Boston Red Sox CEO Struggles to Understand Fan Frustration

Kennedy says ownership's passion for winning is 'hurtful' narrative, but payroll lags behind top spenders

Published on Feb. 16, 2026

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Boston Red Sox CEO Sam Kennedy acknowledged the growing distrust between the team's ownership group and its fanbase, particularly over the last few seasons marked by trades of star players, last-place finishes, and a payroll that lags behind top-spending teams like the Los Angeles Dodgers. Kennedy defended the ownership's passion for winning but admitted the team needs to start producing results on the field.

Why it matters

The Red Sox's strained relationship with their loyal fanbase has become a major storyline, as the team's recent roster decisions and payroll constraints have frustrated many supporters who expect the storied franchise to compete for championships annually.

The details

Kennedy said the only 'hurtful' narrative about the ownership group is the perception that they 'might not care or have the passion for winning.' However, he acknowledged the team's projected $267 million payroll this season, while a franchise high, still falls over $100 million short of the league-leading Dodgers. The Red Sox also have several backloaded contracts that mean their actual cash outlay is lower than the luxury tax payroll figure.

  • The distrust between the Red Sox and their fans began in 2020 with the trade of star outfielder Mookie Betts.
  • The Red Sox have finished in last place in their division in three of the last four seasons.

The players

Sam Kennedy

The president and CEO of the Boston Red Sox.

John Henry

The principal owner of the Boston Red Sox and chairman of Fenway Sports Group.

Linda Pizzuti Henry

The wife of Red Sox owner John Henry and a co-owner of the team.

Tom Werner

The chairman of the Boston Red Sox and a co-owner of Fenway Sports Group.

Mike Gordon

A co-owner of the Boston Red Sox and a member of Fenway Sports Group.

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What they’re saying

“There's only one that, for me, is hurtful, and that's that we might not care or have the passion for winning. That one, I just know it to be untrue. That one gets frustrating.”

— Sam Kennedy, CEO, Boston Red Sox (MassLive)

“You can go do the math and know where we are. 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.”

— Sam Kennedy, CEO, Boston Red Sox (MassLive)

What’s next

The Red Sox will need to show tangible progress on the field this season to begin repairing their relationship with the fan base, who have grown increasingly frustrated with the team's recent struggles and roster decisions.

The takeaway

While Red Sox ownership claims to be committed to winning, the team's actions in recent years - including trading away star players and failing to keep pace with the league's top spenders - have eroded trust with the passionate Boston fanbase. The onus is now on the Red Sox to back up their words with on-field results and a renewed dedication to fielding a championship-caliber team.