Some contracts age like fine wine, and then there are some that feel like a burden. Giancarlo Stanton’s deal is a cocktail mix of both. He had a resurgent year and hit .273/.350/.594 with 24 homers and 66 RBIs in just 77 games. But before the claps settled, in the postseason, he reminded us that consistency is a major question mark for him. And with $54 million still owed until 2028, the massive contract essentially limits the Yankees.

And the Trent Grisham extension mess brought up by Cashman doesn’t make things easy for the Yankees either. And it could be land Stanton to be on the noose for this, because some want him out of the Bronx.

A WFAN insider made it clear about how the Yankees should deal with the mess. “I would rather trade either Dominguez or Jones, or whatever minor leaguers, to get Stevan Kwan here. See what’s left. Bring Kwan in. Put him in left field. Now I’m set. If you have Grisham in center, you bring back Bellinger. He could play some first. Grisham’s not going to play every day in center field. You play him in the center. You could give Judge some days of rest. You put Bellinger in the right. You make Judge DH a little bit. It’s I would still look to bring back Bellinger, add Kwan, and move on from Stanton, and I think that makes them fit better.”

Essentially, they are saying that Stanton is an expensive holdover, standing in the way of the New York Yankees’ outfield alignment. Now this gets us to Trent Grisham and how his accepting a move no one thought he would might have ruined the Yankees’ plans.

Grisham accepted the $22.025 million qualifying offer and ensured that the Yankees have a center fielder of quality. But it also typed things up when it comes to payroll, and that complicates things in left field, where Steven Kwan, projected at $8.5 million, has come out as the prime target for the pinstriped team.

Kwan has high defensive versatility, and it makes him a good fit with Judge and Cody Bellinger, in case Bellinger does return to the Bronx. The Yankees’ payroll, though, is the real challenge. Given that Grisham and Ryan Yarbrough signed, the luxury tax figure sits around $282 million. Adding Kwan or bringing back Bellinger could mean that Jasson Domínguez, Will Warren, or Ben Hess are back into trade discussions.

Things sure did get complicated with Trent Grisham accepting that offer, didn’t they? Some are even calling it the first move of a wrong domino to fall for the New York Yankees. However, if a payroll rise is a concern, they have one key player they can get for a bargain!

Could Corey Seager be the Yankees’ answer at shortstop?

There is no doubt that the Yankees are aggressive this winter, and it’s understandable—the 2025 season has been anything but memorable. They would most likely want to forget the season. Now they are chasing stars like Kyle Tucker, Pete Fairbanks, and even Lucas Giolito. But here is a thing: given they are riddled with big contracts from Grisham to Stanton and more, they need to look beyond the free agency to fill key gaps.

This is where Corey Seager enters the scene.

The Texas Rangers shortstop has emerged as one of the Yankees’ most intriguing trade targets. He is 31 and is due $31.5 million annually through 2021, and it makes him one of the highest-paid players on the Rangers roster. Now Texas is facing the luxury tax issues and can see moving Seager as a smart move financially, given his trade value is high.

As Mac Engel of the Fort Worth Star-Telegram mentioned, “If dealing Seager could potentially net two bats and a pitcher, the Rangers should at least have a serious discussion about it.”

And given that Josh Smith is waiting as a capable replacement, Texas has the right time to explore. For the Yankees, Seager could be a huge upgrade, given Volpe is recovering from shoulder surgery and Caballero is stacked in as the temporary starter. So the Yankees’ shortstop situation is shaky at best. Seager brings offensive and defensive bits for the pinstripes. That said, there is a hurdle—his eight-time no-trade list. Rosenthal had noted that the Braves found themselves blocked by that clause recently.

Now, whether the Yankees are included remains unclear, but if not, then they could be in the prime position to swing a deal with him and transform the middle infield.