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Boston Red Sox owner John Henry is reportedly frustrated with how poorly the team's season has gone this year.

A year ago, the Boston Red Sox were a playoff team. This year, they’re among the worst teams, by record, in all of MLB. It’s not a surprise that fans are frustrated.

Much of that ire is directed at principal owner John Henry. As Fenway Sports Group, which Henry is a founder of, has expanded its portfolio, many fans have grown concerned that the Red Sox are a number on a spreadsheet, and not something that he cares about like he did when he first acquired the team and helped lead them to four World Series wins, including the team’s first in 86 years.

Still, Red Sox spending has not kept up with other big market teams, like the Los Angeles Dodgers, New York Mets, and the New York Yankees. Along with that, since 2018, their last World Series win, Boston has had two playoff appearances and three last-place finishes in the AL East.

So, it’s been notable that John Henry is more visible around the team in 2026. That’s something that MassLive‘s Sean McAdam broke down recently, calling Henry “highly frustrated” with the direction of the team.

McAdam would go on to admit it’s still too early to say how, if in any way, Henry’s increased presence will change things. However, in a season where he was present to hear fans chant to “Sell the team,” it is notable that he has those concerns about the team’s performance.

Boston Red Sox Legend David Ortiz Says John Henry is Worried

No Boston Red Sox player of the John Henry era is more beloved by fans than David Ortiz. A key piece of three World Series teams, Ortiz knows what it takes to win in Boston and has stayed close to the team. So, when Ortiz recently shared that Henry is concerned about the direction of the team, it raised plenty of eyebrows.

“He’s worried. We had a conversation. I can see. I’ve known John a long time, him and the whole team — him and (chairman) Tom Werner, the whole group, they’re working on figuring things out to get this ride better,” Ortiz said at the end of May.

The Red Sox are now 29-40 on the season. That’s 13.5 games back in the AL East and the fourth-worst record by winning percentage in the American League on the whole. It’s put the Red Sox in a position to consider selling at the Trade Deadline.

Ortiz would also address the concern from fans that Henry is apathetic. However, Ortiz attributed that to how he manages his outward emotions.

“The thing is, you see John, and John is someone that he manages his emotions really well. He’s very professional at everything he does. Sometimes, for people, it’s hard for them to understand that part of (him), but he’s worried,” Ortiz said.

“He knows the direction of this team and he’s worried about the team’s situation more than what people think he is.”

Red Sox CEO Sam Kennedy Admits 2026 Season is ‘Embarrassing’

Prior to this weekend’s series win against the Texas Rangers, things were somehow even worse for the Boston Red Sox. At that time, Red Sox CEO Sam Kennedy appeared on local radio, admitting that it’s been an embarrassing season.

“I think it’s important here at the outset to acknowledge how embarrassing, unacceptable, maddening, frustrating — whatever words you want to use— the past two and a half months have been,” Kennedy said. “There’s no way to sugarcoat it. It’s been awful, especially when you consider the stated goal of building upon what happened last season.”

Outwardly, the Red Sox have projected that they want to make trades to improve the roster on the fly. After all, the AL is down this year, and the Wild Card isn’t actually out of reach. However, Kennedy did finally have to admit the team is getting close to pivoting.

“At the current moment, there are a lot of discussions going on in terms of improvement and how we get this thing back on track,” Kennedy said. “But look, let’s be honest, unless things change dramatically, we may have to pivot here from what our initial planning was. It just wouldn’t be responsible to do otherwise.”

Despite that, the Red Sox have outwardly said that they’re not considering firing Chief Baseball Officer Craig Breslow. Not that many reports seem to believe that posturing. In particular, if things keep getting worse under an ever-increasing close eye from ownership.