5 questions for Yankees’ Brian Cashman to answer at GM Meetings

The 2024 MLB GM meetings are set to begin Tuesday in San Antonio, the first stop of what should be a very interesting offseason for baseball — and especially for the Yankees.

GM Brian Cashman will be available to the media to answer a slew of questions after the Yankees lost in the World Series in five games.

This offseason is similar to the one after the 2022 season, where the team had a disappointing end to their playoff run, a superstar hit free agency, and there are questions surrounding the manager.

Although the Winter Meetings will be where the trade and free agent chatter will rev up, there’s plenty for Cashman to answer…

How far will the Yankees go to bring back Juan Soto?

Every question surrounding the Yankees this offseason involves Soto. The talented 26-year-old outfielder has hit free agency for the first time in his already impressive career and could possibly become the highest-paid player in MLB history.

So, what will the Yankees do to make sure their 1-2 punch of Soto and Aaron Judge remains intact? That’s the question Cashman needs to answer. This is similar to when Judge hit free agency, but there are some differences. Without Judge, the Yankees were lost — as we saw when he injured his foot in 2023, leading to New York missing the postseason.

But without Soto, the Yankees are likely still a playoff team. Now, where it’s similar is how much Soto meant to the 2024 team. He checked all of the Yankees’ boxes and provided them with his best offensive season. He also helped the Yanks make it to their first World Series since 2009.

As negotiations commence, don’t expect Cashman to give agent Scott Boras any leverage when speaking on the matter. But his answers should be noteworthy.

How much are Yanks willing to spend this offseason?

Soto will be the No. 1 target this winter, but how much are they willing to spend overall? If Soto goes somewhere else, will the money they were going to use be allocated elsewhere? The Yankees can use a new third baseman, and Alex Bregman is available. Christian Walker is an option at first base if they don’t bring back Anthony Rizzo.

Blake Snell opted out of his contract with the Giants, and the Yankees were in on him last offseason. Would they try and negotiate a deal again?

Even if Soto re-signs, will New York spend for another high-priced bat or arm? There are low-priced prospects like Jasson Dominguez, Ben Rice and others who can fill in certain gaps, but to get over the hump the Yanks may need more.

Status of Aaron Boone

The job security of the manager is always a topic every offseason, but after helping lead this team to the World Series, how much security will Cashman and the organization give Boone?

SNY’s Andy Martino reports that Boone will be back with the Yankees in 2025, as the team will likely exercise their club option, but is a contract extension not far behind?

How will Yanks fix their fundamentals?

On the managing front, the Yankees’ lack of fundamentals were exposed this postseason, especially in the World Series.

Two of the Dodgers’ wins were helped by the Yankees’ poor defense and base running, but is that something that can be fixed in one offseason?

Maybe it’s a lack of accountability. Maybe the roster Cashman put together is to blame. Whatever it is, the GM needs to address how they can fix it or there could be a repeat this upcoming season.

Jasson Dominguez’s role in 2025

There’s no question that Dominguez is the future of the Yankees, but will he be given a starting role next season? Where Soto ends up could impact that decision. If Soto returns, Dominguez is most likely going to start, but if Soto goes elsewhere the team could spend money to bring in an outfielder or two — which could include re-signing Alex Verdugo.

In 18 games in 2024, Dominguez was 10-of-67 with two home runs and one double. Despite being on the postseason roster, Dominguez did not have an at-bat and was used exclusively as a pinch-runner. Next season, the switch-hitting prospect will need to be a more balanced hitter and improve defensively if he wants to be an impactful part of the roster.