Over the next few weeks, we’ll be theorizing about optimal returns at the trade deadline as the Red Sox look to pull off another demolition amid a hopeless season. This week we start with flamethrower melee Aroldis Chapman.
Ah, rumors. Chris Cotillo heard it this week from a veteran scout: Two prospects are back for Aroldis Chapman, one of them a top-100 pick. It’s just the floor. Bob Nightengale – although we can trust him as much as any quirky character in the world – considers him the best hitter on the board of all contenders. With a 2.08 ERA and 14 saves (not surprising considering how many losses this team has) but still 378 in his long career (on pace for the all-time record), the market isn’t treating him like a rental. He treats him like the best he can be. For a 38 year old?! Fine.
The teams making headlines for Chapman are the Dodgers, Mariners, Phillies. In my opinion, there are five real suitors. That’s what Breslow shudder there should be targeting for each of them.
River Ryan (RHP) + Chase Harlan (3B)
Of course, a team that has all the money and continues to assemble super teams in the 2020s wants to add a flamethrower to its bullpen. The problem with the Dodgers is that their best is what Boston doesn’t need. De Paula (No. 8), Hope (No. 17), Quintero (No. 34) are top three prospects…they’re all outfielders. The Red Sox have a logjam in the outfield that won’t be resolved anytime soon between Roman Anthony, Seddan Rafaela, Villier Abreu, Masataka Yoshida, Jarren Duran, the list goes on and on.
The package I’d suggest to overcome all of this: River Ryan (No. 75, RHP) as a top-100 player, plus Chase Harlan, an unranked third baseman quietly posting a 1.025 OPS with ten home runs in the first half. Ryan adds projected depth to the frontcourt rotation that the organization can actually use, especially for a righty. Harlan is the kind of power bat you stock up on when you don’t know who your future third baseman is (yes, I know we have Caleb Durbin, but keeping him at third seems like a huge mistake; I can see him at second and bringing Mayer back to SS, but that’s another topic). Do you hate trading with the new evil empire, a team that makes EVERYONE ELSE look bad? Yeah. Yet you have one of the best farm systems in baseball to root for and Boston still gets what it really needs out of it? Great.
Ryan Sloan (RHP) + Luke Stevenson (C)
At the center of the most specific packaging is Luke Stevenson. I would turn it around. Make Ryan Sloan (#33 Pipeline, #7 BA) the headliner and let Stevenson go with him. Sloan is a top 35 prospect and one of the best pitchers in the AL right now. Stevenson fills a specific gap – the left-handed bat behind the plate at a position where the Sox are weak long-term behind Carlos Narvaez. Do you really trust Connor Wong and Mickey Gaspard in the long run? I don’t think so. This package really works: pitching depth plus positional coverage at a premium spot. If Seattle is serious about October, they know the price. They have a payment system. Adding Chapman to Andres Munoz would be a scary move.
Gage Wood (RHP) + Arun Escobar (2B)
Phyllis puzzles me. They always seem to be one or two pieces behind and never reach their goals on time. Is this a Dombo problem? Who knows. What Philadelphia does have is Gage Wood, a 70-level fastball on par with Andrew Painter (who doesn’t move), a power curve that gives him mid-rotation upside or high leverage depending on how he develops. He is 66 years old in Baseball Prospect. He’s in Single-A, so he’s a few years away, but he has plenty of room to grow. Arun Escobar (2B, Double-A, 21) rounds out the list. Of the five teams in this conversation, the Phillies’ return is the least significant, and Breslow knows it. They can get this deal – just at a discount. I remember the last time the Red Sox sent pitchers to the Phillies at the deadline… I guess it worked better in Boston’s case, huh? (Nick Pivetta for Brandon Workman and Heath Hembree)
Nobody writes about Atlanta, and that’s how it should be. The bullpen has been inconsistent all year – even with Raisel Iglesias dominating the closer position – and Chapman is the type of weapon that contenders acquire when they need an answer late in the postseason lineup – not depth, a second closer who can step in at a moment’s notice. Cam Caminiti (#44) Top 100: 2024 first round, touched 98, six-pitch mix, pre-rotation ceiling. His breaking stuff is kind of a blur together, but the Red Sox pitching lab might be the best place to find that point of differentiation. JR Ritchie debuted in April and would be everything I wanted: seven pitches, 93-95 mph with two fastball shapes, control refined enough to handle heavy pitches. Teasing. But off the list. Boston already has Early and Tolle as elite lefties, so Caminiti is more of an addition than a direct need-filler. This is fine. You can say yes to depth packages like this one.
Ethan Salas (C) + Cruz Schoolcraft (LHP)
This is something worth watching. Ethan Salas was the eighth-best prospect in baseball before a back injury sidelined him in 2025. He’s playing in Double-A San Antonio this year, hitting .320/.396/.546 with five home runs in 28 games, moving up 90 spots in the rankings since the start of the season. Elite defender, left-handed bat, true pop. If Boston was building its ideal long-term power figure around Contreras, this is his profile. Pair him with Cruz Schoolcraft — a 6-foot-8 lefty taken 25th overall in 2025 with a fastball already in the mid-90s — and San Diego puts together the most compelling package in this conversation. A talented top 10 player at a premium position plus a recent first rounder who will be very good. I know I just said that having a lefty in this package seems like overkill for Caminiti, but Schoolcraft intrigues the hell out of me. The only way I would take him is if the Red Sox select Brodie Bumila in this year’s draft. I also know the Padres are closing Mason Miller, but again, you’ll need all the fear in October.
If Breslow is doing it to win, then the San Diego scenario deserves the most attention in my opinion, followed by Seattle. Salas is a potential cornerstone. The Mariners’ package is the most balanced, with Sloan in the top 35 and Stevenson filling a real gap.
Breslow has leverage because he has an asset that everyone seems to want. Is he smart enough to part with it and get the right value back? Less is sold on this one. However, it is absolutely worth tracking in the coming weeks in this lost season.