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

[Brandon Glick]

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+

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

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[mvp 78]

What does re-signing him have to do with the trade? Couldn't they just sign him in the offseason if they wanted to and not have had to give up two prospects? No way is the May trade a B. 

[moonslav59]

If we were going to trade for a pitcher, we could have included Early, Sandlin or Paez with Tibbs and maybe even Romero or Bleis and gotten much better pitchers than May and Matz.

[harmony]

1 hour ago, moonslav59 said:

If we were going to trade for a pitcher, we could have included Early, Sandlin or Paez with Tibbs and maybe even Romero or Bleis and gotten much better pitchers than May and Matz.

Quantity won't compensate for the lack of high-end prospect quality.

A higher-tier prospect or two would be needed to land a higher-tier starting pitcher.

[moonslav59]

2 minutes ago, harmony said:

Quantity won't compensate for the lack of high-end prospect quality.

A higher-tier prospect or two would be needed to land a higher-tier starting pitcher.

I was adding them to a high quality prospect or player.

Was Adam Serwinowski and Van Belle much higher quality? (for Zack Littell)

Randy Dobnak & Enrique Jimenez for Paddock?

Bratt, Drake & Hagaman for Merrill Kelly?

3 prospects for Adrian Houser?

Look, I realize I could be dead wrong on what I thought it might take to get a quality SP'er, especially ones with 2-3 years of control. The fact is, not many quality SP'ers were dealt this July, but I think we had the assets to match or top many of the offers I see above or some deals that were not made.

I think Brez got too stingy and refused to "overpay."

 

[Brandon Glick]

3 hours ago, mvp 78 said:

What does re-signing him have to do with the trade? Couldn't they just sign him in the offseason if they wanted to and not have had to give up two prospects? No way is the May trade a B. 

Re-signing him has a lot to do with it, at least in my estimation. If the plan is to treat him purely as a rental, giving up Tibbs+ makes no sense. If the goal is to keep him around, I can squint hard enough to see the logic.

The thing with a guy like May is, maybe the Red Sox did want to sign him in free agency, but perhaps not enough to beat out 29 other teams to do it. So, they wanted to bring him in now to see what he's got and how he reacts to their system and pitching development team. That kind of information is invaluable, and can really only be ascertained when you have a guy in your building.

Alternatively, maybe the Red Sox knew how much they already loved him and how badly they wanted to sign him in free agency. So, in an attempt to give themselves a leg up in his sweepstakes, they brought him in now with the plan of trying to sell him on Boston for the long-term by showing him how great the franchise/fanbase/internal development team is. Again, something that can really only be simulated during a free agency visit.

[TedYazPapiMookie]

12 hours ago, Brandon Glick said:

Re-signing him has a lot to do with it, at least in my estimation. If the plan is to treat him purely as a rental, giving up Tibbs+ makes no sense. If the goal is to keep him around, I can squint hard enough to see the logic.

The thing with a guy like May is, maybe the Red Sox did want to sign him in free agency, but perhaps not enough to beat out 29 other teams to do it. So, they wanted to bring him in now to see what he's got and how he reacts to their system and pitching development team. That kind of information is invaluable, and can really only be ascertained when you have a guy in your building.

Alternatively, maybe the Red Sox knew how much they already loved him and how badly they wanted to sign him in free agency. So, in an attempt to give themselves a leg up in his sweepstakes, they brought him in now with the plan of trying to sell him on Boston for the long-term by showing him how great the franchise/fanbase/internal development team is. Again, something that can really only be simulated during a free agency visit.

May has played 11 seasons in the minors and majors and is pretty consistent.  He puts up a 4.00 ERA and a 1.14 WHIP normally.  He strikes out slightly less than one batter an inning.  His ERA+ is usually good and he's coming off surgery in 2024.  His 165 ERA+ in 2023 suggests he was trending up before his surgery.  In 2025 his ERA+ of 84 means we are buying low but the upside potential is very good once he's fully recovered from his surgery.   The cost was low and if the pitching staff can help him the rest of the season he was a decent pick-up.  If he performs well in the next month, they can extend him as a solid SP3.

[Deja Doh]

All of these trades have been a fat F.  We got nothing.  The churn adds up to nothing.

[Sawxfan]

6 hours ago, TedYazPapiMookie said:

May has played 11 seasons in the minors and majors and is pretty consistent.  He puts up a 4.00 ERA and a 1.14 WHIP normally.  He strikes out slightly less than one batter an inning.  His ERA+ is usually good and he's coming off surgery in 2024.  His 165 ERA+ in 2023 suggests he was trending up before his surgery.  In 2025 his ERA+ of 84 means we are buying low but the upside potential is very good once he's fully recovered from his surgery.   The cost was low and if the pitching staff can help him the rest of the season he was a decent pick-up.  If he performs well in the next month, they can extend him as a solid SP3.

Since his second Tommy John surgery, May's velocity is way down and he is NOWHERE close to being the same pitcher he used to be! His 7.09era away from Dodger Stadium this year also doesn't give me much confidence.

