There have been few teams in recent memory as dysfunctional and dramatic as the Boston Red Sox. With the team struggling to a 33-46 record through their first 79 games, league-wide attention has shifted to Boston as sellers ahead of the August 3 trade deadline. However, recent comments from both team president Sam Kennedy and Chief Baseball Officer Craig Breslow suggest the two may not be on the same page about the direction the team should take.

“Let’s be honest, unless things change dramatically, we may have to pivot here from what our initial planning was,” Kennedy told WEEI’s The Greg Hill Show on June 11. “It just wouldn’t be responsible to do otherwise,” he continued. In the 14 games since his comments, the Red Sox have gone just 7-7. A seemingly clear sign that the pivot Kennedy alluded to is right around the corner. 

Meanwhile, Breslow has made several comments indicating he still believes the Red Sox can go on a run to get back into the playoff race. Telling Tim Healey of the Boston Globe, “We’re still not at a point where that decision is clear… We’ve got a lot of baseball games to play between now and then, and we’re going to do everything we can to get the ship righted for 2026," ahead of Monday’s 3-2 loss to the Colorado Rockies. 

Breslow again doubled down on his belief in the group on Friday morning on The Greg Hill Show, saying, “It's true we can believe in the roster that we have. We can believe in our players and know that we're capable of playing better... We have to win a lot of baseball games, and we don't have a ton of time to do it. I believe that we're capable of doing it.” 

Miscommunication has been a trademark of the organization for the better part of the last decade, with an ownership group that has changed its organizational philosophies time and time again, dating back to the saga that led to franchise icon Jon Lester signing with the Chicago Cubs in the 2014 offseason. 

Principal owner John Henry has refused to speak with the media since 2020, leaving Kennedy as the ownership group’s forward-facing spokesperson. As a result, Kennedy’s comments should be taken as the stance of Fenway Sports Group. Meaning Breslow’s comments directly contradict his bosses. Just the latest sign of an organization where not everyone is rowing in the same direction. 

Despite everything pointing to the contrary, Breslow remained steadfast that that was not the case, telling Hill, “There's no disconnect."

Regardless of whether the two are on the exact same page, their public comments clearly tell a different story. If the Red Sox are going to right the ship and build a contender moving forward, the organization has to fix its messaging to show a united front rather than two parties at odds. 

The Red Sox will look to secure the series win against the Yankees on Saturday afternoon in game three of a four-game set at Fenway Park. Jake Bennett (1-3, 3.71 ERA) for Boston opposite Gerrit Cole (2-2, 3.62 ERA) for New York. First pitch set for 1:10 p.m. ET. 

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