The will-they-won't-they situationship between Sonny Gray and the Boston Red Sox seems to have come to a conclusion. Insider Alex Speier suggested on the 310 to Left podcast that the Red Sox are comfortable letting Gray walk in free agency.
The expectation is that Boston takes what it would have spent on Gray and instead uses those resources to improve the position player group. Craig Breslow believes that the rotation is in a "really good place" and should be a strength in 2027.
The Red Sox have Garrett Crochet, Payton Tolle, and Ranger Suarez as a more-than-competent top three, and they have considerable starting pitching depth with the likes of Tanner Houck, Johan Oviedo, and Kutter Crawford.
There are issues, though. First, when you add Jake Bennett to the mix, the rotation is extremely left-handed. Second, Brayan Bello's wild 2026 campaign (horrendous starter, dominant reliever) has his place on the roster in peril. Third, all of those depth starters are coming off serious injuries. How much can they be counted on?
Per @alexspeier, the Red Sox seem comfortable letting Sonny Gray walk in free agency and are more likely to put their offseason resources toward position players.
— Matthew Crory (@matthewcrory) November 10, 2026
"I think the rotation is in a really good place. I think it should be a strength of our 2027 team." - Craig Breslow… pic.twitter.com/5PYPlgeRSl
The truth of the matter is Boston doesn't need Gray. He put up an outlier season after two down years, saw his strikeouts decline substantially despite his overall success in 2026, and just turned 37. Committing big money to him, even over just one or two years, could wind up being a poor investment.
What the Red Sox do need is a right-handed starter who is better than Bello. With that in mind, this Gray update makes it feel as if they're walking into a mistake and continuing a frustrating but all-too-frequent trend.
Red Sox focusing on position players and ignoring the rotation, including Sonny Gray, feels like a mistake
Boston could use help in the lineup at a variety of spots. If the club can swing a trade for a top shortstop, like Elly De La Cruz, Zach Neto, CJ Abrams, or Jeremy Pena, Breslow will be happy. However, the Chief Baseball Officer refuses to be locked into chasing one position, or could add pop with a right-handed bat in the outfield, look to upgrade third base, or do a number of other things.
The Red Sox are fortunate to have the kind of flexibility to pursue the best possible option, regardless of position, knowing that they have at least solid players elsewhere, allowing them to create the strongest possible whole.
However, it also sounds like there will be just one significant addition, and that's why it feels like the team is walking into a mistake. We can acknowledge that the lineup needs a boost while also accepting the reality that the rotation could use an upgrade as well. Far too often, whether it be due to John Henry's stinginess or Breslow's stubbornness, we see Boston take this one-or-the-other tactic.
The problem is that the Red Sox play in the AL East. The Yankees might have the best starting rotation in baseball and are thought to be aggressively pursuing upgrades relative to their needs. The Rays are fresh off a World Series appearance and always find creative ways to improve. The Orioles seem hungry to right the wrongs of the past two seasons and return to the playoffs.
If Boston doesn't do enough, the club risks falling behind in the arms race. So while Breslow prepares to say goodbye to Sonny Gray, he should strongly consider adding another top-end right-hander to the Red Sox's rotation mix in addition to upgrading the lineup. The days of either/or must come to an end. It's too competitive out there to run the team this way.
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