Oscar Health (NYSE: OSCR) CFO sells 100,000 shares in planned trade

Q: At what prices did the Oscar Health (OSCR) CFO sell his shares?

The CFO’s shares were sold at weighted average prices of $23.79 and $23.10 per share. Footnotes state these were executed through multiple trades, with price ranges of $22.68–$23.67 and $23.68–$24.09 for the respective sale blocks.

Q: How many Oscar Health (OSCR) shares did the CFO sell in each trade?

CFO Richard Scott Blackley sold 8,741 shares of Class A Common Stock at a weighted average of $23.79 , and an additional 91,259 shares at a weighted average of $23.10 . Together, these Form 4 transactions total 100,000 shares sold.

Q: Does the Oscar Health (OSCR) CFO still hold shares after these sales?

Yes. The Form 4 shows remaining holdings, including 75,000 shares of Class A Common Stock held indirectly by the MQB Irrevocable Trust . The filing also reports continuing direct ownership, indicating the CFO retains a sizable equity position in Oscar Health.

Q: What do the weighted average prices in the Oscar Health (OSCR) filing mean?

Weighted average prices of $23.79 and $23.10 indicate each sale block comprised multiple trades at different prices. Footnotes state the individual trades occurred within ranges of $22.68–$23.67 and $23.68–$24.09 , with full trade details available upon request.

Filing Impact

(Very High)

Filing Sentiment

(Negative)

Form Type

Rhea-AI Filing Summary

Oscar Health, Inc. Chief Financial Officer Richard Scott Blackley reported open‑market sales of 100,000 shares of Class A Common Stock on May 14, 2026. The filing shows two sale tranches: 8,741 shares at a weighted average price of $23.79 and 91,259 shares at a weighted average price of $23.10.

These transactions were effected under a Rule 10b5‑1 trading plan adopted on February 12, 2026 and executed through multiple trades within price ranges of $22.68–$23.67 and $23.68–$24.09. Blackley also reported indirect ownership of 75,000 shares held by the MQB Irrevocable Trust, alongside his remaining direct holdings.

Insider Trade Summary 10b5-1

Net Seller: 100,000 shares ($2,316,031)

Net Sell 3 txns

Insider Blackley Richard Scott

Role Chief Financial Officer

Sold 100,000 shs ($2.32M)

Type	Security	Shares	Price	Value
Sale	Class A Common Stock	91,259	$23.10	$2.11M
Sale	Class A Common Stock	8,741	$23.79	$208K
holding	Class A Common Stock	--	--	--

Holdings After Transaction: Class A Common Stock — 1,225,401 shares (Direct, null); Class A Common Stock — 75,000 shares (Indirect, By MQB Irrevocable Trust)

Footnotes (1)

The transaction was effected pursuant to a Rule 10b5-1 trading plan adopted on February 12, 2026. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.68 to $23.67, 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 $23.68 to $24.09, 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.

Key Figures

Total shares sold: 100,000 shares First sale tranche: 8,741 shares at $23.79 Second sale tranche: 91,259 shares at $23.10 +3 more

6 metrics

Total shares sold 100,000 shares Class A Common Stock open‑market sales on May 14, 2026

First sale tranche 8,741 shares at $23.79 Weighted average price for one block of Class A shares

Second sale tranche 91,259 shares at $23.10 Weighted average price for second block of Class A shares

Price range first block $22.68–$23.67 Trade price range from weighted average footnote F2

Price range second block $23.68–$24.09 Trade price range from weighted average footnote F4

Indirect holdings via trust 75,000 shares Class A shares held by MQB Irrevocable Trust as of May 14, 2026

Key Terms

Rule 10b5-1 trading plan, weighted average price, restricted stock units, Class A Common Stock, +1 more

5 terms

Rule 10b5-1 trading plan financial

"The transaction was effected pursuant to a Rule 10b5-1 trading plan adopted on February 12, 2026."

A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.

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.

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.

Class A Common Stock financial

"security_title: Class A Common Stock"

Class A common stock is a category of a company’s shares that carries a specific set of ownership rights—most commonly defined voting power and claims on dividends—set out in the company’s charter. For investors it matters because the class determines how much influence you have over corporate decisions, the share’s likely dividend and trading behavior, and how it compares in value to other share classes, like choosing a particular seat with different privileges at the company’s decision-making table.

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 →

05/18/2026 - 04:15 PM

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^*

Blackley Richard Scott

(Last)

(First)

(Middle)

75 VARICK STREET, 5TH FLOOR

(Street)

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)

	Director	10% Owner
X	Officer (give title below)	Other (specify below)
	Chief Financial Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/14/2026

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Class A Common Stock	05/14/2026		S		91,259⁽¹⁾	D	$23.1⁽²⁾	1,225,401⁽³⁾	D
Class A Common Stock	05/14/2026		S		8,741⁽¹⁾	D	$23.79⁽⁴⁾	1,216,660⁽³⁾	D
Class A Common Stock								75,000	I	By 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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

Explanation of Responses:

1. The transaction was effected pursuant to a Rule 10b5-1 trading plan adopted on February 12, 2026.

2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.68 to $23.67, 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 $23.68 to $24.09, 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-fact	05/18/2026
	** 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)

Source: View Original Filing on SEC EDGAR

FAQ

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

Oscar Health disclosed that CFO Richard Scott Blackley sold a total of 100,000 Class A Common Stock shares in open‑market transactions. The sales occurred on May 14, 2026 in two tranches at weighted average prices of $23.79 and $23.10 per share.

At what prices did the Oscar Health (OSCR) CFO sell his shares?

The CFO’s shares were sold at weighted average prices of $23.79 and $23.10 per share. Footnotes state these were executed through multiple trades, with price ranges of $22.68–$23.67 and $23.68–$24.09 for the respective sale blocks.

How many Oscar Health (OSCR) shares did the CFO sell in each trade?

CFO Richard Scott Blackley sold 8,741 shares of Class A Common Stock at a weighted average of $23.79, and an additional 91,259 shares at a weighted average of $23.10. Together, these Form 4 transactions total 100,000 shares sold.

Were the Oscar Health (OSCR) CFO’s stock sales made under a 10b5-1 plan?

Yes. A footnote explains the transactions were effected under a Rule 10b5‑1 trading plan adopted on February 12, 2026. Such plans pre‑schedule trades, indicating these sales were arranged in advance rather than timed opportunistically.

Does the Oscar Health (OSCR) CFO still hold shares after these sales?

Yes. The Form 4 shows remaining holdings, including 75,000 shares of Class A Common Stock held indirectly by the MQB Irrevocable Trust. The filing also reports continuing direct ownership, indicating the CFO retains a sizable equity position in Oscar Health.

What do the weighted average prices in the Oscar Health (OSCR) filing mean?

Weighted average prices of $23.79 and $23.10 indicate each sale block comprised multiple trades at different prices. Footnotes state the individual trades occurred within ranges of $22.68–$23.67 and $23.68–$24.09, with full trade details available upon request.