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  4. [Form 4] Playboy, Inc. Insider Trading Activity

Playboy (PLBY) counsel sells 146,420 shares to cover RSU tax obligations

Filing Impact
(Moderate)
Filing Sentiment
(Negative)
Form Type
4

Rhea-AI Filing Summary

Playboy, Inc. General Counsel & Secretary Christopher Riley reported selling a total of 146,420 shares of common stock in early July 2026. These sales on open market dates of July 2 and July 6 were made solely to cover his tax withholding obligations from the settlement of previously granted restricted stock units.

The shares were sold at weighted average prices of $1.2627 and $1.2337 per share, within disclosed intraday ranges. After these transactions, Riley directly holds 1,542,259 shares of Playboy common stock, indicating he retains a substantial equity position.

Positive

  • None.

Negative

  • None.

Insights

Riley’s Form 4 shows routine tax-related share sales while retaining a large stake.

Christopher Riley, General Counsel & Secretary of Playboy, Inc., reported two open-market sales totaling 146,420 common shares. A footnote states the transactions were executed solely to cover tax withholding obligations tied to settlement of restricted stock units, rather than discretionary profit-taking.

The weighted average sale prices were $1.2627 and $1.2337 per share, within specified trading ranges. Following these sales, Riley still directly owns 1,542,259 shares, indicating he maintains a significant equity interest. Because the sales are tax-driven and leave a large remaining position, their informational value for investors is limited.

Insider Riley Christopher
Role General Counsel & Secretary
Sold 146,420 shs ($183K)
Type Security Shares Price Value
Sale Common Stock 74,949 $1.2337 $92K
Sale Common Stock 71,471 $1.2627 $90K
Holdings After Transaction: Common Stock — 1,542,259 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 $1.235 to $1.285, 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 $1.21 to $1.265, 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.
Shares sold July 2, 2026 71,471 shares at $1.2627 Open-market sale of common stock
Shares sold July 6, 2026 74,949 shares at $1.2337 Open-market sale of common stock
Total shares sold 146,420 shares Combined sales to cover tax withholding
Post-transaction holdings 1,542,259 shares Direct ownership after reported sales
Price range July 2 trades $1.235–$1.285 Multiple transactions around weighted average $1.2627
Price range July 6 trades $1.21–$1.265 Multiple transactions around weighted average $1.2337
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 or private transaction financial
"Sale in open market or private transaction"
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Form 4 Insider Transactions: What Each Field Means →

FAQ

What did Playboy (PLBY) executive Christopher Riley report in this Form 4?
Christopher Riley, General Counsel & Secretary of Playboy, reported selling 146,420 shares of common stock in two transactions. Footnotes explain the sales were executed solely to cover tax withholding obligations from the settlement of previously granted restricted stock units.

How many Playboy (PLBY) shares did Christopher Riley sell and at what prices?
Riley sold 71,471 shares at a weighted average price of $1.2627 and 74,949 shares at $1.2337. Footnotes note these are averages across multiple trades within ranges of $1.235–$1.285 and $1.21–$1.265, respectively.

Why did Christopher Riley’s Playboy (PLBY) share sales occur according to the filing?
The filing states the reported share sales were made solely to satisfy Riley’s tax withholding obligations. These obligations arose in connection with the settlement of restricted stock units previously granted to him under the issuer’s compensation practices.

How many Playboy (PLBY) shares does Christopher Riley hold after these transactions?
After the reported sales, Riley directly holds 1,542,259 shares of Playboy common stock. This post-transaction holding shows he continues to maintain a substantial ownership position in the company despite selling shares to cover tax-related obligations.

Were Christopher Riley’s Playboy (PLBY) share sales open-market transactions?
Yes. The Form 4 codes both trades as “S,” described as sales in open market or private transactions. However, the filing clarifies they were executed solely to cover taxes related to the settlement of restricted stock units granted to Riley.

Do Christopher Riley’s Playboy (PLBY) sales indicate a change in his overall stake?
The transactions reduce Riley’s holdings by 146,420 shares, but he still owns 1,542,259 shares directly. Given the tax-withholding purpose disclosed in the footnotes, the sales appear compensation-related rather than a broad reduction of his economic interest.
SEC Form 4
FORM 4UNITED 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)
Director10% Owner
XOfficer (give title below)Other (specify below)
General Counsel & Secretary
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
07/02/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm 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)
CodeVAmount(A) or (D)Price
Common Stock07/02/2026S71,471(1)D$1.2627(2)1,617,208D
Common Stock07/06/2026S74,949(1)D$1.2337(3)1,542,259D
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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount 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 $1.235 to $1.285, 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 $1.21 to $1.265, 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 Riley07/07/2026
** Signature of Reporting PersonDate
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)

Source: View Original Filing on SEC EDGAR