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The Boston Red Sox are about to be faced with some tough decisions as the offseason kicks off now that the World Series has concluded. Since the season is over, every name on the 60-day injured list has to be added back to the 40-man roster during the offseason. These names include: Tanner Houck, Liam Hendriks, Kutter Crawford, Hunter Dobbins, and Triston Casas. All but one (Hendriks) are under team control through 2026. Hendriks held a mutual option with the club, but the team turned down their side of the deal, making Hendriks a free agent. Once the club adds all of those other players to the 40-man roster, their total will sit at 41. Thus, there will be at least one player on the 40-man that will need to be cleared, and certainly more once the Sox begin to add players and protect prospects from the Rule 5 Draft.
Let’s take a look at who some of those candidates could be.
This seems like the most obvious name to be let go during the upcoming 40-man crunch. Grissom was acquired when the Red Sox sent Chris Sale to Atlanta. The hope was that Grissom would slot in as the second baseman of the future since he carried a high draft pedigree and showed in the Braves’ minor league system that he could be a solid contributor on both sides of the ball. Grissom failed to get going though, and the relationship with the team soured over the next two years. Most recently, he was unwilling to discuss what changes he was making in his offensive approach with media members because he “will probably be playing against them soon.” That doesn’t sound like someone who is long for the Red Sox. He was passed over for David Hamilton when Marcelo Mayer went down with a season-ending injury, so that should tell you everything you need to know about Grissom’s standing within the organization.
Arguably the second most obvious name to be let go once the roster crunch begins, Winckowski was barely an afterthought during the 2025 season. He appeared in six games for the Red Sox in 2025. He was then placed on the 60-day injured list in June due to a right elbow flexor strain. The last update we received was in July, when he was reported to have begun his throwing progression. He’s bounced between the starting rotation and bullpen in the past but was penciled in as a low-leverage reliever for 2025 before the injury happened. Effectively, he’s lost his spot in the bullpen because the Red Sox were able to replace him rather quickly. Don’t be shocked to see Winckowski’s name hit the DFA list sooner rather than later this offseason.
Moran came over in a trade with the Twins during December of 2024. The Sox received Moran for Mickey Gasper. It was a deal that didn’t cause much commotion in the world of the Red Sox, but Moran did end up making two appearances for the team in 2025. He threw four innings, struck out five, and worked a 2.00 WHIP and an ERA of 6.75. He’s quite possibly the most expendable pitcher on the 40-man roster and will probably be the first player released once the Red Sox make their first addition of the offseason. He’s a left-handed reliever in a bullpen full of lefties that are miles better than he is. Sometimes, the low-hanging fruit is the correct pick for a reason. Moran may return to the Red Sox on a minor-league deal, but he’s taking up a valuable 40-man spot until then.
Just kidding. But seriously…
There are other possible candidates on the 40-man that could be cleared to make room for all the names that will need to be added during the offseason. Craig Breslow has a great staff around him, which could be growing if his search for an assistant general manager proves fruitful. The first couple of names to purge from the roster seem obvious, but the conversation will grow far more difficult as the winter drags on.
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