AMENDMENT NO. 1 TO THE AMENDED AND RESTATED EXCHANGE AND STOCKHOLDERSAGREEMENT

Exhibit 10.44

AMENDMENT NO. 1 TO THE 

AMENDED AND RESTATED EXCHANGE AND STOCKHOLDERS’ AGREEMENT

THIS AMENDMENT NO. 1 TO THE AMENDED AND RESTATED EXCHANGE AND STOCKHOLDERS’ AGREEMENT (this “Amendment”) is made and entered into as of [__], 2016, by and among Turning Point Brands, Inc. (f/k/a North Atlantic Holding Company, Inc.), a Delaware corporation (the “Company”), North Atlantic Trading Company, Inc., a Delaware corporation (“NATC”), the Persons executing this Amendment on the signature pages hereto and all other persons who are “Stockholders” under the Exchange and Stockholders’ Agreement dated as of June 25, 1997, as amended by the Amended and Restated Exchange and Stockholders’ Agreement dated as of February 9, 2004 (the “Stockholders’ Agreement”), or otherwise bound by the provisions thereof (such Persons, together with any Person who may hereafter become a stockholder party hereto as provided herein being referred to collectively as the “Stockholders” and, individually, as a “Stockholder”). Capitalized terms used and not otherwise defined herein shall have the meanings ascribed to them in the Stockholders’ Agreement.

W I T N E S S E T H

WHEREAS, the Company intends to effect an initial public offering (the “IPO”) of its common stock (the “Common Stock”), pursuant to a registration statement on Form S-1 filed with the U.S. Securities and Exchange Commission;

WHEREAS, in furtherance of the IPO, the Company intends to enter into an underwriting agreement with one or more underwriters (the “Underwriting Agreement”);

WHEREAS, pursuant to Section 8.2 of the Stockholders’ Agreement, Stockholders holding more than 65% of the total number of shares of the Common Stock held by all Stockholders (“Majority Stockholders”) may amend the Stockholders’ Agreement and such amendment shall be binding on all Stockholders and the Company; and

WHEREAS, in furtherance of the IPO, the Majority Stockholders wish to amend the Stockholders’ Agreement to, among other things, delete certain provisions with respect to registration rights for the Common Stock and provide for the termination of the Stockholders’ Agreement upon the closing of the IPO.

NOW, THEREFORE, in consideration of the foregoing premises and the mutual covenants and agreements hereinafter contained, the Stockholders’ Agreement is hereby amended as follows:

“3.3 Restricted Period. During the “Restricted Period” (as hereinafter defined), no Stockholder may, either directly or indirectly:

As used herein, “Restricted Period” means the period commencing on the date of the Underwriting Agreement and ending on the day preceding the day that is six months after the closing of the IPO; provided, however, the Restricted Period shall terminate immediately prior to the consummation of a liquidation, merger, stock exchange or other similar transaction that results in all holders of Shares having the right to exchange their Shares for cash, securities or other property.

Nothing in this Section 3.3 shall prevent the establishment by any Stockholder of any contract, instruction or plan (a “Plan”) that satisfies all of the requirements of Rule 10b5-1(c)(1)(i)(B) under the Exchange Act; provided that it shall be a condition to the establishment of any such Plan that no sales of the Company’s share capital shall be made pursuant to such a Plan prior to the expiration of the Restricted Period; and provided, further, such a Plan may only be established if no public announcement of the establishment or the existence thereof, and no filing with the U.S. Securities and Exchange Commission or any other regulatory authority shall be required or shall be made voluntarily by such Stockholder, the Company or any other person, prior to the expiration of the Restricted Period.

Also notwithstanding the foregoing limitations, (i) any Stockholder may Transfer any or all of its Restricted Securities provided that in each and any such event it shall be a condition to the Transfer that the transferee execute an agreement stating that the transferee is receiving and holding the Restricted Securities subject to the provisions of this Agreement and (ii) any Stockholder may exercise any Company stock options, including the transfer to the Company of the Shares underlying such options solely to pay the exercise price or any withholding taxes in connection with the exercise thereof on a “cashless” or net settlement basis (it being understood that such purchased Shares, after giving effect to the “cashless” or net settlement exercise of options shall not be deemed to be “Restricted Securities”).”

““IPO” shall mean the initial public offering of the common stock of the Company pursuant to a registration statement on Form S-1 filed with the U.S. Securities and Exchange Commission.

“Plan” shall have the meaning set forth in Section 3.3.

“Restricted Period” shall have the meaning set forth in Section 3.3.

“Restricted Securities” shall have the meaning set forth in Section 3.3(a).

“Underwriting Agreement” shall mean an underwriting agreement entered into by the Company and one or more underwriters in furtherance of the IPO.”

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IN WITNESS WHEREOF, the parties have caused this Amendment No. 1 to the Amended and Restated Exchange and Stockholders’ Agreement to be duly executed as of the date first written above.

[Signature Page to Amendment No.1 to 

Amended and Restated Exchange and Stockholders’ Agreement]

[Signature Page to Amendment No.1 to 

Amended and Restated Exchange and Stockholders’ Agreement]