The Yankees and the 2020-21 Offseason Calendar

The Dodgers are the 2020 World Series champions and the 2020-21 offseason begins today. Gotta say, after the shutdown this summer, I’m not looking forward to another long stretch without baseball. Feels like we were just doing this, you know?

Anyway, now that the offseason has begun, it’s time to put together the offseason calendar, and look at what each date means for the Yankees. Let’s get to it.

Today, Oct. 28th: Free agency begins, kinda
Eligible players became free agents at 9am ET this morning. MLB used to make players file for free agency, which was a complete waste of everyone’s time, so now eligible players automatically become free agents the day after the World Series ends. The Yankees have five free agents: J.A. Happ, Erik Kratz, DJ LeMahieu, James Paxton, and Masahiro Tanaka.

(The MLBPA puts out a press release with an official list of free agents on this day each year and if Happ is on it, we’ll know his $17M option did not vest. I’m certain the Yankees avoided that sucker.)

UPDATE: Here is the MLBPA's press release. Happ is not listed. That doesn't necessarily mean his option vested. The two sides could be going in front of an arbitrator to determine his vesting criteria. I can't imagine this will drag out long. The option will determine Happ's employment status and the team's payroll situation going into next year, and both sides want answers quickly.

Friday, Oct. 30th: Most option decisions due
There are some exceptions, but most option decisions are due three days after the World Series ends. The Yankees have two club option decisions:

• Brett Gardner: $10M club option ($2.5M buyout)
• Zack Britton: 2-year, $27M club option (no buyout)

Gardner’s option is a $7.5M decision and I expect the Yankees to decline it and try to re-sign him at a lower salary, perhaps $5M or so. I keep going back and forth on Britton’s option but right now I think the Yankees will pick it up. If the Yankees decline it, Britton then has two days to pick up his one-year player option worth $13M.

Sunday, Nov. 1st: Team qualifying offer decisions and injured list activation
The qualifying offer is a one-year contract set at the average of the top 125 salaries in the game -- it’s worth $18.9M this offseason -- and free agents who reject it are attached to draft pick compensation. LeMahieu is definitely getting a qualifying offer. Tanaka might. No chance on Happ or Paxton. Maybe if Paxton had stayed healthy, but he didn’t, so forget it.

As noted earlier, Britton’s player option decision would fall on this date if the Yankees decline their two-year club option. If they decline their option and he declines his option and becomes a free agent, I don’t think the Yankees would make the qualifying offer. I don’t think they’d walk away from two years and $27M only to offer one year and $18.9M. They'd take the extra year for another $8.1M. LeMahieu is an easy yes, Tanaka is a maybe, everyone else is a no.

This date is also the deadline to activate players off the injured list. There is no injured list during the offseason -- I agree with Jeff Sullivan that the 60-day injured list should be year-round -- and the Yankees have four players on the 60-day injured list: Ben Heller, Tommy Kahnle, James Paxton, and Luis Severino. Paxton came off the injured list when he became a free agent. The Yankees will have enough 40-man roster space to accommodate the other three, so no other moves required on this date. Just activations.

Monday, Nov. 2nd: Free agency begins and awards finalists announced
The five-day exclusive negotiating period ends and free agents will be officially free to sign with any team starting next Monday. Much like the baseball season though (well, a normal baseball season, not this one), baseball free agency is a marathon, not a sprint. There won’t be a rush of signings on Day 1. In fact, I expect this to be a slower than usual free agent period because teams are going to want to get a good idea of their 2021 revenue situation before committing significant dollars to next year’s payroll.

Also on this date, MLB and the BBWAA will announce the three finalists for each of the four major awards (Rookie of the Year, Manager of the Year, Cy Young, MVP), which is something they have been doing for a few years now in an effort to generate buzz. I think it’s working? Hard to tell. Anyway, this year’s finalists will be announced during a live MLB Network broadcast at 6pm ET.

The Yankees have several awards candidates. Gerrit Cole will get Cy Young votes, though the best he can do is finish runner-up to Shane Bieber, I think. These are regular season awards, remember. Votes were cast after the regular season and before the postseason, so the Yankees rocking Bieber in Game 1 of the Wild Card Series had no impact on the Cy Young voting.

LeMahieu and Luke Voit (and Cole?) are going to get MVP votes. Enough to be among the three finalists? Eh. I think Jose Ramirez and Jose Abreu will be top three for sure, leaving one spot for LeMahieu, Voit, Tim Anderson, and Nelson Cruz. The last Yankee to be an MVP finalist was Aaron Judge in 2017. (LeMahieu finished fourth in the voting last year.)

