Tensions have been high around the Boston Red Sox this season. A very frustrating start to the season saw manager Alex Cora and several coaches fired, while fans have been vocal in their frustration for CBO Craig Breslow, as well as Fenway Sports Group as the team’s owners.
Principal owner John Henry has, in particular, been the ire of many Red Sox fans. So, despite his rare public appearances, he appears to have taken some notice.
At the 2026 Sports Business Awards, presented by Sports Business Journal on Thursday night, Henry was given a Lifetime Achievement Award. That gave him the opportunity to step on stage and give a speech, where he made an interesting comment about the fans in Boston.
“When I arrived in Boston 25 years ago, I was told, ‘If you win the World Series in Boston, you’ll never have to buy another drink in this town. It doesn’t actually work that way,” Henry said, being quoted by Chris Cotillo.
John Henry and FSG bought the Boston Red Sox in 2002 for $660 million, a record at the time. At the time, the Red Sox were known for having a passionate fanbase, as well as having gone more than 80 years without winning the World Series. By 2004, Henry saw his Red Sox win it all. Meanwhile, Forbes reports the Red Sox are worth $5.25 billion today.
Seemingly, the relationship has worked out for both sides. However, as Henry did note, fans have grown restless with a recent downturn for the team under his ownership.
John Henry and Fenway Sports Group Have Had Unprecedented Success with the Boston Red Sox
GettyBoston Red Sox Principal Owner John Henry
When looking at the Boston Red Sox franchise since John Henry purchased the team, it’s hard to find a more successful MLB franchise. No other franchise can match their four World Series titles during that time, with the Los Angeles Dodgers and San Francisco Giants tying in second with three. Other teams, like the Houston Astros and St. Louis Cardinals, have two during that time.
In terms of wins and losses, the Red Sox have the fourth-best winning percentage, at .545, since 2002. That’s according to Statmuse. Only the Cardinals, Dodgers, and rival New York Yankees are better off. It’s safe to say the World Series wins make up for the difference there.
2018 was particularly successful. The Red Sox won 108 regular-season games, the most in franchise history, on their way to another World Series. They beat the Yankees, Astros, and Dodgers in those playoffs.
That’s a lot of success, but sports are a matter of what you’ve done for someone lately. Since 2018, things have been difficult, only making the playoffs twice. In that same time, their winning percentage slips to 17th in baseball, at .507.
A Philosophy Change Has Sparked Frustration for Red Sox Fans
GettyJohn Henry in Liverpool
The frustration from fans stems from how the Red Sox have changed their approach since 2018 and shortly after the firing of then-CBO Dave Dombrowski. In particular, taking up a model that emphasizes efficiency and avoiding bloated contracts.
This shift in model coincided with a few changes for Henry and Fenway Sports Group. Several years earlier, FSG had purchased Liverpool FC. It wasn’t the only high-profile investment for FSG. In 2021, FSG purchased the Pittsburgh Penguins. Then, in 2023, it became involved in Boston Common Golf. Meanwhile, FSG owns a majority stake in NESN, the cable station that carries Red Sox and Boston Bruins games, as well as The Boston Globe, the city’s major paper.
All of this has led to criticism that Henry is distracted. Worse, he cares about his other projects more than he currently cares about the Red Sox.
Since 2019, the Red Sox have made the playoffs twice and have had losing records in three seasons. That’s not good enough for fans in Boston, particularly as Forbes reports the Red Sox make $531 on revenue per fan. In 2024, the Red Sox made $120 million in profit, almost double the second-most profitable team, all while spending less and less on free agents.
So, fans have grown frustrated. This season alone there have been multiple “Sell the team” chants audible on the TV broadcasts. Henry was in attendance for one of those chants.
Is that entirely fair? Probably not. Should it be expected, given the high expectations and high cost of being a Boston sports fan? That’s nothing new to John Henry, and the cost of doing business.
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