Most pressing Yankees questions for Brian Cashman at GM meetings

For disconsolate Yankees fans, consider the depths of this time on the calendar last year.

Brian Cashman held court at the GM meetings in Scottsdale, Ariz., where he forcefully defended the club’s operations following an 82-win season and said that the Yankees’ processes and people were “pretty f—ing good.” 

After a 2024 that fell three wins short of a World Series title, the temperature will be turned down at this year’s meetings in San Antonio, but questions remain about a championship drought that has reached 15 years for a team entering another pivotal offseason. 

For the first time since the club’s hopes ended in a wild Game 5 against the Dodgers on Wednesday, Cashman will speak publicly about a season that marked improvement but not enough for a franchise that has made World Series championships — and not appearances — its standard. 

Baseball executives are expected to arrive in Texas on Monday ahead of the official start of the meetings Tuesday.

By the time the meetings conclude Thursday morning, there should be more clarity on how the Yankees plan to handle this offseason, with Cashman set to answer questions such as: 

Do the Yankees need a Juan Soto answer relatively quickly? 

Super agent Scott Boras would not mind taking his time, allowing each team to woo his client and watch a bidding war ensue over the next several months. 

The Yankees — and every other club that is ready to mount a run at Soto — are not sure if they are allocating hundreds of millions of dollars toward one of the most attractive free agents ever in the sport, or whether that money should be spent elsewhere.

Does Cashman feel as if such an enormous domino must fall, one way or another, in a relatively short time?

If Soto slips away, the Yankees would have to pivot quickly. 

What’s the deal with Gerrit Cole? 

The ace opted out of the remaining four years and $144 million of his contract Saturday.

The Yankees can keep Cole from hitting the market by attaching an extra season worth $36 million that would ensure he remains atop their rotation through 2029. 

There has been confusion concerning the deadline for that decision, which was believed to be Sunday before it was determined to be Monday. It was unclear whether the two sides agreed to move it back. 

It is possible the sides are negotiating.

There is a strong case to be made that the Yankees cannot afford to risk losing the face of their rotation and among the best pitchers in baseball, even if he is 34 and beginning to show signs of that age.

There is also a strong case to be made that the Yankees cannot afford to guarantee $180 million to a pitcher if their No. 1 priority is Soto and there are other top starters available. 

 Can the payroll go up? 

The Yankees payroll exceeded $300 million for the first time in 2024, surpassing the highest luxury-tax threshold — the “Steve Cohen tax” — of $297 million. 

At the moment, FanGraphs estimates a $245 million projection for tax purposes next year (which assumes Cole returns) — and that is before a megacontract for Soto and any significant offseason moves. 

If the Yankees sign Soto and retain Cole, would there be room for other additions?

Or is Hal Steinbrenner steadfast on trimming payroll from a level he did not want to reach?

In May, he called the 2024 payroll “not sustainable.” 

“I’ve been a broken record [on this topic]: I don’t believe I should have a $300 million payroll to win a championship,” Steinbrenner said then. “I believe I need a good mix of veterans, who are gonna make a lot more money, but also we’ve put a lot of money into our player development system in the last 5-10 years. And in my opinion, we have one of the better ones in baseball now.” 

Are changes in personnel or coaching necessary to field a more fundamentally sound team? 

The Yankees could swallow mistakes in fielding and baserunning during a regular season that ended with an AL East title and through two rounds of the postseason that ended with a pennant.

But a team that was rated as the worst baserunning club in baseball, according to FanGraphs, and consistently hurt itself defensively paid for its mistakes in the World Series — which climaxed with a three-misplay fifth inning of Game 5 that will be remembered. 

Are the deficiencies a personnel problem that can be addressed through player acquisition?

Or are the deficiencies a structural issue in which the coaching is not strong enough? Speaking of which:

Will Aaron Boone be back? 

The presumed answer is “yes,” but there has been nothing official concerning a manager who just finished the final guaranteed year of his contract with a club option for 2025. 

“We’re certainly happy to have him as our manager,’’ Cashman said during the ALDS. “We’ve got the best record in the American League [and] won the AL East. Now we’ll try to win the postseason and try to climb all the way to the top.” 

For a first time under Boone, the Yankees reached the World Series.

But for a seventh straight time under Boone, they did not complete the mission. Will that matter?