Tuesday, Nov. 3rd: Gold Glove winners announced
The Yankees have two Gold Glove finalists: Gio Urshela at third base and Clint Frazier in right field. Tanaka continues to get snubbed. The last Yankee to win a Gold Glove was Brett Gardner in 2016. Before him it was Mark Teixeira and Robinson Cano in 2012. The Gold Gloves will be selected based on statistics this year, which seems silly given the sample sizes we’re dealing with. Then again, the managers and coaches who usually vote for these awards did not see players outside their region this year, so that’s not a good solution either. The Gold Gloves will be announced during a live ESPN broadcast at 7pm ET.

Monday, Nov. 9th to Thursday, Nov. 12th: Awards week
The BBWAA announces the results of their awards voting this week. Rookies of the Year on Monday, Managers of the Year on Tuesday, Cy Youngs on Wednesday, and MVPs on Thursday. As noted earlier, Cole will make a run at the Cy Young runner-up and LeMahieu and Voit (and Cole?) figure to get MVP votes. The last Yankee to win a major award was Judge in 2017, when he was named Rookie of the Year unanimously. Each award will be announced during a live MLB Network broadcast at 6pm ET.

Wednesday, Nov. 11th: Player qualifying offer decisions due
Players who receive the qualifying offer have 10 days to accept or reject it, and they will spend those 10 days gauging the market. Last year Will Smith signed his three-year, $39M contract with the Braves during the 10-day period, and Ken Rosenthal says Smith’s agent told interested teams to make their best offers quickly or they were going to accept the qualifying offer.

LeMahieu will definitely reject the qualifying offer. He’s in line for a much larger payday and the Yankees would be thrilled if he accepted it. A one-year contract at a lower salary than he’ll likely receive annually on a multi-year deal? Sign me up. Tanaka, if he receives the qualifying offer, seems like a candidate to shop around during the 10-day period, then accept it if nothing good comes along. He loves being a Yankee and might just jump on it. We’ll see.

Monday, Nov. 16th: 2021 Hall of Fame ballot announced
Here are the players eligible for the 2021 Hall of Fame ballot. The screening committee has to go through and pick who will actually appear on the ballot, then the ballot will be announced. There are no notable Yankees among this year’s first timers unless you include A.J. Burnett and Nick Swisher. Good players and long careers, both of them, but nah.

Andy Pettitte will be on the ballot for the third time. He received 11.3% of the vote last year, well below the 75% needed for induction. This will be the tenth and final year on the ballot for Barry Bonds, Roger Clemens, and Curt Schilling. Schilling is probably getting in (he was at 70.0% last year). The other two have been stuck in the 60% range the last few years. Even with the final year boost that has existed historically, it’s hard to see them getting in. Shrug.

UPDATE: I'm an idiot. This year is Year 9 on the ballot for Bonds, Clemens, and Schilling, not Year 10. They still have another year of eligibility remaining after this one. Bonds and Clemens are still likely to fall short this year though.

Friday, Nov. 20th: Rule 5 Draft protection deadline
There was no minor league season this year but non-40-man roster players will still be credited with a year of service. MLB confirmed that weeks ago. That means players who were due to become minor league free agents this offseason will become free agents, and players who were due to become Rule 5 Draft eligible will indeed be Rule 5 Draft eligible.

Of course, no minor league season means teams didn’t have an opportunity to evaluate these guys, both the players in their organization they have to protect, and the players in other organizations they may target. Here are the notable Yankees prospects eligible for this winter’s Rule 5 Draft, via Pinstriped Prospects:

• Catchers: None!
• Infielders: Kyle Holder, Oswald Peraza
• Outfielders: Trey Amburgey
• Righties: Roansy Contreras, Yoendrys Gomez, Glenn Otto, Addison Russ, Trevor Stephan, Alex Vizcaino, Garrett Whitlock
• Lefties: None!

I think the Yankees will add Contreras, Gomez, Peraza, Russ, and Vizcaino to the 40-man to protect them from the Rule 5 Draft. In that case, they’d have to open two 40-man roster spots. Tommy Kahnle is a goner, so that’s one spot. Ben Heller and Mike Ford would seem to be in the most danger for the other spot.

I should note there are usually a bunch of small trades on this date each year as teams move players they aren’t planning to protect. The Yankees acquired random Yankee Dean Anna all those years ago because the Padres weren’t going to put him on their 40-man roster, so they traded him to the Yankees for a non-Rule 5 Draft-eligible prospect. Maybe we’ll see something like that again this year.

Wednesday, Dec. 2nd: Non-tender deadline
This is the deadline for teams to submit a 2021 contract offer to their pre-arbitration and arbitration-eligible players. They don’t have to sign them by this date, but they do have to make an offer, and players who don’t receive an offer become free agents. The expectation within the industry is there will be a large group of non-tenders this offseason as clubs get their payrolls in order following the shutdown.

