5 questions facing the Yankees heading into the winter meetings

The Yankees’ winter began far sooner than the organization anticipated, as they were jettisoned into the offseason Oct. 8 after a Game 4 loss to the Blue Jays in their American League Division Series.

They have made a few moves when it comes to building the 2026 roster, but the true heavy lifting hasn’t yet begun in earnest in constructing next year’s club, one longtime general manager Brian Cashman hopes can net the franchise its first World Series title since 2009.

But the winter meetings — where some of the sport’s biggest moves annually occur — beckon, and this year promises to be no different.

Five questions facing the Yankees with the winter meetings set to begin Sunday in Orlando:

1. Does Cody Bellinger land back in the Bronx?

Cashman hasn’t disputed that bringing back the outfielder, a standout offensively and defensively in 2025, is his top priority, and much of how the rest of the offseason plays out for the Yankees will depend on Bellinger’s decision. For years, it was an article of faith in the game that because of their financial muscle, any player the Yankees targeted inevitably would end up wearing their uniform. But those days, as other big-spending teams such as the Dodgers, Mets and Phillies have emerged, are increasingly in the rearview mirror.

2. How aggressive will the Yankees be in pursuing a rotation piece?

During last month’s general managers' meetings, Cashman expressed appropriate concern regarding his rotation. Three members expected to be significant parts of the rotation — Gerrit Cole, Carlos Rodon and Clarke Schmidt — will begin 2026 on the injured list. Cole and Rodon could be back as soon as May and Schmidt, who underwent Tommy John surgery last July, is expected back far later in the season. But those are all best-case scenarios if the trio’s  rehabs continue without any setbacks, something that is far from guaranteed when it comes to pitchers working their way back from surgery.

3. How much of a priority is the bullpen?

The Yankees appear set at closer with David Bednar, who starred after coming over from the Pirates at the trade deadline, and seem to have a solid collection of arms in front of him: Fernando Cruz, Tim Hill, Camilo Doval and swingman Ryan Yarbrough. But as Cashman acknowledged last month: “We have some quality down there that we need to improve on.” The question is how much the Yankees are willing to spend for those improvements. While many are clamoring for a splashy signing such as Edwin Diaz — especially after the Mets signed Devin Williams earlier this week — recent history says that’s unlikely. Other than signing Aroldis Chapman to a five-year, $86 million deal in December 2016, the Yankees typically don’t spend big on the free-agent reliever market.

4. Could Jasson Dominguez be used as a trade chip?

Dominguez, among the organization’s most hyped prospects of the last quarter-century, faded mostly into the background by the end of last season. Consistent playing time, in the second half especially, simply was not in the cards. Much of that had to do with the consistent production of Bellinger, centerfielder Trent Grisham and, of course, Aaron Judge. Grisham will be back after accepting the $22.025 million qualifying offer, which further complicates the immediate future of Dominguez, who came up through the system primarily as a centerfielder and struggled most of last season in trying to learn leftfield at the major league level. Dominguez is playing winter ball in the Dominican Republic — seeing plenty of time in left — and the Yankees remain high on the good-natured, hard-working outfielder, who won't turn 23 until Feb. 7. But not so high that they wouldn’t dangle him as a trade chip to address some of their significant roster needs, particularly if owner Hal Steinbrenner pulls the reins on spending.

5. What kind of budget is Cashman operating under?

This, really, is the question of the highest significance, one that only Steinbrenner can truly answer. During a Zoom news conference early last week that publicly played to worse reviews than Hulu’s All’s Fair, Steinbrenner said it would be “ideal” if he could bring the payroll under the $319 million it was last season. But he quickly added “that doesn’t mean it’s going to happen.” With 2026 payroll commitments already well north of $200 million and the roster holes what they are, it’s difficult to envision that payroll not surpassing $300 million for a third straight year. Then again, as Cashman recently said: “There’s certain salary levels we’ll tag out at.” What those are when it comes to free agents will hover over the Yankees not only for these winter meetings but for the rest of the offseason.