Grading Yankees' 2025 trade deadline: Did Brian Cashman deliver on all-in promise?

It's possible there's never been a New York Yankees trade deadline with more strongly polarized sides before the action kicked off. There were those who've watched seven weeks of sub-Rockies Yankees baseball and decided they weren't worth investing in — including a few different reporters who hinted the team might even sell a few veterans. There were others, like Brian Cashman, who insisted the Yankees would be all in on a market that didn't seem to have many blockbuster possibilities, on the surface.

Three weeks before the deadline (and before the Yankees' slump worsened in Toronto), Cashman told the media, "We’re going to go to town. We’re going to do everything we possibly can to improve ourselves and try to match up.”

Now that the dust has settled, it's hard to deny Cashman pushed many more buttons than most of us anticipated when the week began. Did he do enough to transform these Yankees from possible playoff team to potential American League champion, all while retaining future flexibility?

Yankees Trade Deadline Grades: Did Brian Cashman succeed or flop?

Ryan McMahon, Colorado Rockies

Instant Grade: C+
Grade after Six Games: B+

McMahon's early success in pinstripes has been that transformative. While it can't be denied that his swing-and-miss profile is a little too Joey Gallo-ish for anyone's taste, and he isn't exactly Eugenio Suárez in the power department (who came kind of cheap, after all), McMahon socked a bases-loaded double that was the difference in his second game, made two slick defensive plays on grounders in his fourth game, and walked off the Rays in his fifth. His stability, mixed with flashes of star quality, at third has been a breath of fresh air. Long may he reign.

Amed Rosario, Washington Nationals

Grade: B

It's hard to get too upset with adding an .800+ OPS bat against left-handed pitching to fill in at third base and in the outfield on occasion, and Rosario has already proven to be a celebration starter and elite vibes guy. This is threatening B- territory, though, only because the Yankees seem averse to using him and they don't plan to have him back up shortstop, forcing Oswald Peraza to remain on the roster (and the Yankees to import another replacement for him). Rosario gets dinged for the awkwardness of the rest of the maneuvering around him.

Austin Slater, Chicago White Sox

Grade: B+

Grade lowered slightly because I'd be embarrassed to hoot and holler over Austin Slater, but the Yankees spent the early portion of the deadline bringing in adult humans to do their baseball jobs. Slater has an .859 OPS against left-handed pitching. He is expected to play the outfield against lefties and hit them. Why it's been so hard for the Yankees to conceive of balance and bench-building in recent years, I have no idea. Slater won't set the world on fire, but he might tag Trevor Rogers a time or two. That has value.

David Bednar, Pittsburgh Pirates

Grade: A

At this time of year ... in this seller's market ... Ben Cherington, you simply cannot give up a top-tier closer like David Bednar in exchange for Rafael Flores, the Yankees' No. 8 prospect, Edgleen Perez, a teenaged catching prospect, and Brian Sanchez, an all-but-unknown young outfielder. Perceptions of trades can shift over time, and Bednar's 2024 struggles were well-documented. But for Pirates owner Bob Nutting to sign off on a deal this underwhelming after reportedly vetoing a trade of the fan favorite in the past ... it's hard not to pat Cashman on the back for a job well done here.

Jake Bird, Colorado Rockies

Grade: C

Easily the grade likeliest to age poorly, and I understand that, but Bird will need to be overhauled by Matt Blake's pitching lab to have value. He comes with the "years of control" that the Yankees love to covet, but the team needs bullpen help now. Bird has a 1.481 WHIP, a 4.50+ ERA for the third time in his four-year career (the other season was 4.33), and just imploded in Cleveland in his final outing before the deadline. His four-seamer doesn't work. His big breaking ball is his calling card. It's hard not to feel Effross-y about this one.

Roc Riggio, traded in this package with 18 homers this season, was always too cool to be a Yankee anyhow.

Oswald Peraza Dealt to Angels

Grade: A+

As depressing as it is to reckon with Peraza's up-and-down-and-further-down-and-oh-my-god-there's-even-more-down Yankees tenure officially coming to a close, they flipped him to a willing participant instead of the inevitable DFA next week.

This grade also improves because the swap was paired almost immediately with...

Jose Caballero, Tampa Bay Rays

Grade: A

After months of watching Peraza merely exist on the roster, the Yankees once again upgraded their bench with intentionality, backing up shortstop Anthony Volpe with the league's leading stolen base threat and a world-class pest. Said it before and I'll say it again: Good teams have players like Jose Caballero on their rosters, and the Yankees have been caught flat-footed too many times in the recent past without one.

Camilo Doval, San Francisco Giants

Grade: A-

Downgraded only a smidge because of Doval's inherent erratic nature that comes with his uncontainable arsenal. Are the Yankees getting the real Doval in 2025, 2026 and 2027, or the one who posted a near-5.00 ERA last season and became a "buy-low" candidate himself? Somehow, the Yankees ended up making the essence of the Bednar trade twice in one day - and I prefer Jesus Rodriguez to anyone the Pirates received.

Overall Grade: A-. It's hard not to fall in love with what the Yankees did. Would adding a name like Merrill Kelly have pushed this over the edge into unimpeachable territory? Do you feel like you missed something without Eugenio Suárez? Other than the nitpicks, it's tough to argue. "Luis Gil is like a trade deadline addition" is the only likely-to-be-uttered phrase that might annoy some people, but let's face it: Cashman killed it, and the preemptive complaining was wrong for once.

And the Yankees still have all their top pitching chips for the offseason, when Joe Ryan and Steven Kwan will once again be available.