Red Sox 2025 Trade Deadline Grades: High-Upside Pitching Doesn't Get Graded on a Curve

In total at the 2025 MLB trade deadline, the Boston Red Sox brought in two players (pitchers Steven Matz and Dustin May) and shipped out three prospects (infielder Blaze Jordan, outfielders James Tibbs III and Zach Ehrhard). It was an underwhelming deadline to say the least, though is it really as bad as it looks?

Like movie, album or video game reviews, grading trades immediately after they come out is a futile task. You're sure to piss someone off by assigning a grade they disagree with, and most people don't even have the same relative scale. Heck, IGN gives practically every single major film that comes out nowadays a 7/10. Nevertheless, they do serve as an easily digestible way to recap an important event, and it's fun to look back on a grade years down the line when the benefit of hindsight has rendered them incorrect and obsolete. For the crowd more interested in the overarching stuff, I'll share my general thoughts on the Red Sox's deadline here before diving into each trade below. 

Given info from trusted sources, my understanding of how the Red Sox approached this deadline is as follows: Craig Breslow's plan was to wait out the market, not with the intention of driving prices down, but with the goal of seeing how other American League contenders handled their business. With the Yankees, Blue Jays, Astros, and Mariners all going all-in at the deadline (and the Rays and Tigers making some solid moves to beef up their rosters), it became clear that the Red Sox would have had to gut the farm system in order to compete with the likes of the newly-formed ruling class in the junior circuit. With a team more built for 2026 and beyond than 2025, Breslow pulled prospects like Payton Tolle and Jhostynxon Garcia from deals, which effectively took them out of the running for Joe Ryan, MacKenzie Gore, and the like. We know they were close on guys like Merrill Kelly and Zac Gallen, too, but the best prospect they were willing to part with was Tibbs, who the Dodgers took more of a liking to than the Diamondbacks.

Let's unpack that briefly. Did the Red Sox do the right thing in the face of the Yankees building a super bullpen or the Astros reuniting with Carlos Correa? Objectively, probably yes. Subjectively, hell no. The team was never dealing Tolle without a controllable starter coming back in return, but their insistence on holding onto every top outfielder on the team just remains a mystery to me. You don't want to deal Jarren Duran (or Wilyer Abreu)? Fine, but then at least make the prospects who are blocked by all those guys, like Garcia, available.

Ultimately, I just think the messaging has been mixed from Breslow and his front office. They shockingly sold Rafael Devers in the middle of a winning streak and swore they would be buyers at the deadline. Technically, they did live up to that promise, but getting rental flyers in Matz and May hardly qualifies as a team doing more than the bare minimum. The Red Sox are in worse shape now in terms of both farm system talent and relative major league talent (i.e., the teams close to them in the standings got better than they did). No matter how you chalk it up, that's a failure.

Boston Red Sox 2025 Trade Deadline Grades

Trade: Boston Red Sox trade INF Blaze Jordan to St. Louis Cardinals for LHP Steven Matz

I have to rewrite this section after the deadline hit because I cannot believe this was the only bullpen move the team made.

Mind you, I wasn't necessarily expecting the team to add another reliever. The bullpen now has five left-handers (Matz, Aroldis Chapman, Justin Wilson, Chris Murphy, Brennan Bernardino), three of whom are due to be free agents at the end of the year. Considering that they picked up a potential closer in Jordan Hicks in the Devers trade, it is absolutely bewildering to me that they didn't deal Chapman given the price closers were going for at the deadline this year. Mason Miller and Jhoan Duran are controllable and in a slightly different tier of reliever, but oh my lord, did you see what the Athletics and Twins got in return for them? 

I like Chapman, and had the team made any other moves that signified they were planning to "go for it" this year, I don't mind the idea of hanging onto your 37-year-old rental closer having a career resurrection in Boston. But Matz and May do not qualify as such. This was an easy chance to upgrade the team for 2026 and beyond without gutting the current roster of an irreplaceable piece, and though that's not technically what I'm grading, Matz is completely and wholly redundant on this team right now. He's great against opposing lefties, but so is, like, half the bullpen.

Blaze Jordan is a good prospect who was having a good year, but he was eminently blocked at just about every infield position. He's not a huge loss, but it's just odd to trade a valuable player for a pitcher who does nothing this roster already couldn't do. Matz—who has a 3.44 ERA and 2.87 FIP in 55 innings this year—will pitch well in Boston until he becomes a free agent in November. Well enough to change literally anything about this team's fate? Probably not. A very nothing-burger move.

Grade: C

Trade: Boston Red Sox trade OF James Tibbs III, OF Zach Ehrhard to Los Angeles Dodgers for RHP Dustin May

This ended up being the "blockbuster" move of the deadline for the Sox, insofar as you don't count Devers and you really stretch the definition of blockbuster. 

I really do like May, who has a tantalizing fastball-sweeper mix and is still only 27 years old. However, his results (4.85 ERA, 4.70 FIP in 104 innings this year) scream mediocrity, and that's about the last thing this rotation needed. His ceiling is that of a No. 2 starter, but his current form is more like a higher-upside Walker Buehler. If he weren't an impending free agent, I could see the logic behind this move, but it's hard to get a guy to change his mechanics/pitch mix/delivery/spin in the middle of the year, especially two months out from free agency. If there's a plan in place to work with him and potentially re-sign him, I can be talked into this being a smart, under-the-radar play. If not, I just don't see it for this team. If it was a rental starter the team was willing to settle for, then why not pony up a little further to go after a sure-thing veteran like Merrill Kelly?

Tibbs is a very good player (.760 OPS across two levels this season), and it's frustrating to see the team use the best prospect acquired in the Devers deal for a rental pitcher who may not be around next spring. Still, I've pounded the drum for the team to use its extreme outfield depth to upgrade the roster, and it did so by letting Tibbs and Ehrhard (.796 OPS across two levels) go. I just don't know if May was the right guy to do it for.

Grade (if re-signed): B

Grade (if not re-signed): D+

What do you think of the Red Sox's deadline moves? What grade would you give Boston for their haul (or lack thereof)?