The Yankees and the 2024-25 Offseason Calendar

The Dodgers are the 2024 World Series champions, the Yankees are the 2024 World Series losers, and the 2024-25 offseason is here. It’s an important offseason for the Yankees. I say that every offseason, but it’s true, and this offseason is more important than most given who’s becoming a free agent. The Yankees have no time to sit around and feel sorry for themselves. Important dates are right around the corner. Here is the 2024-25 MLB offseason calendar and what each date means for the Yankees.

Today, Oct. 31st: Players become free agents, trading resumes

Eligible players (6+ years of service time) became free agents at 9am ET this morning. MLB used to make players file for free agency, which was a waste of time, so now they automatically become free agents the day after the World Series. Seven Yankees became free agents today: Tim Hill, Clay Holmes, Tommy Kahnle, Jonathan Loáisiga, Juan Soto, Gleyber Torres, and Alex Verdugo. Also, trades involving 40-man roster players can resume today. Those get put on hold after the trade deadline each summer.

Sunday, Nov. 3rd: Gold Glove winners announced

There will be an ESPN broadcast at 8:30pm ET. Soto, Verdugo, and Anthony Volpe are the Yankees’ Gold Glove finalists. Soto, eh? I love the guy and hope he’s a Yankee forever, but a Gold Glove caliber defender he is not. Anyway, Volpe won a Gold Glove last season. DJ LeMahieu and Jose Trevino won Gold Gloves the year before. The Yankees have not had Gold Glovers in three consecutive seasons since 2008 (Mike Mussina), 2009 (Derek Jeter and Mark Teixeira), and 2010 (Jeter, Teixeira, and Robbie Canó). They have three chances to make it happen this year.

Monday, Nov. 4th: Free agency, contract options, qualifying offers, 60-day IL activation

The fifth day after the end of the World Series is always a busy one. Here’s what happens on 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 four contract options this offseason:

• Gerrit Cole: Can opt out of final four years and $144M (Yankees can void the opt out adding one year and $36M to his contract)

• Anthony Rizzo: $17M club option ($6M buyout)

• Lou Trivino: $5M club option (no buyout)

• Luke Weaver: $2.5M club option (no buyout)

Weaver is an easy yes, Trivino an easy no. Rizzo should be an easy no, but who knows with this team. I expect Cole to use his opt out and the Yankees to add the tenth year to his contract to void it. You can make a very good argument that letting Cole walk is the right move given his age (34), the decline in whiffs, and the injury issues that began to pop up this season. Monday is decision day.

Qualifying offers: The qualifying offer is worth a record $21.05M this offseason, per Kiley McDaniel, and the deadline to tender it is 5pm ET. Soto is the only lock to get the qualifying offer. Torres is at best a maybe, and Holmes and Verdugo (and Kahnle and Loáisiga) are a no. Because he has received the qualifying offer previously, Cole can not get it again in the event the Yankees decide to let him hit the market.

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 two years ago is by far the most significant free agent to re-sign with his team during the exclusive negotiating period. It very rarely happens. Once a player gets this close to free agency, they test the market. I wouldn’t hold my breath waiting for news about a Soto extension these next five days. In the big picture, this isn’t the NFL or NHL, where there are a rash 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 somehow have only three players on the 60-day IL at the moment: Loáisiga, Trivino, and JT Brubaker. Loáisiga’s a free agent and Trivino will be once the Yankees decline his option. All the free agents mean the Yankees will have plenty of 40-man roster space to fit Brubaker.

Nov. 4-7: GM Meetings in San Antonio

The GM Meetings typically cover off-the-field matters (rule changes, etc.), though there has been an uptick in hot stove chatter and transactions in recent years. When you put each team’s top baseball operations executive in one place, deals get discussed, if not completed. The Yankees made the Aaron Hicks trade at the GM Meetings in 2015. The groundwork for the three-team Curtis Granderson/Ian Kennedy/Max Scherzer trade was laid at the 2009 GM Meetings, then was completed a few weeks later.

