Red Sox Reportedly Feel ‘Real Disappointment’ Over Alex Bregman Exit

Boston Red Sox fans aren’t the only ones upset to see Alex Bregman leave.

Bregman is reportedly signing a five-year, $175 million deal with the Chicago Cubs. An MLB insider indicated that the Red Sox weren’t far off in their bid to keep the third baseman.

Boston offered Bregman a five-year, $165 million contract before he chose the Cubs, per ESPN’s Buster Olney. The Red Sox reportedly thought they’d retain Bregman and feel “real disappointment” that he’s headed elsewhere.

MassLive’s Chris Cotillo and Sean McAdam reported the same $165 million offer with heavy deferrals. A delay in deferral payments and Boston’s refusal to include a no-trade clause were “sticking points” in negotiations.

Bregman signed a three-year, $120 million contract with Boston last offseason but opted out after the 2025 season. He made an indelible impact in that lone year, batting .273/.360/.462 with a 3.5 fWAR in 114 games.

A reunion made sense for the Red Sox, especially after missing the chance to bring back Kyle Schwarber and watching Pete Alonso join the Baltimore Orioles. Bregman established himself as a valuable clubhouse presence for a young squad led by rising star Roman Anthony.

Bregman will instead play for the Cubs, who snapped a four-year playoff drought by going 92-70 in 2025. The 31-year-old will seek his 10th consecutive postseason appearance but first in the National League.

The Red Sox bolstered their lineup by acquiring first baseman Willson Contreras from the St. Louis Cardinals, but they still have questions to answer at second or third base. They’ll reportedly turn their attention to free-agent infielder Bo Bichette.