If the New York Yankees are going to end their World Series drought they will need to make some quality additions ahead of the MLB Trade Deadline. In other words, several players who make the franchise's Opening Day roster won't stick around long enough to experience postseason baseball in the Bronx.
Key Points
Bullet point summary by AI
- The New York Yankees are evaluating their roster ahead of the MLB season with an eye on the upcoming Trade Deadline.
- Three players currently on the roster could be leveraged for veteran additions if the team seeks immediate championship impact.
- These potential moves hinge on performance, platoon dynamics, and contract negotiations that could shift the team's strategy by midseason.
Luminaries like Aaron Judge and Max Fried can rest easy. They are not going anywhere. GM Brian Cashman will not be interested in offloading long-term franchise building blocks during the season.
Some big names that might surprise fans could still be destined to hit the trade block over the next few months. These three players might be leveraged to bring in players who Cashman and the front office believe can have a positive impact on the team's championship equity.
Luis Gil's future with the Yankees is murky, at best
The Yankees are still trying to decide whether Gil will start the season with the big league club or down in the minors. The idea in sending him down to AAA is that he can continue to build up his arm strength as a starter. If he begins the season with the Yankees, he'll have to wait a couple of turns in the rotation to be utilized as the No. 5 starter.
The Yankees are considering optioning Luis Gil to the Minor Leagues, per @BryanHoch
— Talkin' Yanks (@TalkinYanks) March 22, 2026
Gil will remain in Tampa and throw a live batting practice on Wednesday while the Yankees are in San Francisco for Opening Day pic.twitter.com/Qu6q7UzP6N
At the moment, Gil and the Yankees both want to see him continue as a starter. It's easy to envision a scenario where the front office changes their minds if Gil's control and command issues persist. Add in the trouble he's had securing swings-and-misses with his fastball this spring and it's easy to understand why the Yankees are concerned about his long-term future.
None of that means Cashman will give Gil away at the deadline. He still enjoys the patina of his Rookie-of-the-Year Award in 2024. The idea behind moving Gil would be to deal him before his value starts to decline if he's moved to the bullpen. Using him as the centerpiece of a deal to get a veteran star to the Bronx could be a shrewd move for the Yankees this summer.
J.C. Escarra might be the wrong platoon partner for Austin Wells
Carrying two left-handed catchers is far from an ideal outcome for a Yankees front office that believes heavily in platoon splits. Manager Aaron Boone isn't shy with his praise for J.C. Escarra but that doesn't change the reality that he does not hit from the right side of the plate.
Austin Wells seems to be the starter with more upside which could make Escarra the odd man out. A simple trade of Escarra for a right-handed catcher of similar quality would do a lot to improve manager Aaron Boone's lineup flexibility for the stretch run.
A hot start to the season could cement Escarra's status with the team, but the temptation to flip him in favor of a right-handed bat might be too great for Cashman to ignore at the deadline.
Jazz Chisholm could be traded if his contract demands get out of hand
The Yankees are not going to trade Jazz Chisholm unless they've fallen out of contention ahead of the deadline. Only then would they entertain the idea of offloadig a star player who is headed to free agency in the offseason.
Another variable here would be the idea that Chisholm and his representatives start leaking contract demands that New York won't entertain. The talented infielder is not short on self confidence as his desire to rack up 50 home runs and 50 stolen bases this season would illustrate. That supreme confidence could have him looking to become one of the highest paid players in the game.
If the Yankees don't see bringing him back as a realistic financial solution then trading him for a nice prospect haul duruing the season could make sense. That's not an outcome Yankee fans want to see, but Cashman is a pragmatist above all else. The combination of being out of playoff contention and not wanting to break the bank for Chisholm could force the Yankees into a deal.