The Yankees and the 2025-26 Offseason Calendar

The Dodgers are World Series champions and the 1998-2000 Yankees are no longer the last team to repeat as baseball's title winners. It was a good run. The World Series is over and the offseason has already begun, and several important dates are on the horizon. Here is the 2025-26 MLB offseason calendar and what each date means for the Yankees.

Today, Nov. 2nd: Players become free agents, trading resumes

Eligible players (6+ years of service time) became free agents at 9am ET this morning. Eight Yankees became free agents today: Paul Blackburn, Paul Goldschmidt, Trent Grisham, Amed Rosario, Austin Slater, Luke Weaver, Devin Williams, and Ryan Yarbrough. Also, trades involving 40-man roster players resume today. Those get put on hold after the trade deadline each summer.

Sunday, Nov. 2nd: Gold Glove winners announced

There will be an ESPN broadcast at 8:30pm ET. Max Fried is the Yankees’ only Gold Glove finalist unless you count Ryan McMahon, who’s up for one in the NL. No Yankees won a Gold Glove last year, ending a little two-year streak with winners (Anthony Volpe in 2023 and DJ LeMahieu and Jose Trevino in 2022).

Thursday, Nov. 6th: Free agency, contract options, qualifying offers, 60-day IL activation

The fifth day after the end of the World Series is a busy one. Here’s what happens that day, in no particular order.

Contract options: Most contract option decisions are due five days after the end of the World Series. Some contracts specify a different date (the Yankees had to decide on Zack Britton’s 2022 club option after the 2020 World Series, for example), but most are due on this date. The Yankees have three contract options this offseason:

• Cody Bellinger: $25M player option ($5M buyout) (Cubs pay $2.5M either way)

• Jonathan Loáisiga: $5M club option (no buyout)

• Tim Hill: $3M club option ($350,000 buyout)

Loáisiga is an easy no. The Yankees love the guy and it would not surprise me if they bring him back, but it won’t be for $5M. Hill could go either way. The buyout makes it a $2.65M decision and that’s nothing. If it doesn’t work out, you can cut him and move on. Hill’s platoon split is becoming very pronounced, but he did hold lefties to a .181/.224/.220 (.198 wOBA) line with 66.7 GB% in 2025. There’s room in the bullpen for that guy. I think the Yankees will pick up the option, but we’ll see.

Bellinger will reportedly decline his option. The buyout makes it a $20M decision for him and he’s in position to land (much) more than that as a free agent, even if it’s a lower annual salary with more total dollars over however many years. This offseason might be his last chance at a big contract. Bellinger was so good and fit so well this season, though I don’t see him as an absolute must re-sign. There’s definitely a price point where I walk away.

Qualifying offers: The qualifying offer is worth a record $22.025M this offseason and the deadline to tender it is 5pm ET on this date. Bellinger is not eligible for a QO because he received it a few years ago. The only question is Grisham. I think he’s worth a one-year, $22.025M dice roll in 2026. Do the Yankees? They would only receive a compensation 2026 draft pick after the fourth round if he leaves given their luxury tax status. With non-elite free agents (Jameson Taillon, Gleyber Torres, etc.), the Yankees have preferred payroll flexibility (i.e. the player not unexpectedly accepting the QO) to the compensation pick the last few years. None of the other free agents will get a QO. Hi Lev Dev would have with a typical Devin Williams season, which he did not have.

Free agency begins: The exclusive five-day negotiating period ends and free agents become truly free to negotiate and sign with any team as of 5pm ET. Edwin Díaz three years ago is by far the most significant free agent to re-sign during the exclusive negotiating period. It very rarely happens. Once a player gets this close to free agency, he tests the market. I wouldn’t hold my breath waiting for a Bellinger extension these next five days (he’s a Scott Boras client, remember). In the big picture, this isn’t the NFL or NHL, where there are a rush of signings on Day 1. MLB free agency is a marathon, not a sprint.

60-day injured list activation: Players must be activated off the 60-day IL by this date (I think there should be a 60-day IL in the offseason, but there’s not). The Yankees have four players on the 60-day IL at the moment: Oswaldo Cabrera, Gerrit Cole, Jake Cousins, and Clarke Schmidt. The eight free agents mean the Yankees will have plenty of 40-man roster space to fit Cabrera, Cole, Cousins, and Schmidt upon their activation.

Sometime soon (?): Awards finalists announced

The date the BBWAA’s awards finalists will be announced has not yet been revealed, which I don’t get, but whatever. It’s usually the Monday before awards week, which would be this coming Monday, Nov. 3rd. I don’t know for certain they’re coming that day though. Anyway, it’s three finalists for each of the major awards, though it’s really just the top three vote-getters. There’s no second phase of the voting that makes these guys “finalists.” Aaron Judge will be an MVP finalist, Aaron Boone will maaaaybe be a Manager of the Year finalist, and that’s it. No other Yankees figure to be a finalist for a major award.

