The Yankees and the 2023-24 Offseason Calendar

The Rangers are the 2023 World Series champions and the offseason is here. The Yankees have been in offseason mode for over a month now and they should – should – be active this winter. They missed the postseason and posted their worst record since 1992, and there are holes aplenty on the roster. This team isn’t a tweak or two away from contending. With that in mind, here is the offseason calendar and a look at what each date means for the Yankees.

Today, Nov. 2nd: Free agency begins

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. The Yankees have seven free agents: Isiah Kiner-Falefa, Keynan Middleton, Zach McAllister, Frankie Montas, Wandy Peralta, Luis Severino, and Luke Weaver. Some are more vital than others.

Also, Jimmy Cordero’s suspension is over and he comes off the restricted list today, and goes back to counting against the 40-man roster. I’m not sure how it works with Domingo Germán though. He’s not suspended. Unlike Cordero, who had a set activation date, Germán’s stint on the restricted list is open-ended. I think he stays on the restricted list in the offseason? We’re gonna find out soon one way or the other. Either he will be activated today or he won’t.

Sunday, Nov. 5th: Gold Gloves announced

There’s a live broadcast on ESPN at 7:30pm ET. Anthony Volpe and Anthony Rizzo are the Yankees’ two Gold Glove finalists. DJ LeMahieu and Jose Trevino won Gold Gloves last season. The Yankees have not had Gold Glovers in back-to-back seasons since Mark Teixeira from 2009-10. I don’t mean the same player in back-to-back years. I mean Gold Glovers in general in back-to-back years. The Yankees haven't done it in over a decade.

Monday, Nov. 6th: Awards finalists, contract options, qualifying offers, free agency

Monday will be a busy day. Let’s go through each event individually.

Awards finalists announced: Are they really “finalists” if there’s no second vote? Or are they just the top three vote-getters? Whatever. Gerrit Cole will be an AL Cy Young finalist and maybe Volpe will be an AL Rookie of the Year finalist, but probably not. Otherwise that’s it. No other Yankees will be finalists for a major award.

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), but most are due on this date. The Yankees do not have any option decisions this offseason. They owe Josh Donaldson the $6M buyout of his club option, but releasing him eliminated the option decision. (The buyout counted against the 2022-23 luxury tax payrolls. There’s no charge in 2024.)

Qualifying offers: The qualifying offer is worth $20.5M this offseason and the exact deadline to tender the qualifying offer is 5pm ET. Unless they surprise us with Severino, the Yankees do not have any qualifying offer candidates.

60-day injured list activation: There is no injured list in the offseason and players must be activated within five days of the end of the World Series. The Yankees have eight players on the 60-day injured list: Rizzo, Trevino, Nestor Cortes, Jasson Domínguez, Scott Effross, Luis Gil, Lou Trivino, and Ryan Weber. Seven free agents, eight players coming off the 60-day injured list, and one player coming off the restricted list (Cordero) means the Yankees will need to open two 40-man roster spots Monday, possibly three if Germán is activated as well. That won’t be an issue. The Yankees have several easily droppable Quad-A types on the 40-man.

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. There has been speculation the Yankees could reunite with Montas on a one-year prove yourself contract. I could see that coming together during the exclusive negotiating period. Either way, 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.

Nov. 7th to 9th: GM Meetings in Scottsdale

The GM Meetings typically cover off-the-field matters (rule changes, etc.), but when you put each team’s top baseball operations executive in one place, deals get made. The Yankees made the Aaron Hicks trade at the GM Meetings back in the day. The groundwork for the three-team Curtis Granderson/Ian Kennedy/Max Scherzer trade was laid at the GM Meetings, then the trade was completed a few weeks later.

Thursday, Nov. 9th: Silver Sluggers announced

The Silver Slugger finalists will be announced later today but I could not in good conscience give them their own section. Even after missing all that time, Aaron Judge has a good chance to at least be a Silver Slugger finalist, if not win one for the fourth time in his career. Gleyber Torres is the only other Yankee with a chance at a Silver Slugger. I assume second base will go to Jose Altuve or Marcus Semien though.

Nov. 13th to 16th: Awards weeks

That is Rookies of the Year on Monday, Managers of the Year on Tuesday, Cy Youngs on Wednesday, and MVPs on Thursday. Cole will win the AL Cy Young, possibly unanimously, and that’ll be it for the Yankees this awards season. Judge could get some down-ballot MVP votes. Anything more would be a surprise.

Tuesday, Nov. 14th: Qualifying offers and Rule 5 Draft protection deadline

Players used to get 10 days to mull over the qualifying offer. Now the deadline to accept or reject is 4pm ET on Nov. 14th, so they only get eight days this year. Not sure why there’s a set date now. The Yankees don’t have any qualifying offer candidates, but this is the date they will learn who they will have to surrender draft picks and international bonus pool money to sign.

