0001144204-06-017955 Sample Contracts

REGISTRATION RIGHTS AGREEMENT
Registration Rights Agreement • May 2nd, 2006 • 21st Century Holding Co • Fire, marine & casualty insurance • Florida

THIS REGISTRATION RIGHTS AGREEMENT, dated as of September 29, 2004 (the “Agreement”), is entered into by and among 21st Century Holding Company, a Florida corporation (the “Company”), J. Giordano Securities, LLC (the “Placement Agent”), and the Holders (the “Investors”) of the Company’s 6% Senior Subordinated Notes due September ____, 2007 (the “Notes”), and Warrants (the “Warrants”) as set forth on Exhibit A hereto.

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21st CENTURY HOLDING COMPANY 4161 N.W. 5TH STREET PLANTATION, FL 33317 UNIT PURCHASE AGREEMENT
Purchase Agreement • May 2nd, 2006 • 21st Century Holding Co • Fire, marine & casualty insurance • Florida
AMENDMENT TO UNIT PURCHASE AGREEMENT AND REGISTRATION RIGHTS AGREEMENT
Unit Purchase Agreement • May 2nd, 2006 • 21st Century Holding Co • Fire, marine & casualty insurance • Florida

THIS AMENDMENT TO UNIT PURCHASE AGREEMENT AND REGISTRATION RIGHTS AGREEMENT (the “Amendment”) is dated effective as of October 15, 2003 by and among 21st Century Holding Company, a Florida corporation (the “Company”), J. Giordano Securities, LLC (the “Placement Agent”), and the holders of the Company’s 6% Senior Subordinated Notes due July 31, 2006 (the “Notes”) as set forth on Schedule A hereto (collectively, the “Investors”).

21ST CENTURY HOLDING COMPANY LAUDERDALE LAKES, FL 33311 UNIT PURCHASE AGREEMENT
21st Century Holding Co • May 2nd, 2006 • Fire, marine & casualty insurance • Florida

21st Century Holding Company, a Florida corporation (the "Company"), agrees with the Purchasers listed in the attached Schedule A (the "Purchasers") to this Unit Purchase Agreement (this "Agreement") as follows:

21ST CENTURY HOLDING COMPANY 6% SENIOR SUBORDINATED NOTE DUE JULY 31, 2006
Unit Purchase Agreement • May 2nd, 2006 • 21st Century Holding Co • Fire, marine & casualty insurance

This Note is one of a series of Senior Subordinated Notes (herein called the "Notes") issued pursuant to the Unit Purchase Agreement, dated as of July 31, 2003 (as from time to time amended, supplemented or modified, the "Unit Purchase Agreement"), between the Company and the respective Purchasers named therein and is entitled to the benefits thereof. Each holder of this Note will be deemed, by its acceptance hereof, (i) to have agreed to the confidentiality provisions set forth in Section 20 of the Unit Purchase Agreement and (ii) to have made the representations set forth in Section 6 of the Unit Purchase Agreement.

Contract
21st Century Holding Co • May 2nd, 2006 • Fire, marine & casualty insurance

THIS WARRANT AND THE SECURITIES ISSUABLE UPON EXERCISE OF THIS WARRANT HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE "SECURITIES ACT"), OR THE SECURITIES LAWS OF ANY STATE. THE SECURITIES REPRESENTED HEREBY ARE RESTRICTED AND MAY NOT BE SOLD, OFFERED FOR SALE, ASSIGNED, TRANSFERRED OR OTHERWISE DISPOSED OF, UNLESS REGISTERED PURSUANT TO THE PROVISIONS OF THE SECURITIES ACT AND APPLICABLE STATE SECURITIES LAWS OR AN OPINION OF COUNSEL, ACCEPTABLE TO THE COMPANY, IS OBTAINED STATING THAT SUCH DISPOSITION IS IN COMPLIANCE WITH AN AVAILABLE EXEMPTION FROM SUCH REGISTRATION.

21ST CENTURY HOLDING COMPANY
21st Century Holding Co • May 2nd, 2006 • Fire, marine & casualty insurance

THIS WARRANT AND THE SECURITIES ISSUABLE UPON EXERCISE OF THIS WARRANT HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE "SECURITIES ACT"), OR THE SECURITIES LAWS OF ANY STATE. THE SECURITIES REPRESENTED HEREBY ARE RESTRICTED AND MAY NOT BE SOLD, OFFERED FOR SALE, ASSIGNED, TRANSFERRED OR OTHERWISE DISPOSED OF, UNLESS REGISTERED PURSUANT TO THE PROVISIONS OF THE SECURITIES ACT AND APPLICABLE STATE SECURITIES LAWS OR AN OPINION OF COUNSEL, ACCEPTABLE TO THE COMPANY, IS OBTAINED STATING THAT SUCH DISPOSITION IS IN COMPLIANCE WITH AN AVAILABLE EXEMPTION FROM SUCH REGISTRATION.

21ST CENTURY HOLDING COMPANY 6% SENIOR SUBORDINATED NOTE DUE SEPTEMBER 29, 2007
Unit Purchase Agreement • May 2nd, 2006 • 21st Century Holding Co • Fire, marine & casualty insurance

This Note is one of a series of Senior Subordinated Notes (herein called the “Notes”) issued pursuant to the Unit Purchase Agreement, dated as of September 29, 2004 (as from time to time amended, supplemented or modified, the “Unit Purchase Agreement”), between the Company and the respective Purchasers named therein and is entitled to the benefits thereof. Each holder of this Note will be deemed, by its acceptance hereof, (i) to have agreed to the confidentiality provisions set forth in Section 20 of the Unit Purchase Agreement and (ii) to have made the representations set forth in Section 6 of the Unit Purchase Agreement.

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