21st CENTURY HOLDING COMPANY REPORTS 2009 FOURTH QUARTER AND FULL YEAR RESULTS

Lauderdale Lakes, Florida, March 23, 2010 - 21st Century Holding Company (Nasdaq: TCHC), today reported results for the quarter and year ended December 31, 2009 (see tables).

For the three months ended December 31, 2009, the Company reported a net loss of $7.4 million or $0.93 per share on 8.0 million average undiluted and diluted shares outstanding, as compared to a net loss of $2.8 million, or $0.35 per share on 7.9 million average undiluted shares outstanding in the same three month period last year.

For the twelve months ended December 31, 2009, the Company reported a net loss of $10.3 million or $1.29 per share on 8.0 million undiluted and diluted shares versus a net loss of $2.5 million, or $0.31 per share on 8.0 million undiluted shares in the same twelve month period last year.

Net premiums earned decreased $4.5 million or 30.5% to $10.3 million for the three months ended December 31, 2009, as compared to $14.8 million for the same three-month period last year. Net premiums earned decreased $17.1 million or 26.3% to $48.0 million for the twelve months ended December 31, 2009, as compared to $65.1 million for the same twelve month period last year. Gross premiums written increased $11.8 million, or 67.7%, to $29.4 million for the three months ended December 31, 2009, compared with $17.6 million for the three months ended December 31, 2008. Gross premiums written increased $16.2 million, or 18.3%, to $104.4 million for the twelve months ended December 31, 2009, compared with $88.2 million for the twelve months ended December 31, 2008.

Total revenues decreased $2.8 million or 17.5% to $13.2 million for the three months ended December 31, 2009, as compared to $16.0 million for the same three-month period last year. Total revenues decreased $8.6 million or 12.8% to $58.9 million for the twelve months ended December 31, 2009, as compared to $67.5 million for the same twelve month period last year.

Fourth quarter and full year results were adversely impacted primarily by the continued effects of higher reinsurance costs and state-mandated premium mitigation credits. Partially offsetting these factors were higher premium income as the Company resumed writing homeowners insurance after the end of the wind season, the assumption of approximately $12 million of in-force premium from Citizens Property Insurance Corporation (“Citizens”) in December, and the effects of a 19% rate increase on policies written since November 2009.

Mr. Michael H. Braun, the Company’s Chief Executive Officer and President, said, “With the end of the wind season and the approval of a statewide 19% rate increase on voluntary business, we resumed writing new property business in the fourth quarter. As a result, we reported a 67% increase in gross written premiums in the fourth quarter. Offsetting this significant increase, as expected, were the continuing effects of higher reinsurance costs and state mandated mitigation credits. Additionally, on March 22, 2010, Federated National Insurance Company (“Federated National”), a wholly owned subsidiary of the Company, received notice from Demotech, Inc., a rating agency, requiring a capital infusion of $10 million by March 31, 2010 for Federated National to maintain its “A” rating with the agency. We are exploring various options to comply with this requirement.

“The Florida property insurance industry is operating in a challenging environment and while we continue to face substantial headwinds, we believe that 21st Century Holding Company is heading in the right direction. While we will continue to be affected by reinsurance costs and mitigation credits, we expect to see a gradual improvement in operating margin from the flow through of the full effect of the November 2009 rate increase on voluntary business and an anticipated decrease in the cost of reinsurance in the second half of 2010. In addition, we have applied for a 14.9% rate increase on policies assumed from Citizens. ”

The Company will hold an investor conference call at 4:30 PM (ET) today, March 23 2010. The Company’s CEO and its CFO, Peter J. Prygelski, III, will discuss the financial results and review the outlook for the Company. Messrs. Braun and Prygelski invite interested parties to participate in the conference call. A live webcast of the call will be available online at http://www.21stcenturyholding.com (in the Conference Calls section). Listeners interested in participating in the Q&A session can access the conference call by dialing toll free 877-545-1409. Please call at least five minutes in advance to ensure that you are connected prior to the presentation. A webcast replay of the conference call will be available shortly after the live webcast is completed and may be accessed via the Company’s website.

About the Company

The Company, through its subsidiaries, underwrites commercial general liability insurance, commercial residential property, homeowners’ property and casualty insurance, flood insurance, inland marine, personal automobile insurance and commercial automobile insurance in the state of Florida. The Company underwrites general liability coverage as an admitted carrier in the states of Alabama, Louisiana and Texas for more than 300 classes of business, including special events. The Company is approved to operate as a surplus lines/non-admitted carrier in the states of Arkansas, California, Georgia, Kentucky, Maryland, Missouri, Nevada, Oklahoma, South Carolina, Tennessee, and Virginia and offering the same general liability products. The Company is licensed and has the facilities to market and underwrite other insurance carriers’ lines of business, as well as to process and adjust claims for third party insurance carriers. 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, the success of the Company's new growth and marketing initiatives and introduction of its new product lines, inflation and other changes in economic conditions (including changes in interest rates and financial markets); the impact of new regulations adopted in Florida which affect the property and casualty insurance market; the costs of reinsurance and the collectability or reinsurance, assessments charged by various governmental agencies; pricing competition and other initiatives by competitors; our ability to obtain regulatory approval for requested rate changes and/or changes in our capital structure, including regulatory approval of the proposed $10 million capital contribution to Federated National Insurance Company on or before March 31, 2010, and the timing thereof; legislative and regulatory developments; the outcome of litigation pending against us or which is commenced against the Company after the date hereof, including the terms of any settlements; risks related to the nature of our business; dependence on investment income and the composition of our investment portfolio; the adequacy of our liability for loss and loss adjustment expense; insurance agents; claims experience; ratings by industry services (a withdrawal or reduction of our rating(s) could limit us from writing or renewing policies and could cause the Company’s insurance policies to no longer be acceptable to the secondary marketplace and mortgage lenders); 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; the ability of the Company to close the proposed acquisition of HomeWise Insurance Company on a timely basis or at all, or if the transaction is closed, to achieve the contemplated benefits and synergies; and other matters described from time to time by us in our filings with the SEC. Additional risk factors will also be set forth in the Company's Form 10-K for the fiscal year ended December 31, 2009 which will be filed with the SEC by March 31, 2010. 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. The Company undertakes no obligations to update, change or revise any forward-looking statement, whether as a result of new information, additional or subsequent developments or otherwise.

21st CENTURY HOLDING COMPANY
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