Red Sox Free-Agent Case: Will There Be Sonny Days, Or Gray Skies In Boston?

[Ryan Salvaggio]

When the Boston Red Sox acquired Sonny Gray from the St. Louis Cardinals last offseason, the consensus among those who followed the team seemed to be that he was a solid number two option behind Garrett Crochet, and he looked even better as the number three when Ranger Suárez was signed roughly two months later. Now, looking back on the 2026 season, no one could have predicted just how impactful the addition of Gray turned out to be. 

Barring a hamstring injury that caused him to miss 14 games, the 14-year veteran was a pinnacle of consistency for Boston and arguably their most important and impactful starter in a rotation that dealt with injuries to Crochet, Suárez, and Patrick Sandoval, not to mention the natural ups and downs felt by rookies Payton Tolle and Jake Bennett.

Unsurprisingly, Gray has already declined his mutual option, triggering a $10 million buyout. He has more than earned every right to test the open market, but that choice also leaves the Red Sox with a massive hole in the rotation and even bigger question of how to fill it.

Sonny Gray’s 2026 Season At A Glance 

Before the 2026 campaign commenced, no one would have complained if Gray had produced another year similar to the one he had in 2025 in St. Louis. A 14-8 record, 4.28 ERA in 32 starts with 180.2 innings pitched, 201 strikeouts and 1.3 WAR would’ve been sufficient for an arm who was no longer being looked at to be the ace of a staff. As unforeseen circumstances forced Gray into that role however, to say he took it in stride would be an understatement. 

In three fewer starts compared to the year prior, Gray went on to have a top-five finish in the American League in ERA (2.72) and wins, of which he led not only the AL, but all of Major League Baseball with 18. Factor in his 4.3 WAR, good enough for a sixth-place finish among all qualified AL starters, along with a 1.15 WHIP and .234 average against, and in any other year you’d have as good of a case for a Cy Young as ever if not for what Cam Schlittler was able to do in New York. 

What made Gray’s season even more impressive is that it wasn’t built on what made him successful in 2025. In his final season with the Cardinals, Gray was a strikeout machine, possessing a 31.2 chase%, 27.5 whiff%, and 26.7 K%, good for the 81st, 68th, and 79th percentiles, respectively. He was also dominating hitters with his breaking stuff, finishing 2025 with a run value for that pitch type in the 97th percentile.

In 2026, though, it was an elite 91st percentile fastball run value and uptick in his sinker and cutter usage that helped mold him into less of a pitcher who relied on strikeouts, to one who focused on limiting quality contact. Given all of his success, it’s easy to see how he went from an overall pitching run value in the 66th percentile last year to the 90th this year, his best finish since 2023.  

Why the Red Sox Should Re-Sign Sonny Gray 

The fact that Gray is coming off a career year that will undoubtedly have him in the running for some awards is reason enough to want him back. What the Red Sox should also want to consider with Gray, though, is his impact off the field as well as on it. That's something they didn't value enough when they let another veteran sign elsewhere a year ago in Alex Bregman. It’s been well-documented the impact that Bregman had on some of Boston’s young hitters during the 2025 season—just ask Roman Anthony. The same can be said about Gray’s impact on guys like Tolle and Bennett, whom he was regularly seen chatting up in between starts on the top steps of the Red Sox dugout. Gray’s ability to act as a faux pitching coach could prove vital enough to keep around to help further the developments of Boston’s two young southpaws. 

As should be expected, Garrett Crochet will slide back into his role of ace when the 2027 season kicks off. That will easily fill the hole left by Patrick Sandoval, who is once again hitting the open market and is not expected to return. If Gray leaves as well, a second hole is opened up that may not be able to be filled with in-house talent. Brayan Bello, Tanner Houck, Kutter Crawford, and Johan Oviedo are the four most obvious choices to step into Gray’s role, but with Bello’s rotation struggles last year, Houck and Oviedo each only appearing in one game in 2026, and Crawford not touching a big league mound since 2024, it seems like the safest bet would be to run it back with Gray. 

And if the Red Sox do choose to run it back, setting up what is hopefully a fully healthy rotation of Crochet, Suárez, Gray, Tolle, and Bennett or a back-on-track Bello, then you’d be hard pressed to find a better rotation on paper top-to-bottom in not only the AL, but all of MLB. 

Why the Red Sox Should Not Re-Sign Sonny Gray 

If the obvious answer to re-sign Gray is his performance, then the obvious answer for not wanting to re-sign him is age. Not only will he be 37 years old on November 7, but thanks to that career year he just had, plenty of suitors should be lining up for his services. While the consensus seems to be Gray is looking at a chance to secure a three-year deal, the money differs depending on where you look. MassLive’s Chris Cotillo has him projected at a three-year, $75 million deal, while Spotrac projects the same length, but for $58 million, comparable to the likes of Nathan Eovaldi ($25M AAV), Yu Darvish ($18M), Seth Lugo ($23M), and Merrill Kelly ($20M). 

If the Red Sox can somehow get Gray at that $58 million price tag, then it would be foolish to pass up. However, if a bidding war breaks out and the number gets closer to $75 million or more, moving on to a younger option for that kind of money would be the more logical decision. If there is one position that stands out in a relatively weak free-agent class this winter, it’s starting pitching.

The front office could go the route of younger names such as Michael Soroka, Freddy Peralta, Michael King, Tyler Mahle, or Clay Holmes with the idea of longer-term commitments. Or they could look to the same age group as Gray, with names like Kevin Gausman, Nick Martinez, or Chris Bassitt for a cheaper, shorter commitment that also fills the veteran presence hole Gray would leave. As mentioned earlier, although they haven’t been the most reliable options of late, the Red Sox do have the depth of Bello, Houck, Oviedo, and Crawford to cover Gray leaving if they strike out in free agency (and on the trade market).

The Bottom Line

What makes the Sonny Gray situation such a fascinating one is that he very well could have already made his decision on returning months ago. No one was more visibly frustrated with how the Sox's season ended in the Bronx than Gray, who definitely did not agree with being pulled by manager Chad Tracy after just 4.2 innings pitched and two runs allowed in Boston’s 9-2 Game 2 loss. When pressed by the media postgame, amongst other topics, he chose to remain noncommittal about any offseason decisions at that time.

Only time will tell if Gray feels truly mistrusted and wants out. And if so, fans will surely be upset at the Red Sox letting a pitcher of his caliber walk out the door. But those same fans need to ask themselves, can you realistically expect Gray to repeat what he did a season ago as he gets deeper into his 30s? And is it wise for the Red Sox to pony up a long-term, expensive deal for an arm who could be at or beyond 40 years old when said deal is up? 

With other options on the market, and more glaring needs for the front office to address, letting Gray walk if the asking price is too steep will undoubtedly be a painful one to swallow, but a logistical one for the Red Sox to make if it helps improve the team in other areas.

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