These are Yankees' 5 most pressing questions going forward

This story was excerpted from Bryan Hoch’s Yankees Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

NEW YORK -- The pathway between the first-base dugout and the batting cage was 10 bodies deep ahead of a World Series game at Dodger Stadium, where Brian Cashman squinted through California sunshine to peek at his players taking licks in the batting cage.

Though he has carried the title of Yankees general manager for more than two decades, on this afternoon, he was merely a fan with an all-access pass dangling around his neck. There were no roster moves to make, all on-field outcomes out of his control, just an opportunity to stress-watch the games from a suite upstairs.

Yet Cashman recognized then that his busy season was right around the corner, his assignments already in hand for this week’s General Managers Meetings in San Antonio, Texas.

Here are five questions the Yankees are beginning to answer this offseason:

What will their pursuit of Juan Soto look like?

We might as well start with the big one. Yes, the Yankees want to re-sign Soto, and yes, they are bracing for plenty of competition. Cashman and agent Scott Boras had preliminary talks this week, though since Boras said Soto’s free agency will be “a very thorough process” in which he hopes to meet with all interested clubs, a quick resolution shouldn’t be expected.

A rumored target of at least $600 million hasn’t scared off potential suitors, with more than a third of the league reportedly having reached out in hopes of wining and dining the 26-year-old superstar. Should the Yankees retain Soto, he’d surely become the club’s highest-paid player, surpassing Aaron Judge’s $40 million annual salary.

Though managing general partner Hal Steinbrenner has said that keeping payroll above $300 million would be unsustainable for the franchise long-term, there are scenarios where the Yankees could meet Soto’s asking price and still field a competitive team.

“We are more than willing to meet as many times as he would like to meet,” Cashman said. “We certainly have an interest in retaining him, and we’ll put our best foot forward there. But at the same time, that will either lead to us retaining him and signing him back or we’ll be forced to go in a different direction if we can’t.”

Though Cashman said that the Yankees expected Soto to be a “99.9% rental” player at the time of his acquisition from the Padres in December, they did approach Soto about an extension and were told that he wanted to wait until the offseason. For what it’s worth, Boras said that Soto enjoyed his time with the Bombers.

“I think that playing in New York for Juan was really, really comfortable,” Boras said. “He really, really enjoyed his teammates, the Yankee experience. Juan loves winning.”

Can the baserunning and defense be improved?

This topic has gained steam in the wake of the World Series loss to the Dodgers, where the Yankees admittedly did not put forth their sharpest showing in those departments. Two Dodgers, Joe Kelly and Miguel Rojas, have also made public comments about how Los Angeles viewed the Yanks’ discipline as a weakness.

“We had a struggle with our baserunning this year. We were a bad defensive team, without a doubt, at times this year,” Cashman said. “But we also, when you add it all together, we were a really good baseball team that earned the right to win the American League and get all the way to the World Series.”

On the topic of defense, Cashman said that “some of it is inherent to certain players we have.” But the stars who cost them in World Series Game 5, for example, would not have been the suspects included in that group: Aaron Judge, Anthony Volpe, Gerrit Cole and Anthony Rizzo, all of whom are normally sure-handed fielders.

As for the club’s baserunning, Cashman said that “we’re considered one of the best in the business with our baserunning program” organization-wide, adding: “It’s not representative of what you saw with the Major League club, but it is certainly an emphasis for us without a doubt, as it should be.”

Will Aaron Boone return as manager?

That may be the simplest call that Cashman and the club brass face, as the organization holds an option to bring Boone back for an eighth season at the helm. Coming off a World Series appearance, it is difficult to imagine they will not do so (or, perhaps, pursue an extension).

Cashman said that the deadline to trigger Boone’s option is 10 days after the World Series (Saturday, Nov. 9).

“I’m a big Aaron Boone fan,” Cashman said. “I think he’s a great manager and I think we’ve been lucky to have him, but let’s go walk through the process and have the conversations that haven’t been had with people above me.”

As for the coaching staff, Cashman said that would be resolved after Boone’s situation.

What is going on with the right side of the infield?

With Rizzo and Gleyber Torres now free agents, the Yankees are beginning to consider how the ’25 infield will look, and it might be markedly different. The club declined to make a qualifying offer to Torres, making it likely that he will land elsewhere in free agency.

“I think he’ll have a lot of conversations with a lot of teams that have a need in that area, and that also might include us, who knows?” Cashman said. “I appreciate his efforts while he was here.”

They have already had a brief conversation with Boras about free-agent first baseman Pete Alonso, which may be a backup plan to add thump if Soto departs. Cashman mentioned prospect Caleb Durbin as a potential internal fit at second base; Durbin is currently having an excellent showcase in the Arizona Fall League. Oswald Peraza is another choice from within the organization.

The Yanks could also shift Jazz Chisholm Jr. to second base, though that would create a vacancy at third base. Don’t forget, DJ LeMahieu remains under contract and is aiming to play a role for the team in ’25, though at this juncture it does not appear he is being guaranteed a starting job.

How will they rebuild the bullpen?

With Tim Hill, Clay Holmes and Tommy Kahnle all now free agents, the Yankees have a lot of question marks in the late innings.

It was an easy call to pick up Luke Weaver’s $2.5 million option for 2025, a relative bargain in this marketplace, but they’re actively looking for more. Left-hander Tanner Scott will be near the top of their wish list; the Yanks attempted to trade for Scott in July, when he went instead from the Marlins to the Padres.