5 questions Yankees' Brian Cashman must answer at GM Meetings

The 2022 GM meetings will start Monday in Las Vegas, allowing the front office of every MLB team to discuss potential trades and free agent targets.

After a disappointing end to their season, Yankees GM Brian Cashman will have a lot of questions to answer. When your most popular player may walk in free agency, and the gap between the Yankees and Houston Astros has not gotten smaller in five years, there are going to be plenty to ask.

With the Winter Meetings in December being where a lot of the trade/free agent chatter comes in, there will still be plenty of topics for Cashman to discuss, and questions to answer.

What are the Yankees planning to do to bring back Aaron Judge?

This is the biggest story for the Yankees this offseason. After the team and Judge couldn’t agree on a new contract before the start of the season, there’s fear that the face of the franchise may not be in pinstripes in 2023.

While Cashman spoke on the subject of Judge's pending free agency on Friday, he needs to answer what the team is willing to do to bring back Judge. Will they give him the years he’s looking for? Will they incentivize him by naming him the 12th Yankee captain in team history?

We all expect to hear that they want him back, but how far are they willing to go, especially if a bidding war occurs?

How much are the Yankees willing to spend this offseason?

If the Yankees re-sign Judge, it’ll be for a large sum of money. But what about after? Will the organization make some big moves to fill in some of the holes in their lineup and rotation/bullpen? Or will Judge's potential contract be the only big one this offseason?

We’ll likely get a variation of “we’re going to do what’s best for the organization,” but after being swept by the Astros in the ALCS, something clearly has to change. They already shifted to a more defense and speed-focused team, which helped mask a lot of the team’s failings this season -- namely the strikeouts and tendency to have long offensive droughts -- and it worked until the postseason.

With some aces and shortstops on the market, the Yankees can really improve their team -- if they are willing to pay for it.

What do the Yankees need to do to make it back to the World Series?

Every year since 2017 feels the same. A promising season ends in disappointment. 

How can the Yankees make that leap in the postseason to punch their ticket to the World Series? We have some thoughts on how they can do that, but what does Cashman think?

It’ll be interesting to hear if he was proud of the team’s postseason performance and, frankly, his own trade deadline moves. Cashman looks like a genius for getting Harrison Bader, and to a lesser extent Andrew Benintendi, but his move to get Frankie Montas has not looked good, especially when he could have had Luis Castillo.

He could blame the ALCS sweep on injuries, but now that we’re looking toward 2023 what does he think needs to be done to finally make it back to the World Series.

Where do the kids fit in?

Speaking of Castillo, Cashman didn’t grab the right-handed starter because the Cincinnati Reds wanted coveted prospect Anthony Volpe, someone the Yankees did not want to deal.

Since Cashman and the Yankees are clearly keeping the shortstop position open for him, we need to know what their plan is for the young infielder. Will he fight for the spot in spring training or are they set on waiting another year?

What about Oswald Peraza? Now that he’s had a taste of the big leagues, will he play a bigger part on the team in 2023? With Isiah Kiner-Falefa still under contract, and a bevy of shortstops on the free agent market, where does Peraza fit?

It’ll be interesting to hear what Cashman says on the matter as it could give us a hint as to what they plan to do in free agency.

What’s your confidence in Aaron Boone?

Aaron Boone did not have a good postseason. Some questionable bullpen usage and lineup changes have many fans pointing their fingers to him as to why the ALCS wasn’t more competitive.

It was clear that the Astros were the better team, but there were at least two games that were there for the taking, and Boone’s bullpen decisions cost them.

So what did Cashman think of Boone's performance this season? Well, he said in the team's end-of-year news conference on Friday that he thought Boone did a "great job" in 2022, but that was minutes after the Yankees manager finished his conference so give it a few more days and he could have something new to say.

Cashman doesn’t have the power to determine Boone’s fate, but he has Hal Steinbrenner’s ear, and asking him if he believes the manager can bring the Yankees to the next level is a fair question.