Key offseason dates for the Yankees

Not included in our calendar, but Brian Cashman will rappel down a building at some point this winter.

Watching Game 1 of the World Series last night was an unfortunate reminder that the Yankees’ season ended too early. The Bombers front office assuredly is already in preparation for the offseason 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. Additionally, I’ve provided some of the notable award dates at the very end. 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 7 is scheduled for October 30th, so this will come no later than Halloween. Here’s the list of Yankees who will file that day:

  • Didi Gregorius
  • Brett Gardner
  • Dellin Betances
  • Cory Gearrin
  • Cameron Maybin
  • Austin Romine

The Yankees will have exclusive negotiating rights with these players for five days after they become free agents. Once that passes, it’s open season for the other 29 clubs. Last year, the Gardner and the Yankees hammered out a one year deal before exclusivity ended. Perhaps we see the same this year with Gardner and potentially Aroldis Chapman, who could leverage his opt out into a new deal.

Five days after the World Series: Exclusive negotiating window closes, Qualifying Offers, option decisions, and 60-day IL activation

At this point, the Yankees can talk to any free agent they’re interested in (hello, Gerrit Cole). Their own free agents will be able to start speaking with other clubs, too.

Further, the Yankees will have to decide whether or not they want to make qualifying offers ($17.8 million for one year) to eligible players. Everyone on the list above except for Gearrin and Maybin can receive a QO for the Yankees since they were with the team all year and haven’t received on in the past. However, there’s a strong chance the Yankees don’t tender a QO to anyone. Gregorius would be the only arguable case, though he might turn around and accept it which the Yankees may not be keen on.

Next, player/club options. Chapman can opt out of the final two years and $30 million of the deal he signed after 2016. Additionally, the Yankees can pick up Edwin Encarnación’s $20 million option or decline it and make him a free agent. If they decline, they’re on the hook for half of his $5 million buyout. This brings us back to the QO – Chapman would be eligible to receive one and the Yankees undoubtedly would give him one. EE is ineligible to receive a QO.

Lastly, all players on the 60-day injured list must be reinstated. The following are those currently on the 60-day IL (excluding free agents like Betances):

  • Jake Barrett
  • Jonathan Holder
  • Miguel Andújar
  • Greg Bird
  • Jacoby Ellsbury

Given the amount of free agents the Yankees have, the Yankees won’t need to worry about making room on the 40-man roster for this group.

November 11th – 14th: GM Meetings

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 in one place, 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 20th: Rule 5 Draft protection deadline

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. Robert Pimpsner of Pinstriped Prospects has an excellent primer on who’s eligible within the Yankees’ farm system. Here are some notable names not yet on the 40-man that I picked out:

  • Deivi García
  • Nick Nelson
  • Ben Ruta
  • Luis Gil
  • Brooks Kriske
  • Luis Medina
  • Miguel Yajure
  • Estevan Florial
  • Kyle Holder
  • Dermis García
  • Hoy Jun Park
  • Chris Gittens

There are a few obvious guys who will be added to the roster: Deivi, Gil, Medina, and Florial stand out. Wouldn’t surprise me to see Holder and/or Yajure added too.

As hinted at in the last subsection, we could see some 40-man activity on or before this date to clear the way for these minor leaguers.

December 2nd: Non-tender deadline

All players on the 40-man roster with fewer than six years of service time must be offered a contract for the 2020 season at this time. Otherwise, they become free agents. This is more significant for arbitration-eligible players as they are the ones who stand to obtain substantial raises over the near-league minimum salaries earned in their first three service years. I included the list of arbitration-eligible players and their projected salaries in yesterday’s post, but here it is again:

Arbitration20192020 Proj.Increase
James Paxton $        8.575 $      12.900 $   4.325
Aaron Judge $        0.684 $        6.400 $   5.716
Gary Sanchez $        0.670 $        5.600 $   4.930
Tommy Kahnle $        1.388 $        3.000 $   1.613
Gio Urshela $        0.547 $        2.200 $   1.653
Chad Green $        0.568 $        1.400 $   0.832
Greg Bird $        1.200 $        1.300 $   0.100
Jordan Montgomery $        0.597 $        1.200 $   0.603
Luis Cessa $        0.579 $        1.100 $   0.521
Jonathan Holder $        0.522 $        0.800 $   0.278
Tyler Lyons $        0.087 $        0.800 $   0.713
Total $      15.416 $      36.700 $ 21.284

Most everyone will be tendered a contract, though there are a few candidates on the bubble. Greg Bird, Luis Cessa and Tyler Lyons are in jeopardy. Everyone else should be safe.

It’s not too often that the Yankees actually have arbitration hearings with its players, though the most notorious one was the contentious trial with Betances a few years ago. Obviously, both sides like to avoid the process if possible. If not, each side submits figures in mid-January for a February hearing. Keep in mind that even after figures are submitted, the team and player can still agree to a contract and avoid a hearing.

