The Yankees’ 2021-2022 Offseason Calendar

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Now that we’ve had a few days to let the end of the Yankees’ season simmer, it’s time to look forward. Technically, the offseason doesn’t begin until the World Series ends, but for all intents and purposes, the Yankees are in offseason mode.

The next few months could be incredibly tumultuous. Not just for the Yankees, but for MLB as a whole. The collective bargaining agreement expires at 11:59pm on December 1st. Things between the owners and players don’t seem too peachy, so there’s a chance for tense negotiations upcoming. Those negotiations could create a standstill for all trade and free agent activity.

Aside from the front office working on its roster, the group (and ownership) needs to make a decision on Aaron Boone and his coaching staff before anything else happens. Boone’s contract is up, so the team could simply walk away. I imagine the Yankees will have that settled before the World Series ends. So with that, let’s break down the offseason calendar:

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

Game 7 of the World Series is scheduled for November 3rd, so free agency will commence no later than November 4th. Just two Yankees will be major league free agents:

  • Anthony Rizzo, 1B
  • Corey Kluber, RHP

There are going to be a bunch of minor league free agents, though. I’m going to list these players below, but there’s a chance I am not 100 percent accurate with these names based. I had to make these determinations myself. Now with that caveat aside, these are the guys who have played seven seasons in the minors and aren’t on the 40-man roster:

  • Donny Sands, C
  • Max McDowell, C
  • Jason Lopez, C
  • Justin O’Conner, C
  • Kyle Holder, IF
  • Brandon Wagner, 1B
  • Dermis García, 1B
  • Wilkerman García, IF
  • Kaleb Cowart, IF
  • Jonathan Davis, OF
  • Trey Amburgey, OF
  • Ryan LaMarre, OF
  • Thomas Milone, OF
  • Socrates Brito, OF
  • Michael Beltre, OF
  • Isiah Gilliam, OF
  • Juan De Leon, OF
  • Pablo Olivares, OF
  • Frederick Cuevas, OF
  • Brody Koerner, RHP
  • Adam Warren, RHP
  • Nick Goody, RHP
  • David Sosebee, RHP
  • Kevin Gadea, RHP
  • Jio Orozco, RHP
  • Nick Green, RHP
  • Freicer Perez, RHP
  • Jefry Valdez, RHP
  • Carlos Espinal, RHP

The main reason I list these guys, even though they aren’t prospects, is because one (Sands) could sign a major league deal immediately. The 25 year-old catcher had a nice season at the plate and reached Triple-A.

Sands, the team’s 8th round pick in 2015, hit .261/.326/.466 (112 wRC+) with 18 home runs and a 15.0 percent K-rate in 380 plate appearances between Double-A and Triple-A. Per MLB Pipeline, he is a “capable receiver” but an “offensive-minded backup”. Seems like prime fodder to be the team’s third catcher in 2022.

5 days after the World Series

Exclusive free agent negotiating window closes.

In other words, free agents can sign negotiate any team they choose at this date. That means Rizzo and Kluber can talk with other teams. It also means the Yankees can start conversations with one of the big shortstops on the market.

Qualifying offers must be made.

Rizzo isn’t eligible to receive the QO because he was acquired midseason, but it’s not like he or Kluber, who is eligible, were likely recipients anyway. There’s nothing to do here for the Yankees.

Contractual option decisions

Will Gardner return?

Three players could stay or go:

  • Joely Rodríguez, LHP — $3 million team option, $500k buyout
  • Brett Gardner, OF — $2.3 million player option, $1.15 million buyout (or $7.15 million club option)
  • Darren O’Day, RHP — $1.4 million player option

60-day Injured List activation

The Yankees will have to return seven players to the 40-man roster:

  1. Aaron Hicks, CF
  2. Clint Frazier, OF
  3. Miguel Andújar, LF/3B
  4. Darren O’Day, RHP
  5. Tim Locastro, OF
  6. Zack Britton, LHP
  7. Luke Voit, 1B

To do so, the Yankees will need to make a few cuts. There are 47 players on the 40-man right now, but Rizzo and Kluber will reduce that to 45 after the World Series. That’s not a locked in number either, though. Signing Sands to a major league contract and potential option buyouts will make this a moving target.

