Buckley Capital Advisors, an investment management company, released its second quarter 2026 investor letter. A copy of the letter can be downloaded here. The second quarter delivered strong, broad-based gains across the portfolio, with several of the Fund’s largest positions contributing to performance. Buckley Capital returned 36.0% net during the quarter and 29.7% net year-to-date, outperforming the iShares Russell 2000 Value and iShares Russell 2000. The firm remained disciplined in recycling capital by trimming or exiting investments where the thesis had played out or the risk-reward had weakened. Capital was redirected toward businesses where improving fundamentals, catalysts, and attractive valuations support long-term upside. The firm continues to focus on misunderstood small and mid-cap companies with underappreciated earnings power and believes the portfolio is among its strongest in recent years. In addition, please check the firm’s top five holdings to know its best picks in 2026.
In its second-quarter 2026 investor letter, Buckley Capital highlighted Root, Inc. (NASDAQ:ROOT). Root, Inc. (NASDAQ:ROOT) provides insurance products and services. On July 27, 2026, Root, Inc. (NASDAQ:ROOT) closed at $59.65 per share. One-month return of Root, Inc. (NASDAQ:ROOT) was 6.67% and its shares lost 47.47% over the past 52 weeks. Root, Inc. (NASDAQ:ROOT) has a market capitalization of about $944.03 million.
Buckley Capital stated the following regarding Root, Inc. (NASDAQ:ROOT) in its Q2 2026 investor letter:
“We exited most of our Root, Inc. (NASDAQ:ROOT) position at a substantial loss. While we hope to reenter the position in the future, we underestimated how long and how deep the industry headwinds ROOT is facing will persist. Given how soft the commercial auto insurance market is currently, it will be very hard for ROOT to execute in the near term. ROOT is our one material mistake this year thus far, but we have a significant chance of making that money back eventually in the position, as we still believe the long-term story is compelling.”

Root, Inc. (NASDAQ:ROOT) is not on our list of the 40 Most Popular Stocks Among Hedge Funds. As per our database, 24 hedge fund portfolios held Root, Inc. (NASDAQ:ROOT) at the end of the first quarter which was 25 in the previous quarter. While we acknowledge the risk and potential of Root, Inc. (NASDAQ:ROOT) as an investment, our conviction lies in the belief that some AI stocks hold greater promise for delivering higher returns and doing so within a shorter time frame. If you are looking for an AI stock that is more promising than Root, Inc. (NASDAQ:ROOT) and that has 10,000% upside potential, check out our report about this cheapest AI stock.
In addition, please check out our hedge fund investor letters Q2 2026 page for more investor letters from hedge funds and other leading investors.
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Disclosure: None. This article is originally published at Insider Monkey.






