The 2025 MLB season is fully in the books, the Dodgers repeating as champions and burnishing their case as one of the great dynasties in league history. Though the champagne in the clubhouse has hardly dried, the rest of the league, the Yankees included, has been glancing ahead at the offseason for some time, and we can now turn our attention to the offseason calendar.
Below you’ll find all the important dates for the winter. Stay with us as we chart the course through what will hopefully be another
busy offseason for the Yankees.
November 2nd – Free agents file
Eligible players file for free agency a day after the World Series ends. Teams have a five-day window to negotiate with their internal free agents, to tender qualifying offers— set at $22.02 million for this year —to any of their free agents, and to make decisions on club options.
The Yankees have a long list of free agents, headlined by Devin Williams, Trent Grisham, and Cody Bellinger, who opted of his player option for 2026. Luke Weaver, Amed Rosario, Austin Slater, Paul Goldschmidt, and Ryan Yarbrough will also hit free agency. The team has options on Tim Hill and Jonathan Loaisiga, the former of which is much more likely to be exercised.
November 2nd – Gold Glove winners announced (8:30 p.m. ET on ESPN)
The Yankees only have one Gold Glove finalist, Max Fried at pitcher. Jacob deGrom and Luis Severino are the other finalists. Third baseman Ryan McMahon is also a finalist, but in the National League for his work with the Rockies prior to coming over to the Bronx at the trade deadline. You can find the full list of Gold Glove finalists here.
November 6th – Silver Slugger winners announced (6 p.m. ET on “The Baseball Insiders” YouTube stream
Aaron Judge will pick up his fifth career Silver Slugger Award on this day, while Cody Bellinger, Jazz Chisholm Jr., and Ben Rice are all up for awards as well. Find the full list of Silver Slugger finalists here.
November 7th – Free agency opens
Free agency officially opens five days after the World Series ends, and all decisions regarding options and tendering qualifying offers will have been made. All free agents will be free to negotiate and sign with all 30 teams.
November 10th-13th – GM Meetings in Las Vegas
These serve as a prelude to the far more active winter meetings later on the calendar. It’s always possible we see deals here, but more likely teams will still be laying the groundwork for the rest of their winter.
November 10th – Rookie of the Year Awards announced
November 11th – Manager of the Year Awards announced
November 12th – Cy Young Awards announced
November 13th – MVP Awards announced
The Yankees only have one serious contender for the BBWAA awards, with Aaron Judge the favorite to win his second-consecutive AL MVP and his third in four years. The Yankees don’t have any real candidates for Rookie of the Year after managing two finalists (and the winner, Luis Gil) last year, while Max Fried could be a finalist for Cy Young, though his odds of winning are remote.
November 13th – MLB-affiliated Awards announced
MLB will announce a slew of awards on this day on MLB Network. They’ll unveil the All-MLB first and second teams, along with the Hank Aaron Awards, the Comeback Player of the Year Awards, the Reliever of the Year Awards, the DH of the Year Awards, and Executive of the Year Awards.
November 17th – Hall of Fame to announce 2026 ballot for BBWAA elections
November 18th – Deadline for 1) players to accept or reject qualifying offers, and 2) teams to set rosters in advance of Rule 5 Draft
This is a key date in terms of offseason action, with all players who received qualifying offers needing to accept or reject by 4 p.m. ET. Trent Grisham is the only player with a real chance to be tendered a qualifying offer by the Yankees. Teams also need to place any players they want to protect from the Rule 5 Draft on their 40-man roster by this day. The Yankees will likely add Spencer Jones and Elmer Rodriguez-Cruz to the 40-man, as each would otherwise be eligible to be taken in the Rule 5. Here’s a quick primer on the Rule 5 Draft from MLB.com:
Held each December, the Rule 5 Draft allows clubs without a full 40-man roster to select certain non-40-man roster players from other clubs. Clubs draft in reverse order of the standings from the previous season. Players signed at age 18 or younger need to be added to their club’s 40-Man roster within five seasons or they become eligible for the Rule 5 Draft. Players who signed at age 19 or older need to be protected within four seasons… Rule 5 Draft picks are assigned directly to the drafting club’s 26-man roster and must be placed on outright waivers in order to be removed from the 26-man roster in the subsequent season.
