OSCR Executives' Strategic Moves Reflect Varied Insider Trading Amid Market Transition

OSCR: Insider Trading Insights Paint a Varied Picture as Executives Navigate Transition

June 20, 2025 – New York, NY

Oscar Health, Inc. (NYSE: OSCR) has recently experienced a series of varied insider transactions, which offer a potent insight into the company’s internal dynamics and market movements. Over the past month, there have been significant shifts among OSCR's top executives, seeing both stock sales and grants, as well as a notable contrast from past trends.

In the most recent insider activity within the last month, Elbert O. Robinson Jr., a director at OSCR, executed a sale of 25,000 shares at a price of $16.43 each on May 12. This single transaction amounted to $410,750, indicating a strategic move by Robinson amidst a series of bonuses and awards distributed to several directors earlier in the month. On June 4, stock awards of 14,134 shares at no cost were granted to directors, including Boyd Jeffery H., Vanessa Ames Wittman, Laura W. Lang, Siddhartha Sankaran, David Plouffe, and William Gassen, marking an internal strategizing perhaps linked to incentives or future company aspirations.

However, when placing these recent actions within the larger timeframe of the past year, a pattern emerges. Joshua Kushner, an officer, director, and beneficial owner, actively purchased a total of over 1.6 million shares in late 2024, with the transactions executed in mid-November in collaboration with Thrive Partners VII Growth GP, L.L.C. This amounted to substantial investments: $14.4 million at prices ranging from $13.58 to $13.74 in one instance, followed by $5.44 million and $3.18 million at slightly higher share prices.

Comparatively, sales during last year's fourth quarter primarily involved executives such as Richard Scott Blackley, Chief Financial Officer, and Alessandra C. Quane, among others. The sales appeared concentrated in the beginning of December, with Blackley selling 29,939 shares and Quane offloading 16,793 shares, both at prices hovering around $15.93 to $16.52 per share. Such transactions reflected the executives’ strategic portfolio shifts, contrasting with the present month's sales and awards.

From the ownership perspective, insiders hold a modest 4.125% of shares, while institutional investors command a more significant portion, holding 86.78% and indicating strong institutional confidence. Vanguard Group Inc., Blackrock Inc., and JPMorgan Chase & Co. dominate the institutional landscape with notable shares and firm value standings, bolstered by recent incremental percentage changes in their holdings.

The mutual fund landscape closely mirrors institution trends, with prominent funds like the Vanguard Total Stock Market Index Fund and SMALLCAP World Fund Inc. making significant holdings in OSCR.

As OSCR traverses this period with actionable insights from its trading patterns and insider dealings, the upcoming months could see the company reshuffling to align with both its leadership’s vision and market expectations. Investors and analysts alike will be paying close attention to whether these movements signal shifts in company strategy or broader market sentiments impacting OSCR.