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Inside The Red Sox

Did Red Sox CEO Just Accept Blame for Losing Alex Bregman in Free Agency?

It's sure been a crazy year so far
Apr 24, 2026; Los Angeles, California, USA; Chicago Cubs third baseman Alex Bregman (3) rounds the bases after hitting a solo home run during the eighth inning against the Los Angeles Dodgers at Dodger Stadium. Mandatory Credit: William Liang-Imagn Images
Apr 24, 2026; Los Angeles, California, USA; Chicago Cubs third baseman Alex Bregman (3) rounds the bases after hitting a solo home run during the eighth inning against the Los Angeles Dodgers at Dodger Stadium. Mandatory Credit: William Liang-Imagn Images | William Liang-Imagn Images

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It's already been a wild year for the Boston Red Sox, so it's easy to forget that at the start of the year, this was a team still hoping to re-sign Alex Bregman.

Bregman wound up choosing the Chicago Cubs in the second week of January after the Red Sox reportedly balked at the idea of giving him a no-trade clause. Boston's reported offer of five years, $165 million also included more deferred money than the $175 million deal he took with the Cubs.

In the wake of the Red Sox firing manager Alex Cora and five top assistants on Saturday, many have pointed to chief baseball officer Craig Breslow and Red Sox ownership as a more culpable party for the team's disappointing start, and a lot of that criticism has to do with the way Bregman's one-year tenure in Boston played out.

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Kennedy takes blame for Bregman's departure (sort of)

Kennedy
Jul 12, 2024; Boston, Massachusetts, USA; President and CEO of the Boston Red Sox Sam Kennedy applauds before a game against the Kansas City Royals at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images | Paul Rutherford-Imagn Images

During a Tuesday appearance on WEEI's "The Greg Hill Show," Red Sox CEO Sam Kennedy was asked if he owned any blame for not understanding Bregman's importance to the team with regards to roster construction and the team's struggles this season. His response didn't name Bregman, but suggested that there was plenty of blame to go around.

"Absolutely," Kennedy said. "I mean, we have culpability when the franchise is not performing at the level we hold ourselves to. So, short answer is yes, for sure."

Bregman's arrival led to the Red Sox moving longtime third baseman Rafael Devers off his position, and Kennedy was among the leadership convoy that traveled to Kansas City last May to try to convince him to play first base. Devers said no and the Red Sox traded him to San Francisco a month later, only to be left without any veteran star infielders when Bregman left them in free agency.

The Red Sox went on to use most of the money they would have given Bregman on a five-year, $130 million contract for lefty Ranger Suárez, who threw eight scoreless innings for the second time in three outings on Monday.

There's nothing Kennedy or Breslow can do now, but one has to wonder if the organization would like a do-over on Bregman now that the slumping offense has seemingly lacked a leadership presence.

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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@moreviewsmedia.com