Monday, Nov. 11th: Awards finalists announced

Are they really “finalists” if there’s no second vote? Or are they just the top three vote-getters? Whatever. Aaron Judge will be an MVP finalist, and Luis Gil and/or Austin Wells could be a Rookie of the Year finalist. Otherwise that’s it. No other Yankees figure to be finalists for a major award.

Tuesday, Nov. 12th: Silver Sluggers announced

The Silver Slugger finalists will be announced Monday, Nov. 4th. Judge and Soto will win Silver Sluggers, and the Yankees could take home the team Silver Slugger too. Wells has an outside chance behind the plate, but only an outside chance. The slow start and September slump likely killed he won't win it. I assume Sal Perez or Cal Raleigh will get the catcher award.

Monday, Nov. 18th: Hall of Fame ballot released

Here are the players eligible for the 2025 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. Billy Wagner is the only player entering his tenth and final year on the ballot.

A notable former Yankee joins the Hall of Fame ballot this year: CC Sabathia. Also Ichiro Suzuki, though he’ll go in as a Mariner. Sabathia would presumably go in as a Yankee, if he gets in. He won his Cy Young in Cleveland, but Sabathia made more starts, threw more innings, had more strikeouts, etc. as a Yankee than he did in Cleveland and Milwaukee combined. He also won a World Series with the Yankees and received the majority of his Cy Young votes in pinstripes. We’ll see.

Andy Pettitte (seventh year on the ballot) and Alex Rodriguez (fourth) are the two other most prominent former Yankees up for induction this voting cycle. Other former Yankees include Bobby Abreu (sixth), Carlos Beltrán (third), Melky Cabrera (first), Andruw Jones (eighth), Curtis Granderson (first), Russell Martin (first), and Brian McCann (first).

(Also, a certain longtime Yankees blogger will find out whether the Hall of Fame approves his voting status sometime around this date.)

Nov. 18-21: Awards week

Rookies of the Year on Monday, Managers of the Year on Tuesday, Cy Youngs on Wednesday, and MVPs on Thursday. Judge will win MVP, possibly unanimously, and that will probably be it for the Yankees this awards cycle unless Gil or Wells surprise us with a Rookie of the Year win. The awards will be announced during a live MLB Network broadcast at 6pm ET each day.

Tuesday, Nov. 19th: Qualifying offer decisions and Rule 5 Draft protection deadline

Players have until 4pm ET on this date to accept or reject the qualifying offer. Soto will decline it. Torres could take it, and that’s why I lean toward the Yankees not making it. I think they value the payroll flexibility more than the draft pick after the fourth round they would receive if Gleyber declines the qualifying offer and signs elsewhere. As much as 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 (6pm ET, specifically). Here are the notable Yankees’ minor leaguers eligible for the Rule 5 Draft this offseason. It’s not the highest profile group:

• Catchers: J.C. Escarra

• Infielders: Caleb Durbin, Jesus Rodriguez, TJ Rumfield

• Outfielders: none

• Righties: Cole Ayers, Bailey Dees, Zach Messinger

• Lefties: Oddanier Mosqueda

Durbin is a lock to be added to the 40-man roster. Ayers, Dees, and Messinger are all interesting pitch data guys who had success at Double-A this year, and it wouldn’t surprise me to see the Yankees protect one or two. You have to be careful not to stuff your 40-man with fringe prospects though. Roster spots are finite. Rodriguez is a personal favorite more than a serious Rule 5 Draft candidate.

I’m not sure what to think about Rumfield, who performed well enough in Triple-A (.262/.365/.461 and 116 wRC+) and is a very good first base defender, but has iffy ball-tracking data (below average exit velocities, poor pulled fly ball rate, just okay swing decisions). That said, Rumfield is a candidate to get picked by a bad rebuilding team in the Rule 5 Draft, so the Yankees should probably protect him. If anything, they could always trade him later if they’re not sold on him as a big leaguer.

Escarra and Mosqueda will be minor league free agents and thus have to go on the 40-man within five days of the end of the World Series, not at this deadline. I don’t think the Yankees will put either on the 40-man, but I thought they were worth a mention. Mosqueda is a lefty who had a 29.7 K% in Triple-A. Escarra is a lefty bat who slashed .261/.355/.434 (119 wRC+) with a 13.8 K% between Double-A and Triple-A. He frames well and he also plays the four corner positions. Hmmm.

