Grading the Yankees' objectively incomplete trade deadline (with 2 big misses)

In order to set his fumbling Yankees roster back on course after they'd turned a 50-22 start into a tight-beyond-belief Wild Card race, GM Brian Cashman had to deliver a "Reverse 2022."

In other words, he had to take bold chances, making a number of potentially transformative moves -- only this time, he needed to make good trades.

Cashman listened to those who implored him to start early and made an early splash, securing an infusion of athleticism on Saturday afternoon. Unfortunately, that ended up being his biggest difference-making addition.

But ... (sigh) fortunately, this turned out to be a relatively light deadline in general, with only two glaring misses standing out. Only one of those gaffes involved a player actually changing hands.

It's difficult to slam Cashman with as much ease as we did in 2023, when Keynan Middleton and someone named Spencer Howard represented the entirety of a deadline that should've been fueled by selling, not adding middling pieces. He still deserves a few demerits, though, especially for two bummer news drops that hit the wire as the deadline wrapped.

Grading Brian Cashman's 2024 Trade Deadline With New York Yankees

Jazz Chisholm for Agustin Ramirez, Jared Serna, Abrahan Ramirez: B

After watching the rest of the deadline play out, and precious few impact bats (with athleticism) change hands, this Chisholm deal gets bumped up to a B+. The initial grade was slightly lower, but given a handful of games' worth of evidence of how the ex-Marlin can fit with these Yankees, as well as a glimpse of him learning third base on the fly, the price seems more reasonable and the player seems more natural.

Now, the hope was that dealing for Chisholm would lead to a Gleyber Torres/Alex Verdugo/DJ LeMahieu exodus. That won't happen, which probably knocks it down from a B+ due to the impending awkwardness. Gleyber Torres may think he's a second baseman, but Jazz Chisholm actually is.

Mark Leiter Jr. for Jack Neely, Ben Cowles: B+

Cowles is Rule 5 eligible, and the Yankees clearly weren't considering adding him to the 40-man roster after his breakout season in the system (.294 average/.848 OPS). They prefer other infielders and other Bens. Neely seemed like a candidate to help the big-league bullpen right now, but Leiter Jr.'s actually done so at the big-league level. If you're someone who wants to see Cashman either use prospects or lose them, it's tough to argue with him deploying a reliever he clearly didn't trust for one he does.

Leiter Jr.'s going to have to pull a 2021 Clay Holmes to recoup his value, though. He's struggled on the surface this year, and though his wipeout splitter makes him the best strikeout arm in the Yankees' 'pen (already), his 4.21 ERA/2.11 FIP makes him one of the game's unluckiest pitchers. Two months for that luck to turn around in New York. You taking that bet?

Caleb Ferguson to Houston for $750,000 of International Money, High-A Reliever Kelly Austin: A

Other than increasing the likelihood of Ferguson closing out the Yankees in the ALCS, Charlie Morton-style, there's nothing to dislike here. Ferguson had to go, and the Yankees extracted some value for him, setting themselves up for another move with a cleared-out roster spot. And that move was...

Enyel De Los Santos/Minor-League Pitcher Thomas Balboni Jr. for Brandon Lockridge: D

Be honest. Half of the reason you believe this deadline was a downer is because De Los Santos was the last move announced. And you're not wrong! The burly right-hander is somehow still not strong enough to move a single needle. He might even slide right into Ferguson's slot as DFA fodder. 11 bombs in 40 1/3 innings. Welcome to Punk'd.

2 Big Mistakes: Passing on Light Jack Flaherty Package, Failing to up the Ante With Yandy Diaz

Here's where Cashman gets dinged, bringing his overall deadline grade down to a C+.

We were told all along -- at least, after Yusei Kikuchi was traded -- that the rental market prices were crazy, and sellers would be reaping the benefits for the next 24 hours. Someone forgot to tell that to the Tigers, who sent Jack Flaherty to the Los Angeles Dodgers in exchange for Thayron Liranzo, fourth in line for the Dodgers' catching job (and maybe fifth, behind Hunter Feduccia) and Trey Sweeney, formerly a Yankee.

"Well, Sweeney must've broken out in LA," you're surely thinking. I know! But no. Same mid-.700s OPS. Same 13 homers in the elevation-aided offensive environment of the PCL. The Dodgers nabbed Flaherty for two forgotten pieces, something the Yankees absolutely should've done if they were pushing as hard as Bob Nightengale had us briefly believing.

You trade for Flaherty, you use Nestor Cortes Jr. creatively instead of "Wednesday against the Phillies" ... now we're talking.

Only now we're not talking.

According to a report from Ken Rosenthal, the Yankees and Tigers actually reached an agreement for Flaherty, only for Cashman to back out after concerns over the righty's medicals stemming from a recent lower back issue. Cash didn't want to get Montas'd again. We get it. But at the price the Dodgers paid, a gamble still probably would've been worth it, especially without an alternate addition.

Oh, and while we're at it, Yandy Diaz and Pete Fairbanks stayed put in Tampa Bay. Diaz was coveted by the Astros, who ran out of prospects pursuing Kikuchi. The Yankees had an opportunity to make it hurt, and somehow, they pulled up short here, too.

In 2017, the Astros outfoxed the Yankees for Justin Verlander and won the title because of it.

In 2019, the Astros outflanked the Yankees for Zack Greinke, and won the AL because of it.

In 2024, the Yankees had a chance to put the pressure on by deflating Houston's tires with Diaz (or Fairbanks, or both), and came up empty. Revenge is a dish best served with a C+ that was very nearly an A, if either Flaherty or Diaz/etc. had gone down.