3 offseason mistakes Yankees seem uniquely poised to make this winter

The New York Yankees finished 2026 with one of the better pitching staffs in baseball and a good amount of talent in their lineup ... all to bow out in the ALDS for a second straight season. Yankees fans are beyond frustrated, former Yankees are frustrated, and yet nothing's apparently going to change from a leadership perspective. Aaron Boone's coming back in 2027, and Brian Cashman announced on Wednesday that he will receive a new contract, too.

Since Cashman's return has always seemed so obvious and preconceived, I'm not even going to include that in the following rundown of three mistakes the Yankees will hurt themselves with this winter. But if you wanted to include the fact that they didn't part with Boone and are going to re-up Cashman (for how long, who knows), this list could easily be five. Let's get into it.

3 mistakes the Yankees will surely make this winter

1. They won’t trade from their young pitching surplus

The Yankees have too many good starters for a five- or even six-man rotation; meanwhile, they have holes everywhere else (Third baseman? Another outfielder? Bullpen?). Any competent GM would view this as a clear opportunity to trade a Will Warren or a Ryan Weathers for multiple depth pieces. Even Elmer Rodriguez might fetch legitimate value in this market.

Somehow, someway, Cashman will fail to cash in on any of his young, controllable arms, entering the season with an unhappy starter or two and a position player depth chart that doesn't look markedly improved. Yay!

2. They will keep believing in Giancarlo Stanton and fail to trade Ryan McMahon

Stanton and McMahon are "move on from this guy immediately" candidates for entirely different reasons. Stanton literally doesn't play baseball anymore, and McMahon can't field his position at an elite level anymore, which was the only thing he was offering the Yankees in the first place.

Would the Yankees need to eat some cash to move on from these declining pieces? Surely, and it's not like New York's been completely against doing this in the past. But the more likely outcome is that Cashman and the Yanks will rationalize the retention of both Stanton (he'll be load-managed!) and McMahon (he's still under contract!), since it would take legitimately clever front office work to move either without suffering financially.

3. They will underbuild the 2027 bullpen because 2026 went "well"

Speaking of rationalizing things that make no sense, Cashman has a habit of pointing to lucky or singular narratives from the past season and formulating a thesis that those narratives will continue into the next season. He did this when Trent Grisham's qualifying offer came up last winter: Cashman basically said that since Grisham had a career year (which he'd never come close to before, mind you), the Yankees believed Grisham would offer similar production in 2026. That didn't happen, of course.

This year's version of the "Grisham explanation" will apply to the bullpen. Cashman will look back on the success of New York's 'pen in 2026 (even though there were plenty of rocky stretches, and Paul Blackburn probably won't be back) and use this success as a reason not to over-exert himself on the market when it comes to beefing up the staff with relievers.

Look how good Brent Headrick was! He can pitch every night! We're not worried about the bullpen! Meanwhile, Cashman is bound to run Headrick into the ground midway through 2027. And David Bednar, for that matter. The Yankees of recent years derive some weird enjoyment out of entering new seasons with an undermanned bullpen, and then watching the deadline go by without doing much about it. It's hard to expect that to change this winter.

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