There isn’t a whole lot that is more important to a contending playoff team than a strong front half of their starting rotation. The recent addition of Sonny Gray certainly helps the Red Sox move toward that, but there is still work to do if they want to field one of the premier pitching staffs in baseball.
The need for an established starter in the middle of their rotation at the end of the year could not have been more evident when they were forced to ask the freshly-debuted Connelly Early to take the mound in an elimination game on the road in Yankee Stadium. All things considered, Early held his own in that start, but the Red Sox likely don’t want to find themselves in the same situation in 2026.
The Red Sox front office appears to be far from finished this winter
This is presumably the mindset of Boston’s front office headed into winter meetings. Craig Breslow, the Red Sox's chief baseball officer, has been “hesitant to proclaim Sonny Gray as a number two starter because the Sox might acquire another starter this offseason who would slot in front of him,” according to Alex Speier of the Boston Globe.
A number of starting pitchers are on both the free agent and trade market right now that would likely slot in front of the 36-year-old Sonny Gray headed into 2026. Framber Valdez and Ranger Suarez currently headline the free-agent class while starters such as Freddy Peralta, Joe Ryan, and Cole Ragans are some pitchers with buzz as trade candidates that could present themselves as number two starters in the Red Sox rotation.
As it stands now, the rotation has a lot of upside but a lot of question marks as well beyond Garrett Crochet and Sonny Gray. Brayan Bello is coming off of his best season thus far, but posted a handful of underlying metrics that suggest he could have a hard time taking another step forward. Kutter Crawford missed all of 2025, so it’s tough to project what he may provide to the staff. Connelly Early and Peyton Tolle both showed a lot of promise in their brief big league stints, but it can’t be expected that they both will perform at a high level in their first full seasons. For all fans know, Bello, Crawford, Early, or Tolle could be moved at some point this winter.
The Red Sox have plenty of resources to add another starter
There are a lot of directions the front office can take in putting together their pitching staff for 2026, but one thing is for certain — adding another established starter that can join Garrett Crochet and Sonny Gray at the top of the rotation would do a lot in setting the Red Sox up for another playoff berth. They have the resources to make it happen as well, whether that be through the free agent or the trade market.
Alex Bregman and Lucas Giolito both hit the open market which opened up $60 million on the books for the Red Sox which can be used toward adding a Framber Valdez or a Ranger Suarez. Jarren Duran has routinely been brought up in trade talks and could be a valuable piece in bringing in the starter they need. They also have one of the better farm systems in baseball, so a number of prospects could be moved to make a deal happen. The fact of the matter is that the Red Sox have what it takes to make the needed addition, and they appear confident that they are going to get it done.