Turning Point Brands, Inc. — Director's Dealing 2022

May 3, 2022

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: Turning Point Brands, Inc. (TPB)
CIK: 0001290677
Period of Report: 2022-02-03

Reporting Person: Purdy Graham (Chief Operating Officer)

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2022-02-03	Dividend Equivalent Right	$	A	213	Acquired		Common Stock (213)	Direct
2022-04-29	Dividend Equivalent Right	$	D	213	Disposed		Common Stock (213)	Direct

Holdings (Non-Derivative)

Security	Shares	Ownership
Common Stock	138984	Direct

Holdings (Derivative)

Security	Exercise Price	Expiration	Underlying	Shares	Ownership
Options (2022)	$30.46	2032-03-14	Common Stock (12000)	12000	Direct
Options (2021)	$51.75	2031-02-18	Common Stock (9000)	9000	Direct
Options (2020)	$14.85	2030-03-18	Common Stock (11000)	11000	Direct
Options (2019)	$47.58	2029-03-20	Common Stock (5500)	5500	Direct
Options (2018)	$21.21	2028-03-07	Common Stock (8900)	8900	Direct
Options (2017)	$15.41	2027-05-17	Common Stock (5000)	5000	Direct
Options (2014)	$3.83	2024-08-08	Common Stock (5216)	5216	Direct

Footnotes

F1: Granted pursuant to the issuer's 2006 Equity Plan

F2: Granted pursuant to the issuer's 2021 Equity Incentive Plan.

F3: The options vested and became exercisable as to 50% of the underlying shares on August 8, 2014, 25% of the underlying shares on August 8, 2015 and 25% of the underlying shares on August 8, 2016.

F4: Granted pursuant to the issuer's 2015 Equity Incentive Plan.

F5: The options vest and become exercisable as to 34% of the underlying shares on January 1, 2018, 33% of the underlying shares on January 1, 2019 and 33% of the underlying shares on January 1, 2020.

F6: The options vest and become exercisable as to 34% of the underlying shares on January 1, 2019, 33% of the underlying shares on January 1, 2020 and 33% of the underlying shares on January 1, 2021.

F7: The options vest and become exercisable as to 34% of the underlying shares on January 1, 2020, 33% of the underlying shares on January 1, 2021 and 33% of the underlying shares on January 1, 2022.

F8: The options vest and become exercisable as to 34% of the underlying shares on January 1, 2021, 33% of the underlying shares on January 1, 2022, and 33% of the underlying shares on January 1, 2023.

F9: The options vest and become exercisable as to 34% of the underlying shares on January 1, 2022, 33% of the underlying shares on January 1, 2023, and 33% of the underlying shares on January 1, 2024.

F10: The options vest and become exercisable as to 34% of the underlying shares on January 1, 2023, 33% of the underlying shares on January 1, 2024, and 33% of the underlying shares on January 1, 2025.

F11: The total reported in Column 5 includes 2,500 awarded restricted stock units and 136,484 shares of common stock.

F12: Each dividend equivalent right was the economic equivalent of one share of the Company's common stock.

F13: In connection with the vesting and settlement of previously-granted performance-based restricted stock units, which settled in shares of the Company's common stock on February 3, 2022, the reporting person acquired 213 fully-vested dividend equivalent rights pursuant to the terms of the applicable award agreement.

F14: On April 29, 2022, the dividend equivalent rights were disposed of and cancelled in exchange for a cash payment equal to $7,220.85.