1 painful trade and 1 liberating trade Yankees can make at 2025 Winter Meetings

For as pessimistic some Yankees fans want to be after the disappointing 2025 season, there is simply no telling what New York will do to improve the roster for 2026. Conflicting rumors are afoot, and the action at the Winter Meetings hasn't even started yet. Truth be told, while the Yankees could very much limit spending, they aren't the Pirates. Let's relax for a moment.

That said, it's still important to keep some potentially concerning developments in the back of your mind as to not be blindsided if the worst-case scenario unfolds. We know what that is, of course. Trent Grisham's qualifying offer affects spending; the Dodgers, Blue Jays and Mets continue to stockpile top talent; the Yankees bank on young talent to take a step forward and for injured players to rebound; and ... they re-tool in a manner that isn't attractive.

Fans have already heard plenty about one unsettling trade rumor that would undoubtedly set the Yankees back. And if it's going to happen, it'll be this week. But what else might Brian Cashman consider that would surprise us?

1 painful trade and 1 liberating trade Yankees can make at 2025 Winter Meetings

The one painful trade? Moving Jazz Chisholm Jr. As of right now, there's no credible source backing that possibility — only speculation if the Yankees were to limit spending and re-tool. But even if that was the plan, why would you trade Chisholm now? At least wait for the deadline when other teams are getting more desperate.

Just because the Yankees haven't discussed an extension with Chisholm doesn't mean he may as well be traded. He's arguably the best second baseman in the league right now and New York cannot afford to lose his athleticism and incredibly dynamic player profile. Sure, Chisholm wasn't exactly a postseason lightning rod, but there's no denying what he can accomplish in a full regular season with the requisite talent around him. I

If he goes? The Yankees better have a real plan. Because who plays second base once you create that void? Anything short of something like a Ketel Marte trade would be unacceptable.

Then there is, of course, a somewhat painful trade that would greatly lift a sort of weight off the organization's shoulders. Hears us out, but such a move features freeing the payroll of Giancarlo Stanton.

The old heads will love this. We know that. The younger fans? Some might be outright opposed. But those with a realistic perspective of this team understand there is no true championship path in the near future with Big G in the mix. And it's solely because 1) he isn't present enough or 2) he clogs up the DH spot when he is around, and it really hinders Aaron Boone's ability to get creative with the lineup.

Stanton's power presence when he's firing on all cylinders is unlike anything you've ever seen. He's historic. His .254/.322/.605 postseason line in 48 games with the Yankees is the best during the Aaron Judge era. But he's entering his age-36 season and he's only accumulated 11 WAR over his eight Yankees seasons, which is just 2.9 more than his MVP campaign in 2017. He has never eclipsed 40 homers in a year with New York. He's only notched 100 RBI once, and that was his first year here. The offense just isn't elite or consistent enough to justify clogging the lineup through the final two years of his contract. The Yankees' spending habits have proven that Stanton cannot stick around as a clutch postseason luxury as they burn through April-September waiting for him to contribute more meaningfully.

So what if Cashman can clear the remaining $44 million owed to Stanton? That number is actually $64 million, but the Marlins are paying down $10 million in each of the next two years. Does that make him more attractive to a team with an already flexible lineup that only needs power from the DH spot, even if it's for 100 games a year?

The Yankees are limited what they can do in terms of upgrades, and it's not like they have Juan Soto here to mask other lineup deficiencies still. Cody Bellinger, part of the Plan B for Soto, might depart. Stanton is getting older and is still dealing with that double elbow issue that could affect his 2026. If the Yankees want to be a true contender, they will need 140 games out of him ... or they need to get rid of his money.

It won't be easy. It won't feel good. But it might be the best way to forge a new path forward.