The Winter Meetings are where a lot of the offseason craziness begins, and this year the Yankees will need to use this time to figure out a few things. From Dec. 4 to 7, representatives for all 30 teams will be in San Diego to discuss all sorts of business.
For the Yankees, their first order of business involves Aaron Judge. However, there are plenty of other holes on the team's roster to figure out.
Here's what should be on the Yankees’ to-do list…
Resolve the Aaron Judge situation
Judge has been the talk of the offseason. Will he stay or sign elsewhere? The rest of the big free agents could be waiting on what the reigning AL MVP gets before they can set the market for themselves.
For the Yankees, this is the number one order of business at the Winter Meetings. The Yanks are reportedly willing to give Judge something in the range of $300 million for eight seasons, and while it would make him the highest paid position player in baseball, that contract might not woo him to return to the Bronx.
With the San Francisco Giants in on Judge, will the Yankees increase their deal to match or exceed what the outfielder is offered?
SNY’s Andy Martino believes Judge is close to making a decision and he won’t be surprised if it’s done before the Winter Meetings are over.
However this situation ends, the Yankees need to figure it out so they can address the rest of the holes on their roster.
Test Gleyber Torres’ trade market
The Winter Meetings aren’t just for free agent signings, it’s also the place where trades can be done.
It’s no secret the Yankees were close to obtaining Miami Marlins RHP Pablo Lopez for Torres and prospects earlier this year. While New York balked at the deal, it confirmed that the Bombers are ready to move on from Gleyber.
With the infield being flush with talent in the big leagues and minors, the Yankees should test the trade market with Torres. They could possibly get some bullpen arms or package him for another starter to fill out the rotation.
A deal doesn’t necessarily have to get done at the Winter Meetings, but the groundwork could be set for a trade down the line or at the deadline. If Torres is traded, that opens up a lot of possibilities for what the Yankees can do with Anthony Volpe, Oswaldo Cabrera and Oswald Peraza.
Figure out their infield situation
It’s a good problem to have, but the Yankees still have an issue in the infield, specifically that they have too many players for just four positions.
Even if the Yankees can trade Torres, they still have to figure out what to do with Josh Donaldson, DJ LeMahieu, Cabrera, Peraza, Volpe and Isaiah Kiner-Falefa -- who recently signed a one-year deal to avoid arbitration.
Donaldson is due $21 million next season, so it’s unlikely the team just cuts or benches him. However, is IKF now out at shortstop after his poor defensive performance in 2022? The team could use him as a bench player next season, but what of LeMahieu? The Yanks are still waiting to see if he can avoid surgery on his toe, but if he can’t he’ll be out for months. And then the team has Cabrera and Peraza, who got to see some at-bats last season the big league level.
Then there’s Volpe, who the organization loves and is the heir apparent at shortstop for years to come.
Brian Cashman and Hal Steinbrenner have said that their young players will have the chance to compete for starting roles in spring training, but they can also resolve a lot of these issues at the Winter Meetings via trade and free agency.
Enact their Judge backup plan
If Judge decides to sign with another team, the Yankees will need to start looking to fill the hole.
Cashman and the front office likely have their backup plan(s), and they should look to make a splash if Judge leaves.
Whether that’s signing a high-profile free agent like Carlos Correa or making a big trade, they’ll have to do something to show the fanbase that they can move on and be OK -- or at least try.
The Yankees haven’t had a player of Judge’s stature since Derek Jeter, and having him leave in free agency would be something the organization will have to answer for. And one way they can do that is to spend like they haven’t in years.
Will they do it? We’ll have to wait and see.