The Yankees’ winter began far sooner than the organization anticipated, jettisoned into the offseason Oct. 8 after a Game 4 loss to the Blue Jays in the American League Division Series.
There have been a few moves made when it comes to building the roster for 2026, 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’s promises to be no different.
Five questions facing the Yankees as the winter meetings are 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 during his one season in pinstripes in 2025, is his top priority, and much of how the rest of the winter plays out for the Yankees will depend on Bellinger’s decision. For years, it was an article of faith in the game that any player the Yankees targeted inevitably would end up wearing their uniform because of their financial muscle. But those days, as other big-spending teams like 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 as three members expected to be significant parts of it – Gerrit Cole, Carlos Rodon and Clarke Schmidt – will begin 2026 on the injured list. Cole and Rodon could be back as soon as May with Schmidt, who underwent Tommy John surgery last July, expected back far deeper into the season. But those are all best-case scenarios if the trio’s respective 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, a group that includes 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 like 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, by the end of last season had faded mostly into the background, consistent playing time in the second half especially simply 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 who 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 doesn’t turn 23 until Feb. 7. But not so high 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 Brian Cashman operating under?
This, really, is the question of the highest significance and one 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 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 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 hover over the Yankees not only for these winter meetings begin but for the rest of the offseason.
Erik Boland started in Newsday’s sports department in 2002. He covered high school and college sports, then shifted to the Jets beat. He has covered the Yankees since 2009.