Red Sox President Addresses Bregman's Departure

Kennedy says Bregman chose to sign with Cubs despite Boston's interest.

Published on Feb. 16, 2026

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Boston Red Sox president and CEO Sam Kennedy spoke about the team's failed pursuit of free agent Alex Bregman, who signed a five-year, $175 million contract with the Chicago Cubs in the offseason. Kennedy said that if Bregman had wanted to stay in Boston, "ultimately he'd be here." Bregman spent the 2025 season with the Red Sox before opting out of his contract and re-entering free agency.

Why it matters

Bregman's departure is a significant loss for the Red Sox, who were hoping to retain the All-Star third baseman and World Series champion. His signing with the Cubs strengthens their roster and provides veteran leadership as they aim to contend in 2026.

The details

Bregman's new contract with the Cubs includes no opt-outs and a full no-trade clause, as well as significant deferred money that lowers the average annual value for luxury tax purposes to around $31 million. In 2025 with the Red Sox, Bregman hit .273/.360/.462 with 18 home runs and 62 RBIs in 114 games, earning his third All-Star selection despite a quad injury.

  • Bregman signed a five-year, $175 million contract with the Chicago Cubs in early January 2026.
  • Bregman spent the 2025 season with the Boston Red Sox before opting out of his contract and re-entering free agency.

The players

Sam Kennedy

President and chief executive officer of the Boston Red Sox.

Alex Bregman

All-Star third baseman who spent the 2025 season with the Red Sox before signing a lucrative contract with the Chicago Cubs in the offseason.

Jason Heyward

Cubs player who previously signed the largest contract in franchise history.

Dansby Swanson

Cubs player who previously signed the second-largest contract in franchise history.

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What they’re saying

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

— Sam Kennedy, President and CEO, Boston Red Sox (Yahoo Sports)

The takeaway

Bregman's departure is a significant loss for the Red Sox, who were unable to retain the All-Star third baseman despite their interest. His signing with the Cubs strengthens their roster and provides veteran leadership as they aim to contend in 2026, underscoring the challenges the Red Sox face in keeping top talent in Boston.