Nov. 6-7: Silver Sluggers announced

Apparently the Silver Slugger announcement is a two-day event now. Seems unnecessary. It will be the NL on Thursday, Nov. 6th, then the AL the next day. Judge will win another Silver Slugger and Jazz Chisholm Jr. should win one too. Bellinger and Ben Rice are also finalists, as are the Yankees for the team Silver Slugger. They won it last year.

Nov. 10-13: Awards week 

It’s Rookies of the Year on Monday, Managers of the Year on Tuesday, Cy Youngs on Wednesday, and MVPs on Thursday. Judge vs. Cal Raleigh figures to be the closest AL MVP finish since Mike Trout (355 points) beat out Alex Bregman (335 points) for the 2019 award. The awards will be announced during a live MLB Network broadcast each day. A few secondary non-BBWAA awards are scheduled for Thursday too (All-MLB Team, Comeback Players of the Year, Relievers of the Year, etc.).

Nov. 11-13: GM Meetings in Las Vegas

There’s been an uptick in hot stove chatter and transactions at the GM Meetings the last few years. The Yankees made the Taylor Trammell for cash trade with the Astros at the GM Meetings last year. The JR Murphy for Aaron Hicks trade went down at the 2015 GM Meetings. The groundwork for the three-team Curtis Granderson/Ian Kennedy/Max Scherzer trade was laid at the 2009 GM Meetings, then the deal was completed a few weeks later. There are usually a lot of waiver claims these few days as the teams clean up their 40-man roster early in the offseason.

Tuesday, Nov. 18th: Qualifying offer decisions and Rule 5 Draft protection

Free agents have until 4pm ET on this date to accept or reject the QO. If Grisham gets it, he could take it, though I’m not sure he’ll ever have a better chance for a multi-year payday. He was great this year, but I can’t say I expect 34-homer seasons to be the norm. More than anything, this is the date the Yankees will learn which free agents they will have to surrender draft picks and international bonus pool money to sign.

Also, this is the Rule 5 Draft protection deadline (also 4pm ET). Here are the notable Yankees’ minor leaguers eligible for the Rule 5 Draft this offseason. There are a few of their best prospects here:

• Catchers: Manuel Palencia

• Infielders: T.J. Rumfield

• Outfielders: Jace Avina, Spencer Jones

• Righties: Brendan Beck, Chase Hampton, Eric Reyzelman, Elmer Rodriguez-Cruz

• Lefties: Henry Lalane, Allen Facundo, Brock Selvidge

Jones and ERC are locks to be added to the 40-man roster, and I think Hampton is too. He’s thrown 18.2 innings the last two years due to injury and won’t return from Tommy John surgery until the middle of next season, but the stuff was so good before the injuries. Lesser pitching prospects have been Rule 5ed and stashed on the 60-day IL while they rehab. Unless he had a setback we don’t know about, Hampton will be protected.

Selvidge could go either way. He finished the summer healthy and effective with Double-A Somerset. You don’t have to try hard to see a team Rule 5ing him and rostering him in their bullpen. I think Selvidge gets protected. Reyzelman had a bad year and didn’t pitch after Aug. 3rd due to injury. His stuff was down too. I’m not really sure what to make of him at this point. He’s a good relief prospect when he’s right, not a special relief prospect, and I wouldn’t jam my 40-man roster up with a guy like that.

Lalane has thrown 53.2 innings the last three years and hasn’t been healthy the last two years. It’s all shoulder trouble too. The guy’s thrown 18.1 innings above rookie ball. Good prospect when healthy, which isn’t often. There’s just no way Lalane sticks on a big league roster next year. Seems like an easy decision to leave him unprotected, but what do I know. Beck will have some MLB utility. I could see him throwing 100 innings for the Athletics or White Sox in 2026. Avina, Palencia, and Rumfield are just okay prospects.

I should note there are always a bunch of small trades at the Rule 5 Draft protection deadline as teams get their 40-man in order. The Jose Siri trade went down at the Rule 5 Draft protection deadline last offseason, for example. Maybe the Yankees will make one of these small moves this winter.

Nov. 18-20: Owners meetings in New York

The quarterly owners meetings are a bunch of rich guys talking about ways to get richer. The CBA expires next offseason and negotiations with the MLBPA will begin soon. I assume this month's owners meetings will be one of their final strategy sessions. As far as I know, there is no significant imminent business on the docket this month now that the Rays’ sale is complete. Nothing to vote on, etc.

Hal Steinbrenner used to give his “we’re committed to winning a championship/I don’t think you need a [current Yankees’ payroll] payroll to win the World Series” speech at the owners meetings, but the only non-YES interview he’s done in well over a year was the press conference when the Yankees dropped the facial hair policy in February. Probably for the best Hal doesn’t talk much publicly anymore. 

