The Red Sox may be living with John Henry for the long haul, and Sam Kennedy just made that plain.
On August 13, the club’s president and CEO said during his recurring appearance on WEEI’s "The Greg Hill Show" that he expects the Henry family to remain in control in Boston for a long time. Kennedy didn’t leave much room for interpretation, either.
"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.
That’s the reality Red Sox fans are being asked to sit with. For years, plenty of them have wanted Henry to move on, especially in the wake of the Mookie Betts trade and a stretch in which Boston has been uneven in free agency and has either traded away or declined to extend more homegrown talent in favor of lesser outside options. The frustration has only grown in early 2026.
And yet, as much as the grumbling has followed Henry around, his ownership record is not simple to dismiss. Since buying the Red Sox in 2002, Boston has won four World Series titles in the Henry era - more than any other team has managed since 2000 - even while also finishing last in the American League East five times under his watch. That’s the split-screen version of this ownership: championships on one side, ugly lows on the other.
Henry’s Red Sox were also the first team he owned before Fenway Sports Group grew into a much larger sports portfolio. That group now includes Liverpool Football Club of the English Premier League, a stake in Roush Racing and the PGA Tour, and it previously held a controlling stake in the Pittsburgh Penguins before selling that in June 2026. Henry has reportedly wanted to buy a basketball team someday, but according to Kennedy, the Red Sox are not part of that equation.
There have been hints of a different approach lately. Across the 2025-26 seasons, the front office has taken a more aggressive posture, making trades and signing Alex Bregman and Ranger Suarez to hefty free agent deals, even though Bregman’s deal didn’t pan out. Henry was also seen multiple times at Fenway Park during Boston’s 30-5 winning stretch, a run that suggested his baseball appetite may have been stirred again.
Still, the bigger question isn’t whether Henry shows up or spends here and there. It’s whether the organization can avoid the same old churn - the endless cycle of chief baseball officers, the leaked scandals, and the gaps in communication with players and leaders - while also paying enough to stay with the top clubs in the league.
If that happens, Henry staying put may not be a disaster. If the Red Sox keep ducking top-end free agent talent and keep misfiring on how they handle the people inside the room, it could feel like exactly the problem fans feared.
In Other News...
Rafael Devers Is Putting The Red Sox Trade Back Under Fire
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Instead, Devers production has dipped in San Francisco, and the ripple effects are being felt well beyond the Bay Area. The Giants are left sorting through a deal that has not gone the way they hoped, while their general managers mixed comments after the deadline suggested a roster still very much in flux, the sort of uncertainty that can make a trade look different a few months later than it did on the day it was made. [Read more 🡒]
Red Sox May Be Tipping Their Hand With Franklin Arias
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The timing remains unclear, with reports leaving open everything from a debut this year to a longer runway that stretches into 2027. For now, the Red Sox are still evaluating where he could make the most sense down the stretch and, if the club gets there, in October. No official decision has been made on a promotion, which leaves Arias as both a possible answer and a question Boston has not quite settled yet. [Read more 🡒]
Red Sox Bullpen Shuffle Leaves Seth Martinez In A Strange Spot
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Martinez did not get claimed after going on waivers, leaving him in an unusual holding pattern within the organization. He now has the option to elect free agency, but for the moment he remains in the system, a reminder of how quickly a relievers path can change when a team is forced to juggle depth and health at the big-league level. [Read more 🡒]