5 questions for Yankees GM Brian Cashman to answer at 2025 MLB Winter Meetings

The 2025 MLB Winter Meetings are here.

For the Yankees, it’s been a quiet start to the offseason, one that has many fans clamoring for GM Brian Cashman to start making moves to improve a roster that could not return to the World Series in 2025 after flirting with their first title in nearly two decades a year prior.

Although Cashman has been known to work in the shadows in the offseason, this year’s Winter Meetings could prove fruitful for the Yanks.

With plenty of holes to fill and questions to be answered, here are five that the longtime GM needs to address this week…

How much are Yanks willing to spend?

This feels like an annual question for Cashman, but it warrants addressing. Hal Steinbrenner‘s comments about the payroll “ideally” being lower in 2026 have many fans nervous that Cashman will be buying from the bargain bin this offseason.

Perhaps Trent Grisham accepting the qualifying offer affects the team’s spending, but it shouldn’t. Bellinger is a clear priority for Cashman, but it will likely take the team over the $300 million threshold.

Cashman will be asked about this year’s payroll and he won’t answer in a way that gives clarity, but the best way he can is by signing players who will push them over that mark. Currently, the team’s payroll is at around $283.6 million, so one big signing will dispel all questions about the 2026 payroll.

How far is New York willing to go for Cody Bellinger?

Going along with the payroll, Cashman has to answer how far the organization is willing to go to re-sign Bellinger.

Cashman has been in this position before, most recently with Soto, but with options for a free agent plus outfielder relegated to Bellinger and Kyle Tucker this offseason, the Yankees GM needs someone to man left field.

Reports say the Yankees are making a “big effort” to bring back Bellinger, but is that all talk? When Soto was a free agent, the Yankees made a good offer, but the Mets simply went above and beyond for the outfielder’s services. Will Cashman let that happen again when it comes to Bellinger? It’s hard to tell, and Cashman will say it allows Jasson Dominguez and Spencer Jones a chance to win a spot this spring. But it’s an unserious notion considering the team’s expectations.

Devin Williams’ departure and the bullpen

The Yankees went into the 2025 season with Williams as their closer and now he’s on another team. Despite a shaky season, Williams finished strong with the Yanks and a reunion seemed sensible for both sides. But after the right-hander signed a three-year deal with the Mets, it leaves Cashman without a setup man for David Bednar.

Cashman should be asked how close they were of bringing back Williams this offseason, and now that he’s gone, what he plans to do to address the holes. Luke Weaver is a free agent. Are the Yankees in on him? What about other high profile relievers like Pete Fairbanks and Robert Suarez?

Is Spencer Jones going to get a chance?

Jones is the buzziest hitting prospect the Yankees have after the slugger mashed his way up the minor leagues. But at this moment, there’s no space for the outfielder on the roster.

If the Yankees whiff on Bellinger and Tucker, that can change. However, even if Cashman finds a third outfielder this offseason, is there a spot for Jones as a DH or somewhere else? Cashman said previously that Jones has a chance to crack the Opening Day roster in 2026, but is that still true?

Is the trade market better than free agency?

While teams will negotiate and try to outbid the other teams when it comes to free agents, is Cashman’s best path to a formidable roster this offseason via trade?

Cashman has pulled off offseason trades out of the blue before and this year could do so again. There are plenty of starters potentially available via trade (Sandy Alcantara, Edward Cabrera, Tarik Skubal) as well as in the outfield if a deal with Bellinger or Tucker can’t be done. How far is Cashman willing to swim in the trade waters and who is available?

The longtime GM will keep details close to the vest, but it’s worth asking.