Just when it seemed like this October might be different, it wound up being all too familiar for the New York Yankees and their fans. It's not just that they were once again blasted out of the ALDS by a division rival no one saw coming in the spring. It's that it happened in pretty much the exact same way as it always does: with mind-boggling decisions in the field and on the bases, a poor offensive approach and some wild quotes from the clubhouse.
So: Now what? Do you really give this group another bite at the apple and just hope against hope that things will magically play out differently? Even if he wanted to go that route, Brian Cashman probably couldn't, given the pieces that are set to hit free agency this winter. The reality is that we're in for a winter of major change in the Bronx, starting with an All-Star infielder.
2B Jazz Chisholm Jr.
Chisholm Jr. just wrapped up the contract year from hell, from inconsistency at the plate to injuries to even more off-field discourse (some not his fault, some very much his fault). Still, given the paucity of impact position players on the market this winter, somebody is bound to pay up for the services of a tremendous athlete still in his 20s who was performing at an All-Star level as recently as last season.
Will that somebody be Brian Cashman? It feels unlikely right now. New York refused to engage on an extension, although they do that with everybody. It just feels like this relationship has run its course, though, as Chisholm Jr. has become a difficult player to rely on and there seems to be some internal friction as well. If Chisholm Jr. can get something into the nine figures, I'm not sure the Yankees want to go that high with George Lombard Jr. and Anthony Volpe still around and Ryan McMahon clogging up the books for one more year.
OF Trent Grisham
That sound you here is Yankees fans everywhere rejoicing in unison. I still think the decision to extend Grisham the qualifying offer last winter was a defensible one, but his defensive regression became a glaring issue this year and he seemed to get hurt every time he was starting to find a rhythm at the plate.
Grisham clearly isn't a center fielder at this stage of his career, and more importantly, New York already has its Opening Day outfield for 2027 in Aaron Judge, Cody Bellinger, Spencer Jones and Heliot Ramos. That's a pretty solid foursome, and it leaves no room for another lefty bat who doesn't bring value with his glove or on the bases.
RHP Paul Blackburn
This one will hurt a bit more. Blackburn was one of the true success stories of this season, going from a washed-up starter to a crucial part of Aaron Boone's bullpen formula. But that turnaround should fetch him significant money in a weak reliever market this offseason, and it's simply not Cashman's MO to put those kinds of resources into his bullpen.
The more likely path, given New York's track record of unearthing diamonds in the rough just like Blackburn, is that they'll wish him well and then go about finding the next one this winter. That strategy certainly isn't foolproof, but it's the one this Yankees front office seems to prefer.
RHP Will Warren
I'm admittedly going out on a bit of a limb here. Warren has settled in as a perfectly respectable back-end starter, with more room to grow, and the Yankees can't afford to snizz at that given the injury histories involved with Gerrit Cole, Max Fried, Carlos Rodon and Ryan Weathers. They showed just how much they valued him by more or less shutting down any trade rumors surrounding the righty at the deadline.
Now that they've crashed and burned in the ALDS yet again, though, I wonder whether they might be looking to make a splash via trade this offseason. And if they are, he's pretty obviously one of their most appealing assets, given their pitching depth and his big-league track record. If Cashman feels like a real shakeup is needed, this is the first place to look.
UTIL Amed Rosario
Rosario was brought in to provide defensive versatility and mash left-handed pitching. Except he can't really defend anywhere anymore — especially not third base, where he'd be needed most — and his production against lefties cratered this year. He's on the wrong side of 30 now, and there's simply nothing he does well enough to make him valuable to the Yankees moving forward.
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