Longleaf Partners Small-Cap Fund’s Investment in Oscar Health (OSCR) Paid Off

Soumya Eswaran

Wed, February 25, 2026 at 9:58 PM GMT+9 3 min read

In this article:

•                                       StockStory Top Pick 
  

  OSCR

  -1.20%

Longleaf Partners, managed by Southeastern Asset Management, released its “Small-Cap Fund” fourth-quarter 2025 investor letter. A copy of the letter can be downloaded here. Longleaf experienced several environments throughout its experience in small-cap investing. This year, the underlying developments in the Fund’s holdings were more promising than the actual stock price returns when compared to the target of inflation plus 10% and the unusual performance of the Russell 2000. In Q4 2025, the Fund returned 1.13% compared to 2.40% for the Russell 3000 Index and 2.19% for the Russell 2000 Index. The Fund’s yearly return was 7.56% compared to 17.15% and 12.81% return for the indexes, respectively. In 2025, Southeastern demonstrated strong performance by protecting investments during market volatility, emphasizing the value of owning solid, free cash flow-generating companies over speculative fads. In addition, please check the Fund’s top five holdings to know its best picks in 2025.

In its fourth-quarter 2025 investor letter, Longleaf Partners Small-Cap Fund highlighted stocks like Oscar Health, Inc. (NYSE:OSCR). Oscar Health, Inc. (NYSE:OSCR) is a US-based healthcare technology company that aims to simplify healthcare. On February 24, 2026, Oscar Health, Inc. (NYSE:OSCR) stock closed at $12.30 per share. One-month return of Oscar Health, Inc. (NYSE:OSCR) was -17.28%, and its shares lost 21.51% over the past 52 weeks. Oscar Health, Inc. (NYSE:OSCR) has a market capitalization of $3.66 billion.

Longleaf Partners Small-Cap Fund stated the following regarding Oscar Health, Inc. (NYSE:OSCR) in its fourth quarter 2025 investor letter:

"Oscar Health, Inc. (NYSE:OSCR) – Healthcare insurance company Oscar was a contributor for the year as above-market membership growth and sustained expense discipline reinforced confidence in the company’s positioning within the individual health insurance market. We exited our position in the third quarter as the P/V gap closed and industry risks became more apparent. The subsequent drama around the expiration of enhanced Affordable Care Act (ACA) subsidies underscores the ongoing policy uncertainty and challenges facing ACA-centric insurers like Oscar. Overall, the investment was successful for us, aided by management’s execution through a volatile industry backdrop."

Oscar Health, Inc. (NYSE:OSCR) is not on our list of 30 Most Popular Stocks Among Hedge Funds. According to our database, 47 hedge fund portfolios held Oscar Health, Inc. (NYSE:OSCR) at the end of the fourth quarter, up from 40 in the previous quarter. While we acknowledge the potential of Oscar Health, Inc. (NYSE:OSCR) as an investment, we believe certain AI stocks offer greater upside potential and carry less downside risk. If you’re looking for an extremely undervalued AI stock that also stands to benefit significantly from Trump-era tariffs and the onshoring trend, see our free report on the best short-term AI stock.

Story Continues  

In another article, we covered Oscar Health, Inc. (NYSE:OSCR) and shared a list of best long term healthcare stocks to buy. In addition, please check out our hedge fund investor letters Q4 2025 page for more investor letters from hedge funds and other leading investors.

READ NEXT: The Best and Worst Dow Stocks for the Next 12 Months and 10 Unstoppable Stocks That Could Double Your Money.

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

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