Red Sox Roster Crunch: Everything At Stake on the 40-man Roster Prior to Free Agency

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The Boston Red Sox have a lot of roster decisions to make now that the World Series has ended. All roster members who are on the 60-day injured list must be added to the 40-man roster for the postseason. As currently constructed, they will need to clear two additional roster spots to make room for the seven players they currently have on the 60-day IL. Within the first 12 hours of free agency opening, Isiah Kiner-Falefa and Patrick Sandoval both became free agents, and the team traded utility outfielder Nate Eaton (to the Athletics) and fan favorite Tsung-Che Cheng (to the Tigers). While that helps unclog the roster a bit, there are still some decisions to be made.

The Red Sox have a number of candidates they can designate for assignment before November 2. There are a handful of players that the team can DFA in short order without making waves.

Left-hander Raymond Burgos is, in my estimation, the most likely option here. He was a late season call-up who stepped up when the team needed pitching depth, pitching both ends of a doubleheader and eating innings when the bullpen couldn’t afford to be burned. While pitching depth is something that every team needs, there are options beyond Burgos that make more sense in the long run for the organization. He technically has two minor-league options left, but he’s going to have to be DFA’d and then pass through waivers for the team to keep him in the system. His resilience will likely work in his favor as he looks to land a short-term deal somewhere else. He would be welcomed back to the organization on a minor-league deal, but don’t be surprised if he lands somewhere else for 2027.

Outfielder Jahmai Jones was a midseason addition that proved to be a force against left-handed pitching. He platooned in left field with Jarren Duran for most of his tenure in Boston, but with Roman Anthony presumably healthy heading into 2027, Jones is going to be a piece that can be let go without dipping into very much depth. He would be a great piece to have off the bench, but when there are so many names that have to be added back to the 40-man roster that he might be a victim of some roster math.

There's also names to consider like Kutter Crawford, who has missed almost two full seasons, or Zack Kelly, who seems like a prime change-of-scenery candidate after spending more time on the road traveling between Worcester and Boston than he has on the field. If not them, you're most likely going to see a few more trades to clear roster spots.

There’s a handful of guys who don’t seem like they are long for the Red Sox. Depending on how you slice it, that list is headlined by either Masataka Yoshida, Jarren Duran, and even Trevor Story. There are reports that Duran and Yoshida are squarely in the mix to be moved this offseason given their respective contract statuses and past success. Neither player will command a huge return, but finding buyers for either could be easier this offseason since the free-agent market is the weakest it has been in years.

What makes a Story trade far less likely is that he achieved 10-and-5 rights at the conclusion of the 2026 season, so he essentially holds a full no-trade clause. It’s possible he could be moved, but it would have to be a situation where he feels that he could thrive and those are likely to be few and far between at this point in his injury-plagued career.

Should the Red Sox look to move Duran, Yoshida, or Story in a trad, then they’d need to put their foot on the gas to get something done. As they proved with their trades of Eaton and Cheng, it’s possible to make deals immediately after the conclusion of the season, but to move on from a major piece of the roster is a more involved process. It’s possible a deal could be made, but Craig Breslow isn’t known for being the quickest negotiator in the league.

To be able to clear the final few 40-man roster spots, some tough decisions are going to have to be made over the next handful of days. Expect Breslow to explore every avenue available to him, but the roster crunch is only going to get worse when the team has to decide which prospects to protect and when they start signing big-league free agents.