At the outset of trade rumor season back in July, Boston Red Sox righty Sonny Gray was described by Jeff Passan as a “dream” trade target for the Chicago Cubs. In the end it was little more than a dream, of course, as the Red Sox went on a run, didn’t sell, and Gray finished the season in Boston. The Cubs, for their part, actually wound up acquiring a couple similar pitchers in Kevin Gausman and Clay Holmes (i.e., veteran rentals who can pitch in the front half of a rotation), and it does make you think, yeah, Gray might otherwise have been a target.
Fast-forward to October, and we’re on the cusp of free agency. There, Sonny Gray should be freely available, and the Cubs will have a chance to pursue the long-appreciated veteran righty.
Gray, who turns 37 next month, saw his peripherals take a considerable step back in 2026, but his results were just as good as they’ve been for years now:
(via FanGraphs)As you can see, Gray’s weathered the inevitable velocity decline well, though his strikeout rate has dipped from 30.3% in 2024 to 26.7% in 2025 to just 21.8% in 2026. That would be the thing to watch, because his results were largely the product of no walks and outstanding contact management – things we know the Cubs really appreciate, but also things we know can go poof later in a pitcher’s career.
Sonny Gray came up in a quartet of pitchers mentioned at The Athletic as standout names for the Cubs to pursue this offseason, with each of the other three having been discussed around here previously as pretty obvious targets (Tarik Skubal, Freddy Peralta, and Michael King). Among the comments from Sahadev Sharma and Patrick Mooney:
“Having a Vanderbilt connection isn’t a prerequisite, but it probably doesn’t hurt that the Cubs have a Gold Glove shortstop (Dansby Swanson), a bench coach (Ryan Flaherty) and a general manager (Carter Hawkins) with ties to the same SEC program. Chicago’s relative proximity to the Nashville area, where Gray’s family is rooted, could also be a plus for a pitcher at this late stage of his career.
The intermittent speculation about Gray and the Cubs goes all the way back to the early stages of the Theo Epstein regime, when the organization hired Derek Johnson away from Vanderbilt to be a minor-league pitching coordinator around the time Gray began to emerge with the Oakland A’s ….
[T]he Cubs would be drawn to his groundball rate, which ranked in the top 10 among all major-league pitchers who qualified for the ERA title this year.
If Gray wants to take it one year at a time, the Cubs have historically shown a willingness to boost a deal’s average annual value in exchange for the flexibility of a short-term commitment.”
With the Cubs losing nearly an entire rotation’s worth of free agent starting pitchers, and with questions aplenty about the few guys who’ll be returning, this is an offseason where the Cubs will have to import multiple starting pitchers. A guy like Sonny Gray may not look like the most premium option out there, but it’s not at all hard to imagine him being an important part of a successful offseason.
Because of the age and the questions on the peripherals, I can imagine a world where Sonny Gray is not getting a monster contract, and could fit right in as a second or even third signing for the Cubs this offseason.
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