Red Sox CEO Sounds Bitter About Alex Bregman's Offseason Departure

Boston's front office failed to retain the star third baseman, who signed with the Cubs instead.

Published on Feb. 17, 2026

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The Boston Red Sox are entering the 2026 season without star third baseman Alex Bregman, who opted out of his contract with the team and signed a lucrative deal with the Chicago Cubs. Red Sox CEO Sam Kennedy expressed frustration over the team's inability to keep Bregman, suggesting the player had no desire to take a hometown discount to remain in Boston.

Why it matters

Bregman's departure is a significant loss for the Red Sox, who have also traded away star player Rafael Devers in the offseason. The team's front office is facing criticism for not doing enough to retain their top talent, which could impact fan sentiment and the team's performance in the upcoming season.

The details

The Red Sox made a $40 million offer to Bregman before he opted out and signed with the Cubs for $10 million more. Red Sox CEO Sam Kennedy expressed bitterness over the team's inability to keep Bregman, saying "If Alex Bregman wanted to be here, ultimately, he'd be here." However, Bregman was under no obligation to take a hometown discount, and the Cubs' higher offer was the deciding factor in his decision to leave Boston.

  • Bregman opted out of his contract with the Red Sox in the 2025 offseason.
  • Bregman signed a deal with the Chicago Cubs in February 2026.

The players

Alex Bregman

A star third baseman who played for the Boston Red Sox before opting out of his contract and signing with the Chicago Cubs in the 2026 offseason.

Sam Kennedy

The CEO of the Boston Red Sox, who expressed frustration over the team's inability to retain Bregman.

Caleb Durbin

The player who is taking over third base for the Red Sox in Bregman's absence.

Willson Contreras

The player who is taking over first base for the Red Sox in the 2026 season.

Rafael Devers

A star player who was traded away by the Red Sox in the offseason, further depleting their roster.

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What they’re saying

“If Alex Bregman wanted to be here, ultimately, he'd be here. There's many different parts of a contract negotiation. We did not come to an agreement. So obviously, he's a Chicago Cub and wish him well until the end of the year.”

— Sam Kennedy, CEO, Boston Red Sox (The Athletic)

What’s next

The Red Sox will need to find a way to replace Bregman's production and leadership on the team, as they look to remain competitive in the 2026 season.

The takeaway

The Red Sox's inability to retain star players like Bregman and Devers raises questions about the team's commitment to building a winning roster and keeping their top talent. This offseason has been a disappointment for Red Sox fans, who are hoping the team can rebound and remain competitive in the upcoming season.