This story was excerpted from Bryan Hoch’s Yankees Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.
NEW YORK – Early in his press conference addressing the Yankees’ offseason, general manager Brian Cashman likened his club to “a prize fighter getting into the ring,” noting, “You’ve got to be on your ‘A’ game or you’re going to take a punch that’s going to knock you out.”
Sometimes that blow has come one win shy of the World Series. Other times — like this year – it arrived in the early rounds. Either way, that knockout blow has been sending the Yankees to the canvas around this time every fall since their most recent championship in 2009.
If the Yankees are to script a different ending in 2026, they must continue to fine-tune what’s already in place and reinforce weak spots over the next several months. Here are some key questions that will shape the winter:
Which players are free agents?
Eligible Yankees free agents include: RHP Paul Blackburn, 1B Paul Goldschmidt, OF Trent Grisham, IF Amed Rosario, OF Austin Slater, RHP Luke Weaver, RHP Devin Williams and LHP Ryan Yarbrough.
Are any of them likely to receive qualifying offers, and what is the deadline for that?
With the qualifying offer valued this year at $22.025 million, Grisham is the only candidate who might make sense, coming off a career-best performance and set to test free agency in search of a multi-year deal.
The Yankees won’t risk that figure on Weaver or Williams. Bellinger received a qualifying offer from the Cubs in 2024 and is not eligible for it again. Qualifying offers can be made through the fifth day after the World Series, and a player has a week after that to accept.
Which players have options, what’s the dollar figure and impact on payroll and when does it need to be decided upon?
LHP Tim Hill has a $3 million club option for 2026 that the club seems inclined to exercise. RHP Jonathan Loáisiga has a $5 million club option for 2026 that is likely to be declined. The deadline for players and teams to make 2026 option decisions is five days after the end of the World Series.
Who might be a non-tender candidate, and when does the club have to make that decision?
Among those are: RHP Jake Bird, RHP Jake Cousins, RHP Scott Effross, RHP Ian Hamilton, and RHP Mark Leiter, Jr.
The non-tender deadline is Nov. 21. If a club does not tender a contract, the player immediately becomes a free agent.
Who needs to be added to the 40-man roster this winter to avoid the Rule 5 Draft and do they have a crunch for roster spots?
OF Spencer Jones and RHP Elmer Rodriguez-Cruz are both locks to be added to the 40-man roster. RHP Chase Hampton seems to be a strong bet, even as he recovers from Tommy John surgery.
Also likely to be considered are RHP Brendan Beck, RHP Harrison Cohen, RHP Eric Reyzelman and RHP T.J. Rumfield.
The Yankees currently have 44 players on their 40-man roster, including four on the 60-day injured list. They’ll have nine players filing for free agency, including Bellinger. They’ll have to make those calls by Nov. 18.
What kind of help do they need, and will they be active in free agency?
The Yankees’ biggest holes are in the outfield and bullpen, though the rotation is uncertain with Carlos Rodón, Gerrit Cole and Clarke Schmidt all set to begin the year on the injured list. So is shortstop, with Anthony Volpe set to miss the beginning of the year as he recovers from left shoulder surgery.
With Bellinger and Grisham both set to test free agency, they must import at least one outfielder capable of handling a full workload. At present, their outfield would consist of Aaron Judge, Jasson Domínguez and potentially Jones, their No. 4 prospect per MLB Pipeline.
In the infield, their current plan would be to start José Caballero, but they would prefer him in a 10th man/utility role. As for the relief crew, they underperformed in the second half and will have a new look this winter.
David Bednar, Fernando Cruz and Camilo Doval gave them a good start, but Weaver and Williams were both large pieces of the 2025 blueprint and could be elsewhere by Opening Day.
Who might they target?
The general sense is that the Yanks will prioritize retaining Bellinger this offseason, but they’ll have company in the free agency market, coming off a year in which Bellinger hit .272/.334/.480 with 29 homers and 89 RBIs and posted a 4.9 fWAR.
Kyle Tucker’s name figures to be mentioned frequently in media reports, and he’d also be an appealing fit, but there are voices within the organization who prefer Bellinger’s defensive versatility. Bo Bichette headlines the shortstop market, but the Yankees appear committed to continuing with Volpe when healthy.
A serious run at Pete Alonso seems unlikely with Ben Rice seemingly in line to take over as the full-time first baseman, but Edwin Díaz makes sense if the Yankees wanted to check in Queens. They’ll also look overseas: The Yankees have been connected to two Japanese stars — corner infielders Munetaka Murakami and Kazuma Okamoto.
There are many within the organization who’d welcome a reunion with Michael King, who’s expected to decline a $15 million mutual option from the Padres.
Who might they be willing to trade?
Cashman often says no one is untouchable, and so there should be plenty of players in the organization who generate interest this offseason.
Here’s an interesting case: Jazz Chisholm Jr. is coming off a season in which he hit 31 homers and stole 31 bases, just the third Yankee to have a 30/30 year (joining Bobby Bonds and Alfonso Soriano, the latter of whom did it twice).
Chisholm is going into his third arbitration year and is eligible for free agency after 2026; thus far, the Yankees haven’t given any signals about a potential extension. Do they see him as their second baseman of the future — and if not, could they move him?
There’s a similar question about Domínguez, who was relegated to a bench role in the second half. Are the Yankees ready to commit to him as an everyday starter, and if not, are they stunting his development?
