Oscar Health (OSCR) is trading at $14.43, up $2.21 (+15.29%) on the day as of market open.
Oscar Health CEO Mark Bertolini made headlines this week after buying 1 million OSCR at $11.92 each — a $11.92M personal bet on the health insurer’s turnaround. The stock jumped ~11% Wednesday morning on the news.
The purchase was disclosed in a regulatory filing after Tuesday’s close. Bertolini, who previously served as CEO of Aetna, made the transaction on Monday, April 6.
But the deal wasn’t a typical open-market purchase. The Form 4 filed with the SEC describes it as a private placement — meaning Oscar issued 1 million new shares directly to its CEO at the $11.92 closing price, the same price used that day to withhold stock for tax purposes on newly vested performance units.
The company received $11.92M in fresh capital, while Bertolini’s stake increased to 10.87%, or 10,196,876 shares. Net dilution to other investors was minimal.
Oscar’s 2025 financials paint a company that’s growing fast but still burning cash. Full-year revenue hit $11.7B, up from $9.18B in 2024. Membership reached a record 3.4 million. Net losses for the year came in at $443.2M, with operating losses of $396.4M.
For 2026, the company is guiding for $18.7B–$19B in revenue — roughly 60% year-over-year growth — while targeting a medical-loss ratio of 82.4%–83.4%. Analysts are projecting EPS of $0.77 for 2026, which would mark a turn toward profitability.
That’s a big target to hit. And Bertolini just wrote a personal check suggesting he thinks they will.
Compare that to the bigger players: UnitedHealth Group posted $113.2B in Q4 2025 revenue, up 12.3% year-over-year. Centene and Molina Healthcare grew in single digits. Oscar’s growth rate is in a different league, even if profitability hasn’t arrived yet.
It’s worth noting what this isn’t. A traditional open-market purchase — where an executive buys at the ask price, absorbs slippage, and risks an immediate loss — is typically seen as the stronger signal. That says: “I like this price, right now.”
A private placement is a different kind of move. Bertolini didn’t wake up and put in a market order. He acquired stock at a pre-set fair market value price, part of a coordinated transaction tied to vesting. The company got cash; he got stock.
Still, Bertolini could have sold his vested shares to cover taxes and walked away with cash. Instead, he chose to own more. At current prices, he holds roughly $125M worth of Oscar stock.
OSCR stock had already gained ~7% on Tuesday after the U.S. government confirmed a 2.5% Medicare Advantage reimbursement hike for 2027 — higher than the prior proposal to keep rates flat.
Oscar’s Q1 2025 earnings are scheduled for May 6 before the market open.
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