Insider Selling: Oscar Health (NYSE:OSCR) CFO Sells $695,125.02 in Stock

Posted by Brian Himes on Jun 7th, 2026

Oscar Health, Inc. (NYSE:OSCR – Get Free Report) CFO Richard Scott Blackley sold 31,683 shares of the stock in a transaction dated Tuesday, June 2nd. The stock was sold at an average price of $21.94, for a total transaction of $695,125.02. Following the completion of the transaction, the chief financial officer directly owned 1,074,977 shares of the company’s stock, valued at $23,584,995.38. This trade represents a 2.86% decrease in their position. The transaction was disclosed in a legal filing with the SEC, which is accessible through the SEC website. The transaction was executed under a pre-arranged Rule 10b5-1 trading plan. The sale was made to cover tax withholding obligations related to the vesting of equity awards.

Richard Scott Blackley also recently made the following trade(s):

On Thursday, May 14th, Richard Scott Blackley sold 100,000 shares of Oscar Health stock. The stock was sold at an average price of $23.16, for a total transaction of $2,316,000.00.

Oscar Health Stock Up 4.2%

OSCR stock opened at $24.59 on Friday. The stock has a market capitalization of $7.41 billion, a P/E ratio of -41.68, a price-to-earnings-growth ratio of 1.71 and a beta of 2.37. The company has a current ratio of 1.11, a quick ratio of 1.11 and a debt-to-equity ratio of 0.26. Oscar Health, Inc. has a 12 month low of $10.69 and a 12 month high of $25.58. The firm has a 50-day moving average price of $18.39 and a 200-day moving average price of $16.06.

Oscar Health (NYSE:OSCR – Get Free Report) last issued its quarterly earnings data on Wednesday, May 6th. The company reported $2.07 earnings per share (EPS) for the quarter, beating analysts’ consensus estimates of $1.11 by $0.96. The business had revenue of $4.65 billion during the quarter, compared to analyst estimates of $4.90 billion. Oscar Health had a negative net margin of 0.30% and a negative return on equity of 3.26%. The firm’s quarterly revenue was up 52.6% on a year-over-year basis. During the same quarter last year, the business earned $0.92 EPS. As a group, equities research analysts anticipate that Oscar Health, Inc. will post 0.47 EPS for the current fiscal year.

Trending Headlines about Oscar Health

Here are the key news stories impacting Oscar Health this week:

Positive Sentiment: Wells Fargo upgraded Oscar Health from “strong sell” to “hold”, easing bearish sentiment even though its $20 target remains below the current share price. Zacks.com
Positive Sentiment: Oscar Health’s recent earnings showed a major EPS beat, which supports the stock’s fundamental story despite revenue coming in below estimates.
Neutral Sentiment: A company co-founder shifting into an advisory leadership role looks like an internal reorganization rather than a disruptive change. Oscar Health Co-Founder Shifts to Advisory Leadership Role
Neutral Sentiment: Multiple insiders, including CFO Richard Scott Blackley and CAO Victoria Baltrus, sold shares under pre-planned 10b5-1 programs to cover tax obligations on vested equity awards, which is less concerning than discretionary selling.
Negative Sentiment: Director Mario Schlosser sold 34,120 shares, the largest insider sale in the latest batch, which may pressure sentiment even though it was pre-arranged.

Institutional Inflows and Outflows

Hedge funds have recently added to or reduced their stakes in the company. Jones Financial Companies Lllp raised its holdings in Oscar Health by 7,473.3% during the 1st quarter. Jones Financial Companies Lllp now owns 2,272 shares of the company’s stock worth $30,000 after purchasing an additional 2,242 shares during the last quarter. Strs Ohio bought a new position in Oscar Health during the 1st quarter worth approximately $30,000. Fifth Third Bancorp raised its holdings in Oscar Health by 148.7% during the 4th quarter. Fifth Third Bancorp now owns 2,363 shares of the company’s stock worth $34,000 after purchasing an additional 1,413 shares during the last quarter. Quarry LP raised its holdings in Oscar Health by 439.8% during the 3rd quarter. Quarry LP now owns 1,803 shares of the company’s stock worth $34,000 after purchasing an additional 1,469 shares during the last quarter. Finally, Tsfg LLC bought a new position in Oscar Health during the 3rd quarter worth approximately $38,000. Institutional investors own 75.70% of the company’s stock.

Wall Street Analyst Weigh In

A number of brokerages recently issued reports on OSCR. Zacks Research upgraded shares of Oscar Health from a “hold” rating to a “strong-buy” rating in a report on Thursday, May 7th. Robert W. Baird raised their price objective on shares of Oscar Health from $15.00 to $19.00 and gave the company a “neutral” rating in a report on Thursday, May 7th. UBS Group raised their price objective on shares of Oscar Health from $15.00 to $20.00 and gave the company a “neutral” rating in a report on Thursday, May 7th. Wells Fargo & Company set a $20.00 price objective on shares of Oscar Health and gave the company an “equal weight” rating in a report on Thursday. Finally, Wall Street Zen lowered shares of Oscar Health from a “strong-buy” rating to a “buy” rating in a report on Saturday. One investment analyst has rated the stock with a Strong Buy rating, two have issued a Buy rating, eight have assigned a Hold rating and one has assigned a Sell rating to the stock. According to data from MarketBeat, the company presently has a consensus rating of “Hold” and a consensus price target of $20.22.

Get Our Latest Stock Analysis on Oscar Health

About Oscar Health

(Get Free Report)

Oscar Health, trading on the New York Stock Exchange under the ticker OSCR, is a technology-driven health insurance company headquartered in New York, New York. Founded in 2012 by Mario Schlosser, Joshua Kushner and Kevin Nazemi, the company was built with the goal of simplifying healthcare coverage and enhancing member experience. Oscar leverages a proprietary digital platform to streamline plan enrollment, claims administration and member support, distinguishing itself in the individual, family and small group insurance markets.

The company’s primary products include on-exchange individual and family medical plans under the Affordable Care Act, off-exchange plans, as well as Medicare Advantage offerings.