Friday, Nov. 21st: Non-tender deadline

Teams don’t have to sign their pre-arbitration and arbitration-eligible players to 2026 contracts by this date, but they must make an offer. The non-tender deadline used to be Dec. 2nd every offseason, then a few years ago MLB and the MLBPA agreed to move it up to the Friday before Thanksgiving, giving non-tendered players a little more time to find a job. I count eight non-tender candidates:

• Catchers: none

• Infielders: Braden Shewmake, Jorbit Vivas

• Outfielders: none

• Righties: Michael Arias, Jake Cousins, Scott Effross, Ian Hamilton, Mark Leiter Jr.

• Lefties: Allan Winans

Leiter is projected for $3M through arbitration, a somewhat pricey sum for a soon-to-be 35-year-old middle reliever who has a 4.89 ERA (4.07 FIP) as a Yankee and wasn’t on the ALDS roster. Everyone else listed above is a non-tender candidate for 40-man roster management reasons, not salary reasons. Hamilton, Shewmake, Vivas, and Winans are all out of options now (and could be DFAed before this date).

Cousins had Tommy John surgery in June and that will wipe out most or all of his 2026. Guys like him, the significantly injured 31-year-old journeyman middle reliever, are difficult to carry on the 40-man all winter. A non-tender get a player off the 40-man without exposing him to waivers. The Yankees could non-tender Arias, Cousins, Vivas, et al, then try to re-sign them to a minor league contract. They did that with Domingo Germán once upon a time.

Mid-to-late November: Hall of Fame ballot released

Here are the players eligible for the 2026 Hall of Fame ballot. This is not the day the voting results are announced. This is the day the ballot itself will be revealed. The screening committee goes through the first time eligible players and picks who will appear on the ballot, then announces it to the public. Manny Ramirez is the only player entering his tenth and final year on the ballot.

No slam dunk first ballot Hall of Famer joins the ballot this year. The best newcomer will be Cole Hamels. Carlos Beltrán’s voting percentage has crept up from 46.5% to 57.1% to 70.3% in his three years on the ballot. You need 75% for induction, and, historically, once you get to 70%, you get in. Beltrán has seven more years to go on the ballot. He’ll get in eventually, if not this year. Andruw Jones looks like the only other player on the BBWAA’s ballot with a chance to get in this winter (66.3% last year).

Andy Pettitte (eighth year on the ballot) and Alex Rodriguez (fifth) are the two most prominent Yankees up for induction this voting cycle. Jones (ninth), Bobby Abreu (seventh), and Beltrán (fourth) are the only other players with Yankees ties who will be on the ballot this winter. (The date the ballot is released has varied over the years and I haven’t been able to track it down.)

Early December: Competitive balance draft picks awarded

These are the extra draft picks given to teams in the bottom 10 in revenue and market size (there’s overlap between the two groups, so there are 14-15 of these picks, not 20). The Yankees do not get one of these picks (duh), though I note this because competitive balance picks are the only tradeable draft picks. Only once have the Yankees traded for a draft pick. They received the No. 38 pick in the Sonny Gray deal with the Reds and used it on lefty T.J. Sikkema, who they sent to the Royals in the Andrew Benintendi trade. Sikkema is now with the Reds, bringing things full circle. These picks are announced sometime during the week before the Winter Meetings.

Sunday, Dec. 7th: Hall of Fame’s Contemporary Baseball Era Committee voting results announced

The Hall of Fame split the Veterans Committee into several Eras Committees years ago and this winter the Contemporary Baseball Era Committee will meet. The 16-person committee will consider “players who made their greatest impact on the game since 1980.” The eight-person ballot will be revealed sometime in November and could include someone relevant to the Yankees (Don Mattingly?).

Dec. 7-10: Winter Meetings in Orlando

The Winter Meetings are the busiest few days of the offseason. The biggest signings and trades tend to happen at the Winter Meetings, plus there’s an endless supply of rumors. The Yankees have made their most significant offseason transactions at the Winter Meetings the last few years. Last year they traded for Bellinger and signed Max Fried at the Winter Meetings. The year before was the Juan Soto trade. The year before that was re-signing Judge. Go back a ways and the Yankees signed Cole and CC Sabathia at the Winter Meetings. Odds are their biggest offseason move(s) will happen during this week.

Tuesday, Dec. 9th: Draft lottery

Irrelevant to the Yankees this offseason but I’m including it for the sake of completeness. Only non-postseason teams are eligible for the lottery, which determines the top six picks. Picks 1-6 are lottery picks, picks 7-18 are the remaining 12 non-postseason teams in reverse order of the standings, and picks 19-30 are postseason teams in order of their finish. The Yankees are locked into the No. 35 pick. Here are the lottery odds, if you’re curious.

