When the story of the 2026 Boston Red Sox is told–and we have no clue yet whether it will be a triumphant tale of season-long redemption or a footnote in the history books of a team having a magical month before flaming out down the stretch–starting pitcher Sonny Gray figures to have a prominent role. It was Gray, after all, who might well have jump-started the Red Sox resurgence back in mid-June, when he declared bluntly, “We’re just not a good team right now, that’s a fact.”
Boston was 29-43 at that point. The Red Sox are 26-8 since.
Maybe it’s a coincidence, or maybe that was the wake-up call the team badly needed. But Gray, who has been the ace of the staff with Garrett Crochet injured, has certainly been one of the big drivers to help get the team back on track here in 2026. And though he is in the final year of a three-year, $75 million contract he brought with him when he was acquired in a trade with the Cardinals last winter, there is an increasing chance that he could be around longer.
Red Sox Extending Sonny Gray ‘Makes Sense’
That’s according to the beat writer duo of Chris Cotillo and Sean McAdam of MassLive, who say the Red Sox and Gray–who was a top trade candidate when the team was floundering in June–could instead re-up on an extension.
They pointed out that president Craig Breslow took that path with Aroldis Chapman last season, after Chapman was supposed to be a short-term addition and head back to free agency. Instead, the Red Sox extended him.
They write: “A similar strategy with Gray might make sense. The veteran, after silencing doubters about his ability to pitch in a big market with a fantastic first four months in a Red Sox uniform, is said to ‘definitely’ be interested in a contract extension with Boston, though conversations haven’t picked up as the Red Sox have focused on turning around their season.”
Sonny Gray’s Market Comes With Questions
Of course, the question in such a situation is always, how much? Gray is in an odd position because he turns 37 in November, and the Red Sox are his fifth team in eight seasons. He has been a solid starter all along, but not the ace he has been this year, with a league-best 12-2 record and a 2.78 ERA.
His advanced numbers are not jaw-dropping, as his WHIP of 1.163 is only slightly below his career number (1.195) and his strikeouts per nine innings is 7.8, lowest in 10 years.
Spotrac has Gray’s market value at $18 million per year, warranting a $54 million contract over three seasons. Is that too much and too long for Gray? Should he get more of a short-term deal at a bigger number? His contract value is a tough nut to crack.
Red Sox Rotation Needs Stability
McAdam and Cotillo bring up the trade of Connelly Early, though, as a reason for the Red Sox to move quicker on an extension for Gray, to give the rotation some stability.
They write: “Gray … has enjoyed his time in Boston. While he could cash in on his strong year with a high-dollar, short-term deal in free agency this winter, there’s a possibility the Red Sox strike to lock him in for 2027 before he can test the market. Moving Early increased the need for future rotation help, too.”
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