We’re within two weeks of the MLB Trade Deadline, and things are pretty unsettled across the league. In the 12-team, three-Wild Card playoff era, it gets harder and harder to discern buyers from sellers, with so many teams within striking distance of a postseason spot. This year, a number teams that many figured would be also-rans, like the Cardinals and Marlins, are contending, while some presumed contenders, like the Mets and Tigers, are fading. Some teams that looked sure to sell not long ago
(looking at you, Boston), look like they might buy, while other teams that perpetually seem to go all in (hello, San Diego, might now need to sell.
We have little idea what anyone’s going to do over the next couple of weeks, and that includes the Yankees. The baseline assumption is that they’ll buy, because of course they will, they’re the Yankees. But beyond that, exactly what kind of deadline New York has is an open question.
To my eye, the last decade of Yankees’ trade deadlines gives us a few archetypes. There’s the most flashy one: the full-scale renovation, the deadline that sees the Yankees part with buckets of prospects for several major-league contributors. Seasons like 2025 and 2017 come to mind for this archetype, and 2022 also might fit the standard as well. After that, there’s a deadline of still-impactful but more measured buying, where Brian Cashman makes a few significant moves, without overhauling a third of the roster at once. Years like 2018, 2021, and 2024 are probably the best examples here. And then there are the years where the Yankees mostly stand still, content to make one or two moves without really shaking the boat; think 2019, 2020, and 2023. There’s also, lastly, the Selling Deadline, which the Yankees have pursued just once this century in 2016, though the odds of that kind of deadline are low (but not zero with Aaron Judge still hurt!).
Which type of deadline do you think is most likely in 2026? For my money, the solid deadlines of 2018, and 2021, and 2024 feel like the best analogs. 2018 saw Cashman add a few pitchers (J.A. Happ, Lance Lynn, and Zack Britton), while taking a flyer on a bat in Luke Voit. In 2021, he brought in Anthony Rizzo, Joey Gallo, and Andrew Heaney, while in 2024 it was Jazz Chisholm Jr. and Mark Leiter Jr. That kind of deadline, where the Yankees target a few legitimate big-league contributors but don’t go crazy, generally feels like the median outcome for a Cashman deadline.
But there’s always a chance things go off script, in either direction. Maybe the Yankees see fit to turn over the roster like they did last year, or maybe they’ll make like 2023, the last time they entered the deadline with an injured Judge, when Cashman added an interesting relief arm in Keynan Middleton before calling it a day.
What do you think? Which route is most likely? And which do route do you think would be best for the Yankees with the roster in its current state?
On the site today, our Trade Deadline target series rolls along, with John analyzing Luis Arraez, a player the Yankees were often linked to a couple years ago. John will also profile Carsten Charles Sabathia on the occasion of his 46th birthday, while Matt will hand up the day’s Rivalry Roundup. Later, Michael recaps the last week of action down on the farm, and Peter delivers his At-bat of the Week.
Today’s Matchup
New York Yankees vs. Pittsburgh Pirates
Time: 7:10 p.m. EST
TV: YES Network, SportsNet Pittsburgh
Venue: Yankee Stadium, Bronx, NY