Wednesday, Dec. 10th: Rule 5 Draft

Last offseason was the first time the Yankees did not lose a player in the Rule 5 Draft since the 2014-15 offseason. Was that a one-off, or the start of a new trend? My guess is the former and the Yankees will have a player(s) taken this year. The Yankees haven’t made a Rule 5 Draft pick of their own since Cesar Cabral and Brad Meyer in 2011, though Erik Boland reported they “probably” would’ve taken righty Evan Reifert had he gotten to their pick last year. Reifert walked 12 batters in 6.1 Grapefruit League innings with the Nationals and was returned to the Rays in mid-March. His Triple-A season was uneventful. The smart bet is on the Yankees not making a Rule 5 selection this offseason.

Monday, Dec. 15th: 2025 international signing period closes

At 5pm ET, specifically. I have no idea how much bonus pool space the Yankees have remaining, though they added some in the Oswald Peraza trade at the deadline. There has been a trend the last few years of teams trading for pool money in the closing days of the signing period, and using it to sign players they were expected to sign when the next year’s signing period opens in January.

The Yankees did exactly that last year. They picked up bonus pool money in the Carlos Narváez/Elmer Rodriguez-Cruz trade with the Red Sox, and used it to sign shortstop Stiven Marinez ($1.65M bonus). The Yankees were going to sign Marinez one way or the other, but getting that extra pool money in December allowed them to sign Marinez as part of their 2024 international class, freeing up $1.65M for the 2025 signing period. Perhaps the Yankees have another move like that in the works this winter.

Friday, Jan. 9th: Arbitration filing day

The deadline for teams and their arb-eligible players to file salary figures for next season is 8pm ET with a soft 1pm ET deadline for contract agreements. The player files what he believes he should be paid and the team files what they believe he should be paid. This is just the filing deadline and the two sides can still work out a contract of any size after this date. The vast majority of arb-eligible players sign before this deadline. The Yankees have 14 arb-eligible players this winter. Here are their projected salaries.

Thursday, Jan. 15th: 2026 international signing period opens

The Yankees have a $5.44M bonus pool for next year’s signing period, per Jesse Borek. They can trade for an additional 60%, so they can max out at $8.704M. I’ll have more on the prospects the Yankees are expected to sign in the coming weeks. I can tell you they are expected to sign shortstop Wandy Asigen, MLB Pipeline’s No. 2 prospect. The signing period opens at 9am ET.

Tuesday, Jan. 20th: 2026 Hall of Fame class announced

Again, Beltrán and Jones look like the only players with a chance to get voted in by the BBWAA this year. Depending what happens with them, the rest of the BBWAA’s ballot, and the Contemporary Baseball Era Committee, there’s a chance of a zero-person induction class next year. (Or at least the best chance of one since the empty 2021 class.) I would not count on Pettitte (27.9% last year) or A-Rod (37.1%) getting in this year or ever. Their voting trajectories are not close to approaching 75%.

Monday, Jan. 26th to Friday, Feb. 20th: Arbitration hearings

If the team and an arb-eligible player can’t agree to a contract, they’ll argue their cases in front of a three-person panel, and the panel will pick either the salary the player filed or the salary the team filed back on Jan. 9th. Nothing in between. The two sides can still negotiate a contract up until a hearing, and heck, they can even rip up the panel’s ruling and agree to a new contract after a hearing, though I can't remember that ever happening.

The Yankees beat Leiter in an arbitration hearing last offseason. It was their first hearing since beating Dellin Betances in 2017. Before that, their last hearing was beating Chien-Ming Wang in 2008. The Yankees and Judge were so close to a hearing three years ago that Judge said he was logged into the Zoom call when they got his one-year contract for 2022 done. Some teams are very antagonistic toward their players and go to a lot of hearings (see: Rays). The Yankees are not one of them. Leiter last year was not the norm.

Mid-February: Spring Training begins

Next year is a World Baseball Classic year. Players participating in the WBC will have an earlier reporting date than everyone else. Judge is captaining Team USA and Chisholm is expected to play for Great Britain. Those are the only WBC-bound Yankees we know about right now, but there will be others. Here is the WBC bracket and schedule (full-size version):

As for Spring Training, MLB still hasn’t released the Cactus and Grapefruit League schedules for some reason. Usually we get them in August. The regular season schedule was late this year and so is the Spring Training schedule. MLB be slackin’. Figure pitchers and catchers will report the week of Feb. 9th and the Yankees will play their first Grapefruit League game on or around Friday, Feb. 24th.

Wednesday, March 25th: Opening Day!

Or, rather, Opening Night. The Yankees begin next season in San Francisco and they are the only game on the schedule that day. It’s a Netflix exclusive too. The rest of the league begins their seasons the next day. The home opener is Friday, April 3rd, against the Marlins. The Marlins? The Marlins. Here is the 2026 schedule.