Yankees’ captain Aaron Judge takes BP at Seattle
Yankees’ captain Aaron Judge takes BP at Seattle
NEW YORK – As the World Series begins Friday, the Yankees will be plotting how to reach those heights in 2026.
There’s potentially less heavy lifting to do than last winter, when the Yankees heavily pursued their own superstar free agent Juan Soto – only to lose a bidding war against the Mets, necessitating a complete pivot.
That shift led the Yankees to free agents Max Fried and Paul Goldschmidt and the trade for Cody Bellinger, who is the centerpiece to their current winter plans.
Without a reunion with Bellinger, the Yankees’ winter work becomes much more difficult.
When does MLB free agency start?
Eligible players on expiring contracts have begun declaring free agency, but the formal period begins a day after the World Series ends (the trade market re-opens, too).
Teams will have five days to extend (or not) a qualifying offer to their own free agents, with the QO reportedly set at $22 million for the 2026 season.
A player who accepts the QO is under contract at that salary for 2026. Those who reject it become free agents, and any player extended the offer will no longer be subject to a future QO.
Will Trent Grisham be a Yankee in 2026?
Unlike Bellinger (not subject to a QO, having previously received one), Trent Grisham has a good chance of being extended a qualifying offer.
But Grisham has a better chance of receiving a multi-year offer in free agency, though not at that annual average salary. By extending the QO, the Yanks are at least protected and have flexibility.
Should Grisham accept it, the Yanks could trade him or keep him if they lose Bellinger to free agency. If Grisham rejects it, the Yanks receive a form of draft pick compensation by the signing club.
Yankees’ 2025-26 free agent list
In addition to Grisham and Bellinger, fellow outfielder Austin Slater, first baseman Paul Goldschmidt, infielder Amed Rosario and pitchers Luke Weaver, Devin Williams, Paul Blackburn and Ryan Yarbrough are free agents.
Relievers Tim Hill and Jonathan Loaisiga have club options for 2026, with Hill having the better chance of remaining a Yankee. Bellinger has a player option for 2026 but is expected to trigger his $5 million buyout.
Yankees potential 2025 award winners
During the week of Nov. 17, the Baseball Writers’ Association of America will announce its voting results for Manager of the Year, Rookie of the Year, pitching’s Cy Young Award and the MVP in each league.
This could be a very close AL MVP race between Aaron Judge, the reigning MVP, and Seattle Mariners‘ switch-hitting slugging catcher Cal Raleigh, who crushed 60 home runs.
Judge led the league in OPS (1.144), batting average (.331) and runs scored (137), part of an outstanding portfolio that could net him a third career MVP award.
The Yankees’ captain is also an AL finalist for the Hank Aaron Award, honoring the league’s most outstanding hitter, to be presented at MLB’s own awards show Nov. 13.
Max Fried could be among the Top 5 in the Cy Young Award balloting. Before that, Fried is a finalist for a Rawlings Gold Glove Award, to be announced Nov. 2.
Yankees third baseman Ryan McMahon is also among the finalists for a Gold Glove Award at his position, though he’s in the NL category, having played the majority of 2025 with the Colorado Rockies.
When does the baseball General Managers Meetings take place?
In fabulous Las Vegas, Nov. 10-13, at which time the groundwork for trades and free agent acquisitions begins, although the occasionally early offseason swap or signing might occur.
When is MLB’s non-tender deadline?
By Nov. 21, teams must decide whether to tender contracts to arbitration-eligible players.
A non-tendered player becomes a free agent, and the Yankees’ non-tender candidates include right-handed relievers Mark Leiter Jr., Scott Effross and Ian Hamilton.
When do the MLB Winter Meetings begin?
MLB’s annual Winter Meetings take place Dec. 8-10 at Orlando, Fla., at a resort on the Disney World campus.
At this time last year, the Yankees lost Soto and moved quickly to sign Fried in free agency, followed shortly after by the signing of Goldschmidt and the trade for Bellinger.
This year, any drama or mystery about Bellinger’s signing might play out during these meetings (he’s also represented by Scott Boras), which might once again shape the Yankees’ winter course.
Additionally, the Yankees could be seeking to add a veteran starting pitcher, bullpen help and right-handed hitting complementary pieces at catcher and the corner infield spots, on short-term commitments.
Oh, and if there are serious trade talks involving the likes of Tarik Skubal, Paul Skenes or Freddy Peralta, expect the Yanks to be among the inquiring clubs.
Yankees’ potential arbitration cases: Mid-January
Led by Jazz Chisholm Jr., heading into his free agent walk year, the currently Yankees have 14 arbitration-eligible players, about 10 of which could be exchanging salary figures.
During GM Brian Cashman’s era, the Yankees rarely take players to arbitration, though Mark Leiter Jr. was an exception last year (he lost his case vs. the team).
Along with Chisholm, Yankees players in line to file for arbitration include David Bednar, Clarke Schmidt, Fernando Cruz, Anthony Volpe, Camilo Doval, Luis Gil, Jake Cousins, Oswaldo Cabrera and Jose Caballero.
When do Yankees pitchers and catchers report in 2026?
While it’s not yet official, Yankees pitchers and catchers figure to report to spring training at Tampa, Fla., on or about Feb. 10, at Steinbrenner Field.
When is Yankees’ Opening Day?
The 2026 Yankees are scheduled to open with a standalone MLB game at San Francisco against the Giants on Wednesday, March 25, at a yet-to-be-determined time.
After beginning with road series against the Giants and Seattle Mariners, the Yankees return for their home opener at Yankee Stadium on Friday, April 3, against the Miami Marlins.