Investing legend Peter Lynch once noted that insiders sell for any number of reasons, but they buy for only one — they think the company’s stock price will rise. The CEO of beleaguered health insurer Oscar Health (NYSE:OSCR | OSCR Price Prediction) just made a big purchase of company stock, suggesting a vote of confidence in Oscar, whose shares are down almost 10% year-to-date but off more than 45% from their 52-week high.
Yet, this purchase wasn’t a typical open-market buy that most executives make when attempting to show their belief in their company’s recovery. So let’s take a closer look at whether Mark Bertolini’s $12 million purchase is as bullish as it appears on the surface.
Taking a Different Route
On April 6, Bertolini bought 1,000,000 shares at $11.92 each using his own cash, according to the Form 4 he filed with the SEC. The move raised his direct ownership of Oscar stock to 10.87% with 10,196,876 shares. As Lynch suggested, insider purchases mean the executive is betting personal capital that future results will beat today’s price. But here is where Oscar’s story gets nuanced.
Bertolini did not buy these shares on the open market. The Form 4 explicitly calls it “shares of Class A common stock purchased from the issuer by the reporting person in a private placement transaction.” The company issued 1 million new shares directly to him at $11.92 — the same price it used that day to withhold 1,000,001 shares for taxes on 5,733,334 newly vested performance stock units. Oscar’s net share count barely budged; the company received $11.92 million in fresh cash while Bertolini’s economic stake grew.
Private placements skip the public exchange for speed and zero market impact. No road show, no underwriter fees, no temporary price pressure. SEC rules still require the price to reflect fair market value — here, the closing price on the vesting date — so the deal stayed at arm’s-length.
Oscar, which ended 2025 with $396.4 million in operating losses, pockets capital without diluting other shareholders in any meaningful way. The transaction will appear in the next 10-Q under “unregistered sales of equity securities.”
A Tech-Driven Insurer Looking to Make a U-Turn
Oscar Health fits the profile of a high-growth name worth watching. Full-year 2025 revenue hit $11.7 billion, up from $9.18 billion in 2024. Membership reached a record 3.4 million. For 2026, Oscar guided total revenue between $18.7 billion and $19 billion — roughly 60% growth — while projecting a medical-loss ratio of 82.4% to 83.4%. Analysts forecast 2026 EPS of $0.77 after a $443.2 million net loss in 2025. The stock closed yesterday at $12.97 per share, up from Bertolini’s purchase price.
Compare that to peers. UnitedHealth Group (NYSE:UNH) posted $113.2 billion in Q4 2025 revenue — up 12.3% year-over-year but far slower than Oscar’s pace — while Centene (NYSE:CNC) and Molina Healthcare (NYSE:MOH) grew in the single digits. Oscar’s tech platform, which simplifies individual and small-group plans, delivers at a faster pace, yet the company still trades at a negative P/E because profitability remains a work in progress. That’s exactly the setup where an insider buy can matter.
Is This as Bullish as a Classic Insider Buy?
Granted, a classic open-market purchase — where the CEO pays the ask price, absorbs slippage, and risks the stock dropping the next day — carries a louder signal. That move screams, “I like the valuation right now.” A private placement feels more like a tidy alignment exercise: the CEO reinvests at the same fair-market-value price the company uses for compensation accounting. The net-zero dilution and instant cash infusion help the balance sheet without broader shareholder pain.
That said, Bertolini still wrote an $11.92 million personal check. He could have sold vested shares to cover taxes and walked away richer. Instead, he chose to own more. When all is said and done, the CEO now holds roughly $125 million in Oscar stock at current prices. In short, the signal is positive but tempered. It shows confidence without the full-throated roar of an open-market buy.
Key Takeaway
Oscar Health’s path to sustained profits rests on hitting that $18.7 billion-plus 2026 revenue target and keeping the medical-loss ratio below 83.4%. Bertolini’s buy adds one more data point that management believes the numbers will work.
Smart investors shouldn’t back up the truck on this alone. Instead, watch Oscar’s Q1 results due May 6 before the market opens. If revenue growth stays above 50% and adjusted EBITDA narrows further, the stock’s current $3.86 billion market cap could look like a bargain versus slower-growing giants like UnitedHealth. Until then, treat the $12 million vote as encouraging homework, not a buy-at-any-price trigger. You’ll sleep better knowing the CEO just did the same.
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