What if the Yankees Made Some CRAZY Deadline Moves?

What if the Yankees Made Some CRAZY Deadline Moves?

…Mid July Thoughts from Cary Greene

(July 20, 2026)

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With the Trade Deadline now only a little over a week away, its no secret that the Yankees are prioritizing catching and relief pitching, but what if Brian Cashman and the Yankees decided to expand on this thinking and do something very out of character for a team run by a term I coined a few years ago, known as Stienbrenneromics. What if Hal Steinbrenner decided to authorize Cashman to enact drastic change in order to give the Yankees the strongest possible chances of winning a World Series this season?

How could the Yankees, a team with a farm system rated as the third worst in MLB by MLB.COM even make drastic moves? Well, the answer is pretty simple actually. They’d have to be willing to take on some bad contracts and actually, what’s the harm in doing that? The existing CBA comes to an end after the final inning of the World Series is played. Besides paying tax-related penalties per the existing CBA, there would be no further, future repercussions for lavish spending.

What if the Yankees decided to take on a few bad contracts in order to boost their championship aspirations, which players would they target and, might they be able to get the selling teams to take on some of the monies owed to the players the Yankees might be interested in.

It is time to have some fun.

Writing this article is causing me to go drastically beyond my comfort zone. Those that know me here know that I’m all about c-Value. Bad contracts create a lack of financial flexibility and they can doom an organization for many years, but with the CBA expiring, what’s the harm in doing a little cherry picking?

What should a free-wheeling cherry picking strategy look like? There’s no question that the current Yankees priorities need to be addressed. As mentioned, the Yankees are presumably targeting help at catcher while they’re also looking to improve the bullpen. The two catchers the Yankees covet most are likely not realistic trade targets. With the Twins currently tied for a Wild Card berth, they’ve made it clear that they’re not interested in trading Ryan Jeffers. Cashman still needs to try like heck though to entice the Twins because the Yankees lineup really does need a right-handed slugger in it.

Meanwhile, the Rockies haven’t indicated that Hunter Goodman is available either and while the Yankees can certainly attempt to dazzle the A’s with a massive package for Shea Langeliers, it’s very doubtful that the A’s would make their All-Star catcher available. If by some miracle, Langeliers was there for the plucking though, it would likely take the Yankees parting with George Lombard Jr. to get him. Personally, that’s a trade I think I’d have to make if I were Brian Cashman.

Catching has been in demand over the past several seasons and there really aren’t a lot of selling teams at this year’s Deadline, so the Yankees will need to lower their expectations if they are to acquire a catcher to pair with Austin Wells.

Enter Kyle Higashioka, who is currently with the Rangers, might be available for the right price. Texas needs pitching desperately and they also need a versatile player who can play infield and outfield. The Yankees have Oswaldo Cabrera or J.C. Escarra available for an even swap that gives the Rangers more surplus value than they’d be giving up.  Also available are Max Schuemann, Camilo Doval or even Anthony Volpe, should the Rangers wish to expand the trade. If not Higashioka, there are other backup catchers out there who could help the Yankees. Even Jose Trevino’s name has been connected to the Yankees in back page rumors.

If the Yankees do have to make do with a lesser option at catcher, I’m all the more convinced that if they want to win a championship, they have no choice but to start working Ben Rice in at catcher as the season winds down. This means they will need an upgrade at first base, unless Paul Goldschmidt can regain his earlier season form.

It looks like finding a catcher won’t be all that difficult. In terms of upgrading the bullpen though, Cashman will truly have his work cut out for him. Over a month ago, the chatter amongst us in the comments sections of various articles has explored whether or not the Yankees trading for relievers like Mason Miller, Aroldis Chapman or Garrett Whitlock makes sense. Relief pitching will be extremely expensive at this year’s Deadline, as many contending teams are prioritizing relief pitching.

Presently, the Yankees have the seventh best bullpen in baseball. Given that David Bednar, Brent Headrick, Fernando Cruz and Paul Blackburn have all been very effective this season, Brian Cashman’s goal will be to acquire either a lock down closer or a very good high leverage reliever. The Red Sox are a half a game out of the Wild Card presently, so I’m not sure they’ll be in the mood to part with either Chapman or Whitlock and the Padres are presently only 3 ½ games behind in the Wild Card standings so the idea of them trading Miller seems a bit far fetched as well.

