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Red Sox Weigh Roster Moves as Bregman Extension Talks Stall

Formal negotiations for a potential $184 million to $200 million extension remain unopened as Boston explores roster changes for payroll relief.

ARLINGTON, TEXAS - MARCH 27: Alex Bregman #2 of the Boston Red Sox is seen in the dugout during a game against the Texas Rangers at Globe Life Field on March 27, 2025 in Arlington, Texas. (Photo by Richard Rodriguez/Getty Images)
BOSTON, MASSACHUSETTS - JULY 10: Walker Buehler #0 of the Boston Red Sox pitches against the Tampa Bay Rays during the first inning at Fenway Park on July 10, 2025 in Boston, Massachusetts.
BOSTON, MA - JULY 13: Catcher Connor Wong #12 of the Boston Red Sox congratulates Aroldis Chapman #44 after their 4-1 win over the Tampa Bay Rays at Fenway Park on July 13, 2025 in Boston, Massachusetts.
BOSTON, MA - JULY 13: Alex Bregman #2 of the Boston Red Sox connects on a hit during the eighth inning against the Tampa Bay Rays at Fenway Park on July 13, 2025 in Boston, Massachusetts.

Overview

  • Neither the Red Sox nor Alex Bregman have begun formal extension talks despite mutual interest in a long-term deal.
  • Industry estimates place Bregman’s extension value between $184 million and $200 million based on his All-Star-caliber first half.
  • GM Chaim Bloom has publicly voiced a desire to keep Bregman in Boston but acknowledged there is no set timeline for negotiations.
  • To clear payroll space for a mega-deal, Boston is considering trading outfielder Jarren Duran or allowing veteran closer Aroldis Chapman to depart.
  • ESPN insider Jeff Passan affirmed that neither Bregman nor Chapman will be moved before the July 31 trade deadline as the team pushes toward the postseason.