The Boston Red Sox have made it clear: they’re not done. After adding infielders Isiah Kiner-Falefa, Brendan Rodgers, and Tsung-Che Cheng, the front office is still hunting for more - specifically, a legitimate bat that can elevate the lineup. But here’s the twist: Boston’s looking to deal from its prospect pool, not its big-league roster.
That points to one thing - pitching prospects. And the Red Sox have no shortage of them.
With a farm system flush with arms, Boston is in a strong position to swing a deal. But not all prospects are created equal. Let’s break down the key names who could be in play - and what it might take for the Red Sox to part with them.
Payton Tolle: The Crown Jewel
If there’s a name Red Sox fans should know by now, it’s Payton Tolle. He’s the top-ranked prospect in Boston’s system for a reason. After rocketing through three levels in 2025 and debuting in the majors by late August, Tolle has cemented himself as a front-of-the-rotation candidate - not just in theory, but in practice.
At 6-foot-6 with a fastball that pops and a presence that screams “ace,” Tolle cracked Baseball America’s Top 100 list and climbed as high as No. 17. He’s not just a future piece - he’s a near-term contributor with serious upside.
That’s exactly why trading him would be a massive move. Unless Boston is getting a bona fide franchise-changing bat - think superstar infielder territory - Tolle’s likely staying put. He’s the kind of arm you build around, not deal away lightly.
Connelly Early: MLB-Ready and Rising
Next up is Connelly Early, a lefty who’s already dipped his toes into the big leagues and shown he belongs. He’s polished, he’s got strikeout stuff, and he’s projected to slot in as a solid mid-rotation starter.
That blend of MLB experience and projectability makes him a valuable asset - both for the Red Sox and for teams looking to add controllable arms. Compared to Tolle, Early might be a bit more movable, especially if Boston is chasing a middle-of-the-order bat. But even then, it would take a serious return to pry him loose.
Early’s the kind of piece that could headline a deal - but only if the bat coming back is a clear upgrade to the lineup.
Kyson Witherspoon: High Ceiling, High Interest
Drafted 15th overall last year, Kyson Witherspoon is one of the most intriguing names in Boston’s pipeline. He hasn’t thrown a professional pitch yet, but his college resume - highlighted by a nasty five-pitch mix and elite strikeout numbers - has scouts buzzing.
He’s a classic projection arm: not quite ready now, but with the tools to develop into a mid-rotation starter or better. That makes him a fascinating trade chip. Teams love upside, and Witherspoon offers it in spades.
Because he hasn’t debuted yet, his value is based more on potential than performance. That could make him more tradable than Tolle or Early - especially if Boston is crafting a multi-player package. Witherspoon could easily be the centerpiece of a deal for a proven bat.
Juan Valera: Raw Talent, Real Upside
Juan Valera isn’t a household name yet, but he’s not far off. Still working his way through High-A, the young right-hander has a live arm and the kind of projection that keeps player development staff excited.
He’s not at the level of Tolle or Witherspoon, but Valera’s upside gives him value - especially in a package. Other teams might see him as a cost-controlled developmental piece, someone they can mold over time.
He’s unlikely to headline a trade, but as a second or third piece in a bigger deal, Valera could help push talks across the finish line.
Anthony Eyanson: Middle-Tier Depth with Upside
Eyanson, a third-round pick out of LSU, brings a solid mix of strikeout stuff and pitchability. He’s not at the top of Boston’s prospect list, but he’s a valuable depth piece - the kind of arm that rounds out a rotation pipeline.
He’s young, projectable, and could appeal to teams looking to bolster their farm with arms that aren’t too far off. In a trade scenario, Eyanson likely serves as a sweetener - not the main attraction, but a name that adds value to a package.
Marcus Phillips: Long-Term Play
Marcus Phillips, another early-round pick from last year’s draft, is still raw. He’s got the tools and starter profile, but he’s further away from the majors and still honing his command.
That longer development timeline lowers his immediate trade value, but it also makes him a more flexible piece for Boston to include in deals. He won’t headline anything, but as a filler in a multi-player package, Phillips fits the bill.
What This All Means for Boston
The Red Sox are in an enviable position: they’ve got a farm system stocked with arms, and they’re using that depth to try to land a bat that can help now. But it’s a balancing act.
Boston has to weigh the short-term need for offense against the long-term importance of building a sustainable rotation. Tolle and Early are close to contributing - or already have. Witherspoon, Valera, Eyanson, and Phillips represent the next wave.
The front office knows it can’t keep everyone. That’s just the math of modern roster building. But if the right bat becomes available - and the return justifies the cost - don’t be surprised if one or more of these names ends up on the move.
The Red Sox aren’t just tinkering. They’re targeting. And if they hit the mark, this team could be a lot more dangerous by Opening Day.