There are a few players on the 40-man bubble. I’ll rank seven in the order I think most likely to be cut on or before this day:

  1. Rob Brantly, C
  2. Tim Locastro, OF
  3. Greg Allen, OF
  4. Andrew Velazquez, SS
  5. Chris Gittens, 1B
  6. Lucas Luetge, LHP
  7. Rougned Odor, INF

Chances are the Yankees won’t need to get past five of these guys, and perhaps there could be as few as three or four to start depending on the contract buyouts.

November TBD: Owners’ Meetings

This is usually scheduled for November as part of the 30 owners’ quarterly meetings. I’m sure the main topic will be the CBA.

November TBD: GM Meetings

This also is typically in November. 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 19: 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’21” or “R5” are eligible). Rather than list everyone, I’ve whittled it down to notable first-time eligible minor leaguers and notable repeat-eligible players:

  • New players: Josh Breaux, Brandon Lockridge, Randy Vasquez, Everson Pereira, Matt Sauer
  • Notable Repeats: Oswaldo Cabrera, Ron Marinaccio

We’ll do some more robust coverage on the Rule 5 guys as this deadline approaches.

December 1st: Non-tender deadline

I count 19 (!) players eligible for arbitration this winter. That’s a lot of players getting raises. I’ve listed them below. Those with asterisks are players who were Super Two eligible and thus will go through the process four times (rather than three).

  1. Aaron Judge (3rd time)
  2. Gary Sánchez (3rd)
  3. Joey Gallo (3rd)
  4. Jameson Taillon (3rd)
  5. Chad Green (3rd)
  6. Gio Urshela (3rd*)
  7. Jordan Montgomery (3rd*)
  8. Wandy Peralta (3rd)
  9. Luke Voit (2nd*)
  10. Gleyber Torres (2nd*)
  11. Clint Frazier (2nd*)
  12. Clay Holmes (1st)
  13. Miguel Andújar (1st)
  14. Domingo Germán (1st)
  15. Tyler Wade (1st)
  16. Jonathan Loáisiga (1st)
  17. Kyle Higashioka (1st)
  18. Tim Locastro (1st)
  19. Lucacs Luetge (1st)

Voit is going to get talked about as a non-tender candidate, but I really just can’t see it. I really don’t think the Yankees will non-tender anyone here, in fact (assuming Locastro is cut earlier, as I mentioned). They may trade a few of these guys before this deadline, but a straight non-tender? I doubt it.

December 5th-9th: Winter Meetings

Last year’s Winter Meetings went virtual due to COVID-19, but I expect a more normal event this offseason. Traditionally, this is when a lot of the big transactions go down. Who knows what it will be like this year given the labor situation.

January 14th: Arbitration figure exchanges

Teams and eligible players exchange contract amounts for the upcoming season and a hearing date is scheduled for February. This date doesn’t mean two sides can’t settle, though. The Yankees rarely go to arbitration hearings, and when they do, they tend to be ugly. Look no further than the club’s hearing with Dellin Betances a few years back.

February 2022: Spring Training Begins

Players will officially report to camp mid-month and the first game is on February 26th. The rest of the game schedule is here.




A look at the Yankees payroll entering the offseason


  1. Scott

    Weissert deserves a nod here as a notable rule 5 repeat. He had a good year from start of AA through end of AAA season. Was named to the top 30 mid season prospect and was a reliable guy in late innings out of the pen.

  2. Mark12211

    Did anyone see the Cashman conference? It seems impossible to field a lineup with more athleticism and contact-hitting ability and a strong spine up the middle by only replacing the Shortstop. Yankees are already over the payroll threshold for 2022 if the CBA doesn’t increase it significantly.–

    Brian Cashman has said that he subscribes to the theory of building with a “strong spine” of the diamond, first instilled in him decades ago by the late Yankees superscout Gene Michael. Teams that boast solid performers at catcher, shortstop, second base and center field are usually well-equipped to be contenders.

