With the holiday season upon us, baseball executives and agents will be shopping in Orlando, Florida next week.
There, the Winter Meetings officially begin on Monday, though the Sunshine State should start expecting arrivals on Sunday. Last year, the Yankees found out they lost the Juan Soto sweepstakes to the Mets the night before the meetings formally began.
This year, the Yankees are once again trying to retain a Scott Boras-repped outfielder following a successful one-year audition in the Bronx. That would be Cody Bellinger.
However, the Bombers have other wants and needs. With that in mind, here are a few questions facing the club ahead of the Winter Meetings.
WILL BELLINGER RETURN?
Brian Cashman hasn’t been shy about his desire to retain Bellinger, who thrived with the Yankees this past season after being acquired from the Cubs. The general manager has said he would “love” to keep the 30-year-old, who would slot into left, and that the Yankees would be “better served” if that happens. Bellinger, meanwhile, said he was “absolutely” interested in a reunion after the Yankees’ season ended with the ALDS.
However, Bellinger is a fit for other contenders, and he is looking for a lucrative long-term deal after previous trips to free agency yielded prove-it and option-heavy contracts. If the Yankees don’t re-sign Bellinger, it will leave them short an impact bat. Kyle Tucker, a better and younger corner outfielder, is also a free agent, but he will cost more than Bellinger.
Bellinger’s free agency will have an impact on young Yankees outfielders Jasson Domínguez and Spencer Jones. If the veteran stays, either neophyte could become a trade chip. If not, Domínguez and Jones could find themselves in competition this spring.
COULD ROTATION GET A SIGNIFICANT BOOST?
The Yankees have a lot of starting pitchers. However, Gerrit Cole, Clarke Schmidt and Carlos Rodón will all start the season on the injured list, and the first two are coming off Tommy John surgery. Meanwhile, Max Fried, Cam Schlittler and Will Warren are all coming off career-high workloads. Swingman Ryan Yarbrough, recently re-signed, and Luis Gil, make up the rest of the projected Opening Day rotation, assuming more injuries don’t occur during spring training and the early parts of the season.
That’s not a safe assumption. So while the Yankees aren’t necessarily in dire need of a frontline starter, they have more than a few reasons to pursue one.
Japanese free agent Tatsuya Imai is of interest to the Yankees, as is reentry to his home country’s market. However, it remains to be seen just how pricey bidding will get. With Dylan Cease already getting a seven-year, $210 million deal from the Blue Jays, the free agent market for starters is off to an expensive start.
The Yankees may find a trade more palatable; Minnesota’s Joe Ryan and Miami’s Sandy Alcantara are among the names to keep an eye on.
WHO WILL JOIN BULLPEN?
The Yankees already have a closer in David Bednar, so going after someone like Edwin Díaz or Robert Suarez would not be cost-efficient for a team that has generally avoided lofty contracts for relievers.
That said, the Yankees do have some holes in their bullpen with Devin Williams agreeing to a deal with the Mets and Luke Weaver a free agent. Camilo Doval is currently positioned as Bednar’s setup man, and he demonstrated how erratic he can be after being acquired from the Giants last summer.
The Yankees should specifically be looking for velocity and command, two things they lacked last year, for their bullpen. Kyle Finnegan, Brad Keller and Hunter Harvey are intriguing free agent options, but don’t be surprised if the Yankees pursue a trade for relief help. They could also turn to one of their young incumbent starters, such as Warren or Gil, if they add to the rotation.
HOW MUCH ARE YANKEES WILLING TO SPEND?
The answer to this question will color all others, but don’t expect the Yankees to announce their payroll plans for 2026. Hal Steinbrenner recently declined to offer a number, but he did say it would be “ideal” for the team to be under the $319 million it spent last season. However, he immediately acknowledged that that may not happen.
As of Thursday night, the Yankees’ projected competitive balance tax payroll for 2026 sat at $283.6 million, per Cot’s Contracts, putting them a smidge below the second-highest penalty threshold of $284 million.
The highest threshold in 2026 is $304 million. It will be tough for the Yankees to avoid that and field a championship caliber team given the aforementioned holes – they also need to improve their bench – on their roster.
