For the next few weeks we’ll be doing some theorizing on optimal returns at the trade deadline as the Red Sox look to do another tear down amidst a hopeless season. This week, we kick things off with the flamethrowing closer Aroldis Chapman.

Ah, rumors. Chris Cotillo heard it from a veteran scout this week: two prospects back for Aroldis Chapman, one of them a top-100 type. That’s only the floor. Bob Nightengale—though we can trust him as much as any bizzaro world character we can—has him rated as the top reliever on every contender’s board. With a 2.08 ERA and 14 saves (not surprising considering how many losses this squad has)— but still 378 in his long career (closing in on the all-time record), the market isn’t treating him like a rental. It’s treating him like the best available. For a 38 year old?! Ok.

The teams making headlines for Chapman are the Dodgers, Mariners, Phillies. In my opinion, there are five realistic suitors. Here’s what Breslow shudder should be targeting from each one.

River Ryan (RHP) + Chase Harlan (3B)

Of course the team that has all the money and continues to assemble super teams in the 2020s wants to add a flamethrower to their bullpen. The problem with the Dodgers is their best stuff is the stuff Boston doesn’t need. De Paula (#8), Hope (#17), Quintero (#34) land as their top three prospects…they’re all outfielders. The Red Sox have an outfield logjam that isn’t getting cleared any time soon between Roman Anthony, Ceddanne Rafaela, Wilyer Abreu, Masataka Yoshida, Jarren Duran, the list goes on and on.

The package I’d push for snakes past all of that: River Ryan (#75, RHP) as the top-100 piece, plus Chase Harlan, an unranked third baseman quietly posting a 1.025 OPS with ten home runs through the first half. Ryan adds projectable front-end rotation depth the organization can actually use, especially in a right-hander. Harlan is the kind of raw power bat you stockpile when you don’t know who your future third baseman is (yes, I know we have Caleb Durbin, but keeping him at third feels like a giant mistake; I see him at second and slotting Mayer back to SS but that’s another piece). Do you hate trading with the new evil empire, the team that makes EVERYONE ELSE look bad? Yeah. Still, having one of the best farm systems in baseball to root from—and Boston still gets what it actually needs out of it? Fine.

Ryan Sloan (RHP) + Luke Stevenson (C)

The most specific package out there has Luke Stevenson at the center. I’d flip it. Make Ryan Sloan (#33 Pipeline, #7 BA) the headliner and let Stevenson come with him. Sloan is a top-35 arm, one of the better pitching prospects in the AL right now. Stevenson fills a specific gap—a left-handed bat behind the plate at a position the Sox are thin at long-term behind Carlos Narváez. Do you really trust Connor Wong and Micky Gaspar long term? I don’t think so. This package does real work: pitching depth plus positional coverage at a premium spot. If Seattle is serious about October, they know the price. They have the system to pay it. Adding in Chapman to Andres Muñoz would be a scary punch.

Gage Wood (RHP) + Aroon Escobar (2B)

The Phillies puzzle me. They always seem to be one or two pieces away and never hit their marks at the deadline. Is that a Dombo issue? Who knows. What Philadelphia does have is Gage Wood—70-grade fastball, tied with Andrew Painter (who isn’t moving), power curve that gives him mid-rotation upside or a high-leverage floor depending on how he develops. Baseball Prospectus has him at 66. He’s at Single-A, so he’s a few years away but a lot of room to rise. Aroon Escobar (2B, Double-A, 21) rounds out the package. Of the five teams in this conversation, the Phillies return is the thinnest and Breslow knows that going in. They can close this deal—just at a discount. I do remember the last time the Red Sox sent pitching pieces to the Phillies at the deadline…I think it worked out better for Boston, eh? (Nick Pivetta for Brandon Workman and Heath Hembree)

Nobody’s writing about Atlanta, and they should be. The bullpen has been inconsistent all year—even with Raisel Iglesias dominating as closer—and Chapman is the kind of arm contenders acquire when they want an answer at the back of a postseason roster—not depth, a second closer who can step in at any time. Cam Caminiti (#44) is the top-100 piece: 2024 first-rounder, touched 98, six-pitch mix, front-of-the-rotation ceiling. His breaking stuff kinda blurs together but the Red Sox pitching lab might be the best place to find that differentiation point. JR Ritchie debuted in April and would have been a piece I wanted: seven pitches, 93-95 mph with two fastball shapes, control refined enough to handle high-leverage innings. Tantalizing. But off the list. Boston already has Early and Tolle as elite lefties, so Caminiti is a depth add rather than a direct need-fill. That’s fine. You can say yes to depth packages like this one.

Ethan Salas (C) + Kruz Schoolcraft (LHP)

This is the one to watch. Ethan Salas was the eighth-best prospect in baseball before a back injury wiped out his 2025. He’s at Double-A San Antonio this year slashing .320/.396/.546 with five home runs through 28 games, climbing 90 spots in the rankings since the season started. Elite defensive catcher, left-handed bat, real pop. If Boston was drawing up their ideal long-term power piece behind Contreras, this is the profile. Pair him with Kruz Schoolcraft—6-foot-8 lefty, taken 25th overall in 2025, fastball already in the high 90s—and San Diego has assembled the most compelling package in this conversation. A rebounding top-10 talent at a premium position, plus a recent first-round arm who’s going to be very good. I know I just said having a lefty in this package seems redundant with Caminiti, but Schoolcraft intrigues the hell out of me. Only way I would take him out is if the Red Sox draft Brody Bumila in this year’s draft. I also know the Padres have Mason Miller closing, but again, you need all the scary you get come October.

If Breslow is doing this to win, San Diego’s scenario is the one worth chasing hardest to me, followed by Seattle. Salas is a potential cornerstone. The Mariners package is the most balanced return—Sloan is a top-35 arm and Stevenson fills a real gap.

Breslow has the leverage here having the asset everyone seems to want. Is he smart enough to part with it and get the right value back? Less sold on that. Still, this is absolutely worth tracking in the weeks ahead in this lost season.