One Red Sox Free Agent They Can't Afford to Lose (and One They Can)

Who will be back with the Boston Red Sox in 2027?

Sep 8, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Patrick Sandoval (43) throws a pitch against the Los Angeles Angels in the first inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images | IMAGN IMAGES via Reuters Connect

One thing that is a positive about the Boston Red Sox is the fact that they actually don't have a lot to worry about this offseason when it comes to internal free agents.

This offseason, there are just a few guys likely heading to the open market, unless Boston gets some sort of extension done. It's still too early in the offseason for the Red Sox to do anything tangible, but let's look ahead at one guy Boston should keep, and one guy it can afford to lose.

Can't Afford To Lose

Sep 11, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Sonny Gray (54) pitching during the first inning against the Kansas City Royals at Fenway Park. Mandatory Credit: Natalie Reid-Imagn Images | IMAGN IMAGES via Reuters Connect

Sonny Gray

Gray has a $30 million mutual option that is likely going to be one of the most talked-about topics around the team over the next few weeks. The Red Sox are going to have to make a decision about the option within five days of the World Series coming to an end. At the end of the day, a $30 million option for a 36-year-old hurler doesn't seem particularly likely to be picked up. In fact, mutual options almost never get picked up in general.

Still, of the guys who could become free agents this winter, Gray is the one Boston should absolutely want to keep with some sort of extension. He was Boston's ace all season. Imagine what the 2026 Red Sox could've looked like with a healthy Gray and Garrett Crochet all season?

Plus, of course, Payton Tolle, Ranger Suarez and Jake Bennett, among others. That's the type of rotation that could win a championship. Gray also is right-handed, which is an important topic here. The Red Sox are full of lefties and need at least one righty. Gray should be the guy.

Can Afford To Lose

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

Patrick Sandoval

Sandoval made just 15 appearances in a Red Sox uniform after signing with the club ahead of the 2025 season. He had a 5.12 ERA in 70 1/3 innings of work. Down the stretch, he was very important for Boston, especially as other hurlers dropped due to injuries. While this is the case, the Red Sox are stacked with left-handed pitchers and can afford to let Sandoval walk.

When you have guys like Crochet, Tolle, Suarez and Bennett, you don't really need another left-handed starter. Or, more specifically, you don't need to pay for one in free agency. Boston's cash would be better spent elsewhere. Sandoval did everything the Red Sox could've asked for down the stretch after being hurt for a while. But the Red Sox would be fine looking elsewhere.