All the talk throughout the 2026 MLB season will finally come to a head. All the noise, speculation, and rumors, all for this moment. With the New York Yankees out of the playoffs, they have nothing left to play for, but will still face critical decisions over the winter. Jazz Chisholm Jr. will be the biggest free-agent drama in The Bronx, but not the only one.
Indeed, the Yankees’ qualifying-offer dilemma with Chisholm Jr. will only get more expensive this offseason, but there may not be a decision to make after all. Especially after the tough note on which the season ended for Jazz and the fanbase, as Chisholm Jr. lectured Yankees fans after being booed in Game 3 of the ALDS. In addition to Chisholm, there are several other players whose contracts are expiring and who will demand a firm decision from the front office.
These are all the position players currently in the Yankees organization with contracts expiring at the end of 2026: Jazz Chisholm Jr., Trent Grisham, Paul Goldschmidt, and Amed Rosario. All of them signed one-year deals coming into the season, though in different situations, and could all be allowed to walk by the Yankees.
Chisholm Jr. and Grisham didn’t meet expectations after signing to avoid arbitration and on a $22 million qualifying-offer deal, respectively. As for Goldschmidt, he’s 39 years old. Even after the early playoff exit, he made it clear he loves competing, but it remains to be seen if New York will have him back next spring.
Trent Grisham #12 of the New York Yankees.
Bullpen free agents
Other big free-agency storylines for the Bronx Bombers revolve around their bullpen. Going into the offseason, the Yankees have all of their starting pitchers locked in at least through 2028. The same can’t be said about their relief options, though.
According to Spotrac, the following pitchers are set to hit free agency: closer David Bednar and relievers John Schreiber, Tim Hill, Ryan Yarbrough, Paul Blackburn, and Michael Fulmer.
Aaron Boone’s future
Make no mistake, Boone isn’t a free agent. For two reasons: the main one is that he’s a manager, and managers don’t go through free agency. Secondly, he’s under contract in The Bronx. The Yankees’ manager is signed through the 2027 MLB campaign. However, he may not be able to play out the full length of his two-year extension signed back in 2025 (club option for the 2027 season).
With the Pinstripers falling short of the end goal—which is always to hoist the World Series trophy—the pressure has only mounted for Boone, and fans are asking for heads to roll. Fans may not light their torches and walk toward Yankee Stadium, but they are making themselves heard, and many want out of the Aaron Boone experience.
The Yankees aren’t obliged to, but it’s all trending toward them having to make a decision on Boone soon. And even if Cam Schlittler took the playoff elimination off Boone’s shoulders, the die may already be cast.
Key takeaways
- Jazz Chisholm Jr., Trent Grisham, Paul Goldschmidt, and Amed Rosario all have expiring contract deals in 2026.
- David Bednar, John Schreiber, Tim Hill, Ryan Yarbrough, Paul Blackburn, and Michael Fulmer are set for free agency.
- Aaron Boone remains under contract with the New York Yankees through the 2027 MLB campaign.
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