As for the Rule 5 Draft protection deadline, the deadline itself is 6pm ET. Here are the notable Yankees minor leaguers eligible for the Rule 5 Draft this offseason:

• Catchers: Josh Breaux, Antonio Gomez, Carlos Narvaez, Agustin Ramirez
• Infielders: Jesús Bastidas, Andrés Chaparro, Jared Serna, Alex Vargas
• Outfielders: Elijah Dunham, Brandon Lockridge
• Righties: Clayton Beeter, Sean Boyle, Carson Coleman, Matt Sauer, Mitch Spence
• Lefties: Edgar Barclay

The Yankees got their Rule 5 Draft protection heavy lifting out of the way early when they added Domínguez and Austin Wells to the 40-man roster in September, and called them up. Beeter is the only slam dunk protection candidate, though the case can be made Barclay, Coleman, Sauer, and/or Spence should be added to the 40-man as well.

These days the Rule 5 Draft is the “pitchers with interesting pitch data” draft. Low minors hitters like Gomez, Ramirez, and Serna are unlikely to be selected, and, even if they are, there is basically no chance they stick on a big league roster all next season. Dunham had a poor year and Coleman missed the season with injury. Maybe a team takes him anyway given his premium fastball data?

Chaparro and Narvaez will be minor league free agents this offseason, so the deadline to add them to the 40-man roster is really Monday. Otherwise they’ll become free agents and likely sign with a team that offers a clearer path to MLB playing time. Rather than lose them for nothing, the Yankees could add them to the 40-man, then trade them. They did that with Donny Sands two years ago. Narvaez had a nice year in Triple-A. Chaparro did not.

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 deadline each year.

Nov. 14th to 16th: Owners meetings in Arlington

The quarterly owners meetings are a bunch of rich guys talking about ways to get richer, though there will be some actual baseball stuff this time around. The Athletics’ proposed relocation to Las Vegas is up for a vote. The A’s need 22 of the other 29 owners to vote their way for approval and I would be shocked if it doesn’t pass.

“It’s my plan (to vote in November),” Rob Manfred told Evan Drellich (subs. req’d) last week. “First of all, the relocation committee has been meeting on a very regular basis. Three times this week, to give you a feel for the level of activity. Once I have a pretty good sense of where they’re headed – not finalized – I have to consult with the executive council, and then after that consultation, I prepare a recommendation to the clubs.”

The A’s relocation is probably something Hal Steinbrenner should vote against? They’re moving from MLB’s tenth largest media market to the smallest, so the A’s will collect revenue sharing in perpetuity once they’re in Las Vegas. In the Bay Area, there’s at least a chance to move out of revenue sharing payee status with a good team and a new ballpark (like the Giants). That chance won’t exist in Las Vegas.

The Yankees pay more into revenue sharing than any other team, so you’d think they would be against anything that sends more revenue sharing dollars elsewhere. Hal could even cast a token protest vote and the relocation will still probably pass. Maybe I’m wrong here. Probably am. Either way, the A’s move to Las Vegas figures to become officially official on this date.

Friday, Nov. 17th: Non-tender deadline

Teams do not have to sign their players to 2024 contracts by this deadline but they must make an offer. The non-tender deadline used to be Dec. 2nd every offseason, but 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. The Yankees have no fewer than 12 non-tender candidates, by my count:

• Catchers: none
• Infielders: none
• Outfielders: Jake Bauers, Franchy Cordero, Estevan Florial, Billy McKinney
• Righties: Albert Abreu, Matt Bowman, Jimmy Cordero, Domingo Germán, Lou Trivino, Ryan Weber
• Lefties: Anthony Misiewicz, Nick Ramirez

Like I said earlier, the Yankees have several easily droppable Quad-A types on the 40-man, and more than a few of these guys won’t even make it to the non-tender deadline. They’ll be dropped from the 40-man long before this date. Germán is the big name here. Do the Yankees keep him, or do they finally move on?

Monday, Nov. 20th: Hall of Fame ballot released

Here are the players eligible for the 2024 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. Gary Sheffield is the only player entering his tenth and final year on the ballot.

Adrián Beltré, Joe Mauer, and Chase Utley are the notable first timers joining the ballot this year. So is Phil Hughes. We launched RAB two months before the Yankees called Hughes up for the first time and now here he is joining the Hall of Fame ballot. This is me:

Andy Pettitte (sixth year on the ballot) and Alex Rodriguez (third) are the most prominent former Yankees up for induction. Others include Hughes, Sheffield, Bobby Abreu (fifth), Carlos Beltrán (second), Andruw Jones (seventh), and Chase Headley (first).

Friday, Dec. 1st: Competitive balance draft picks awarded

Those are the extra draft picks given to teams in the bottom 10 in revenue and/or market size. 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’m sure I’ll go on my annual “the Yankees should trade for an extra draft pick(s)” rant one of these days.

Sunday, Dec. 3rd: Veterans Committee results announced

The Hall of Fame split the old Veteran Committee into several Eras Committees years ago and this winter the Contemporary Baseball Era Non-Players Committee will meet. That’s a mouthful, eh? There are eight former umpires, managers, and executives on this year’s ballot.

