Re-Grading Red Sox's 2025 Trade Deadline Performance One Year Later

When the Boston Red Sox finally reach the 2026 trade deadline, they’ll be in a different spot than they were a year ago when Craig Breslow put together a performance that could only be described as “underwhelming.” With the Red Sox sitting at 59-51, good for third in the American League East and second in the AL Wild Card (both five games back coincidentally), the goals seemed obvious enough: acquire some help for the rotation and potentially another late-inning arm to help solidify the back-end of what was an impressively strong bullpen. 

Of course, we know Breslow answered those questions by acquiring left-handed reliever Steven Matz from the now-frequent trade partner St. Louis Cardinals, and right-handed starter Dustin May from the Los Angeles Dodgers, who should probably find themselves on the same “Do Not Trade With” list as the Milwaukee Brewers, given their consistent ability to seemingly send the Red Sox a lesser piece/pieces than what the Sox are sending them. 

Our managing editor, Brandon Glick, graded out these deals when they occurred, which you can find here. But now almost a full year removed, with neither player on the current iteration of this Red Sox roster, it’s time to take a big picture look back and re-grade Boston’s 2025 deadline acquisitions. 

Trade #1: Red Sox acquire LHP Steven Matz from the Cardinals for 1B/3B Blaze Jordan

When the Red Sox entered the 2025 deadline, most people assumed that if they were going to acquire some sort of bullpen help, it would be of the late-inning, right-handed variety to not only ease the workloads of arms like Garrett Whitlock, Greg Weissert, and Justin Slaten, but to also make up for the failure that was Jordan Hicks.

Instead, Breslow opted to acquire veteran lefty Steven Matz, a move that was surprising to say the least and met with some skepticism due to the fact the bullpen already featured four southpaws in Aroldis Chapman, Justin Wilson, Brennan Bernardino, and Chris Murphy. In return, they sent the Cardinals No. 19th-ranked infield prospect Blaze Jordan, who was tearing up Triple-A Worcester at the time, slashing .298/.341/.480 with six home runs and 25 RBIs in 44 games. However, he seemed to be locked out of any infield position given the team's glut of options at the corners.

Almost a year later, and this deal is definitely the harder of the two to put a grade on. Initially, it garnered a ‘C’ and was justifiably labeled a “nothing-burger move” by Glick. As previously mentioned, Jordan looked like an easily expendable prospect and Matz came in sporting a respectable 3.44 ERA, 2.92 FIP, and 20.7 K% in 55 innings pitched with St. Louis. With the Red Sox though, Matz was borderline dominant with a 2.08 ERA, .218 average against, and 2.4 BB% in 21 regular season appearances to go along with two scoreless outings in Boston’s Wild Card series loss versus the Yankees. He ended up only being a gun-for-hire though, as he signed with the Rays on a two-year, $15 million deal this past winter with the opportunity to once again work as a starter. The move hasn't really panned out for Tampa Bay as he currently owns a 5.65 ERA and 5.55 FIP across 14 outings split between the rotation (10) and bullpen (4). 

As for Blaze Jordan, this is where the old “hindsight is 20/20” saying comes into play. After slugging .313 with a .921 OPS, 11 home runs and 35 RBIs in 57 games for Triple-A Memphis, the Cardinals called him up to make his major league debut on June 12 and he’s done nothing but hit since, slashing .286/.306/.486 with one home run, seven RBIs and an impressive 11.1 K% and 16.7 Whiff% in just nine games. That's production I’m sure disgruntled Red Sox fans don’t want to see given the team’s continued offensive woes. 

While Jordan’s production could definitely be used in this abysmal Red Sox lineup, the fact still stands he probably wouldn’t have a spot on this club at first or third base with the additions of Willson Contreras and Caleb Durbin (or even designated hitter, which has constantly been used to try and solve Boston’s outfield logjam situation). When it comes to Matz, the Red Sox got exactly what they needed from him as a shutdown arm a year ago and seem to have dodged a bullet given his struggles this year opting to not bring him back. 

Grade: B+

Trade #2: Red Sox acquire RHP Dustin May from the Dodgers for OF James Tibbs III and OF Zach Ehrhard

When it comes to the second of Boston’s two 2025 deadline acquisitions I want to put this as lightly as I can… everything about this trade was an abject failure. Let’s start with the lead up to it. By now, everyone knows this ended up being a panic move by Craig Breslow, a deal that was one of those that trickled in after the deadline came and went, after numerous failed attempts throughout the afternoon to acquire a more dependable and solidified arm like Merrill Kelly and the tease that was Joe Ryan, who the Sox had consistently been linked to. 

Now to the player himself. Upon being dealt to Boston, May was the owner of a 4.85 ERA, 4.74 FIP, and 44.4% hard-hit rate across 16 games (15 starts) and looking like he was about to fall out of L.A's crowded rotation. With the Red Sox, things took a turn for the worse, as his numbers imploded to a 5.40 ERA, 5.39 FIP, even worse 45.6% hard-hit rate, and career-worst .307 average against in just six games (five starts) before having his short-lived Sox tenure end due to a right elbow neuritis injury. He, like Matz, would end up leaving Boston in the offseason for St. Louis where he has pitched to a pedestrian 4.30 ERA in 15 starts.

And just when you think things couldn’t get any worse, we turn to the two prospects Boston sent the Dodgers’ way: James Tibbs III (No. 10 prospect via MLB’s rankings) and Zach Ehrhard (No. 17). Upon getting to the Dodgers organization, both reported to Double-A Tulsa and performed relatively well, with Tibbs hitting .269 with a .900 OPS, and seven homers to go along with 32 RBIs in 36 games and Ehrhard hitting for .282 with an .857 OPS, five homers, and 20 RBIs in 30 games. As for this season, where they both currently reside at Triple-A Oklahoma City, this is where Red Sox fans who haven’t been paying attention might want to avert their eyes. 

Starting with the latter, in 67 games Ehrhard is slashing .288/.394/.490/.884 with 11 home runs, 53 RBIs and 29 extra-base hits. As for Tibbs III, he not only has racked up a line of .291/.415/.585/1.000 with 20 homers and 62 RBIs, but also leads all PCL hitters in home runs, walks (57), extra-base hits (39), total bases (161) and runs (64), per of OKC Comets Communications & Broadcast Assistant Logan Bourandas on X).

When Glick first graded this trade, he put a caveat on it that it would be a ‘B+’ if May was re-signed and a ‘D+’ if he wasn’t, which made sense given the price the Red Sox were giving up to get him but the flashes of potential and ability May had shown in the past to hopefully be a solid middle of the rotation arm. Given the absolute train-wreck that ensued everywhere you look with how this trade shaped up, I think it’s pretty obvious what this deal deserves.

Grade: F-

Final Verdict and Grade

With almost a full calendar year to now look back on those who described the 2025 Red Sox trade deadline as “underwhelming” seemingly hit the nail on the head. Steven Matz gave them exactly what was needed, and while the Blaze Jordan departure doesn’t look ideal on paper right now, there was no true path to him contributing like he has on the Cardinals.

On the flip side, at the time it was believed Dustin May wasn’t the right move for the rotation and that could not have been more of the truth; that trade not only hurt the Sox in-season with his horrendous performance and an injury that left the rotational depth weakened heading into the playoffs, but could come back to haunt them in a major way if Tibbs and/or Ehrhard grow into contributing big leaguers.

Overall Grade: C-