) per share
 from continuing
 operations       $      0. 29 $      (2.80)$       1.56 $      (1.77)
                   ------------ ------------ ------------ ------------
Basic net income
 (loss) per share
 from discontinued
 operations       $         -- $      (0.06)$       0.17 $      (0.02)
                   ------------ ------------ ------------ ------------
Basic net income
 (loss) per share $       0.29 $      (2.86)$       1.73 $      (1.79)
                   ============ ============ ============ ============
Fully diluted net
 income (loss) per
 share from
 continuing
 operations       $       0.28 $      (2.80)$       1.48 $      (1.77)
                   ------------ ------------ ------------ ------------
Fully diluted net
 income (loss) per
 share from
 discontinued
 operations       $         -- $      (0.06)$       0.16 $      (0.02)
                   ------------ ------------ ------------ ------------
Fully diluted net
 income (loss) per
 share            $       0.28 $      (2.86)$       1.64 $      (1.79)
                   ============ ============ ============ ============

Weighted average
 number of common
 shares
 outstanding         6,384,386    5,925,952    6,189,040    5,786,803
                   ============ ============ ============ ============

Weighted average
 number of common
 shares
 outstanding
 (assuming
 dilution)           6,589,257    6,279,826    6,533,575    6,248,663
                   ============ ============ ============ ============

Dividends declared
 per share        $       0.08 $       0.08 $       0.24 $       0.24
                   ============ ============ ============ ============
21st CENTURY HOLDING COMPANY
                          Balance Sheet Data
                              (Unaudited)

                                                  Period Ending
                                              09/30/05     12/31/04
                                             ------------ ------------

Total Cash & Investments                    $ 95,251,216 $ 90,509,879
Total Assets                                $153,824,591 $163,601,372
Unpaid Loss and Loss Adjustment Expense     $ 36,128,129 $ 46,570,679
Total Liabilities                           $117,402,051 $138,624,637
Total Shareholders' Equity                  $ 36,422,540 $ 24,976,735
Common Stock Outstanding                       6,393,716    6,047,942
Book Value Per Share                        $       5.70 $       4.13
Premium Breakout
                                                ------------------
                                                 9 Months Ending

Line of Business                              09/30/05     09/30/04
----------------                             ------------ ------------
Automobile                                       19.0%        21.4%
Homeowners'                                      61.0%        63.8%
General Liability                                19.6%        13.2%
Mobile Home Owners                                0.4%         1.6%
                                             ------------ ------------
Gross Written Premiums                          100.0%       100.0%


                                       Loss Ratios

                       3 Months Ending            9 Months Ending
Line of Business    09/30/05      09/30/04    09/30/05      09/30/04
----------------   ------------ ------------ ------------ ------------
Automobile             54.9%        108.3%       60.6%         90.3%
Homeowners'           105.0%        308.0%       66.0%        165.3%
General Liability       6.8%          9.9%       17.0%         17.7%
All Lines              66.7%        209.1%       53.8%        115.8%