STOCK TITAN

Oscar Health CFO sells 28,869 shares at $31.45

Oscar Health’s CFO sold shares under a Rule 10b5-1 plan primarily to cover tax withholding while retaining over one million shares.

(High)
(Negative)
Form Type
4

Rhea-AI Filing Summary

Oscar Health, Inc. (OSCR) reported that Chief Financial Officer Richard Scott Blackley sold 28,869 shares of Class A Common Stock on September 3, 2026 at a weighted average price of $31.45 per share, in transactions executed between $30.97 and $31.96, pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy his tax withholding obligations on vesting equity awards. After this sale, he directly holds 1,046,108 shares, which include shares to be issued upon vesting of restricted stock units, and indirectly holds 56,250 shares through the MQB Irrevocable Trust.

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Insights

Analyzing...

Insider Blackley Richard Scott
Role Chief Financial Officer
Sold 28,869 shs ($908K)
Type Security Shares Price Value
Sale Class A Common Stock F1, F2, F3 28,869 $31.45 $908K
holding Class A Common Stock -- -- --
Holdings After Transaction: Class A Common Stock — 1,046,108 shares (Direct); Class A Common Stock — 56,250 shares (Indirect, By MQB Irrevocable Trust)
Footnotes (3)
  1. F1. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy the Reporting Person's tax withholding obligation upon the vesting of previously granted equity awards.
  2. F2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $30.97 to $31.96, 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 at which the transactions were effected.
  3. F3. Includes shares to be issued in connection with the vesting of one or more restricted stock units.
Shares sold 28,869 shares Class A Common Stock sold by CFO on September 3, 2026
Weighted average sale price $31.45 per share Average price for CFO’s September 3, 2026 sale
Sale price range $30.97–$31.96 per share Range of prices for the multiple sale transactions
Direct holdings after transaction 1,046,108 shares CFO’s direct Class A Common Stock position after sale, including RSU-related shares
Indirect holdings after transaction 56,250 shares Shares held through the MQB Irrevocable Trust after the reported transaction
Rule 10b5-1 plan date August 8, 2025 Date the instruction letter governing the sale was entered into
Transaction date September 3, 2026 Date of the reported sale of Class A Common Stock
Rule 10b5-1 regulatory
"The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025"
Rule 10b5-1 is a regulation that allows company insiders to buy or sell their shares at predetermined times, even if they have access to non-public information. It acts like setting a schedule in advance for transactions, helping prevent accusations of unfair trading. This rule provides a way for insiders to plan trades transparently, giving investors confidence that these transactions are not based on hidden information.
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.
restricted stock units financial
"Includes shares to be issued in connection with the vesting of one or more restricted stock units"
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.
irrevocable trust financial
"56,250 shares are held indirectly through the MQB Irrevocable Trust"
An irrevocable trust is a legal arrangement where an owner transfers assets into a separate entity managed by a trustee and gives up the power to modify or reclaim those assets. For investors it matters because putting stock or other holdings into such a trust can change who controls and benefits from the assets, affect taxes and creditor protection, and influence how easy it is to sell or value those holdings—like placing valuables in a locked safe overseen by someone else.

FAQ

What insider transaction did Oscar Health (OSCR) disclose for its CFO?

Oscar Health disclosed that CFO Richard Scott Blackley sold 28,869 shares of Class A Common Stock on September 3, 2026 at a weighted average price of $31.45 per share, with individual trades between $30.97 and $31.96.

Was the OSCR CFO’s September 2026 share sale made under a Rule 10b5-1 plan?

Yes. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025, which provided for sales to satisfy the CFO’s tax withholding obligations on vesting equity awards.

How many Oscar Health (OSCR) shares did the CFO hold after the reported sale?

After the sale, the CFO held 1,046,108 shares of Class A Common Stock directly, including shares to be issued upon vesting of restricted stock units, and 56,250 shares indirectly through the MQB Irrevocable Trust.

What price range were the OSCR shares sold for by the CFO on September 3, 2026?

The reported weighted average sale price was $31.45 per share. The shares were sold in multiple transactions at prices ranging from $30.97 to $31.96, inclusive.

Why did the Oscar Health (OSCR) CFO sell shares in this Form 4 filing?

The filing states the sale was made to satisfy tax withholding obligations arising from the vesting of previously granted equity awards, under a pre-arranged Rule 10b5-1 instruction letter dated August 8, 2025.

Does the OSCR CFO still have a significant ownership stake after this Form 4 transaction?

Yes. Following the reported sale, the CFO continues to hold over 1.0 million shares directly plus 56,250 shares indirectly through the MQB Irrevocable Trust, as disclosed in the filing.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Learn about SEC filing dates
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).
X
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*
Blackley Richard Scott

(Last)(First)(Middle)
75 VARICK STREET, 5TH FLOOR

(Street)
NEW YORK NEW YORK 10013

(City)(State)(Zip)

UNITED STATES

(Country)
2. Issuer Name and Ticker or Trading Symbol
Oscar Health, Inc. [ OSCR ]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
Director10% Owner
XOfficer (give title below)Other (specify below)
Chief Financial Officer
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
09/03/2026
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
Class A Common Stock09/03/2026S28,869(1)D$31.45(2)1,046,108(3)D
Class A Common Stock56,250IBy MQB Irrevocable Trust
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. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy the Reporting Person's tax withholding obligation upon the vesting of previously granted equity awards.
2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $30.97 to $31.96, 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 at which the transactions were effected.
3. Includes shares to be issued in connection with the vesting of one or more restricted stock units.
Remarks:
/s/ Melissa Curtin, Attorney-in-fact09/08/2026
** 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)

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