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Red Sox Boss Hints at Bregman's Departure to Cubs
Boston CEO Sam Kennedy suggests Alex Bregman chose to leave the Red Sox for the Cubs in free agency.
Published on Feb. 16, 2026
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Boston Red Sox CEO Sam Kennedy made some eyebrow-raising comments about the team's failure to re-sign star third baseman Alex Bregman this offseason. Kennedy implied that Bregman's camp was responsible for the breakdown in contract negotiations, hinting that Bregman's demand for a no-trade clause was a sticking point. Bregman ultimately signed a lucrative deal with the Chicago Cubs, leaving the Red Sox without one of their top offensive threats from last season.
Why it matters
Bregman's departure is a significant loss for the Red Sox, who are now projected to have a less powerful lineup in 2026. The team's leadership has emphasized the need to add more power, making Bregman's exit all the more painful. This saga also raises questions about the Red Sox's willingness to accommodate star players' contract demands, especially when it comes to no-trade clauses.
The details
According to multiple sources, Bregman was willing to make concessions to re-sign with the Red Sox, but the main sticking point was his request for a no-trade clause. The Red Sox reportedly refused to grant that, citing organizational policy. When pressed on the issue, Red Sox CEO Sam Kennedy suggested that Bregman's camp was responsible for the failed negotiations, saying "If Alex Bregman wanted to be here, ultimately, he'd be here." Kennedy declined to confirm whether the Red Sox would have given Bregman a no-trade clause if he had asked for one.
- Bregman opted out of his three-year, $120 million contract with the Red Sox at the end of the 2025 season.
- The Red Sox held their first full-squad workout of the 2026 season on Sunday, February 16, 2026.
The players
Sam Kennedy
The CEO and president of the Boston Red Sox.
Alex Bregman
A 31-year-old All-Star third baseman who played for the Red Sox in 2025 before opting out of his contract and signing with the Chicago Cubs in free agency.
Rafael Devers
A former Red Sox player whose tenure with the team ended last spring, which was cited as a factor in Bregman's desire for a no-trade clause.
What they’re saying
“We're so grateful to Alex Bregman and what he meant to us, but when you have choices the way he did – you work really hard to be in a position to become a free agent and perform at that level. He chose a different path, and we wish him well.”
— Sam Kennedy, CEO and President, Boston Red Sox (Chicago Tribune)
“If Alex Bregman wanted to be here, ultimately, he'd be here.”
— Sam Kennedy, CEO and President, Boston Red Sox (Chicago Tribune)
What’s next
The Red Sox will have to find a way to replace Bregman's production and leadership in the lineup, with FanGraphs' ZiPS projections estimating no player on their roster will reach 20 home runs this season.
The takeaway
The Red Sox's failure to re-sign Alex Bregman highlights the challenges the team faces in retaining star players, especially when it comes to accommodating contract demands like no-trade clauses. This saga raises questions about the team's organizational policies and their willingness to be flexible in order to keep their top talent.
