Boston Red Sox CEO Says He Can't Understand Obvious Fan Gripe

Over the last few seasons, distrust between the Boston Red Sox and the ownership group has become rampant.

It began in 2020 with the Mookie Betts trade, and has only gotten worse throughout a trio of last-place seasons, trading away Rafael Devers, then letting Alex Bregman walk in free agency. The Red Sox have also been blown past by the Los Angeles Dodgers, New York Mets, and a handful of others in terms of spending on payroll.

On Sunday, Red Sox CEO Sam Kennedy discussed the team's up-and-down relationship with its fans, and seemed to wrestle in real time with the fact that the ownership group, to which he is the No. 1 conduit, didn't have Bostonians in the palm of its hand.

If you like our content, choose Sports Illustrated as a preferred source on Google.

Sam Kennedy depicts one "hurtful" narrative

Jun 29, 2025; Boston, Massachusetts, USA; A closeup view of the Green Monster before a game at Fenway Park between the Boston Red Sox and the Toronto Blue Jays. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

According to Kennedy, of all the narratives the fans have about him and owners John Henry, Linda Pizzuti Henry, chairman Tom Werner, and the rest of Fenway Sports Group, there's only one that's bothersome.

“There’s only one that, for me, is hurtful, and that’s that we might not care or have the passion for winning,” Kennedy said, per Chris Cotillo of MassLive. “That one, I just know it to be untrue. That one gets frustrating.

“There’s one way to address that, however: win.”

As Cotillo also reported, the Red Sox's projected collective bargaining tax payroll this season is around $267 million -- which would be the highest in franchise history, but still would come up over $100 million short of where the Dodgers have pushed their spending.

Expecting the Sox to keep up with the Dodgers may be unreasonable, but the Red Sox also have several backloaded contracts that signify that their cash outlay is actually lower than that CBT payroll by a good amount, even with penalties figured in.

“You can go do the math and know where we are,” Kennedy said. “I think it just shows that John and Linda and Tom and Mike Gordon in ownership are continuing to put the resources necessary into the Boston Red Sox to be successful. Now, we’ve got to go out and do it.”

More MLB: Introducing Red Sox's Larger-Than-Life Teenager With Unlimited Potential