December 9th – 12th: Winter Meetings

Normally, this is when all of the fun stuff happens. Free-agent signings, big trades, etc. Last season’s Winter Meetings weren’t terribly exciting, though there were a few significant deals such as the three-team deal that included Carlos Santana, Yandy Díaz and Edwin Encarnación.

Last year, the Yankees reportedly came to an agreement with JA Happ during the Winter Meetings. There’s no way to predict what will go down this year. But, like the other 29 clubs, the Yankees will be in San Diego for this year’s get together.

The Rule 5 draft is held at the end of the Winter Meetings. The Yankees usually lose someone in this process, though in recent years, they’ve been returned. Nestor Cortes, Mike Ford, Caleb Smith and Nick Green are examples of those who the Yankees received back later. Luis Torrens (Padres) is a player they lost for good.

February: Spring Training!

Pitchers and catchers report on February 12th while everyone else joins in on the fun on the 17th. The first game for the Yankees is scheduled for February 22nd.

March 26th: Opening Day!

The Yankees start the 2020 season in Baltimore. It’s a Thursday for those wondering. The Yankees’ home opener isn’t until April 2nd against the Blue Jays.

Award Season and Hall of Fame Voting

I know this is going out chronological order, but I wanted to get the key roster and game dates out of the way first. Here are when various awards will be announced this year along with players/staff under consideration:

  • November 3rd: Gold Gloves (Brett Gardner, DJ LeMahieu, Aaron Judge)
  • November 7th: Silver Sluggers (DJ LeMahieu, Gleyber Torres, Aaron Judge)
  • November 11th: Rookies of the Year
  • November 12th: Managers of the Year (Aaron Boone)
  • November 13th: Cy Young Awards
  • November 14th: Most Valuable Player Awards (DJ LeMahieu)
  • January 21st: Hall of Fame voting results (Derek Jeter)


We were all wrong about DJ LeMahieu [2019 Season Review]


The Two Halves of James Paxton [2019 Season Review]


  1. RetroRob

    Miguel Yajure will be protected. If not, he’ll be gone in a heartbeat. He’s already pitched in AA briefly, and is ticketed for AA and AAA in 2020. Could move quickly based on reports. He’s too valuable of a property to risk that he might be returned. A team like the Orioles could simply hide him in their bullpen for a season before sending him back to AAA in 2021 for finishing school. If for some reason the Yankees couldn’t fit him, they’d trade him. He’d have good value. He could be in the majors as a starter by 2021.

    I suspect Bird is gone. I believe he has options, so maybe they send him back to AAA. They’d have to use two 40-man spots to hold both Bird and Ford.

    • Wire Fan

      I also think Yajure is protected. Or a typical Cashman 40 man trade to a team with 40 man space for a prospect or two that is not 40 man/Rule 5 eligible for a year or two.

      I think Holder is also added. The 26th man next year will make it easier for a rebuilding team to carry an infielder who at least will have value with the glove. And gives that team chance to see if the bat improved or is more of a juiced ball thing. Though the Yankees do have Wade and Estrada already on the 40 (wouldn’t surprise me if one of those guys was dealt)

      I suspect teams will be more careful about protecting guys with the 26 man roster coming next year, especially lower level guys who often haven’t been protected in the past. Teams like the O’s, Tigers, Royals, etc, can easily eat one or two 26 man roster spots for a year and then demote them to the minors the following year (like the Pads did with Torrens).

      • RetroRob

        Yes. They will maximize his value, either by protecting him or trading him. I’d bet on the former. He’s getting very good reviews. I suspect the Yankees would rather bet on his upside than trade him for some lottery tickets.

        Agreed on Holder. They’ll protect him too, especially if one of Wade or Estrada is moved.

  2. DJ Lemeddardhieu

    I’d make resigning Brett and Austin and Dellin #1 priority this offseason, Derek. I’d like to see Cameron back as well but I just don’t think we have room for him unless we trade Tauchman and Stanton decomposes. Gearrin never should have been brought here in the first place. Let Didi and Aroldis walk.

    I’d trade Bird in the offseason for a spare tire and a case of Natural Light. Keep Andujar in case Gio turns back into a pumpkin next year and DH. Tie Holder and Ellsbury together and put them in the lion’s den at the Bronx Zoo.

    As I said before, I wouldn’t give Gary or Bird a raise. Not even one penny. They’ve done nothing to earn it and Gary doesn’t need any more money to buy food.

    Opening Day will be here before we know it. Now is a good time to rest and forget about baseball. I usually take winters off but I told these guys I’d help them get this blog off the ground so I’ll be around driving up traffic to the site like I always do. This place has the potential to surpass RAB and become a permanent fixture that always strives for greatness and never goes away, like Papa John’s.

Powered by WordPress & Theme by Anders Norén