Oscar Health Stock Rides Higher As Insider Joshua Kushner Ups Stake: Retail Bets On Trump Boost

Following the latest purchases, the later-stage venture capital fund of Thrive Capital holds 6.08 million Oscar Health shares.
Analysts say the Medicare Advantage risk/reward improved with the election of Trump but warned that areas of concerns still exist.
Analysts say the Medicare Advantage risk/reward improved with the election of Trump but warned that areas of concerns still exist. | Photo Courtesy of Leeloo The First via Pexels
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Shanthi M·Stocktwits
Updated Mar 05, 2026   |   2:29 PM EST
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Shares of Oscar Health, Inc.  ($OSCR), a New York-based provider of health insurance, will likely extend their gains from Monday following disclosure regarding insider buying.

Joshua Kushner, the brother of President Donald Trump’s son-in-law Jared Kushner, co-founded the company in 2012.

Oscar Health shares rallied nearly 7.50% on Monday after the company said in a statement that Anahata Foundation, a charitable foundation established  by the company’s CEO Mark Bertolini, purchased 933,333 shares in the company on the open market in the week of Nov. 11.

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Later in two filings with the SEC, the company disclosed that Thrive Partners VII Growth GP along with Claremount VII bought 344,522 Oscar Health shares, valued at $5.44 million, last Thursday. 

Following the transaction, Thrive Partners VII Growth GP, the later-stage venture capital fund from Thrive Capital, directly holds 6.08 million shares in the company.

Joshua Kushner is the Managing Partner at Thrive Capital and Claremount VII.

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"All shares were purchased in accordance with the daily volume and other limitations and requirements of Rule 10b-18," the company said in the filing.

Thursday’s buy represented follow-on purchases from Nov. 11 when Joshua Kushner bought 1.056 million shares.

On Monday, Wells Fargo lowered its price target for Oscar Health from $27 to $21 but the firm maintained an Overweight rating on the stock, the Fly reported. The price-target cut was due to the premise that the enhanced exchange subsidies will expire by 2026. 

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The Medicare Advantage risk/reward improved with the election of Trump but warned that areas of concerns still exist, the analysts added.

Earlier this month, Oscar Health reported a wider-than-expected loss despite top-line exceeding estimates.

In premarket trading, as of 9:08 am ET, Oscar Health shares were up 2.38% at $16.36.  The stock has gained nearly 75% year-to-date.

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The insider buying gave retail enough confidence to take a position in the stock. A user on Stocktwits said the heavy insider buying is bullish for the stock and said the $15-ish level is a good entry point.

Trump’s victory, though expected to bear fruit for healthcare companies only in the out-years, was a reason for another user to get bullish on the stock.

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Read Next: XPeng Stock Kicks Into To Top Gear After Q3 Beat, Positive Guidance: Retail Sentiment Soars

For updates and corrections email newsroom@stocktwits.com 

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