Boston Red Sox fans have long ceased their optimism that the team might be able to buy ahead of the August 3 trade deadline. The front office, on the other hand, remained optimistic for much longer.
Buster Olney reported on June 3 that Red Sox chief baseball officer Craig Breslow was scouring the trade market to find a right-handed bat to save the team (when the Sox were already 6.5 games back of a Wild Card spot). Red Sox CEO and president Sam Kennedy has recently conceded that Boston might have to pivot to selling, but it's the way he said it that has upset fans.
"It's brutal. We have rarely found ourselves in that situation, and when you do, like every trade deadline, you have to do what's in the best interest of the organization," Kennedy said in a June 17 pregame appearance on NESN. "It's brutal and truly, sort of, unthinkable, given the expectations."
Kennedy is in the unfortunate position of being the mouthpiece for ownership, which refuses to entertain Boston media. Kennedy has to try and make John Henry's messaging as palatable as possible, which wouldn't be easy for anyone.
But the Red Sox absolutely have been in this position before, and recently. Boston has finished in last place three times since 2020 and seems destined to do the same this year. The Red Sox haven't been this far under .500 since 2020 or this miserable at Fenway Park for decades, but they've been deadline sellers in recent memory (subscription required).
Red Sox fans are tired of Sam Kennedy and the front office's reasoning for selling at the trade deadline
Multiple rival executives been quoted saying they knew the Red Sox's offense would be underwhelming. Alex Speier of The Boston Globe on June 10 reported some unfortunate quotes from rival executives, including one that called the Red Sox's lineup "punchless" (subscription required). Another said they have a "lot of guys on the team who satisfy the model but are role players who are being overexposed.”
Rivals certainly didn't have high expectations for the Sox, which raises questions about where the internal hope came from. Sure, some players have regressed from 2025, like Jarren Duran, Trevor Story and Carlos Narváez, but Boston knew it needed a power bat and neglected to sign one.
Boston's front office has not been interested in doing what's best for the organization since about 2019. Reuniting with Alex Bregman or signing Pete Alonso or Kyle Schwarber would've been best for the club, but since they demand actual money and not league minimum or utility player salaries, the Red Sox wouldn't pay up.
Red Sox fans are tired of the excuses they've heard year in and year out from ownership. Boston has been in rebuilding mode for the better part of a half decade and there's seemingly no end in sight despite making the playoffs just one year ago.
Kennedy words will ring hollow until real change is made in the Red Sox organization. But after Breslow's seemingly inevitable firing, the endless cycle of leadership changes will begin again. If the Red Sox want to buy instead of sell at the trade deadline, they have to actually try in the offseason and spend money on proven free agents rather than makeshift trade candidates they try to shove into bigger roles than they've ever held.
The Red Sox's surprise at their underwhelming offense is exhausting, as is the constant falling short of expectations. Kennedy speaking as if they aren't a recurring pattern in Boston over the last few years makes things even worse.
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