The Boston Red Sox 2026 season ended much sooner than anyone in the organization would have liked to see, falling to the rival New York Yankees in the wild-card series.
Boston was swept over a two-game series, with the team not looking overly competitive throughout the matchup. Now, the Red Sox enter into the offseason following a disappointing end to what could have been a special year.
So, heading into the crucial offseason, the Red Sox’s front office does have a lot of big questions to answer. One of the biggest comes from free agency, where Boston has some key contributors either entering the market or having the ability to do so.
Sonny Gray Free Agency Prediction
MLB analyst Joel Reuter of Bleacher Report has put together predictions for one free agent from every team in the league this offseason. For Boston, it was starting pitcher Sonny Gray, with Reuter predicting Gray to leave the team this winter.
Gray has an option on his current contract, and he will likely decline it to land a larger contract, or potentially even retire. The veteran has been rumored to be considering retirement this offseason, but that all remains to be seen.
“Gray is a lock to decline his end of a $30 million mutual option in favor of a $10 million buyout. After going 18-5 with a 2.72 ERA, 1.15 WHIP and 149 strikeouts in 169.0 innings, he should have no problem finding more guaranteed money. A healthy Garrett Crochet can replace him atop the Red Sox rotation, with Payton Tolle, Ranger Suárez, Jake Bennett and Brayan Bello behind him,” Reuter wrote.
Gray was excellent for the Red Sox this past season, helping the team hold down the fort in the starting rotation. While his end to the year was a little rough, he could easily help this group moving forward, with Boston understanding his overall worth to the organization.
But given where Boston is coming into next season, Gray may be one of the odd men out from the starting rotation. However, having a solid veteran like this could be beneficial, and the Red Sox will have a tough decision to make whether to retain one of their more productive pitchers.
Should Boston Re-Sign Sonny Gray?
If Gray is willing to come back on some sort of a discount, the Red Sox should even think twice about signing him. However, given the year that he just put together, Gray will likely be trying to land the final large contract of his MLB career.
Gray was dominant this season, and he could help a team in need of another starter going forward. Due to his age, the right-hander would likely only sign a one- or two-year deal, but it could be for higher money.
This may take the Red Sox out of the overall bidding, especially with the depth that the team has for the rotation next season. But this all will depend on Boston’s willingness to spend this winter, mixed with Gray’s desire to either keep playing or call it a career this offseason.
Red Sox Given Interesting Free Agency Prediction on Sonny Gray