Every Red Sox Player Set for Free Agency After Yankees ALWCS Blowout

The Boston Red Sox's 2026 season is officially over and now the focus will turn to 2027.

It's going to be a long few months, to say the least. Boston clearly has to find a way to add even more pieces — specifically from a power standpoint — and more importantly, has to find a way to keep its guys healthy. Losing to the New York Yankees for the second straight year in the wild-card series is a clear sign of this. On top of all of this, the 2027 season is completely up in the air in general with the collective bargaining agreement set to expire after the 2026 season comes to a close across baseball. It's a tricky time, to say the least.

Teams are going to have to make offseason decisions quickly before a potential lockout takes over. One thing that is a positive for Boston is the fact that there aren't too many guys to worry about from a free agency standpoint heading into the offseason. Let's dive in.

Patrick Sandoval — UFA

Sep 27, 2026; St. Petersburg, Florida, USA; Boston Red Sox pitcher Patrick Sandoval (43) delivers a pitch during the seventh inning against Chicago Cubs at Tropicana Field. Mandatory Credit: Pablo Robles-Imagn Images | IMAGN IMAGES via Reuters Connect

Sandoval signed a two-year deal with Boston before the 2025 season and ended up pitching in just 15 games total with the organization. All of those appearances came down the stretch this season and he logged a 5.12 ERA. The talent is there and he'll be even further removed from his injury next season. But Boston is loaded with lefties and so, at this moment, it doesn't seem likely that Sandoval will return.

Isiah Kiner-Falefa — UFA

Sep 30, 2026; Bronx, New York, USA; Boston Red Sox second baseman Isiah Kiner-Falefa (2) warms up before game two of the Wildcard round for the 2026 MLB Playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | IMAGN IMAGES via Reuters Connect

A veteran utility man through and through. When Kiner-Falefa was on the field this season, he was impactful for Boston. He also was a veteran voice in the clubhouse. Boston has a lot of guys who can play all over the infield. Because of that, it would be a bit surprising if Kiner-Falefa was back in 2027. But he was a solid piece of the puzzle in 2026.

Sonny Gray — Mutual Option

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

Gray is the most interesting player here to watch. He just put together one of the best seasons of his big league career, despite the fact that he's 36 years old. Gray had a 2.72 ERA in 29 regular season starts and then was good in Game 2 of the wild-card series against the New York Yankees. But he has a $30 million mutual option that isn't very likely to be picked up. In fact, the vast majority of mutual options in baseball do not get picked up. So, it would seem as though Gray is going to head to free agency. If he were to retire, that would change things. Also, if the Red Sox and the righty found some sort of path to an extension, that would also change things.

Garrett Whitlock — Club Option

Sep 17, 2026; Arlington, Texas, USA; Boston Red Sox pitcher Garrett Whitlock (22) throws to the plate against the Texas Rangers during the ninth inning at Globe Life Field. Mandatory Credit: Raymond Carlin III-Imagn Images | IMAGN IMAGES via Reuters Connect

Whitlock technically could become a free agent after the season because of the fact that he has a club option for the 2027 season. But there's no need for concern. That will almost certainly be picked up.

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