Since John W. Henry bought the Boston Red Sox in 2002, the organization has dabbled in the extremes. Boston has enjoyed more World Series titles than any other team since 2000 with four titles in the Henry era. It's also finished last in the American League East five times under his ownership.
In many recent seasons, including early in 2026, Red Sox fans have called for Henry to sell the team. Since the Mookie Betts trade, Boston has been an inconsistent player in free agency, and traded or neglected to extend more home grown stars in favor of lesser free agent or trade options.
Red Sox CEO and president Sam Kennedy on August 13 said during his recurring appearance on WEEI's "The Greg Hill Show" said that he expects the Henry family to be in charge in Boston for a long time. Los Angeles Dodgers owner Mark Walter purchased the Los Angeles Lakers 14 months ago and flipped the team for a $2 billion profit, but Henry, who also hopes to buy a basketball team someday, reportedly doesn't plan on selling the Red Sox to get there.
"John Henry, Linda Henry, Henry family, are never selling the Boston Red Sox — and that's a soundbite you can play forever more, I'd bet anything on that," Kennedy said.
Red Sox's Sam Kennedy says John Henry will 'never' sell the team
"John Henry, Linda Henry, Henry family, are never selling the Boston Red Sox." Red Sox President and CEO Sam Kennedy joins! #RedSox #FenwaySportsGroup #MLB #Sports #fyp pic.twitter.com/k3udsSHXA2
— The Greg Hill Show (@TheGregHillShow) August 13, 2026
Red Sox fans are certain to have conflicting feelings about Kennedy's announcement on Henry's ownership. It would be hard for even the most jaded fans to argue that Henry's tenure as team owner has been a failure, given the Red Sox's World Series success over the last two decades, but Henry's mentality has changed over the years.
The Red Sox were the first sports team Henry bought before he founded Fenway Sports Group, which owns Liverpool Football Club of the English Premier League, a stake in Roush Racing and the PGA Tour, and it once owned a controlling stake of the Pittsburgh Penguins before selling it in June 2026. Henry's priorities have changed since he bought the Red Sox and said change is reflected in the team's spending practices, which has resulted in generally poorer performances in baseball's most competitive division.
The front office has shown signs of change over the 2025-26 seasons, being aggressive with trades and signing Alex Bregman and Ranger Suarez to hefty free agent deals (even though Bregman's didn't pan out). Henry was pictured multiple times at Fenway Park during Boston's 30-5 winning stretch and his passion for baseball might be sparked again.
Henry keeping the Red Sox might not be the worst thing, if he can keep the endless cycling through chief baseball officers and leaked scandals to a minimum, as well as spending enough to keep up with the best competition in the league. If the Red Sox keep refusing to pay top-end free agent talent and fail to communicate with their leaders and players, it may well be the worst thing.
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