Alex Bregman opting out of his contract with the Boston Red Sox to become a free agent was a foregone conclusion. All of Red Sox Nation knew it was going to happen unless he missed the entire season. Now, fans are hoping that the front office recognizes the impact he had both on and off the field and brings him back for the long term.
Headed into the 2025-26 offseason, the Red Sox are looking to make splashes. As Craig Breslow said (in similar verbiage), it's much harder to get from 89 wins to 92 than from 81 to 89. Luckily for the Red Sox, their needs seem pretty clear. Their entire outfield is set (with backups), catcher seems locked down for now, Trevor Story is manning one of the middle infield positions, and most of the starting rotation is set.
Boston heads into the offseason needing to bring Bregman back (or figure out third base), add a No. 2 starter, upgrade at first base, figure out who is manning the middle infield with Story, and flush out the middle of the bullpen. It seems clear that a reunion with Bregman is a top priority, but one Red Sox insider noted that it isn't that simple.
Scott Boras' usual tactics might prevent Alex Bregman was returning to Boston
Sean McAdam of MassLive said that the Red Sox may not be able to wait around for Bregman to make a decision this offseason while they have other needs to fill (subscription required). Bregman's agent, Scott Boras, likes to wait out to market to get the best possible price for his client, but this could backfire if Bregman hopes to reunite with the Red Sox.
Boston is going to need to make waves this offseason at the higher end of the market, and those players tend to find homes quickly. Bregman isn't going to be cheap, somewhere in the $30 million per year range, and they might need to use that money elsewhere to make upgrades.
It's a sad reality for Red Sox fans who fell in love with Bregman this season. His presence at the plate lengthened the lineup, and his leadership in the clubhouse to the many rookies who found their way to Fenway's first base dugout was invaluable. Red Sox Nation hopes the Sox can convince him to make Boston his permanent home for the rest of his career. Fans also know that this team has World Series aspirations, and to realize them, it needs to make other upgrades.
Of course, this wouldn't be a problem if the ownership group spent whatever it took to make the team great, but that isn't the case. The hope now is that the Sox make a competitive offer early in the offseason, and he wants to stay, so he takes it.