Playboy (PLBY) general counsel sells 181,570 shares for RSU tax obligations

Rhea-AI Filing Summary

Playboy, Inc. General Counsel and Secretary Christopher Riley reported selling 181,570 shares of common stock in two transactions at weighted average prices of $1.7494 and $1.7763 per share. According to the footnotes, these sales were made solely to cover tax withholding obligations from the settlement of previously granted restricted stock units. After these transactions, he directly holds 1,688,679 shares of common stock.

Insights

Insider trading & governance analyst

Riley’s sales are tax-driven RSU settlements, not discretionary selling.

The filing shows Christopher Riley completed two open-market sales totaling 181,570 shares of Playboy, Inc. common stock at weighted average prices near $1.75 per share. Transaction codes indicate sales, but the footnotes clarify their purpose.

The company notes these shares were sold solely to satisfy Riley’s tax withholding obligations tied to the settlement of previously granted restricted stock units. This characterizes the activity as a mechanistic, compensation-related event rather than a directional bet on the stock.

Following the transactions, Riley still directly owns 1,688,679 shares, indicating he retains a substantial equity position. Overall, this looks like routine equity compensation and tax management, with limited informational value about his outlook on the company.

Insider Trade Summary

Net Seller: 181,570 shares ($320,084)

Net Sell 2 txns

Insider Riley Christopher

Role General Counsel & Secretary

Sold 181,570 shs ($320K)

Type	Security	Shares	Price	Value
Sale	Common Stock	90,896	$1.7763	$161K
Sale	Common Stock	90,674	$1.7494	$159K

Holdings After Transaction: Common Stock — 1,688,679 shares (Direct, null)

Footnotes (1)

1. Represents shares sold solely to cover the reporting person's tax withholding obligations in connection with the settlement of restricted stock units previously granted to the reporting person. Pursuant to the Issuer's current practices, the disclosed sale of shares was made in connection with the settlement of restricted stock units, solely to cover taxes related to such settlement. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions ranging from $1.68 to $1.81, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions ranging from $1.74 to $1.805, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Key Figures

Shares sold 2026-05-04: 90,674 shares at $1.7494 Shares sold 2026-05-05: 90,896 shares at $1.7763 Total shares sold: 181,570 shares +3 more

6 metrics

Shares sold 2026-05-04 90,674 shares at $1.7494 Open-market sale of common stock

Shares sold 2026-05-05 90,896 shares at $1.7763 Open-market sale of common stock

Total shares sold 181,570 shares Two tax-related sales covering RSU withholding

Holdings after transactions 1,688,679 shares Direct ownership following reported sales

Price range 2026-05-04 $1.68–$1.81 Multiple trades within this range; weighted average $1.7763

Price range 2026-05-05 $1.74–$1.805 Multiple trades within this range; weighted average $1.7494

Key Terms

restricted stock units, tax withholding obligations, weighted average price, open-market sale

4 terms

restricted stock units financial

"in connection with the settlement of restricted stock units previously granted"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

tax withholding obligations financial

"shares sold solely to cover the reporting person's tax withholding obligations"

weighted average price financial

"The price reported in Column 4 is a weighted average price."

Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.

open-market sale financial

"transaction_action": "open-market sale""

An open-market sale is when a shareholder sells existing shares directly on a public exchange to any willing buyer, rather than through a private deal. Think of it like putting goods on a busy market stall where price is set by supply and demand; for investors it matters because such sales increase available supply, can put short-term downward pressure on the stock price, and signal changes in liquidity or investor confidence.

Form 4 Insider Transactions: What Each Field Means →

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Riley Christopher

(Last) (First) (Middle)

C/O PLAYBOY, INC.

10960 WILSHIRE BLVD, SUITE 2200

(Street)

LOS ANGELES CALIFORNIA 90024

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Playboy, Inc. [ PLBY ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	General Counsel & Secretary

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/04/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	05/04/2026		S		90,674(1)	D	$1.7494(2)	1,779,575	D
Common Stock	05/05/2026		S		90,896(1)	D	$1.7763(3)	1,688,679	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. Represents shares sold solely to cover the reporting person's tax withholding obligations in connection with the settlement of restricted stock units previously granted to the reporting person. Pursuant to the Issuer's current practices, the disclosed sale of shares was made in connection with the settlement of restricted stock units, solely to cover taxes related to such settlement.

2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions ranging from $1.68 to $1.81, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

3. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions ranging from $1.74 to $1.805, inclusive. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Remarks:

	/s/ Christopher Riley	05/05/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

FAQ

What insider transaction did Playboy (PLBY) report for Christopher Riley?

Christopher Riley reported selling 181,570 shares of Playboy common stock in two transactions. The sales occurred at weighted average prices of about $1.75 and $1.78 per share, as disclosed in the Form 4 insider trading report.

Why did Christopher Riley sell Playboy (PLBY) shares in this Form 4?

The filing states Riley’s sales were made solely to cover his tax withholding obligations. These obligations arose from the settlement of restricted stock units that had previously been granted to him as part of his equity compensation.

How many Playboy (PLBY) shares does Christopher Riley hold after these transactions?

After the reported transactions, Christopher Riley directly holds 1,688,679 shares of Playboy common stock. This post-transaction holding shows he retains a significant equity stake in the company despite the tax-related share sales.

At what prices were Christopher Riley’s Playboy (PLBY) shares sold?

The reported weighted average prices were $1.7494 per share for 90,674 shares and $1.7763 per share for 90,896 shares. Footnotes explain that each block consisted of multiple trades within stated price ranges around those averages.

Do Christopher Riley’s Playboy (PLBY) share sales signal a bearish outlook?

The filing describes these sales as solely to cover tax withholding on vested restricted stock units. Such tax-driven transactions are generally viewed as routine compensation and tax management, rather than a discretionary decision reflecting an insider’s view of the stock.