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Tax-driven Oscar Health (OSCR) CEO sale of 1.24M shares under 10b5-1

Filing Impact
(Very High)
Filing Sentiment
(Very Negative)
Form Type
4

Rhea-AI Filing Summary

Oscar Health, Inc. Chief Executive Officer Mark T. Bertolini reported open-market sales of a total of 1,238,996 shares of Class A Common Stock on June 29–30, 2026. Footnotes explain these sales were made to satisfy tax withholding obligations related to deferred settlement of performance stock units that vested on April 3, 2026, under a pre-arranged Rule 10b5-1 instruction letter entered on November 10, 2025 and amended on March 24, 2026. The reported weighted average sale prices ranged from about $27.78 to $30.61 per share. Following these transactions, Bertolini directly holds 7,751,570 shares of Class A Common Stock, which the disclosure notes includes shares to be issued upon future vesting of restricted stock units.

Positive

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Negative

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Insights

Large CEO sale is tax-driven and pre-planned, limiting signal.

Oscar Health’s CEO, Mark T. Bertolini, reported selling 1,238,996 shares of Class A Common Stock across June 29–30, 2026. All transactions are coded as open-market sales, with weighted average prices between roughly $27.78 and $30.61 per share.

A key footnote states the sales were to satisfy tax withholding obligations tied to deferred settlement of performance stock units that vested on April 3, 2026. The activity was executed pursuant to a Rule 10b5-1 instruction letter entered on November 10, 2025 and amended on March 24, 2026, indicating a pre-planned, mechanical process rather than discretionary market timing.

After these transactions, Bertolini still directly owns 7,751,570 shares of Class A Common Stock, and the position disclosure notes that this figure includes shares issuable upon vesting of restricted stock units. The combination of a large remaining stake, tax-driven motivation, and 10b5-1 planning makes this filing more routine in nature, with limited implication for Oscar Health’s underlying business performance.

Insider Bertolini Mark T
Role Chief Executive Officer
Sold 1,238,996 shs ($35.77M)
Type Security Shares Price Value
Sale Class A Common Stock 488,654 $28.35 $13.85M
Sale Class A Common Stock 135,590 $28.97 $3.93M
Sale Class A Common Stock 555,826 $29.17 $16.21M
Sale Class A Common Stock 58,926 $30.08 $1.77M
Holdings After Transaction: Class A Common Stock — 7,887,160 shares (Direct, null)
Footnotes (1)
  1. Represents sale of shares to satisfy tax withholding obligations in connection with the deferred settlement of performance stock units that vested on April 3, 2026. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on November 10, 2025 and amended and restated on March 24, 2026. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.74 to $29.73, 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. Includes shares to be issued in connection with the vesting of one or more restricted stock units. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $29.74 to $30.61, 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. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $27.78 to $28.77, 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. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.78 to $29.29, 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.
Total shares sold 1,238,996 shares Net open-market sales on June 29–30, 2026
Sale price 1 $28.97 per share Weighted average price for 135,590 shares sold on June 30, 2026
Sale price 2 $28.35 per share Weighted average price for 488,654 shares sold on June 30, 2026
Sale price 3 $30.08 per share Weighted average price for 58,926 shares sold on June 29, 2026
Sale price 4 $29.17 per share Weighted average price for 555,826 shares sold on June 29, 2026
Post-transaction holdings 7,751,570 shares Direct Class A Common Stock ownership after reported sales
Rule 10b5-1 instruction letter regulatory
"The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on November 10, 2025..."
performance stock units financial
"...tax withholding obligations in connection with the deferred settlement of performance stock units that vested on April 3, 2026."
Performance stock units are a type of company award that grants employees shares of stock only if certain performance goals are met. They motivate employees to work toward specific company achievements, aligning their interests with those of shareholders. For investors, they can influence a company's future stock supply and reflect management’s confidence in reaching key targets.
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.
weighted average price financial
"The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions..."
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.
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Form 4 Insider Transactions: What Each Field Means →
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*
Bertolini Mark T
(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)
XDirector10% Owner
XOfficer (give title below)Other (specify below)
Chief Executive Officer
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
06/29/2026		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 Stock06/29/2026S(1)555,826D$29.17(2)8,434,740(3)D
Class A Common Stock06/29/2026S(1)58,926D$30.08(4)8,375,814(3)D
Class A Common Stock06/30/2026S(1)488,654D$28.35(5)7,887,160(3)D
Class A Common Stock06/30/2026S(1)135,590D$28.97(6)7,751,570(3)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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Explanation of Responses:
1. Represents sale of shares to satisfy tax withholding obligations in connection with the deferred settlement of performance stock units that vested on April 3, 2026. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on November 10, 2025 and amended and restated on March 24, 2026.
2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.74 to $29.73, 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.
4. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $29.74 to $30.61, 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.
5. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $27.78 to $28.77, 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.
6. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.78 to $29.29, 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.
Remarks:
/s/ Melissa Curtin, Attorney-in-Fact07/01/2026
** 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

FAQ

What did Oscar Health (OSCR) CEO Mark Bertolini report in this Form 4 filing?

Oscar Health CEO Mark T. Bertolini reported selling 1,238,996 shares of Class A Common Stock on June 29–30, 2026. The sales were tied to tax withholding on vested performance stock units and executed under a pre-arranged Rule 10b5-1 instruction letter.

How many Oscar Health (OSCR) shares did the CEO sell and at what prices?

Mark T. Bertolini sold a total of 1,238,996 Oscar Health Class A shares. Reported weighted average sale prices ranged from about $27.78 to $30.61 per share, with individual transactions disclosed at averages like $28.97, $28.35, $30.08, and $29.17.

Why were Oscar Health (OSCR) CEO Mark Bertolini’s shares sold according to the filing?

The filing states the shares were sold to satisfy tax withholding obligations from deferred settlement of performance stock units that vested on April 3, 2026. This indicates the transactions were primarily driven by tax requirements, not discretionary portfolio changes by the CEO.

Were Oscar Health (OSCR) CEO share sales made under a Rule 10b5-1 plan?

Yes. The filing explains the sales were executed pursuant to a Rule 10b5-1 instruction letter entered into on November 10, 2025 and amended and restated on March 24, 2026. Such pre-planned instructions typically automate trades regardless of short-term market conditions.

How many Oscar Health (OSCR) shares does CEO Mark Bertolini own after these transactions?

After the reported June 29–30, 2026 transactions, Mark T. Bertolini directly holds 7,751,570 shares of Oscar Health Class A Common Stock. The disclosure notes this figure includes shares that will be issued upon the vesting of one or more restricted stock units.

What kinds of equity awards are referenced in Oscar Health (OSCR) CEO’s Form 4?

The Form 4 references performance stock units that vested on April 3, 2026 and restricted stock units that will vest in the future. Shares tied to these equity awards drive both the tax-withholding share sales and the inclusion of future issuable shares in the CEO’s reported holdings.