Kahnle is an obvious non-tender candidate -- he is scheduled to become a free agent next offseason and will miss next year rehabbing from Tommy John surgery, so the Yankees aren’t going to pay him to rehab and then potentially walk away -- and I think Heller and Ford are as well. Heller and Ford could be re-signed to minor league contracts. They’d remain in the organization as non-40-man roster players in that case.

Domingo German could be non-tendered as well, depending how the Yankees feel about his actions and suspension under the domestic violence policy. Hal Steinbrenner recently called the incident, the details of which are not public, “horrific.” German was quite good in 2019, the last time he pitched, but the Yankees might walk away. We’ll see.

Monday, Dec. 6th to Thursday, Dec, 10th: Winter Meetings in Dallas
The GM Meetings that are held each November have already been cancelled and will be held remotely. I can’t imagine the Winter Meetings will go on as scheduled. It’s way too many people in an enclosed space for too many days. I don’t see how they could be done safely during the pandemic and, frankly, they're not imperative. Almost everything that happens at the Winter Meetings can be done remotely. I think it’s only a matter of time until MLB announces the Winter Meetings are cancelled. In that case, we’d lose out on what is traditionally the busiest and most hectic week of the offseason. Stupid pandemic.

Thursday, Dec. 10th: Rule 5 Draft
The Rule 5 Draft is the unofficial end of the Winter Meetings. Everyone heads home afterward. The Yankees figure to lose a player or two this year because they always lose a player or two -- the Tigers used the No. 1 pick in last year’s Rule 5 Draft on righty and former Yankees prospect Rony Garcia, who allowed 20 runs in 21 innings with Detroit -- but don’t expect them to select a player. The 40-man roster is tight and the Yankees haven’t taken a player in the Rule 5 Draft since grabbing random Yankee Cesar Cabral and Brad Meyer in 2011. This isn’t a pool they swim in. That said, I do think the Rule 5 Draft will be more active than usual as teams seek inexpensive talent following the shutdown.

Friday, Jan. 15th, 2021: Arbitration filing deadline and international signing period opens
This is the deadline for teams and their arbitration-eligible players to file salary figures for next year. 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 continue to discuss (and agree to) a contract of any size after this date, though many teams are file-and-trial these days, meaning they use the filing deadline as a hard deadline, and cut off contract talks after this date. The vast majority of arbitration-eligible players will agree to contracts prior to the filing deadline. Only a handful actually file each year. The Yankees have 12 arbitration-eligible players this winter, though one is Kahnle, who is getting non-tendered.

Also on this date, the 2021 international signing period opens. The first day of the signing period was moved back from July 2nd, 2020 because of the pandemic, and also because MLB is laying the ground work for an international draft. Now the signing period is set neatly in one calendar year. The Yankees have been connected to Dominican shortstop Hans Montero and Venezuelan catcher Jesus Galiz. They were expected to sign Dominican catcher Samuel Basallo as well, but he's signing with the Orioles instead. The Yankees have about $4.2M to spend this signing period (they forfeited $1M to sign Cole) and teams aren't allowed to trade for additional space this year.

Mid-January: 2021 Hall of Fame class announced
Pretty good chance Schilling is the only player voted in this year. It’s a weak ballot. Clemens is the only former Yankee with a chance to get in and I think he’ll fall short again. Induction weekend was canceled this past July because of the pandemic, so the 2020 Hall of Fame class will be honored alongside the 2021 class at induction weekend next July. Derek Jeter is part of that 2020 Hall of Fame class.

Early-to-mid February: Arbitration hearings
If the two sides 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. 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 unusual. The two sides are typically done talking once they file.

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 Luis Severino were literally minutes away from a hearing two years ago when they agreed to his four-year extension. As always, bet against the Yankees going to a hearing. They have been more willing to do so in recent years though, and who knows how the payroll squeeze and weirdness of this season will affect how willing each side is to go to a hearing.

Sunday, Feb. 14th: Pitchers and catchers report to Spring Training
In theory, at least. We’ll see how things go with the pandemic. Pitchers and catchers reporting day marks the beginning of the new season but is a non-news day. Nothing really happens this day. Guys take their physicals and that’s it. Workouts begin the next day.

Saturday, Feb. 24th: Grapefruit League opener
Again, in theory. The Yankees are scheduled to host the Tigers at George M. Steinbrenner Field in Tampa on this day. I hope it happens.

Thursday, April 1st: Opening Day!
Once again, in theory. The Yankees are scheduled to begin the 2021 regular season at home against the Blue Jays. They play six games at home (Blue Jays and Orioles) to start the season then go out on a six-game road trip to Tampa and Toronto. Let’s all hope next season can start on time, shall we?