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Red Sox Insider Drops Strong Hints on Sonny Gray's Future

One-and-done, or run it back?

Aug 15, 2026; Pittsburgh, Pennsylvania, USA; Boston Red Sox starting pitcher Sonny Gray (54) delivers a pitch against the Pittsburgh Pirates during the first inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | IMAGN IMAGES via Reuters Connect

When the Boston Red Sox are eliminated from the ongoing playoffs, there's not much we can do on the free agency front besides reading the tea leaves.

The biggest name the Red Sox have heading to free agency from their own roster is starting pitcher Sonny Gray, assuming his $30 million mutual option isn't picked up. These days, mutual options are becoming more of a formality than a legitimate question, so don't expect to see that deal stay intact.

Gray was the Red Sox's ace all season, even though he wasn't expected to be when he was traded to Boston in November. But he's exiting his age-36 season, and with Garrett Crochet expected to return to the top of the rotation next season, those tea leaves might be saying something about the low likelihood of Gray's return.

Have we seen last of Gray as a Red Sox?

Aug 26, 2026; Miami, Florida, USA; Boston Red Sox pitcher Sonny Gray (54) delivers a pitch against the Miami Marlins during the first inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images | IMAGN IMAGES via Reuters Connect

On Sunday, insider Sean McAdam of MassLive wrote that Gray was "expected" to leave the Red Sox in free agency in the middle of an opinion column, though he wasn't reporting that Gray definitively would not come back.

"Even with the likely loss of Sonny Gray, their starting rotation is excellent, led by a now healthy Garrett Crochet. Payton Tolle and Jake Bennett will only get better and Ranger Suarez is proven and dependable," McAdam wrote.

"The back end of the bullpen is superb, and so is the team’s overall defense — as evidenced by their three Gold Glove finalists. Further, Gray is expected to be their only significant loss in free agency."

As great as Gray was all season, you could make the case that the under-the-hood numbers suggest regression is coming next year — which could still mean a solid year for someone if his ERA takes a jump up from where it landed at 2.76. After all, he had an ERA over four with the St. Louis Cardinals last season, and that wasn't indicative of his true talent either.

It felt like the partnership between Gray and the Red Sox could easily be ending when he bemoaned being taken out of Game 2 of the Wild Card Series in the fifth inning. Time will soon tell whether that was a premonition.

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