With Major League Baseball just days removed from a thrilling end to the World Series, the offseason is already in motion.
On Sunday, 137 players officially became free agents, thus beginning a five-day window to exclusively negotiate with the team they ended the 2025 season with. Eight Yankees were part of that pool: Paul Blackburn, Paul Goldschmidt, Trent Grisham, Amed Rosario, Austin Slater, Luke Weaver, Devin Williams and Ryan Yarbrough.
A few more Yankees could join that group, as Cody Bellinger is expected to decline his $25 million player option. The Yankees also have a $5 million club option for Jonathan Loáisiga that they are sure to decline, though they are expected to pick up Tim Hill’s $3 million club option.
Of course, the Yankees will have to add some external pieces if they want to dethrone the Blue Jays in the American League East and contend with a Dodgers squad that has won back-to-back championships. With that in mind, let’s take a look at what awaits the Yankees this offseason.
Nov. 6: Five Days Removed From The World Series
Thursday at 5 p.m. ET is the deadline for teams and players to make decisions on options; reinstate players on the 60-day injured list; and to tender qualifying offers. Once the clock strikes 5 p.m., major league free agents can sign with any club.
Outfielder Kyle Tucker is the top free agent on the market and is someone the Yankees should pursue seriously, but the expectation is that the team will instead prioritize the cheaper Bellinger after he opts out. In addition to the outfield, the Yankees also need to address their bullpen. Adding another starter – trading for someone like Freddy Peralta, Joe Ryan or Sandy Alcantara seems feasible – and a right-handed bench bat who can play third and first would help, too.
Once Bellinger opts out of his contract, the Yankees will have a projected payroll of $253.9 million for 2026 before making any moves, per Cot’s Contracts. That would put them over the first luxury tax threshold of $244 million. The other thresholds are set at $264 million, $284 million and $304 million for 2026.
In addition to the Bellinger, Loáisiga and Hill options, the Yankees will have to decide if they want to give Trent Grisham the one-year, $22.025 million qualifying offer by Nov. 6. If they do, he has until Nov. 18 to accept or reject it.
It’s a fascinating decision for both sides, as Grisham is coming off a career year at the plate, belting 34 homers with a 129 wRC+. After never coming close to such production previously, cashing in on a long-term deal would be his ideal outcome. However, his .191 average, .651 OPS and 87 wRC+ from 2022-2024 could ward off potential suitors, even if his offensive metrics suggest he can remain a force at the plate. So could his declining defensive metrics in center field, which signal a future shift to the corners.
Teams must forfeit a draft pick when they sign external free agents who received a qualifying offer – the Yankees would get a compensatory 2026 pick after the fourth round for Grisham – so that will also work against the 29-year-old.
If Grisham were to accept the qualifying offer, he’d be getting a significant raise to stay in a city he’s enjoyed. The Yankees, meanwhile, would pay a high but short-term price to retain their center fielder without having to rush top prospect Spencer Jones. But with Bellinger a focus and some concerns surrounding Grisham, it’s unlikely the Yankees extend a long-term offer to the latter.
As for reinstating players to the 40-man roster, four Yankees ended the year on the 60-day injured list: Gerrit Cole, Clarke Schmidt, Oswaldo Cabrera and Jake Cousins.
Nov. 10-13: General Managers Meetings
Brian Cashman and others in charge of their teams’ baseball operations will gather for a few days in Las Vegas. American League GMs are scheduled to speak on Nov. 12.
Nov. 13: Will Aaron Judge Win His Third MVP?
The MVP Awards will be announced next week. In the AL, Aaron Judge is looking for his second straight MVP and third overall. However, he could face stiff competition from Mariners catcher Cal Raleigh, who became the first backstop to hit 60 home runs as Seattle won its first AL West title since 2001.
Judge leads Raleigh in most offensive categories, but some voters will add weight to the latter’s case because so much goes into being a big league catcher. How many choose to do that will determine who wins the award.
Nov. 18: 40-Man Roster Protections
In addition to Nov. 18 being the deadline for qualifying offer decisions, teams must add eligible prospects to their 40-man roster by 6 p.m. if they want to protect them from the Rule 5 Draft in December.
The Yankees have two Rule 5 eligible players who are sure to be added: Jones and Elmer Rodriguez-Cruz. There’s a good chance the top-100 prospects impact the team in 2026.
Other notable Rule 5 eligible prospects include pitchers Brendan Beck, Chase Hampton, Brock Selvidge, Allen Facundo, Henry Lalane, Eric Reyzelman and Harrison Cohen, catcher Manuel Palencia, first baseman T.J. Rumfield and outfielder Jace Avina.
Nov. 18-20: Owners Meetings
With MLB facing an uncertain labor future – the Collective Bargaining Agreement expires after the 2026 season – owners will meet in New York City. Yankees owner Hal Steinbrenner hasn’t spoken to reporters in a group setting since the team lifted its longstanding beard ban in spring training.
Nov. 21: Tender Deadline
The Yankees have 14 arbitration eligible players, including Jazz Chisholm Jr., David Bednar and Anthony Volpe. Most will be tendered a contract. Those who are not will become free agents.
The Yankees have a few non-tender candidates in relievers Cousins, Mark Leiter Jr., Scott Effross and Ian Hamilton.
Dec. 7: Hall of Fame Announcement
Results from the Hall of Fame’s Contemporary Baseball Era Committee ballot will be announced following votes from a 16-person panel.
Committee candidates for 2026 – which are different from the candidates that the Baseball Writers’ Association of America votes on – include former Yankees Don Mattingly, Roger Clemens and Gary Sheffield. Barry Bonds, Carlos Delgado, Jeff Kent, Dale Murphy and Fernando Valenzuela are also on the ballot.
Dec. 8-11: Winter Meetings
The entire baseball world will head to Orlando, Florida as the Hot Stove heats up. Don’t be surprised if Tucker, Bellinger and a slew of other free agents sign by the end of the meetings.
The MLB Draft lottery for the June amateur draft is Dec. 9. The Rule 5 Draft is set for Dec. 10.
Jan 8: Deadline To Agree With Arbitration Eligible Players
This is the final day for teams and arbitration eligible players to reach a one-year contract. If an agreement can’t be reached, the two sides then exchange desired salary figures and schedule an arbitration hearing for February.
Last winter, Leiter became the first Yankee since Dellin Betances in 2017 to go to arbitration. He lost and made $2.05 million after filing at $2.5 million.
February: Spring Training
Neither MLB nor the Yankees have released spring training schedules, but pitchers and catchers will likely report sometime during the second week of February. Position players will arrive soon after, followed by the start of exhibition games and the World Baseball Classic.
The Yankees will open the 2026 season in San Francisco on March 25.
