The Boston Red Sox are saying they are not done after the acquisitions of infielders Isiah Kiner-Falefa, Brendan Rodgers, and Tsung-Che Cheng. They want more, but are looking for a trade that's "prospect-based" (h/t @tylermilliken_).
This most likely means the Red Sox are looking to trade prospects in a package for a "legit bat" rather than trading any of the players on their current roster, per Peter Abraham of the Boston Globe.
Reading between the lines, the endless pitching prospects that the Red Sox have will be something that teams want to take a dig at. The headliners are obvious, with Payton Tolle and Connelly Early, but more are in the wings.
1. Payton Tolle
Payton Tolle is arguably Boston's best prospect and their crown jewel in most aspects. He ranks at the very top of the Chowder's Red Sox 2026 Top 30 Prospects system. In 2025, he had a meteoric rise to the Majors, climbing quickly from High-A through Triple-A, making his MLB debut in late August. His combination of size and his projected fastball were tools that earned him a place in the Top 100 prospects list, ranked as high as #17 by Baseball America.
Boston sees Tolle as a future front-of-the-rotation arm, with a real chance to contribute in 2026. That high upside makes him one of the least likely candidates to be traded for a position bat this winter.
Why?
It's because the Red Sox would realistically only move him in a package worthy of a superstar infielder, not just an everyday bat. Given how he's already made the majors and will most likely be back there again, along with his strong profile, trading Tolle would be a rather dramatic gamble. That is unlikely for Breslow to give him up unless Boston had absolute certainty of landing a franchise anchor.
2. Connelly Early
Connelly Early enters 2026 as a highly regarded left-handed starter with both minor and major-league experience. He's ranked near the top of Boston's prospect lists and made meaningful contributions late in 2025, demonstrating his strikeout ability and polished command relative to many of his peers.
His MLB experience and potential to settle into a mid-rotation role make him extremely valuable to Boston's long-term rotation picture. Compared with Tolle, Early might be slightly more tradeable because he's closer to MLB readiness and could be packaged more easily for an impact bat.
However, trading Early for an infielder like a middle-of-the-order run-producer would still be a steep price. Boston would have to be sure the return significantly upgrades the lineup without depleting too many complementary arms.
3. Kyson Witherspoon
Kyson Witherspoon was picked 15th overall by the Red Sox last year in the MLB draft and is one of the most exciting high-upside arms in the system. He dominated in college with a high strikeout rate and a five-patch mix that projects well in a starter's role. He ranks high in the Chowder and Champions top-30 prospects, and while he won't debut immediately, scouts see his future as a mid-rotation starter or even better once he progresses this year.
Due to him not pitching at the professional level just yet, Witherspoon represents a pure future asset, which is enticing to other clubs because of his projection and relatively lower MLB exposure risk. That could make him more tradable than both Tolle and Early if Boston wanted to build a deal around multiple pieces for a bat. But given his position in the system hierarchy, trading him in a package would be an ideal part as a centerpiece.
4. Juan Valera
Juan Valera appears right behind Witherspoon in my top 30 rankings. As a young right-hander still working his way through High-A, Valera boasts intriguing arm talent and projectability. While not as heralded as Tolle, Early, or even Witherspoon, his presence on these lists shows scouts view him as a real starter option down the road.
Valera's youth and projection have value on both sides of trade conversations. Boston values him as future rotation depth, but other clubs might see him as a cost-controlled arm to develop. That dynamic could make him more tradeable in a package where Boston attaches Valera with a higher-profile arm like Witherspoon to reach the infielder they target. But on his own, he probably doesn't command enough value to land a frontline bat yet.
5. Anthony Eyanson
Anthony Eyanson, picked out of LSU in the third round, showed promise in college with strikeout ability and multiple quality pitches in his arsenal. Though not as high as Tolle or Valera in the system boards, he's a solid middle-tier arm in Boston's rotation pipeline.
His relative youth and projectability make him an intriguing piece in trade discussions, particularly if bundled. He alone won't be a primary piece, but as a secondary arm in a larger package, he can sweeten the deal. Teams looking to restock rotation depth might value him, especially if paired with another name like any of the above.
6. Marcus Phillips
Marcus Phillips, one of the three right-handers picked out of the first few rounds in the MLB Draft last year by Boston, brings raw talent and a starter profile that scouts find appealing. As with many recently drafted arms, Phillips' timeline is longer, and he's still mastering command and development entering his age-22 season.
Since Phillips is further from the majors and is more speculative than anything, his trade value is lower than Tolle's or Early's. However, that also makes him easier for Boston to part with if trying to build a deal for an everyday infielder. He won't be enough on his own, obviously, but as a filler name in a package, he'll more than fit the mark. He could help bridge the gap between Boston's depth and another club's asking price.
Conclusion
As the Red Sox eye a legitimate bat to push them into contention, the decision to trade from their pitching depth isn't taken lightly. Boston's farm, which is still strong despite recent graduations, features several high-ceiling arms that could fetch impact hitters in the right deal.
The organization must balance immediate offensive needs with long-term rotation sustainability, knowing that moving the right piece could swing a blockbuster. The Red Sox don't have to worry about making a 'wrong' decision, but also need to be wise about who they want to keep and where they will put these pitchers in the rotation when everything's all set and done.