The biggest questions facing the Yankees entering the winter meetings

NEW YORK — With the baseball world heading to Dallas for the winter meetings on Sunday, one gigantic question is hovering over the Yankees and the rest of the league: where will Juan Soto sign?

The Yankees are hoping to retain the 26-year-old right fielder after a dazzling 2024 season in the Bronx, but the pennant winners have also been competing with the Mets, Red Sox, Blue Jays and Dodgers as Soto seeks a contract that will exceed a decade in length and $600 million in earnings. It’s unclear exactly when Soto will make his decision, but a choice is expected no later than the conclusion of the meetings on Thursday.

Of course, Soto’s future is not the only pressing question facing the Yankees as they enter the winter meetings ...

How much are the Yankees willing to spend on payroll?

After exceeding a $300 million payroll for the first time in franchise history in 2024, Hal Steinbrenner would love to avoid the highest luxury tax threshold, set at $301 million, in 2025 if he can. That said, Steinbrenner said he had yet to think about parameters for an operating budget at MLB’s owners meetings last month.

Even if Soto re-signs for a record-setting average annual salary, the Yankees could still make more moves and stay under $301 million if Steinbrenner wants, as several in-house free agents have taken money off the team’s books. The Yanks will have to make additional moves in some form or another, as they have questions at first, second or third — Jazz Chisholm Jr. can play either position and center — and left. Steinbrenner also said to expect a “deep dive” on the pitching staff.

There are free agents who can fill all of those needs, but the Yankees may want to take a harder look at the trade market if they make a sizable commitment to Soto. The Yankees could also shed some salary by trading well-paid veterans such as Marcus Stroman, Nestor Cortes, Trent Grisham and Jose Trevino.

What could Yankees’ Plan B look like if Soto leaves?

If Soto picks one of his other suitors, the Yankees will have a lot of earmarked money to play with. It would be interesting to see how they spread it around, though that path is certainly not their first choice.

Would they spend big on high-end starters like Corbin Burnes or Max Fried, two starters they Zoomed with this week? Do they try to replace Soto’s generational bat with a few hitters, such as some combination of Christian Walker, Willy Adames, Alex Bregman and Anthony Santander? How about a break in typical strategy and spending big on a top-shelf reliever such as Tanner Scott or Jeff Hoffman?

Again, the Yankees could go after some of these free agents even if Soto splits. But he’s their top priority, and the team he chooses will determine just how much money the Yankees have to work with.

Would Yankees be comfortable with multiple rookies starting?

Soto and the Yankees’ potential desire to stay under the $301 million threshold could also determine how reliant the team is on cost-efficient rookies. Jasson Domínguez could be an option in left or center depending on what moves the team makes, while Caleb Durbin is a candidate to start at second base.

Domínguez didn’t exactly lock himself into a full-time starting job with a September audition last season, but the highly-hyped prospect is still well-regarded within the organization and expected to factor into the Yankees’ 2025 plans. The same goes for Durbin, whose bat-to-ball skills have positioned him for a “big role,” as Aaron Boone said, even if he doesn’t start. If the Yankees don’t re-sign Soto, they could pursue one of the aforementioned free agent third basemen and move Chisholm back to second. That would limit Durbin to more of a utility role.

Will Boone get an extension?

With agents, managers and front office personnel meeting up in Dallas, could Boone get an extension?

The skipper had his 2025 club option picked up earlier this offseason, but Boone is guaranteed nothing beyond that after taking the Yankees to the World Series for the first time as a manager this past season. Last month, Steinbrenner said he would discuss Boone’s situation with Brian Cashman but added “there’s no huge rush.”

The Yankees could also add onto Gerrit Cole’s deal, though there’s nothing necessarily imminent there either. The ace opted out of the remaining four years and $144 million on his contract at the start of the offseason. The Yankees had the ability to void that opt out by adding an extra year and $36 million to his deal, but they didn’t do that. Instead of testing free agency, Cole then essentially changed his mind about opting out. At the time, it was suggested that the Yankees, Cole and his agent, Scott Boras — who also reps Soto and will be in Dallas — could discuss an extension at a later date.

“Any discussions they want to have, we’ll have,” said Steinbrenner, who is close with Cole.