The 2020-2021 Offseason Calendar

Do you want to stay, DJ?

It’s pretty annoying to see the Rays go up 2-0 on the Astros, isn’t it? The Yankees should be doing that. Instead, the organization is now looking ahead to 2021. There’s still a couple of weeks remaining in the playoffs, meaning the offseason has yet to begin, but the front office is certainly preparing for the moves to come. Let’s take a look at some of the significant dates Brian Cashman and his staff face in the coming weeks and months. We’ll link to this in our sidebar for reference all winter long.

Day after the World Series: Eligible players file for free agency

Game 4 is scheduled for October 24th and Game 7 is set for the 28th, so players will file for free agency no later than the 29th. The following Yankees will file that day:

  • DJ LeMahieu
  • Masahiro Tanaka
  • James Paxton
  • JA Happ*

The Yankees will have exclusive negotiating rights with these players for five days after they become free agents. The Yankees and Brett Gardner came to an agreement in 2018’s exclusive window, in case you’re wondering.

*We still haven’t gotten official clarification on what’s going to happen to Happ this offseason. Apparently, either he and the Yankees need to renegotiate the option, or they need to go to arbitration.

5 days after the World Series

Exclusive free agent negotiating window closes

This is pretty straightforward. The Yankees can start making calls to the representatives for the other 29 clubs’ free agents. Meanwhile, LeMahieu and other Yankees’ free agents can start chatting with the rest of the league.

Qualifying offers must be made

This year’s qualifying offer is approximately $18.9 million, according to The Athletic’s Evan Drellich. All of the Yankees’ free agents are eligible to receive the QO, but I only expect LeMahieu to get it. Assuming that occurs and LeMahieu signs elsewhere, the Yankees would receive a compensation pick after the fourth round of the 2021 draft.

Contractual option decisions

Is this it for Gardner?
  • Zack Britton: This is a funky one. The Yankees have to decide on Britton’s 2022 season — yes, 2022 — worth $14 million. If the Yankees decline, Britton can subsequently opt out of his 2021 contract ($13 million).
  • Giancarlo Stanton: The postseason star can opt out of the remaining 7 years and $218 million on his deal. He reportedly won’t, though. Reminder: the Marlins owe the Yankees $30 million if Stanton stays, so the Yankees are really on the hook for $188 million.
  • Brett Gardner: The Yankees hold a $10 million club option on the longtime outfielder for next season. However, this is really a $7.5 million decision. He’s due a $2.5 million buyout if the Yankees decline his 2021 option.

Injured list activation

The following three players must be removed from the 45-day injured list and returned to the 40-man roster:

  • Luis Severino (Tommy John surgery)
  • Ben Heller (Biceps nerve injury)
  • Tommy Kahnle (Tommy John surgery)

No subsequent 40-man moves will need to be made to re-add these players. The Yankees will have enough free agents to open up spots at this time, unless someone re-signs quickly.

November date TBD: GM Meetings

The GM meetings will be held remotely this year. I can’t find the official dates for this, but it will be in November. I’ll update once there’s clarification.

There usually aren’t many transactions to announce during this period, but it’s certainly an opportunity for groundwork on future deals to be made. Any time you have all 30 general managers getting together, trades are going to be discussed. For what it’s worth, the Aaron Hicks deal went down during the GM meetings a few years back.

November 17th – 19th: Owners’ Meetings

Unlike the GM Meetings, this is still scheduled to occur in person — for now. The big news that’s expected to come out of this? Approval of new Mets owner Steve Cohen.

November 20th: Rule 5 Draft Protection

The Yankees will have to add a few players to the 40-man roster in order to protect them from the Rule 5 Draft that occurs at the end of the Winter Meetings. You can see all of the players eligible for the Rule 5 draft on the Yankees’ Roster Resource page (players with “Dec’20” or “R5” are eligible). Rather than list everyone, I’ve whittled it down to notable first-time eligible minor leaguers:

  • RHP Alexander Vizcaino
  • RHP Addison Russ
  • SS Oswald Peraza
  • RHP Trevor Stephan
  • RHP Garrett Whitlock
  • RHP Roansy Contreras
  • RHP Glen Otto
  • RHP Daniel Bies
  • RHP Yoendrys Gomez
  • LHP Alfredo Garcia

Here are other notable players who are eligible, but not first timers.

  • SS Kyle Holder
  • RHP Daniel Alvarez
  • 1B Chris Gittens
  • INF Oswaldo Cabrera

Holder, Alvarez, Russ, and Vizcaino were all in the Yankees’ 60-man player pool this summer and seem like strong candidates, though not all of them are locks especially since Holder and Alvarez were passed over just a year ago.

