Red Sox CEO: Alex Bregman Chose a Different Path

Bregman's potential signing with the Red Sox had a ripple effect on the entire roster

Apr. 11, 2026 at 12:03am

Got story updates? Submit your updates here. ›

A cubist, geometric painting depicting a baseball game in motion, with players and the field fragmented into overlapping planes of color and shape, conveying the complexity and tension of the Red Sox's offseason decisions.The complex negotiations between the Red Sox and Alex Bregman expose the team's struggles to retain top talent and the ripple effects on the roster.Fort Myers Today

Boston Red Sox CEO Sam Kennedy recently commented that if Alex Bregman truly wanted to be with the Red Sox, he would be there. The Red Sox reportedly offered Bregman a five-year, $165 million deal, but the sticking point was the team's unwillingness to grant him a full no-trade clause. This led Bregman to sign a five-year, $175 million deal with the Chicago Cubs instead. Kennedy's comments have fueled speculation about the negotiations and the Red Sox's decision-making process, especially in light of the team's trade of Rafael Devers to the San Francisco Giants.

Why it matters

Bregman's potential signing with the Red Sox wasn't just about adding a star player; it had a ripple effect on the entire roster. His arrival would have led to a position shift for Rafael Devers, which reportedly frustrated the young slugger. This tension ultimately culminated in Devers' shocking trade to the Giants, leaving a gaping hole in the Red Sox lineup. The Red Sox's offseason moves have left fans with more questions than answers, and the upcoming season will be a crucial test of the team's ability to rebuild and contend without two of its former cornerstones.

The details

The Red Sox reportedly put a five-year, $165 million deal on the table for Bregman, but the sticking point was the team's unwillingness to grant him a full no-trade clause. This provision would have given Bregman significant control over his future with the team. Kennedy remained tight-lipped on whether Bregman specifically requested the no-trade clause, emphasizing the Red Sox's policy of not discussing the intricacies of negotiations.

  • In January 2026, Bregman signed a five-year, $175 million deal with the Chicago Cubs.
  • The Red Sox traded Rafael Devers to the San Francisco Giants during the offseason.

The players

Sam Kennedy

The Boston Red Sox CEO, who made the comments about Bregman's potential signing with the team.

Alex Bregman

The star player who signed a five-year, $175 million deal with the Chicago Cubs instead of joining the Red Sox.

Rafael Devers

The young slugger who was traded to the San Francisco Giants after reportedly being frustrated by the position shift that Bregman's arrival would have caused.

Willson Contreras

The Red Sox's only significant addition this offseason, who does not fill the power void left by Devers.

Roman Anthony

A player the Red Sox signed this offseason, likely using some of the money freed up by the Devers trade.

Ranger Suárez

Another player the Red Sox signed this offseason, likely using some of the money freed up by the Devers trade.

Got photos? Submit your photos here. ›

What they’re saying

“If Alex Bregman wanted to be here, ultimately, he'd be here.”

— Sam Kennedy, Boston Red Sox CEO

“We try not to talk about organizational policy and the finer points of negotiations. Just doesn't serve you well.”

— Sam Kennedy, Boston Red Sox CEO

“You can't replace someone like Raffy as an individual, an exceptional hitter.”

— Sam Kennedy, Boston Red Sox CEO

“We all have to do what's in the best interest of the organization...Would we have done things differently leading into it? Absolutely.”

— Sam Kennedy, Boston Red Sox CEO

What’s next

The judge in the case will decide on Tuesday whether or not to allow Walker Reed Quinn out on bail.

The takeaway

This case highlights growing concerns in the community about repeat offenders released on bail, raising questions about bail reform, public safety on SF streets, and if any special laws to govern autonomous vehicles in residential and commercial areas.