The MLB free‑agent sweepstakes for three‑time All‑Star third baseman Alex Bregman came to a dramatic conclusion on Saturday as he signed with the Chicago Cubs by agreeing to a five‑year, $175 million deal. Left out in the cold are the Boston Red Sox, who had expectations of bringing the 31-year-old first baseman back into the fold.
MLB Rumors: Red Sox Surprised By Bregman’s Free Agency Decision
Bregman, who played the 2025 season with the Red Sox, opted out of the final two seasons of his three‑year, $120 million deal to test free agency for a second consecutive offseason. Boston front office officials believed they had positioned themselves to retain him, reportedly extending a five‑year, $165 million offer that would’ve kept Bregman in Fenway Park through 2031, and $205 million total including his 2025 contract with the team.
The Red Sox believed they were going to land Bregman with their 5-year, $165 million offer. Including his ‘25 deal, they would’ve paid him $205m over six years, w deferrals. Real disappointment in the organization today.
— Buster Olney (@Buster_ESPN) January 11, 2026
But those expectations were dashed when the Cubs came in with a higher overall guarantee.
The Cubs’ deal, which includes a full no‑trade clause and no opt‑outs, marks a significant financial commitment from Chicago and the richest average annual value in franchise history at roughly $35 million per season. That offer ended up being too rich for Bregman to pass up, even if the Red Sox had hoped their longstanding relationship would carry more influence.
For Boston, the outcome represents a bitter offseason disappointment. General manager Craig Breslow and manager Alex Cora were vocal throughout the winter about their desire to bring Bregman back, praising his clubhouse leadership and his offensive contributions. During the 2025 MLB season, Alex Bregman posted a .273 batting average with 18 home runs and 62 RBI while with the Red Sox.
Yet, despite those efforts, Bregman chose the Cubs, whose offer not only surpassed Boston’s in total value but also provided him long‑term stability and control late in his career.
The Red Sox now face the offseason’s next challenge. The must replace a key bat and clubhouse presence who helped them reach the postseason for the first time in four years. With Bregman off the board, Boston will likely turn attention toward other free agents like Ketel Marte and Bo Bichette or seek trade options to bolster their lineup.