I should note there are always a bunch of small trades league-wide at the Rule 5 Draft protection deadline as teams get their 40-man in order. The Yankees picked up Tim Locastro (the first time) in a minor trade when the Diamondbacks needed a 40-man spot to protect a young player from the Rule 5 Draft in 2018. There are several deals like that at the protection deadline each year. Maybe the Yankees will make one this offseason.

Nov. 19-21: Owners meetings in New York

The quarterly owners meetings are a bunch of rich guys talking about ways to get richer. They voted on the Athletics’ proposed relocation to Las Vegas at last November’s meetings, but there’s nothing as significant on this year’s docket. Because the owners meetings are in New York, I’m sure some local reporters will be there, and Hal Steinbrenner will say he wants to make Soto a Yankee for life while also giving his usual “I don’t think you need a [current Yankees’ payroll] payroll to win the World Series” speech.

Friday, Nov. 22nd: Non-tender deadline

Teams do not have to sign their pre-arbitration and arbitration-eligible players to 2025 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 nine non-tender candidates:

• Catchers: Jose Trevino

• Infielders: Jon Berti

• Outfielders: Trent Grisham, Duke Ellis

• Righties: JT Brubaker, Scott Effross, Mark Leiter Jr.

• Lefties: Nestor Cortes, Tim Mayza

Nestor will only get non-tendered if his flexor strain turns into a surgery that wipes out all or most of next season, though he was healthy enough to pitch in the World Series, which is promising. If anything, the Yankees will tender him and trade him. They’re not cutting a healthy Cortes loose. Trevino’s salary will jump over $3M in 2025, which is what free agent backup catchers get every offseason. I think the Yankees keep Trevino, but non-tendering him wouldn’t be that insane.

Berti is looking at close to $4M through arbitration and that’s an awful lot for a soon-to-be 35-year-old bench guy who can’t stay healthy and isn’t much of a hitter. Would Berti get that much as a free agent? Would he even get a Major League contract? Berti’s spot is an obvious place to save a few bucks, even with the Yankees likely going cheap on the infield around Volpe and Jazz Chisholm Jr.

Grisham could go either way. He would be an expensive bench player, but he was an expensive bench player in 2024, and the Yankees aren’t in position to dump a legitimate center fielder. I think they should keep him. I would also understand a non-tender. Ellis is a DFA candidate who could be long gone by time the non-tender deadline arrives. No need to keep a pinch-running specialist on the 40-man.

Effross has not been healthy and effective at the same time since 2022, though his projected arbitration salary is small enough that I bet the Yankees keep him. Brubaker can start and there are reasons to believe Leiter is better than he showed after the trade. I think all three (Brubaker, Effross, Leiter) get tendered. Mayza’s looking at $4M or so, per MLBTR. That’s a no. The other three are all projected for well under $3M.

Sunday, Dec. 1st: 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 those two groups, so there are 14 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. I’ll go on my annual “the Yankees should trade for an extra draft pick(s)” spiel one of these days.

Sunday, Dec. 8th: Veterans Committee voting results announced

The Hall of Fame split the Veterans Committee into several Eras Committees years ago and this winter the Classic Baseball Committee will meet. They consider “players, managers, executives, pioneers and/or umpires who made their greatest impact on the game” before 1980. The eight-person ballot will be revealed Monday, Nov. 4th. Odds are someone with Yankees ties will be on the ballot (Thurman Munson?).

Dec. 8-11: Winter Meetings in Dallas

The Winter Meetings are when all hot stove hell breaks loose. The offseason’s biggest signings and trades tend to happen at the Winter Meetings, plus there are an endless supply of rumors. The Yankees have made their most significant offseason transactions at the Winter Meetings the last few years. Last year it was the Soto trade, the year before it was re-signing Judge, and a few years back it was signing Cole. Those moves all happened at the Winter Meetings.

Tuesday, Dec. 10th: 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. More on the Yankees’ 2025 draft slot coming soon.

