Jim Cramer Shows Bullish Sentiment Toward Oscar Health Because of CEO Mark Bertolini

By Syeda Seirut Javed | January 22, 2026, 3:09 AM

Oscar Health, Inc. (NYSE:OSCR) is one of the stocks Jim Cramer recently looked at. Starting the lightning round, a caller asked if the company has the setup for a breakout year, and Cramer replied:

I’m going to tell you the truth, if Bertolini weren’t running that company, I would say [bear buzzer], but because he is, and I like him a lot, I’ll go with that [bull buzzer].

A laptop and a computer monitor display a detailed stock market technical analysis chart. Photo by Jakub Zerdzicki on Pexels

Oscar Health, Inc. (NYSE:OSCR) provides medical insurance plans for individuals, families, and small businesses. Longleaf Partners Small-Cap Fund stated the following regarding Oscar Health, Inc. (NYSE:OSCR) in its third quarter 2025 investor letter:

Oscar Health, Inc. (NYSE:OSCR) – Healthcare insurance company Oscar reversed course from being a contributor last quarter to a detractor this quarter. We wrote to you in our previous letter about the shifts in sentiment and how we sold shares into the positive feelings at the end of the second quarter when the stock went over $20 per share. July ended up being a rough month for Oscar and its industry as claims losses were much worse than expected in the first half of the year. Oscar was unfortunately unable to lose much less than others because of the way this unique market works, and this hurt our appraisal. As the stock recovered later in the quarter, we sold the rest of our position as our price to value gap had closed. This ended up being a successful overall investment, and we are grateful to our partners at the company for leading it through volatile industry times.

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Disclosure: None. This article is originally published at Insider Monkey.

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