If neither the Red Sox or the Padres emerge as potential trade partners, the Yankees will be forced to look elsewhere to accomplish their main goal. Attractive partners at that point might be the Mets or the Royals. In particular, the Yankees might be interested in a trio of Mets relievers including old friend Luke Weaver along with Huascar Brazobán and Brooks Raley. Cashman might also want to inquire with the Royals about Daniel Lynch IV’s availability.

Depending on how things shake out when/if Carlos Rodon and or Clarke Schmidt return from the DL, Internal bullpen reinforcements also exist for the Yankees. When the dust settles post Trade Deadline, it remains to be seen if there will be any Yankees Minor League pitchers that could be called up to likewise buttress the bullpen.

Assuming the Yankees two main priorities can be traded for at the Deadline, it’s now time to pose the million dollar question. Where else does this roster need help and are there any bad contracts out there that the Yankees could absorb, if only Hal Steinbrenner would agree to doing so?

There is no question that the Yankees desperately need a middle of the order bat. Counting on Giancarlo Stanton to come back and be productive really feels like a stretch right now. There is a strong chance that Stanton is done for the season and unfortunately, the Yankees have about a week and half to come up with a replacement for Big G. If he does return though, at some point, the Yankees would have to use him to give their dreams of a championship the best possible chances.

Clearly, the Yankees need help at third base and when Judge does come back, he likely won’t be used in the field in order to protect him. I’ve written a few times already that the Yankees should attempt to land Luis Arraez and they could then shift Jazz Chisholm over to third base for the remainder of the season. A plan like that is realistic, but there are other options out there and don’t forget, I promised CRAZY Deadline moves would be revealed in this article. The Yankees need help on offense, but their inability to play fundamental, reliable defense has also been a glaring weakness.

Without further ado, let’s get Crazy!

Crazy Deadline Move #1

Needing to inject a few sparks into their stagnant offense, while trading with the Giants for Luis Arraez, the Yankees also agree to take Rafael Devers in an expanded trade. The two teams would have to haggle over how much of Devers’ contract the Giants would agree to pay, but if ever a player needed a change of scenery, Devers would be the very epitome of THAT guy!

There’s no arguing that Devers doesn’t have a ton of offense left in his lightning quick left handed stroke. Devers also plays first base well enough to get by. Towards the end of the season and into the Playoffs, the Yankees could even shift Ben Rice to catcher and, if Paul Goldschmidt’s bat remains playable, they would have Rice, Goldy or Stanton and Devers all in the lineup together. Imagine that! Not only would the Yankees catching issues be fixed, but the lineup is suddenly lethal. Assuming Judge is deployed in the outfield for the playoffs, here’s the Yankees lineup:

1.     Arraez 2B*

2.    Judge RF

3.    Rice C*

4.    Bellinger LF*

5.    Goldschmidt 1B / Stanton DH

6.    Devers DH* / 1B

7.    Chisholm 3B* / Rosario

8.    Grisham CF*

9.    Caballero SS

Crazy Deadline Move #2

Somehow, some way, the Yankees pull off a trade with the Rangers for Corey Seager. The Yankees would need to eat a ton of contract here. Seager is a proven winner and a proven post season legend. He’s exactly the kind of player the Yankees lack. However, he’s been on the DL three times this season, so there are injury red flags associated with this move.

Would the Rangers consider trading Seager? Possibly, but it’s really not likely. However, if it happened, it would make for headline Yankees news. Now consider for a moment, if both of my crazy moves were made, the Yankees postseason lineup now looks like the below. Would it be good enough to get by a Dodgers team that likely will land Tarik Skubal - barring a Brewers intervention.

1.     Arraez 2B* (hits LHP exceptionally well)

2.    Judge RF

3.    Seager SS* (hits LHP well)

4.    Rice C*

5.    Bellinger LF* (terrific reverse splits)

6.    Goldschmidt 1B / Standon DH

7.    Devers DH* / 1B (struggles vs LHP)

8.    Chisholm 3B* / Rosario

9.    Grisham CF*