4 big moves at Winter Meetings Yankees fans should be anticipating

The Winter Meetings begin on Sunday, and that’s when the ball will get rolling on various free agency/trade dealings. That’s the case almost every year, but with a limited class of free agents and high-profile trade candidates, it’s even more valid heading into the 2023 season.

As always, the New York Yankees are at the forefront of the discussion, but they’re faced with an Aaron Judge-sized conundrum they’re not particularly used to. When’s the last time something like this presented itself to the Yankees in a tumultuous offseason? Back in 2014 with Robinson Canó? The whole 2010 ordeal with Derek Jeter? Back in 2007 with Alex Rodriguez?

One could argue Judge’s case is vastly different than all of those, however. We’ll get to that later on.

As for other things that need to be taken care of, general manager Brian Cashman will undoubtedly be busy over the next couple weeks. He usually strikes in both big and small ways early on in December, and fans should expect a combination of both before the holidays.

What’s on the docket? What should Yankees fans be anticipating leading up to Sunday and through Wednesday night? We think we have an idea.

4 big moves Yankees fans should anticipate at the Winter Meetings

4. Gleyber Torres Trade

This is No. 4 because there’s somewhere around a 50-50 chance it happens. At the very least, traction will be gained on this front as Cashman gauges the market.

Gleyber Torres is currently playing winter ball in Venezuela after the Yankees reluctantly allowed it (they first said no, and then relented), so perhaps the team is trying to give him what he wants and get ahead of a trade as soon as possible in the event he has a poor showing or suffers an injury.

There are complications here, though. DJ LeMahieu is not healthy at the moment, and his status for Opening Day could be in jeopardy based on how his toe injury progresses/if he needs surgery. If he’s not going to be ready for 2023, it’ll be difficult for the Yankees to deal Torres, because that would mean Isiah Kiner-Falefa is still on the team/getting a ton of reps, or that Oswaldo Cabrera will be the starting second baseman and unable to be more of the super utility player that many envision him to be.

Then again, if the Yankees really need to clear some salary and address other areas of the roster, Torres is the No. 1 option to be traded. Though no longer an impressive/integral Yankee, he’s still a young, controllable asset other teams would covet.

Might be best to rip off the Band-Aid, move on, and sign a stopgap second base option who could fill in for DJLM for the time being, then be one of the last guys off the bench for the remainder of the season.

3. Low-Leverage Starting Pitcher Signed (or Traded For)

A classic Cashman move that happens twice per year — once in the offseason, and then again at the trade deadline. The man loves acquiring mediocre pitching to fill out the back end of the starting rotation. It’s rarely ever the “right” move, but you can bet he’ll be doing it again after Jameson Taillon hit free agency.

Right now, Cashman said he’s content entering the 2023 season with Gerrit Cole, Nestor Cortes, Luis Severino, Frankie Montas and Domingo German as his starting rotation … but come on. Montas offered nothing to be inspired by, and German is better suited to make spot starts and come out of the bullpen for long relief appearances.

Don’t expect a high-profile signing or trade, though. There are not a whole lot of options on either market. Justin Verlander, Jacob deGrom and Carlos Rodón probably aren’t happening. Think more like Jose Quintana or Michael Wacha. Even the middle class options of Chris Bassitt and Nathan Eovaldi don’t seem within the Yankees’ reach. As for the trade market, it’s barren. Guys like Shane Beiber, Lucas Giolito and Pablo Lopez have been floated as possible trade candidates, but they’ll cost a steep price. And who else is selling? Most of the AL isn’t, whereas the NL doesn’t have a whole lot to offer.

Prepare to be underwhelmed! Hope to be surprised.

1. Contract for Aaron Judge by Conclusion of Winter Meetings

When the Yankees want or need a player, they get said player. Regardless if it’s Hal or George. Hal’s just more conservative in his overall spending/bidding. The man paid a stupid $324 million for Gerrit Cole because he needed an ace. He knew he overpaid. The world knew he overpaid. But he did it. Because it was needed.

Judge is needed. Far more than Cole. Far more than anybody else in modern day Yankees history. If the Yankees lose him, they’re back to the drawing board. Without him, they miss the playoffs in 2021 and probably lose the division in 2022. This team is flawed with Judge, so imagine life without him? Now that’s something Cashman and Steinbrenner wouldn’t be able to stomach.

Multiple MLB insiders have suggested Judge will probably sign a deal at or shortly after the Winter Meetings. ESPN’s Jeff Passan said “all signs point to Judge returning” to the Yankees. He’s had a meeting with the San Francisco Giants and that’s it (at least of what’s been widely reported). If he’s going to leave the Yankees, it’ll be for a winning environment that can finish in October or an insane amount of money the Yankees would’ve never been willing to offer ($375 million? $400 million?).

Judge knows that if his free agency lags beyond the Winter Meetings, his price tag is more than likely going to decrease. He’s not going to want to be in a Bryce Harper or Manny Machado situation. The Yankees make the most sense. They always have.

Expect Cashman to make a few moves to round out the roster and then meet with Judge to settle this once and for all. If it doesn’t get done at the meetings, expect it shortly thereafter. Judge is a good guy. He wants this done before Christmas so Yankees fans can enjoy the holiday.

He is a man of faith, right?

ESPN senior writer pitches ‘One Big’ Yankees move to make Red Sox miserable

ESPN has predicted that, in a world where the Yankees aren't allowed to re-sign Aaron Judge, they should boldly go after Xander Bogaerts.