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Root investor letter highlights persistent commercial auto headwinds
Buckley Capital said it exited most of its Root position at a substantial loss, citing the commercial auto insurance market as too soft to support near term execution.
Buckley Capital Advisors described Root, Inc. as its key near term miss in a second quarter 2026 investor letter, pointing to insurance industry headwinds that it expects to persist. In the letter, the firm said it redirected capital toward companies where it sees improving fundamentals, catalysts, and attractive valuations.
Root, Inc., an insurance products and services provider, closed at $59.65 per share on July 27, 2026. Its shares were up 6.7% over one month, but down 47.5% over the past 52 weeks, and the company’s market capitalization was about $944.0 million.
Buckley said it exited most of its Root position at a substantial loss, adding that it underestimated how long and how deep the industry pressures would last. The firm argued that with the commercial auto insurance market currently soft, it would be difficult for Root to execute in the near term, while still calling the long term outlook compelling.
The letter also framed Root as Buckley’s one material mistake so far in 2026, while leaving open the possibility of reentering the stock if conditions improve. Buckley said it continues to focus on small and mid cap companies it views as misunderstood with underappreciated earnings power.