Item 2.02 and Item 8.01 Results of Operations and Financial Condition and Other Events

On October 29, 2009, 21st Century Holding Company (the "Company") issued a press release announcing its decision to reject an unsolicited proposal from Homeowners Choice, Inc. ("HCII") to acquire all of the outstanding shares of the Company's common stock for approximately $5.30 per share, primarily with shares of HCII's common stock, as not being in the best interest of the Company's shareholders. The rejection of the proposal was communicated in a letter dated October 29, 2009 from Bruce Simberg, the Chairman of the Company's Board of Directors to Paresh Patel, the Chairman of HCII's Board of Directors. The press release ("Press Release") announcing the rejection, including the full text of the rejection letter delivered to Mr. Patel, is attached as Exhibit 99.1 to this Current Report of Form 8-K and is incorporated herein by this reference.

In the Press Release, the Company reported that it expected to report a net loss in the third and fourth quarters of 2009.

In the Press Release, the Company announced that its Board of Directors has authorized the repurchase ("Stock Repurchase Program") of up to $4 million of the Company's common stock from time to time in the open market. The Stock Repurchase Program will be implemented by a broker pursuant to Rule 10b-18 of the Securities Exchange Act of 1934 ("Exchange Act") and other applicable Exchange Act rules and regulations and is expected to commence immediately.

Item 9.01. Financial Statements and Exhibits.

(d) Exhibits Exhibit No. Description 99.1 21st Century Holding Company Press Release, dated October 29, 2009.

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