Wednesday, Dec. 11th: Rule 5 Draft

The Yankees lose a few players in the Rule 5 Draft every winter. Last year it was Carson Coleman, Matt Sauer, and Mitch Spence. The vast majority get returned though. Their only notable losses in recent years are Spence, Trevor Stephan, and Garrett Whitlock, and Stephen and Whitlock were four years ago now, when a bunch of guys slipped through the cracks after the canceled minor league season. The 2020 Rule 5 Draft was one the best ever. Chances are the Yankees will have another player(s) taken this year. The Yankees have not made a Rule 5 Draft pick since Cesar Cabral and Brad Meyer in 2011. I don’t expect that to change this offseason. The Rule 5 Draft is not a talent pool they swim in.

Sunday, Dec. 15th: 2024 international signing period closes

At 5pm ET, specifically. I normally don’t note this each year because all the top international prospects have been off the board for months, but this date applies to Roki Sasaki, if the Chiba Lotte Marines do go ahead and post him before Dec. 15th. Joel Sherman says the Marines are expected to announce their decision soon after the Japan Series, which will end no later than Sunday, Nov. 3rd.

It would make sense for the Marines to wait until the 2025 signing period opens on Wednesday, Jan. 15th to post Sasaki – they could announce the decision to post him sooner, but not actually post him until Jan. 15th – once the bonus pools reset. That would give teams more money to play with, not that money seems to matter to Sasaki. It would potentially net the Marines a larger posting fee, however. Sasaki wants to come to MLB. That much is known. Whether the Marines will let him is a mystery.

Thursday, Jan. 9th: Arbitration filing day

The deadline for teams and their arb-eligible players to file salary figures for next season is 8pm ET. 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 signed all their arb-eligibles prior to the filing deadline last year. They have 10 arb-eligible players this winter. Here are MLBTR’s salary projections. I’ll have a more detailed breakdown soon.

Wednesday, Jan. 15th: 2025 international signing period opens

The Yankees have a $6.2616M bonus pool this signing period, per Ben Badler. They can trade for an additional 60%, so they can max out at $10.01856M. Here are MLB Pipeline’s top 50 international prospects. The league’s media arm finally realized they shouldn’t report on early agreements that are against the rules, so we don’t know who the Yankees are expected to sign yet.

Tuesday, Jan. 21st: 2025 Hall of Fame class announced

Ichiro is a slam dunk and all signs point to Wagner getting into Cooperstown this voting cycle, his tenth and final year of eligibility. He received 73.8% of the vote last year and, historically, when a player comes that close to the 75% threshold, he gets in the next year. I would not count on Pettitte (13.5% last year) or A-Rod (34.8%) getting in this year or ever. Their voting trajectories are not close to approaching 75%. Sabathia? I think he’s got a good chance to get into the Hall of Fame one day. I’m not sure it’ll be on the first ballot though.

Jan. 27th to Feb. 14th: 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 continue to negotiate a contract up until a hearing, and heck, they can even rip up the panel’s ruling and agree to a contract after a hearing, though I can't remember that ever happening.

The Yankees last went to an arbitration hearing with Dellin Betances in 2017. Before that, their last hearing was with Chien-Ming Wang in 2008. The Yankees and Judge were so close to a hearing two years ago that Judge said he was logged into the Zoom call when they got his one-year contract for 2022 done. I’d bet against the Yankees going to a hearing this offseason. Both sides try to avoid one and they usually do.

Mid-February: Spring Training begins

The Yankees open their Grapefruit League schedule at home against the Rays on Friday, Feb. 21st. They have not yet announced when pitchers and catchers will report, though it’s usually 10 days before the first spring game, so figure Tuesday, Feb. 11th, or thereabouts. Position players will report 3-4 days later. Here is the Grapefruit League schedule.

Thursday, March 27th: Opening Day!

The Yankees open next season at home with three games against the Brewers. Three games with the Brewers, three games against the Diamondbacks, then a road trip through Pittsburgh and Detroit, then a homestand that begins against the Giants. An NL heavy start to 2025, it will be.