Inside The Red Sox

Why Alex Bregman Left Red Sox, According to Boston's CEO

Red Sox Nation might not be so understanding...
Jackson Roberts|
Feb 11, 2026; Mesa, AZ, USA; Chicago Cubs Alex Bregman (3) gets ready to hit during spring training camp at Sloan Park. Mandatory Credit: Rick Scuteri-Imagn Images
Feb 11, 2026; Mesa, AZ, USA; Chicago Cubs Alex Bregman (3) gets ready to hit during spring training camp at Sloan Park. Mandatory Credit: Rick Scuteri-Imagn Images | Rick Scuteri-Imagn Images

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For all the other side quests this offseason brought with it, the failed pursuit of Alex Bregman felt like the No. 1 story for the Boston Red Sox.

Bregman signed a five-year, $175 million deal with the Chicago Cubs. The Red Sox were reportedly willing to go as high as $165 million, but their offer also included more deferred money than Chicago's, and they wouldn't give the three-time All-Star a no-trade clause.

To most people, it would be fair to say the Red Sox didn't adequately match the Cubs' offer. But to listen to Red Sox chief executive offer Sam Kennedy, the whole saga was somehow about something else.

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Kennedy says Bregman leaving wasn't about offer, no-trade clause

Alex Bregman
Sep 30, 2025; Bronx, New York, USA; Boston Red Sox third base Alex Bregman (2) hits a single during the first inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

On Sunday, Kennedy spoke at JetBlue Park in Fort Myers, and gave an answer about why Bregman didn't re-sign with the Red Sox that doesn't seem as if it will go over well with the fan base as a whole.

"We're so grateful to Alex Bregman and what he meant to us," Kennedy said. "But look, again, when you have choices the way he did, you work really hard to become a free agent and perform at that level. He chose a different path, and we wish him well. We look forward to seeing him at the end of the season at Fenway."

When pressed for a follow-up about the no-trade clause part of the equation, Kennedy essentially dodged the question and put the onus for Bregman's departure squarely on Bregman.

“If Alex Bregman wanted to be here, ultimately he’d be here," Kennedy said.

The Red Sox have taken plenty of heat for what they self-professed to be a team policy about not offering no-trade clauses. That heat seems particularly well-founded if they're not even willing to accept that it could have contributed to Bregman wanting to jump ship.

Now, could it ultimately work out better for Boston that instead of spending the money on Bregman, they got starting pitcher Ranger Suárez at a lower price point and traded for Caleb Durbin as his de facto replacement? Sure, but that doesn't mean the process was sound at all times.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org

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