Five Things the Yankees Did At the Deadline That Surprised Me

…Post Deadline, thoughts by Cary Greene

August 11, 2025

Five Big Surprises:

I was very surprised to see the Yankees not trade Trent Grisham at the Deadline, but hanging onto him makes plenty of sense. Fangraphs says that so far this season, Grisham would be worth $17.3 million if he were a free agent this season. He'll likely finish with a value over $20 million and there’s no question he’s been invaluable to the Yankees this season. It also means that he has undeniably played his way into a very large payday this coming offseason.

On those grounds, I don't see a reality in which the Yankees look to re-sign him. If he were traded this season at the Deadline, he might have fetched a prospect equivalent in value to say -- Carlos Lagrange. Lagrange happens to be the Yankees #2 prospect, but oddly his MTV is far below those of #3 Spencer Jones and #4 Cam Schlittler - so Lagrange might not be a good prospect to pick for this illustration.

Therefore, if not someone like Lagrange, definitely another team's #5 to #10 ranked prospect, of course dependent on the strength of the farm system in question. Maybe Ben Hess is a better prospect comparison to use. For the stretch run, someone like Hess (or Lagrange) would not have made the kind of impact to this year's team that Grisham will, which is likely why Cashman chose to hang onto Grisham and allow the Yankees playoffs chase to benefit from his on field presence.

No question that Grisham has been great (not just good) this season for the Yankees. He's in the 85th percentile of all MLB hitters this season and he plays an extremely important position defensively - center field. He's also not been great in CF for the Yankees this season and I blame that on Yankee stadium's expansive CF real estate more than I do on Grisham - who is relatively slow afoot for someone who plays his position. Speed-wise, Grisham is in the 37th percentile and his arm is a smidge above average.

All this said regarding Grisham’s value and the sound reasons for keeping him, I really thought Cashman would get an offer for Grisham that he couldn’t refuse and I expected the offer to be in the form of a good bridge reliever. Alas, the offer never happened and I can’t say that I’m disappointed in any way, as it’s been a lot of fun watching Grisham play this season. If the Yankees are to make a playoffs run, they’ll need Grisham to continue to be at his best.

Two other Deadline surprises were that the Yankees hung on to both Bryce Cunningham and Carlos Lagrange, I didn't think there was any chance they'd come out of the Deadline having not dealt one or both of them.

Another huge surprise was two fold. First, the Yankees didn’t trade Cam Schlittler for an established starter or an impact player. I was pleased to see Cashman recognize the value of keeping Schlittler but even more surprising was the Yankees decision to give both Will Warren and Schlittler continued starts - which come on the heels of the team designating Marcus Stroman for assignment. This is a great sign that Cashman's eyes are beginning to turn towards the Yankees future.

Figuring Schlittler would be moved for a veteran pitcher, specifically either Seth Lugo or Sonny Gray, I was very glad to see Cashman hold the line and not trade the promising Schlittler. Perhaps the main reason I felt this way was that Luis Gil has made his way back to the mound for the Yankees and this thinking combines with the reality that fifth starters don’t really impact the postseason once it begins - though they can certainly help a team fighting for their playoffs lives the Yankees are - in getting “there” - to the postseason!

Finally, the last thing that surprised me was that Cashman didn’t trade Ben Rice. I fully expected Rice to be traded but instead, the Yankees chose to keep the impactful Rice around and instead, Rafael Flores (whom the Pirates sent straight to Triple-A once they acquired him), who is still a season away from a call-up, was dealt.

Cashman has earned high grades from most insiders for the moves he made (and didn’t make) at this year’s Deadline. Most of the Yankees top prospects didn’t get dealt away, and yet Cashman has provided answers to all of the Yankees needs. He’s using Schlittler and Warren as the fifth starter that the team needed and he’s thrown quality players at all other areas of team need. Will this strategy pan out? That’s a fair question to ponder.

From here on out - we can all sit back in front of our television sets, or streaming devices, and watch how all of Cashman’s decisions turn out. We can also assume that because Cashman kept all of his top prospects, that his job is in no way in jeopardy. After all, Cashman kept the Yankees' future candle burning bright, while also improving the team dramatically, so on some level, shouldn’t what he accomplished be seen as a win?

Unfortunately, the Yankees are still dropping like a rock in the standings folks and in fact I’m beginning to wonder if the Yankees will manage to slide right out of the postseason picture in the coming months. One thing is certain, if the Yankees don’t turn things around soon, they’re in serious trouble. There isn’t a ton of time left to make up ground.