One of the eight candidates has ties to the Yankees: Lou Piniella. Piniella played for the Yankees from 1974-84 and won two World Series titles (1977 and 1978). He also managed the Yankees from 1986-87, and again late in 1988. Piniella won a World Series as Reds manager in 1990 and he managed the Mariners during their glory years from the mid 1990s to early 2000s.

Piniella is on the ballot as a manager, though the voters are supposed to consider the entirety of the person’s baseball career. Sweet Lou retired with 1,705 hits as a player and 1,825 wins as a manager, the 17th most all-time. Piniella missed by a single vote in 2019. I reckon he’ll get over the threshold this year (12 votes are needed from the 16-person committee).

Dec. 3rd to 6th: Winter Meetings in Nashville

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 re-signed Judge at the Winter Meetings last season and signed Cole at the Winter Meetings in 2019.

Tuesday, Dec. 5th: Draft lottery

The Yankees missed the postseason and thus have a chance at the No. 1 pick in the 2024 draft through the lottery. It’s a very small chance, but it’s better than the 0% chance they’d have under the old rules. The top six picks are determined through the lottery. Here are the Yankees’ odds for those picks:

• No. 1: 0.5%
• No. 2: 0.5%
• No. 3: 0.6%
• No. 4: 0.7%
• No. 5: 0.9%
• No. 6: 1.1%

That’s a 1-in-200 chance at the No. 1 pick and a 1-in-23 chance at a top six pick. Last year the Twins moved up from No. 13 to No. 5, so fingers crossed the Yankees get similar luck.

Picks 7-18 are set in reverse order of the standings. The most likely outcome is the Yankees get the No. 16 pick through reverse order of the standings, then that pick is moved back 10 spots to No. 26 because of their luxury tax status. I should note that, if the Yankees do move into the top six, the 10-pick penalty is applied to their second rounder, and they keep the top six pick.

Wednesday, Dec. 6th: Rule 5 Draft

The Rule 5 Draft is Wednesday now, not Thursday. It used to mark the unofficial end of the Winter Meetings. Everyone would get together Thursday morning, make their picks, then get on a plane and go home. That is no longer the case for whatever reason.

The Yankees lose a few players in the Rule 5 Draft every year (last year it was Zach Greene and Wilking Rodríguez), though the vast majority get returned. Their only notable recent losses are Trevor Stephan and Garrett Whitlock three years ago, 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.

Given all those non-tender candidates and thus 40-man roster flexibility, maybe the Yankees will take someone in the Rule 5 Draft this year? They haven’t made a pick since taking Cesar Cabral and Brad Meyer in 2011. Maybe they'll grab a bullpen arm or a bench piece. That would be a fun little wrinkle. Been a while since we’ve had a Rule 5 Draft player around these parts.

Friday, Jan. 12th: Arbitration filing deadline

The deadline for teams and their arb-eligible players to file salary figures for next season. 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 except Gleyber. He signed about two weeks later. The Yankees have an MLB-leading 17 arb-eligible players this winter.

Monday, Jan. 15th: International signing period opens

The Yankees have a $4.6522M bonus pool this signing period and can trade for an additional 60%, so they can top out at $7.45952M. There are indications the Yankees will sign Dominican OF Francisco Vilorio. The public rankings suggest he’s a good prospect but not one of the very best available this signing period. It seems the Yankees will spread their money around next year rather than give most of it to one player a la Domínguez and Roderick Arias.

Tuesday, Jan. 23rd: Hall of Fame class announced

All signs point to Todd Helton getting into Cooperstown this voting cycle. He received 72.2% of the vote last year and, historically, when a player comes that close to the 75% threshold, he gets in the next year. Billy Wagner (68.1% last year) is within striking distance too, and Beltré is a great first ballot candidate. I would not count on Pettitte (17.0% last year) or A-Rod (35.7%) getting in, this year or ever. Their voting trajectories are not close to approaching 75%.

Jan. 29th to Feb. 16th: Arbitration hearings

If the team and player can’t agree to a contract, they’ll argue their cases in front of a three-person arbitration panel, and the panel will pick either the salary the player filed or the salary the team filed. 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 that’s extremely rare.

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 minutes away from a hearing last year (Judge said he was logged into the Zoom call for his hearing when they got his one-year contract for 2022 done), but I would 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 on the road against the Tigers on Sunday, Feb. 24th. Their first home game is the next day against the Blue Jays. The Yankees have not yet announced when pitchers and catchers will report, though it’s usually 10 days before the first spring game, so figure Wednesday, Feb. 14th, or thereabouts. Position players will report 4-5 days later. Here is the Grapefruit League schedule.

Thursday, March 28th: Opening Day!

The Yankees open next season with a four-game series in Houston. I was going to make a joke about the Yankees starting 0-4, but those idiots swept the Astros in Houston this year. Anyway, four games in Houston, three games in Arizona, then home for a six-game homestand. The home opener is Friday, April 5th, against the Blue Jays. There’s no off-day after the home opener next year. I guess if it gets rained out, there will be plenty of chances to make it up against Toronto. Five months until Yankees baseball returns to the Bronx.