Mark T. Bertolini, serving as the Chief Executive Officer of Oscar Health, Inc. (NASDAQ: OSCR), executed a substantial divestiture of company equity, moving $35,767,321 worth of stock across multiple transactions on June 29 and June 30, 2026. The sales were carried out at weighted average prices ranging between $28.35 and $30.08 per share. This executive activity coincides with a period of heightened market valuation for the insurer, as the stock has since appreciated to $31.90, trading in close proximity to its 52-week high of $30.66. This price action follows a remarkable 98% surge over the preceding six months. According to data from InvestingPro, the current valuation appears slightly elevated relative to a calculated Fair Value of $30.96, positioning the equity among companies identified as overvalued.
The transactions involved the disposition of Class A Common Stock. On June 29, Mr. Bertolini sold 555,826 shares at a weighted average price of $29.17 per share, with individual execution prices ranging from $28.74 to $29.73. Later that same day, an additional 58,926 shares were sold at a weighted average price of $30.08, with prices ranging from $29.74 to $30.61. The following day, June 30, saw the sale of 488,654 shares at a weighted average price of $28.35, with transaction prices falling between $27.78 and $28.77. Concluding the reported sales, 135,590 shares were disposed of at a weighted average price of $28.97, with individual share prices ranging from $28.78 to $29.29. In total, Bertolini sold 1,238,996 shares of Class A Common Stock.
These sales were undertaken to satisfy tax withholding obligations stemming from the deferred settlement of performance stock units that vested on April 3, 2026. The transactions were carried out pursuant to a Rule 10b5-1 instruction letter, initially entered into on November 10, 2025, and subsequently amended and restated on March 24, 2026. Following these transactions, Mr. Bertolini directly holds 7,751,570 shares of Oscar Health Class A Common Stock. This figure includes shares to be issued in connection with the vesting of one or more restricted stock units.
In other recent news, Oscar Health has seen significant developments. Barclays upgraded Oscar Health's stock rating to Overweight from Equalweight, increasing the price target to $35.00, citing potential for a multi-year re-rating and margin recovery. Similarly, Wells Fargo upgraded the company's stock to Equal Weight from Underweight, with a new price target of $20.00, expressing confidence in the exchange market's trajectory for 2026. Meanwhile, Raymond James maintained an Outperform rating with a $30.00 price target following a federal judge's decision affecting marketplace regulations, noting the change in the open enrollment period.
Oscar Health also announced updates to Mario Schlosser's role, transitioning him from President of Technology and Chief Technology Officer to Co-Founder & Advisor to the CEO, where he will continue to support AI and digital health initiatives. Additionally, options trading activity in Oscar Health surged, with 52,384 contracts traded, highlighting investor interest. These recent developments provide a comprehensive look at Oscar Health's current market position and strategic changes.