    Cashman indicated he would look to upgrade over the in-house shortstop options of Gio Urshela and Andrew Velazquez, with Urshela penciled in as the starting third baseman.

    This offseason presents a loaded free-agent crop at shortstop, including Carlos Correa, Marcus Semien, Corey Seager and Trevor Story.

    Cashman said that he aims to field a lineup with more athleticism and contact-hitting ability than the ’21 roster displayed. The expected return of switch-hitting centerfielder Aaron Hicks could help settle some defense and balance issues.

    Notably, Cashman was non-committal when asked if he envisions Gary Sánchez as the starting catcher in ’22.

    According to Cot’s Baseball Contracts, the Yankees appear to have cleared the 2021 luxury tax threshold of $210 million. Adding a $135 million base payroll to the estimated $80 million in arbitration salaries would produce a total salary budget of $215 million for 2022

  3. Anthony Rizzeddardo

    You forgot November 2: Sox win the World Series, Derek. They are such a better organization than us from top to bottom. And it really goes to show you how much a good manager matters. The Sox were a World Series winning club with Cora, last place without Cora, and now on the brink of another World Series with Cora. We need a fighter like Cora who isn’t afraid to get his hands dirty. Why hasn’t Boone been fired yet? Fire him immediately and hire Carlos Beltran or Buck or Coney or anybody with an ounce of toughness because Boone is a feckless clown.

    The Sox are on the brink of winning their 3rd WS of the decade to the Yankees 0 and their 5th WS of the century to the Yankees 1. And Boone says that the Rays and Sox have caught up to us. The Sox passed us 15 years ago and the Rays 10 years ago. And the Jays are a year or two away from passing us. And the Sox keep winning with different cores trading away their best players and we keep the same rotten core and do nothing. Both Cash and Boone shoulda been fired by now which makes me worry they’re going to be retained. Why can’t they fish up some old racist emails on those two.

  4. Bill Toncic Jr

    Orlando Cabrera needs to be added to the 40 man .Had an outstanding year. MVP in NE AA & was strong in his short time with SWB.

  5. What about Ridings and Sears for rule 5? If he didn’t blow out his elbow Ridings seems a given. I think they’ll have to protect a bunch. Vasquez, Breaux, Periera, Cabrera, Marinaccio. Unless they trade some. Sands is slightly closer to the bigs but Breaux will start at AAA and is younger. Both are bat first. I can see them signing then trading Sands.

  6. Kiwi

    Can the Yankees DFA Britton to create a 40 man roster spot given he’ll miss the year, which is the last year of his deal anyway? Thanks.

    • Derek

      Yes but they likely have insurance on his contract, which will cover some portion of salary while he’s on the IL. Releasing him would nullify the policy.

      • Kiwi

        Thanks for that. Hopefully protecting that money doesn’t cost them another Whitlock.

        • Wire Fan

          This is a team that gave away Cessa to squeeze under the LT threshold and gave away extra prospects in the Rizzo and Gallon deals just to save a few million in LT payments.

          If given the choice between a few million in insurance and protecting a fringe 40 man prospect, I think it is pretty clear which direction they will go.

  7. Wire Fan

    MLBTR’s arbitration projections
    Jameson Taillon – $4.7MM
    Joey Gallo – $10.2MM
    Gary Sanchez – $7.9MM
    Aaron Judge – $17.1MM
    Chad Green – $4.1MM
    Wandy Peralta – $1.7MM
    Jordan Montgomery – $4.8MM
    Gio Urshela – $6.2MM
    Luke Voit – $5.4MM
    Gleyber Torres – $5.9MM
    Clint Frazier – $2.4MM
    Miguel Andujar – $1.7MM
    Tyler Wade – $700K
    Clay Holmes – $1.0MM
    Jonathan Loaisiga – $1.7MM
    Domingo German – $2.1MM
    Lucas Luetge – $1.1MM
    Tim Locastro – $700K
    Kyle Higashioka – $1.2MM

  8. dasit

    you forgot the deadline to fire boone, which was 6 days ago


    Interesting article on MLBTR projecting arb salaries
    Quick addition Yankees have about $80 million in salary to arb eligible players

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