It has been a tumultuous season for Boston Red Sox principal owner John Henry and the rest of the Fenway Sports Group. At 25-33, Boston has been one of the most underwhelming teams in baseball, leading to calls from fans for the group to sell the team. However, Henry received a strong vote of confidence on Monday afternoon from three-time World Series Champion and Hall of Famer David Ortiz, who spoke to the media about the ownership group at a charity golf event. 

The last five seasons have been the most contentious of Fenway Sports Group's 24-year run as the owners of the Boston Red Sox. After nearly two decades of dominance that brought Boston its first four World Series titles since the late 1910s, a change in organizational philosophy saw the Red Sox pivot from perennial big spenders to a team focused on building a more sustainable contender on the backs of homegrown talent. 

Since winning the 2018 World Series, the Red Sox that fans had come to know and love were slowly dismantled as the newfound philosophy took over. And as the shift towards sustainability wore on, so did the losing seasons.  After trades that sent franchise staples like Mookie Betts and Rafael Devers to the West Coast, and botched negotiations that led to Xander Bogaerts signing with the Padres, fans slowly began to turn on Henry and FSG, painting them as cheap and caring more about their bottom line than the product on the field.

Things came to a head quickly in 2026, with the team having self-proclaimed World Series aspirations that they have fallen well short of through the first 58 games. With the Red Sox struggling to a 9-19 record at Fenway Park, chants of 'sell the team' can be heard on a near-nightly basis at America's Most Beloved Ballpark. 

Despite calls from fans to move on from the Red Sox, FSG has remained steadfast in its belief, not only in the 2026 roster, but also that they are on the right path toward becoming perennial contenders under the new philosophy. 

But until the results on the field start to show that their belief is well-founded, the chants won't be going anywhere anytime soon. 

“I don’t blame them,” Ortiz told WBZ’s Dan Roche at the David Ortiz Soirée of Hearts charity golf tournament when asked about fans' calls for Henry to sell the team. "We got them used to winning." Despite the Hall of Fame Designated Hitter's understanding of the chants, he still believes that Henry is as committed as ever to winning. "On the other hand, the front office, Fenway Sports Group, John Henry, he always finds a way to get the fans what they deserve, and I'm pretty sure that's gonna happen moving forward," Ortiz said. 

Ortiz described a conversation he had with Henry last week in an interview with the Associated Press, saying, "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." 

While Ortiz's vote of confidence in ownership should help quell some fans' concerns, it is worth noting that since his retirement after the 2016 season, he has served as a "special assistant" to the Red Sox, meaning he is still technically an employee of Henry. 

For many fans, though, ownership's "worry" about the team will fall on deaf ears, as the team has made the playoffs just twice since the 2018 season while continuing to charge some of the highest ticket and concession prices in baseball. For Fenway Sports Group, it is, to put it plainly, a put-up-or-shut-up time in Boston.

The Red Sox are off on Monday night after taking two of three from the Cleveland Guardians. They'll return home for a three-game set with the Baltimore Orioles that gets underway on Tuesday night. Connelly Early (5-2, 2.95 ERA) gets the start for the Red Sox opposite Shane Baz (2-5, 4.48 ERA) for the Orioles. First pitch from Fenway Park set for 6:45 p.m. ET. 

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