[Hugh2]

I’m a huge fan of judging a trade on its merits alone.  I don’t think we should consider what happens after a contract expires to be a grading factor.

what if they extend him in lieu of someone else who ends up performing much better? Doesn’t make sense to assign a higher grade in that scenario but we do.  
 

my two cents

[moonslav59]

3 hours ago, Sawxfan said:

Since his second Tommy John surgery, May's velocity is way down and he is NOWHERE close to being the same pitcher he used to be! His 7.09era away from Dodger Stadium this year also doesn't give me much confidence.

We keep relying on has been pitchers to somehow regain their past level of performance.

They come cheaper for a reason.

[Nick]

I keep thinking there's something special about Bres, but no. He's just a another guy earning a paycheck.

I went nuts over Bres not promoting Anthony to the major leagues. When it happened, he struggle but we kind of knew that he was the real deal.

His triple A manager said "Anthony has nothing more to learn at AAA". Yeah that's what he said,

Meanwhile the Ivy League sissy, Bres, continued to spew lies about Anthony. He needed this and that....He can learn more......

How many games did we lose by not promoting him sooner?

I KNOW THAT I'M NOT THE ONLY ONE THAT FELT HE SHOULD HAVE BEEN CALLED UP. THE SAME GOES FOR MAYER. HE HAD A GREAT SPRING TRAINING. HE WAS PROVEN DEFENSIVE PLAYER.

So I give Bres a grade of C. For every Crochet, he has come up with 3 duds.

For life of me, I don't have any idea why Yoshida is still in our lineup. He rolls more balls to second baseman than my grandmother who baked 24/7.

[moonslav59]

Promoting Mayer, earlier, might have helped, too.

I agree on Anthony.

The Sale and Priester trades hurt us, badly, but IMO, Brez has made way more plus moves than bad ones, and not just Crochet.

Bregman, Chapman & Wilson to name just 3. (I was not high on the Chapman & Wilson when signed.)

Narvaez was brilliant. Plus, it was the Yanks we robbed.

Sticking with Rafaela & finding PAs for Romy vs lefties.

While the farm's pitching improvement is speculative, I feel he has already flipped the script on a decades long issue with developing good to great pitchers on the farm. Even if we fail at this, I applaud the immense effort made to boost the staff, at every level.

Okay, the Sale and Priester deals hurt like hell. He's barely traded pitchinga way, and those two ended up being bad choices to trade. Other pitchers traded included pitchers coming back, except for the O'Neill trade. (Maybe I missed another one.)

Brez has added these pitcher w MLB IP for the Sox from '24-'25 (30+ IP):

Crochet, Chapman, Giolito, Wilson, Criswell, Fitts, Buehler, Sandoval, Slaten, Weissert & Booser

Chase Anderson & Newcomb

5-25 IP: I Campbell, Hicks, Burdi, Hendriks, Paxton, B Keller, B Horn, Alcala, L Garcia, L Sims & Priester

While Bloom set the bar very low, this is a pretty good report card.

In just 2 seasons, he's added these pitching prospects (SP.com rankings)

1. Tolle

4. Witherspoon

6. Clarke

9. Sandlin (trade)

15. Phillips

16. Eyanson

20. Fajardo (trade)

27. Delzine

28. Wehunt

29. C Cason

34. Holobetz (trade)

41. Travieso

45. J Bello (trade)

Futrell, D Reyes & B Morgan

Gartrell, Cordero, Aita, Tygart, Brooks, Foutch, Finley, Patton, Neely, Judice & others

I gotta say, that's an impressive 2 years of additions.

[Hugh2]

.

[Kimmi]

On 8/2/2025 at 11:57 AM, Nick said:

I keep thinking there's something special about Bres, but no. He's just a another guy earning a paycheck.

I went nuts over Bres not promoting Anthony to the major leagues. When it happened, he struggle but we kind of knew that he was the real deal.

His triple A manager said "Anthony has nothing more to learn at AAA". Yeah that's what he said,

Meanwhile the Ivy League sissy, Bres, continued to spew lies about Anthony. He needed this and that....He can learn more......

How many games did we lose by not promoting him sooner?

I KNOW THAT I'M NOT THE ONLY ONE THAT FELT HE SHOULD HAVE BEEN CALLED UP. THE SAME GOES FOR MAYER. HE HAD A GREAT SPRING TRAINING. HE WAS PROVEN DEFENSIVE PLAYER.

So I give Bres a grade of C. For every Crochet, he has come up with 3 duds.

For life of me, I don't have any idea why Yoshida is still in our lineup. He rolls more balls to second baseman than my grandmother who baked 24/7.

Those of you who were clamoring for Anthony to be called up were right about how special he is.  After struggling for a bit, he seems to have found his bearings.  He is currently the player I have the most confidence in when at the plate.  

I'm not upset that Breslow waited to call him up.  It seems to me that he is pretty high on Duran, Rafaela, and Abreu, which I agree with.  Our deadline trade acquisitions were not what most of us hoped, but the best part of it for me is that we still have all of our outfielders.