Our Stock of the Week is Oscar Health, Inc. (OSCR). Oscar is a technology-led health insurer offering individual and family health plans, along with its +Oscar platform that licenses its technology stack to other players in the healthcare system.

An IPO back in 2021, the price action quickly soured, with the stock subsequently spending the next two years losing about 93% of its value. In March 2023, however, shares saw a one-day gain of about 60% after OSCR announced Mark Bertolini, the former CEO of Aetna, as the new CEO, with the board giving Bertolini a mandate to run the company like an insurance company, with tighter underwriting and pricing discipline, exiting less profitable geographies and product lines, and keeping the ACA marketplace as the core focus. The company also leaned harder into its tech angle, licensing its +Oscar platform to other insurers and providers and rolling out AI tools like Oswell, positioning technology as a means to help control costs.

The turnaround began to show results with full-year 2025 showing a record 3.4 million members and $11.7 billion in revenue, while Q!26 results showed continued improvement, with net income coming in at $679 million. However, it wasn’t until April 8th that the stock started making sustained progress out of a two-year range, pushing past long-term resistance in early June and back toward post-IPO highs a month later.

Along the way, Q2 results on August 6th showed 70% revenue growth and a 46% membership increase, with management raising full-year guidance once again, which prompted Barclays and Goldman Sachs to lift their targets to $39 and $30, respectively. Then at an Investor Day on September 16th, management raised its long-term outlook further, introducing a 2029 EPS target of at least $4, lifting 2026 operating income guidance by $100 million, and guiding to 2027 EPS above $2.25. That drew another wave of price target increases, with Raymond James moving to $42 from $34, Barclays to $49, and Baird and Stephens both raising targets as well.

Over the past several weeks, the stock has been been carving out a near-term base at highs, with support along the rising 50-day moving average, and could be building cause for a run at those brief record highs from back in 2021. As always, we won’t chase strength on Monday morning, but will look to aggressively trade the stock as the chart develops.

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This post is for educational purposes only! This is not advice or a recommendation. We do not give investment advice. Do not act on this post. Do not buy, sell, or trade the stocks mentioned herein. We WILL actively trade this stock differently than discussed herein. We will sell into strength and buy or sell at any time for any reason. We will actively trade into any unusual activity. At the time of this post, principals, employees, and affiliates of Shark Investing, Inc. and/or principals, clients, employees, and affiliates of Hammerhead Financial Strategies, LLC, directly or indirectly, controlled investment and/or trading accounts containing no positions in OSCRat the time this was published. To accommodate the objectives of these investing and/or trading accounts, the trading in these shares will be contrary to and/or inconsistent with the information contained in this posting.