Red Sox CEO sounds off on Alex Bregman leaving Boston to join the Cubs

Chicago visits Fenway Park to close out the 2026 regular season.
Eric Canha-Imagn Images

All winter, the near-universal expectation was Alex Bregman and the Boston Red Sox would eventually find common ground and he'd re-up with the club long-term.

Then, Jed Hoyer and the Chicago Cubs entered the picture and played spoiler, ultimately signing the three-time All-Star to a five-year, $175 million deal that included full no-trade protection, something Boston reportedly refused to do.

Red Sox CEO Sam Kennedy held court with the media in Florida over the weekend, weighing in on Bregman's decision to leave Boston, saying, "If Alex Bregman wanted to be here, ultimately, he’d be here.”

Well, that's a nice talking point, but it also boils down to the organization's apparent refusal to give him what he sought in his next contract. Cubs fans are no stranger to a front office and ownership group sticking to its principles in free agent negotiations - and what can happen when teams refuse to budge. This time, though, Chicago was on the right side of the equation and landed a player they'd long desired.

Alex Bregman delivered in Boston - and took full advantage of it

After getting off to the best start of his career, Bregman suffered a quad injury in May and missed nearly two months before returning to the Red Sox lineup. Despite the missed time, he still finished the year with 3.5 bWAR, a 128 OPS+ and 46 extra-base hits, setting himself up to opt out of his deal with Boston and test free agency once again.

“We’re so grateful to Alex Bregman and what he meant to us,” Kennedy said. “But look, in the end, 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 and looking forward to seeing him at the end of the season at Fenway (when the Cubs play the Red Sox Sept. 25-27).”

Losing Bregman this winter after trading franchise cornerstone Rafael Devers last summer has Kennedy, ownership and the Red Sox front office on thin ice with a frustrated fan base that failed to make a major offensive splash this winter. Meanwhile, expectations and vibes are high in Mesa, where Bregman and the Cubs have their eyes set on a World Series title.

Loading recommendations... Please wait while we load personalized content recommendations