November 18th-20th – MLB Owners Meetings in New York
November 21st – Non-tender deadline
This is the final day teams can decide whether to tender a contract toa player on their 40-man roster. This most typically occurs with arbitration-eligible players a club decides to cut. The Yankees’ most likely non-tender candidates are Jake Cousins, Ian Hamilton, Scott Effross, and Mark Leiter Jr.
December 7th – Hall of Fame to announce Contemporary Baseball Era inductees
December 8th-11th – MLB Winter Meetings in Orlando
The centerpiece of the MLB offseason will take place in Orlando, FL this time around. Last year’s edition saw some serious bombshells: Juan Soto to the Mets, Garrett Crochet to the Red Sox, Max Fried to the Yankees. This season will surely be no different. It’s very possible the Winter Meetings are where free agents like Kyle Tucker and Alex Bregman find homes, not to mention some big-time trade candidates, headlined by AL Cy Young favorite Tarik Skubal.
December 9th – MLB Draft Lottery (5:30pm ET, MLB Network)
December 10th – MLB Rule 5 Draft, and Hall of Fame to announce Ford C. Frick Award winner (John Sterling is a finalist)
The Winter Meetings will feature more than just rumors and signings and trades, as MLB will hold their annual draft lottery, and the Meetings will conclude with the Rule 5 Draft. Tragicomically, the Rockies are ineligible for the lottery this year, as MLB rules prevent teams from receiving lottery picks in three-consecutive seasons. The Yankees are currently slated to pick 25th in the first round of the 2026 MLB Draft.
Once the Winter Meetings close, we’ll have something of a dry period on the calendar, which will be otherwise filled by the various rumors and transactions of the time.
January 15th – 2026 international free agent signing period opens
This is when teams are able to officially sign top international amateur talent. The top IFA last year was Roki Sasaki, who got $6.5 million from the Dodgers. The biggest signing the Yankees made was infielder Mani Cedeno, for $2.5 million.
January 22nd – Hall of Fame to announce any BBWAA ballot inductees
The Yankees again stand to have plenty of former players on the ballot this year. Carlos Beltrán, a Yankee from 2014 to 2016, is poised to be elected after earning 70.3 percent of the vote share last year (75 percent is required for election). Alex Rodriguez (fifth time on the ballot), Andy Pettitte (eighth), and Bobby Abreu (seventh) will also appear, though none is likely to come close to hitting the threshold. There also don’t appear to be any strong first-time candidates, with Cole Hamels probably in possession of the most plausible case.
Mid January – Salary Arbitration figures exchange date
We don’t have an exact date yet, but at some point in January, teams will have to come to agreements with their arbitration-eligible players, or else each side will have to exchange salary figures before going to arbitration. Last year, the Yankees went to arbitration with Mark Leiter Jr. and won. The Yankees’ most prominent arb-eligible players this year will be Jazz Chisholm Jr., David Bednar, Camilo Doval, and Clarke Schmidt.
February 10th (estimate) – Yankees pitchers & catchers report
Pitchers and catchers reported for the Yankees on February 11th this year, so they’ll likely report right around this date in 2026.
March 5th – World Baseball Classic begins (WBC organization is why we don’t know the spring training schedule yet)
The WBC will be held next year, which is why we don’t have more precise spring training dates just yet.
March 17th – World Baseball Classic ends
March 25th – Yankees @ Giants for Opening Day
The Yankees’ 2026 season will start on the road in San Francisco. They’ll play a standalone opening game, broadcast on Netflix on a Wednesday night.
