Is the New York Yankees Window Closing?

By E.J. Fagan

October 31, 2025

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NOTE: The following comes from EJ Fagan's substack page and is shared with permission.

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I noticed something interested about the Yankees roster that I think is worth discussing. Here is the distribution of ages for players under the Yankees team control in 2026:

Brian Cashman has pretty well staggered the Yankees roster by age. It sure looks purposeful to me. They don’t have any real Baby Boom on the roster, where a bunch of players are likely to get old at the same time. I imagine a python that just ate a big meal, where the big lump has to work its way down the snake’s body before it can eat again.

A well-staggered roster is great for a baseball club that wants to win into perpetuity. If you have sign three guys to long term deals who are all the same age, they will all be entering their decline years at the same time. You all but guarantee a long fallow period following a few years where the contending window is open.

For example the 2013-2016 Yankees suffered from Derek Jeter, Alex Rodriguez, Jacoby Ellsbury, CC Sabathia and Mark Teixeira all declining at once but still occupying roster spots and commanding big salaries. It was a rough few years for the years before they could clear them off the books.

But there’s a downside to staggering ages: you never load up for a championship. Maybe the reason why the Yankees feel perpetually trapped in the low-to-mid 90 win range is that they have decided to never set themselves up for a 2013-2016 period again.

Implications

How does this distribution impact the Yankees offseason plans? Cody Bellinger is going to be 30. The Yankees don’t have any long term commitments to 30 year olds. He would be entering his decline years right around the time that Stanton, Cole and Rodon come off the books. Trent Grisham and Kyle Tucker are both a year younger, where the Yankees similarly have no long term commitments.

The gap in the 29-31 range (McMahon is signed to a pretty cheap contract for just two more years, Bednar is a free agent after 2026), makes a monster deal for someone like Kyle Tucker a lot less risky. When he enters his mid-30s, the Yankees will have shed themelves of a few more old guys, allowing them to sign someone else in their late 20s. The logic is similar for Cody Bellinger, although I suspect that he’ll require less of a mega contract.

Jazz Chisholm and Bo Bichette are both entering their age 28 seasons. I’d rather extend Jazz, but either make sense as a long term second baseman.

It also rules out big contracts for a Kyle Schwarber (32), Pete Alonso (31), Framber Valez (32), Alex Bregman (31), but they might be willing to commit to Michael King (30), Dylan Cease (30) or Ranger Suarez (30).

What about younger guys? Rice and Wells are under team control into their 30s, so I don’t expect them to get extended. Warren and Volpe aren’t very good yet. Schlittler and Dominguez make a lot more sense.

Bottom Line: Window?

I don’t think that the Yankees should push all of their chips into the 2026 pot. While guys like Rodon, Judge, Fried and especially Cole are getting older, but all I suspect that all three will be productive for some time. And Rodon and Stanton aren’t that far away from the end of their contracts.

But at the same time, the Yankees have a pretty strong core of guys deep into their 30s. Aaron Judge is still in GOAT-mode. Fried, Rodon and Cole are a pretty strong playoff rotation. Jazz Chisholm and Ben Rice are great. Other than their new outfield vacancies, the team lacks obvious holes. The farm system is pretty weak other than like two hitters and four starters.

I’m not sure when the window is going to be open any wider than it is right now.

The Yankees should be adding this offseason. They have room for another long term contract, but should also look for shorter term options to improve the roster along the lines of the trades for Bednar, Chisholm and especially Cody Bellinger. That might mean trading from their still-solid stable of minor league starting pitching.

We’ll talk a lot about all of the Yankees options for this offseason, but I wanted to get the big picture out of the way.

See you after the World Series - Go Jays!