May 18, 2025; Boston, Massachusetts, USA; A Boston Red Sox hat and glove rests on the railing by the dugout prior to a game against the Atlanta Braves at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images Bob DeChiara-Imagn Images

Boston Red Sox Next Contract Extension Should Be Obvious

Originally posted on Boston Red Sox on SI
By Patrick McAvoy | Last updated Aug 31, 2025 12:00 PM ET

The Boston Red Sox have been proactive, rather than reactive this season.

Boston has proved over and over again this season that things are different. The Red Sox entered the season after an aggressive offseason that featured Garrett Crochet, Aroldis Chapman, and Alex Bregman coming to town among other moves.

The Red Sox extended Crochet and have also been aggressive with their top prospects this season. Kristian Campbell started the season in the big leagues and landed a long-term deal. Roman Anthony eventually made the jump to the big leagues and landed a long-term extension himself. The Red Sox signed Walker Buehler this past offseason and cut ties with him rather than waiting it out until the offseason. Boston also just promoted No. 2 prospect Payton Tolle to the big leagues in the same season that he started with the High-A Greenville Drive.

On top of all of these moves, the Red Sox reportedly got another extension done on Saturday. Boston has gotten a historic season from Chapman this season and responded with an extension for the 2026 season to go along with an option for 2027.

The Red Sox should hand out one more contract extension

All of this is to say that the Red Sox's front office isn't messing around. After a few down years for Boston, the window is opening up. Craig Breslow has made it clear he isn't afraid to hand out a deal early. So, who could be the next option? That, seemingly is obvious.

Boston's next extension should be Alex Bregman. This isn't a ground-breaking statement. Earlier in the season, there was some chatter about the possibility. Right now, it doesn't seem likely. Bregman has talked about having discussions after the season because he wants to focus on helping the team stack up wins and make it back to the postseason.

While this is the case, Bregman is the type of game-changer Boston has been looking for over the last few years. The Red Sox found him and he was an All-Star this year and has been a leader in the clubhouse. The Red Sox just inked Chapman to an extension and the club's next deal should be Bregman. It's easier said than done, but this team is trending up and it's not a coincidence that this was the case after he came to town.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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