Yankees GM Brian Cashmanwill head to the annual MLB GM Meetings, taking place in Las Vegas this week and speak to reporters for the first time since New York was ousted in the ALDS by the Toronto Blue Jays.
Many could see the 2025 season as a failure for the Yanks, after making it to the World Series a year prior, so Cashman and his front office will have plenty of questions to answer about how he plans to get New York its first championship since 2009.
It won’t be easy, of course, as the Blue Jays and other American League upstarts like the Red Sox and Mariners are waiting to take their shots this offseason and in 2026.
Don’t expect Cashman to lay his cards on the table at the GM Meetings. But we can glean something from when he speaks, whether it’s about the needs of the team or where current players are on the depth chart.
Here are five questions Cashman should be asked this week…
Has his stance on Anthony Volpe changed?
One of the many questions Cashman received during his end-of-season news conference was about shortstop Volpe.
The third-year infielder had a difficult 2025, which — whether manager Aaron Boone admits it or not — was impacted by his injured shoulder. Volpe has since undergone surgery and will look to man the shortstop position when he returns sometime during the season. However, is Volpe’s role as the starting shortstop in hand?
Cashman didn’t commit to the shortstop position back in October, but he said he believes in Volpe and that there is still growing to do.
“I believe in the player, still. I think we believe in the player,” Cashman said. “It doesn’t mean that we don’t play with, on any level, all aspects of roster assessments. He’s 24 years old. I don’t think New York’s stage is too big for him, I just think he’s still finding his way. The age is something that there’s a lot of value to reminding yourself about.”
Jose Caballero is on the roster and probably has an inside track to break camp as the starting shortstop, but there are some intriguing options like Bo Bichette available.
Sep 3, 2025; Houston, Texas, USA; New York Yankees second baseman Jazz Chisholm Jr. (13) runs to first base on a single during the fifth inning against the Houston Astros at Daikin Park. / Troy Taormina-Imagn Images
Is there interest in extending Jazz Chisholm Jr.?
Cashman has had some great trade deadline deals the last few seasons, and the addition of Chisholm in 2024 helped the team make it to the World Series. In Chisholm’s first full season in pinstripes, he was even better, having arguably his best offensive season en route to an All-Star selection and a Silver Slugger.
But does that mean Cashman has the stomach to have extension talks with his infielder?
Chisholm will enter the final year of his contract in 2026, but an extension could buy out his final year of arbitration and keep the 27-year-old in the Bronx for a long time.
Cashman, however, is not one to give out extensions. But he should be asked if Chisholm is an exception, especially after the production he’s provided and how selfless he’s been, playing third base whenever asked.
What’s the plan for the outfield?
Aaron Judge is the only name Boone can write in as a starting outfielder next season. Cody Bellingeropted out of his contract and will explore free agency, and Trent Grisham‘s contract also expired — though the Yankees extended him the qualifying offer.
Cashman needs to fill out left field and center field, so what is his plan for them this offseason? The qualifying offer shows the Yanks are willing to bring Grisham back, but it doesn’t guarantee his return. And then, how hard are they going to try and re-sign Bellinger? The former NL MVP had a great first season in the Bronx and said he’d welcome a return.
There’s also the bevy of free agent outfielders, like Kyle Tucker, who are available. We don’t expect Cashman to give away which of the outfielders he wants the most, but perhaps a hint of where he’s leaning could be gleaned.
New York Yankees outfielder Spencer Jones (78) celebrates after hitting a three-run home run against the Philadelphia Phillies in the third inning during spring training at BayCare Ballpark / Nathan Ray Seebeck – Imagn Images
Where do Jasson Dominguez and Spencer Jones fit?
Speaking of the outfield, the Yankees have two youngsters who could fill one — or both? — spots to start the 2026 season. Dominguez made the team out of spring training in 2025, but the young switch-hitter had growing pains at the plate and in the outfield. Once a highly-touted prospect, Dominguez’s first full season in the bigs did not go the way the team had hoped.
It also didn’t help that Grisham simply outplayed the youngster, taking away precious at-bats while New York was in the midst of maintaining a playoff spot.
Cashman should be asked if Dominguez is a part of their plans and whether he has the stomach to deal him.
And then there’s Jones. The young slugger burst out in the minors last season, going on a power tear through Double-A and Triple-A. Cashman said that Jones “put himself in the conversation” of making the Opening Day roster, but how true is that? Also, is Jones a trade candidate if the outfield spots are filled up with external signings?
This could be the best time to trade Jones, whose stock has never been higher.
Do the Yankees have enough pitching to withstand injuries?
The Yanks will be without Gerrit Cole, Clarke Schmidt and Carlos Rodon to start the 2026 season. While the team has viable arms, do they have enough to get through a 162-game season?
Max Friedwill anchor a starting rotation that will likely include Luis Gil, Will Warren, and Cam Schlittler. That’s a lot of question marks that need to be answered.
The Yankees can sign a free agent starter like Dylan Cease, Michael King or Zac Gallento help their bludgeoned rotation, which would possibly clear the way for them to trade some of their young arms.
Cashman is always candid when it comes to pitching, in that he can never have enough of it. Perhaps that’s the case this offseason, and Cashman should answer that.