The Yankees are headed into another winter with a familiar kind of mess on their hands: a roster with real pitching depth, obvious holes in the everyday lineup, and leadership that appears set to run it back. Aaron Boone is returning in 2027, Brian Cashman said on Wednesday he’ll get a new contract, and that combination alone tells you how much change is actually coming.
That’s why the most likely offseason mistakes feel almost baked in already. The Yankees finished 2026 with one of the better pitching staffs in baseball and a lineup that had enough talent to matter, and still got knocked out in the ALDS for the second straight year.
The frustration is obvious. The fix, less so - at least if you’re expecting the front office to act boldly.
The first swing and miss: not trading from the pitching surplus. New York has more starters than it can reasonably use in a five- or even six-man rotation, but that strength hasn’t translated into the rest of the roster.
Third base? Another outfielder?
Bullpen help? There’s room to improve in plenty of places.
A smart front office would turn one of those young arms - Will Warren, Ryan Weathers, even Elmer Rodriguez - into multiple depth pieces and make the club better everywhere else. Instead, the more likely path is holding onto all of them and entering the season with at least one unhappy starter and a position-player group that still feels thin.
The second mistake is the easiest one to see coming: staying attached to Giancarlo Stanton and Ryan McMahon. Stanton plans to make his spring debut next week and play a full season despite tennis elbow preventing him from doing simple tasks pic.twitter.com/dvlQ5VUsYP
- Talkin' Yanks (@TalkinYanks) February 26, 2026
Those two are “move on from this guy immediately” candidates for different reasons. Stanton, as the source puts it, literally doesn’t play baseball anymore.
McMahon’s issue is defense; he can’t field his position at an elite level anymore, and that was the main thing he brought to the Yankees in the first place. Yes, moving either one might mean eating money.
But New York has done that before. The more likely outcome is that the Yankees convince themselves Stanton can be load-managed and McMahon is worth keeping because he’s still under contract.
And then there’s the bullpen, where the Yankees are primed to make the same mistake in a different year. Cashman has a track record of looking at one season’s outcome and treating it like a blueprint for the next, even when the logic doesn’t really hold up.
The source points to last winter’s Trent Grisham situation, when the Yankees treated his career year as something they could expect to repeat in 2026. That obviously didn’t happen.
Now the same kind of thinking could hit the bullpen. Cashman could point to how well the relief corps worked in 2026 - even with rocky stretches and the likelihood that Paul Blackburn won’t be back - and decide the group doesn’t need major help.
Brent Headrick looked great, sure, and David Bednar is part of the picture too. But that’s exactly how teams get themselves in trouble: by assuming a good season guarantees another one, then entering the next year light on arms and waiting too long to fix it.
That’s the pattern the Yankees seem most likely to repeat this winter: not cashing in the pitching surplus, hanging onto declining veterans, and convincing themselves the bullpen is stronger than it actually is.
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