Latest on Red Sox, Sonny Gray's Future

The Boston Red Sox could very well end up losing Sonny Gray this winter in free agency.

iJun 18, 2026; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Sonny Gray (54) pitches against the Toronto Blue Jays during the first inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | IMAGN IMAGES via Reuters Connect

The World Series will begin on Friday between the Milwaukee Brewers and the Tampa Bay Rays. Shortly after the World Series comes to a close, the Boston Red Sox will have to make their first big decision of the offseason.

Option decisions have to be made within five days of the World Series coming to an end. For the Red Sox, the two guys to think about are Sonny Gray, who has a mutual option, and Garrett Whitlock, who has a club option. It would be a shock if Whitlock's option wasn't picked up, to say the least. When it comes to mutual options, they are almost never picked up. Could the Red Sox and Gray shock baseball? Sure. But, again, they are almost never picked up. And it doesn't seem like this one will be either. MassLive.com's Christopher Smith noted that Gray is expected to opt out of his deal with Boston after the World Series.

"The Red Sox will have little roster flexibility because they have only three pending free agents coming off the 40-man roster. Only two players — Isiah Kiner-Falefa and Patrick Sandoval — will become free agents the day after the World Series ends," Smith wrote. "Sonny Gray also is expected to opt out of his contract to become a free agent within a five-day window following the conclusion of the World Series."

The Red Sox Star Is Expected To Enter Free Agency

Sep 23, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Sonny Gray (54) delivers a pitch against the Cleveland Guardians during the first inning at Fenway Park. Mandatory Credit: Gregory Fisher-Imagn Images | IMAGN IMAGES via Reuters Connect

The reason why it's rare to see mutual options get picked up is because of the fact that the value rarely matches the performance from the previous season. You'll tend to see guys pick up their side of the option if they didn't have an explosive season.

In that case, you tend to see the team decline their end of the option. On the other hand, if a player has a great season, you tend to see them opt out and head to free agency in hopes of getting a multi-year deal.

When it comes to Gray, he fits that second category. He had one of the very best seasons of his big league career in 2026. Gray made 29 starts for Boston and logged a 2.72 ERA and led the league with 18 wins. Gray's 2.72 ERA was his lowest mark since he logged a 2.67 ERA as a rookie back in 2013, although he pitched in just 12 games that season.

Gray should cash in. At 36 years old, this is likely Gray's last shot at a multi-year deal. He should go for it and it sounds like he will be.