The players I’d say are locks? Vizcaino and Contreras. You can probably make a case for Gomez and Peraza, but they’re both so far away from the majors. We haven’t done much prospect stuff this year thanks to the lack of a minor league season, so we’ll have to delve in deeper into these candidates as the protection deadline approaches.

December 2nd: Non-tender deadline

The Yankees have a ton of arbitration eligible players this year:

  • Aaron Judge (2nd year)
  • Gary Sánchez (2nd)
  • Gio Urshela (2nd)
  • Chad Green (2nd)
  • Jordan Montgomery (2nd)
  • Gleyber Torres (1st)
  • Luke Voit (1st)
  • Miguel Andújar (1st)*
  • Clint Frazier (1st)
  • Tommy Kahnle (4th)
  • Luis Cessa (2nd)
  • Jonathan Holder (2nd)
  • Ben Heller (1st)*

*Service time is murky this year, so these players might qualify for super two treatment and be first-time eligible.

There are a few non-tender candidates here. Tommy Kahnle is the most obvious one because he won’t pitch in 2021 due to Tommy John surgery. He made $2.625 million in arbitration last year. I also think Luis Cessa, Jonathan Holder, and Ben Heller are on the chopping block. Cessa is out of options and will probably eclipse a $1 million salary in 2021, so there are some savings there if the Yankees’ are looking to cut corners. Same for Holder, though he has a minor league option remaining. Heller? He’s hurt again (biceps nerve injury) and would clear some space.

Once the MLB Trade Rumors arbitration salary estimates are released, I’ll update this post with the projected figures.

December 6th – 10th: Winter Meetings

I don’t expect the Winter Meetings to go down traditionally this year, though they haven’t been canceled or reconfigured yet.

A lot went down at last year’s Winter Meetings. The Yankees signed Gerrit Cole! We also saw the departure of Didi Gregorius. It tends to be the busiest period, transaction-wise, in the offseason baseball calendar. This year could be a lot different though, for obvious reasons.

February 2021: Spring Training Begins

The Yankees’ spring training game schedule is already out. They host the Tigers at Steinbrenner Field on February 27th. Pitchers and catchers should report a couple of weeks before that with the position players coming not long thereafter.


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  1. MikeD

    Britton will be an interesting choice. I’m not saying this because Chapman has blown two straight deciding postseason games, but I’d actually prefer Britton as the closer and Chapman as the power setup arm. I’ve compared Britton to Mariano in the sense that neither is the classic, high-K reliever, but their ability to limit hard contact is valuable.

    One option is to turn what would amount to a two-year deal if they trigger the option into a three-year deal. Negotiate it to a lower AAV, but more guaranteed money for Britton. I believe his stuff will age well.

    Of course, this scenario is based on the Yankees wanting to pay him and not let him leave. Even in what is expected to be a depressed market, I can see him doing quite well. The Phillies for one would love to add him.

    If they move Cessa and Holder, and let Britton leave, they’re going to have a lot of work to do on rebuilding the pen.

  2. Dani

    QO to DJ obviously is a no-brainer. I’d offer Tanaka too because it’s hard to replace him and if he accepts it’s not the worst deal in the world. Paxton is a no because of his injury history.

    As great as Britton has been … no way I’m picking up that option. If he opts out … so be it. I’ve never been a fan of handing out big deals to relievers, if you look around the league that seems to backfire like 90% of the time. I expect the Yanks to trade for at least one cheap-ish setup type reliever this winter to replace Kahnle and possibly Britton.

    It’ll be interesting to see what they do to fill the holes in the rotation. Bauer might be big jerk but damn, he’d fit perfectly. Him + trading for another solid #3 type starter … sign me up for that.

    btw: I really hope they don’t use Covid as an excuse to cut the payroll (but we all know that’s exactly what’s gonna happen).

    • MikeD

      I’d be surprised if they didn’t offer Tanaka a QO. if he accepts, you get a quality starting pitcher on a one-year deal for $18.9M, which is three million below what he was paid this year. I doubt he accepts since he’ll get a multi-year deal on the open market. Even if the AAV is less than the QO, it’s more guaranteed money. If the Yankees are interested in bringing him back long term, they can negotiate from the QO.

  3. Billy

    Monty is in his 2nd year of arbitration, right? I also thought Wade and German were 1st time eligible this year?

    • Derek

      You’re right on Montgomery, I will update. I think Wade falls short of Super 2 status. As for German, I’m not sure. The suspension might have cost him a year of service which would delay things.

  4. mikenyc2007

    wonder if they could opt out of Britton, yet qualify him….net savings if they don’t think he will age well in a few years, and if he signs elsewhere the Yanks get a pick… if he stays, he basically is making the same as Chapman anyway

    • mikenyc2007

      edit… read the option wrong :). my bad

      • Derek

        They could qualify him if: 1) the Yankees decline 2022 and 2) Britton subsequently opts out of 2021.

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