There’s little doubt that the Yankees have some very serious organizational problems going on. Key players are making mistakes that good Little League teams don’t make and that reflects very poorly on Yankees manager Aaron Boone and his coaching staff. Still - players win games and Cashman made a few deals to acquire some players that the Yankees obviously believe will impact the team in a positive way.

We’ll never know whether a new manager and or a coaching shake up would have done wonders for this year’s Yankees - or perhaps some of the past teams during the current championship drought that the organization is suffering through. Hal Steinbrenner has perpetually opted not to make in-season leadership changes and Brian Cashman, left to his own druthers, likewise has stuck with Aaron Boone as the team’s manager. Cashman has prioritized Boone’s ability to relate to players and deal with the New York media - in short, Cashman likes Boone’s ability to relate and communicate.

What’s been lost in all of this has been the team’s on field performance - or lack thereof. This is why I’ve been telling myself that perhaps, the things Cashman didn’t do at this year’s Deadline will turn out to be a blessing in disguise for whatever the organization’s future holds. After all, the Yankees have a smidge over $202 million already on the books for next season and they’re already a three-time CBT offender, so Hal Steinbrenner is likely not going to authorize Cashman to shop for free agents at Bergdorf Goodman for free agents this winter.

Therefore, what Cashman didn’t do at this year’s Deadline is clearly part of a larger plan to lower payroll by promoting internal MiB talent as much as possible. I’m already imagining what the Yankees lineup, rotation, bullpen and bench might look like next season. I’m assuming Cody Bellinger declines his player option and decides to test the open market, given that Scott Boras is his agent. I doubt Bellinger will be back next season due to Hal Steinbrenner’s unwillingness to violate certain CBT thresholds. Likewise, I’m expecting Trent Grisham to earn a fairly large, multi-year contract from another team as he’s played his way into a significant raise for 2026 and beyond, so it’s doubtful that Grish will return as well.

Without Grisham and Bellinger, the Yankees will be dangerously thin in center field and at first base, so Cashman will likely hunt for a cheap, backup center fielder and possibly, he might actually spend big for a middle of the order bat capable of playing first base.

Another current Yankees that probably isn’t likely to be brought back is Amed Rosario, as he’s also on an expiring contract, but the Yankees might possibly have some spare payroll to allocate in his direction as he could be a key utility player for a team like the Yankees. In short, Rosario is a good fit and he shouldn’t be too expensive to bring back, but will the Yankees throw some minor free agent dollars at him? Somehow, I doubt they will spend on a journeyman like Rosario, who barely plays for the Yankees as it is.

Lastly, we’re likely seeing the last of Devin Williams in pinstripes, as he’s on an expiring contract as well. He simply hasn’t panned out.

More than likely, the Yankees will need to sign a starter or two next offseason as the priority of upgrading the rotation might be where they chose to spend the bulk of whatever scant payroll they throw at the wall next offseason.

A short list of Free Agents many Yankees fans will be clamoring for Cashman to sign include Kyle Tucker, Munetaka Murakami, Alex Bregman, Pete Alonso, Kyle Schwarber, Dylan Cease, Mike King and Framber Valdez. There are numerous other lower tier options available as well obviously.

It would be amazing if the Yankees decided to eat the remaining $34 million left on Giancarlo Stanton’s contract and then splurge for an ideal DH like Schwarber, but I don’t see Cashman doing that in any reality that exists. Likewise, the Yankees signing Tucker to a huge, multi-year deal seems very unlikely. Murakami plays third base, but he’s fallen off quite a bit this season and the Yankees have George Lombard Jr. coming up anyway so I don’t see Murakami being seriously courted by the Yankees either.

While it would be a fine form of revenge for the Mets signing Juan Soto, it’s also hard to imagine that Cashman would pay significant, long time dollars for Alonso and while we’re at it, Bregman is another star the Yankees will likely pass on this coming offseason.

Cashman will probably look to spend whatever budget he has on mid-tier starters so it remains to be seen who he targets, but I’m not expecting a sizable deal for a Cease type starter.

I’ll sign off with this and ask you this, will the below lineup win a World Series, or does Cashman need to do significant work to improve the team?

Lineup: 

1.     Dominguez LF

2.    Jones CF

3.    Judge RF

4.    Rice C/1B/DH

5.    Stanton DH

6.    Chisholm 2B

7.    McMahon 3B

8.    Wells C/DH

9.    Lombard SS