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SEPTEMBER 4, 2010
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Contact: Peter J. Prygelski, CFO, 21st Century Holding Company
(954) 308-1252 or (954) 581-9993

21st CENTURY HOLDING COMPANY SIGNS AGREEMENT IN PRINCIPLE TO ACQUIRE HOMEWISE INSURANCE COMPANY AND OTHER INSURANCE RELATED BUSINESS FROM HOMEWISE HOLDINGS

Lauderdale Lakes ,  Florida ,  March 23, 2010
21st Century Holding Company (Nasdaq: TCHC) announced today that it has signed an agreement in principle with HomeWise Holdings, Inc. to acquire HomeWise Insurance Company and HomeWise Management Company. The agreement in principle also includes a renewal rights agreement to acquire certain insurance policies from HomeWise Preferred Insurance Company. Terms of the proposed transaction were not disclosed. The proposed transaction is subject to customary definitive documentation, regulatory approval and the completion of satisfactory due diligence. Due diligence has already begun and is expected to be completed in the next several weeks. The Company expects to close the transaction prior to June 1, 2010.

HomeWise Insurance is based in Tampa and provides homeowners property coverage in Florida and Louisiana through a leading network of experienced, independent agents; it reported approximately $38.2 million in gross written premium in 2009, and statutory surplus of $20.3 million.

Mr. Michael H. Braun, 21st Century Holding Company’s Chief Executive Officer and President, said, “We are pleased to have signed this agreement with HomeWise, a top-ranked Florida insurance company with a high quality book of business. Once completed, the transaction should yield substantial, immediate benefits for 21st Century Holding Company shareholders. Synergies include greater diversification of risk within Florida and into Louisiana, the ability to write more premium for each dollar we spend on reinsurance and expense savings from combining our two companies. We believe the transaction, when completed, will be accretive to our earnings. We anticipate that the acquisition of HomeWise Insurance Company and renewal rights agreement with HomeWise Preferred Insurance Company to generate over $100 million in annual premium.”

About the Company
The Company, through its subsidiaries, underwrites commercial general liability insurance, homeowners' property and casualty insurance, flood insurance, 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 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; 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 us in our filings with the SEC, including, but not limited to, the Company's Annual Report on Form 10-K for the fiscal year ended December 31, 2008. 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.  


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