Oscar Health CEO Mark T. Bertolini sold 597,942 shares on June 25, 2026, at $28.60 per share, for a total value of about $17.10 million. Because the CEO is the company’s top operating decision-maker, trades from this role tend to draw attention, and the dollar size here is notable. The filing indicates the sale was made under a Rule 10b5-1 plan, which is a pre-set trading arrangement that schedules sales in advance. That matters because it reduces the chance the trade was timed around new, nonpublic information. While investors often watch insider selling for clues, planned sales like this are generally viewed as less informative about management’s current view of the business than an open-market sale made at the insider’s discretion. This transaction also fits a recent pattern: Bertolini reported another large sale within the last 30 days, selling about $16.21 million on June 29, following this $17.10 million sale on June 25. Back-to-back sales by the same insider can reflect an ongoing plan execution or personal financial planning, so the key takeaway is the size and repetition, tempered by the fact both trades were reported as pre-scheduled.