The Boston Red Sox made it back to the postseason in 2025. The winter that’s followed has been busier, messier, and way less settled.
With 87 days until they open the 2026 season, the Red Sox have been active without being definitive. They’re making moves that raise the floor while leaving the ceiling very much up for debate.
Boston finished 89-73 last season and grabbed an American League Wild Card spot. The run ended quickly, with a loss to the New York Yankees in the Wild Card Series, but it still counted as progress for a club that’s spent too many recent seasons chasing direction as much as wins.
Craig Breslow took that energy into the winter.
The Red Sox’s Chief Baseball Officer added a veteran stabilizer to the rotation by trading for Sonny Gray, a move designed to bring reliability and innings after a year where both felt optional. They also reshaped the lineup by acquiring Willson Contreras, adding a right-handed bat with flexibility and edge. Someone who’s been through October and doesn’t blink.
Those are real upgrades. They’re also not finishing touches.
The Bregman Situation Changes Everything
The offseason pivot point came when Alex Bregman opted out of his contract. Boston would like him back, but the opt-out reopened a problem they thought they had solved. Instead of continuity, the Red Sox are now back in decision mode, weighing whether to recommit to Bregman or pivot toward another core-altering move.
That’s where things get interesting. Names have hovered around Boston all winter – not as leak-heavy rumors but as logical alternatives if the club decides to reshape the infield rather than simply restore it. Either direction would matter.
Waiting too long on both risks ending up with neither.
At the same time, the Red Sox have kept another card on the table throughout the offseason, a signal that Boston’s at least open to moving a controllable, high-energy piece if it helps balance the roster or unlock something bigger. That kind of chatter doesn’t linger all winter by accident.
The problem is that all of this still feels like a setup.
Questions Remain
The rotation behind Gray has questions. The lineup depends heavily on decisions that haven’t been made yet. The direction is flexible, but flexibility has a shelf life – especially in an American League East that doesn’t wait for anyone to finish thinking.
The Red Sox are better than they were a year ago. They’re also still deciding who they want to be.
At some point soon, the offseason stops being about options and starts being about consequences.
