The Boston Red Sox have shockingly few players hitting free agency this offseason. While one would think that would make it easy to keep the band together, there are a few factors that will make it difficult to reunite with a couple of these guys, despite their value to the franchise.
For one, the Red Sox need to find a way to revitalize the roster. Following their second consecutive early playoff exit at the hands of the New York Yankees, changes need to be made. That doesn't necessarily mean that the players hitting the market are at fault for Boston's fate, but there are only so many resources to go around, meaning they could still be squeezed out.
The other, darker side of things is that it takes two to tango, and not all of the Red Sox's upcoming free agents will be willing to return to Boston.
2 impending free agents the Red Sox will miss next season
Sonny Gray
The Red Sox and Gray share a $30 million mutual option for the 2027 season. However, these sorts of options rarely get picked up, as both sides need to say yes for things to kick into place. That doesn't mean that Boston can't try to re-sign Gray and entice him with either a higher salary, more years, or both, but any overtures are likely to fall on deaf ears.
Gray was extremely unhappy with Chad Tracy's decision to pull him in the fifth inning of the AL Wild Card Series, which ultimately could be the straw that broke the camel's back. If that wasn't enough, Gray had publicly mulled retirement as his next step after the 2026 season.
Following the Game 2 defeat, he seemed to walk back those previous musings. Whether that was because he was still amped up after the Red Sox's drama-filled playoff exit, or he's actually changed his mind, remains to be seen.
If Gray pitches in 2027, it probably won't be in a Red Sox uniform. That's a blow for the club, as high-end front-of-the-rotation starters don't grow on trees, much less ones who can likely be had with a short-term commitment.
Isiah Kiner-Falefa
Isiah Kiner-Falefa gave the Red Sox's relatively solid play for his role as a backup infielder who is better known for his glove than his bat. Still, he provides a level of veteran savvy that is valuable to a perennial contender like Boston. On top of that, he's shown a kind of veteran leadership that helped get the team through hard times.
Isiah Kiner-Falefa: “Uncompetitive. We got boat-raced … To lose in the Wild Card is unacceptable.”
— Chris Cotillo (@ChrisCotillo) October 1, 2026
The problem with bringing him back is that the Red Sox have a good amount of infield depth. Curtis Mead will be available for the full 2027 season. Andruw Monasterio and Anthony Seigler are both younger utility options with more upside. Kristian Campbell will likely get a shot in 2027, and Trevor Story is still kicking around.
Kiner-Falefa made $6 million in 2026. Someone will likely give him something similar to be their primary utility infielder in 2027. The Red Sox don't have that role available for him, and with other needs can't afford to spend the money nor the roster spot on a player whose contributions might mostly come in the clubhouse versus in the field.
Add us as a preferred source on Google