Here Are MLB’s Important Offseason Dates, Including Some Cubs-Specific Notes

With the Dodgers’ super-spreader event World Series win secured, Major League Baseball managed to conclude its truncated 2020 season by the skin of its teeth. That means we can now move on to talk of the offseason, which figures to consist largely of the fallout from league owners’ desire to slash spending and potential negotiations on carrying over some of this season’s rules changes.

It’s also possible that, despite all we’ve heard from the owners since at least May about how much money they’re losing, a few teams will be willing to spend big this winter. The Mets have been talked about as big players in free agency as new owner Steve Cohen — assuming New York City indeed approves the sale — looks to get splashy with his investment. In what figures to be a depressed market, what has been a joke of a franchise lately could suddenly become very attractive to the likes of George Springer and JT Realmuto.

The past two or three winters have taught us that free agency can stretch well into spring training and even the regular season but this offseason figures to be a little different. Along with some of that same stagnation, we’re likely to see more non-tenders than ever before. The Rule 5 Draft might also be more active, while $18.9 million qualifying offers should be somewhat scarce given the state of the market.

Exactly when and how everything will play out is anyone’s guess, but we do know when things can start to happen. Below are all the pertinent dates and deadlines for various meetings, options, and offers.

October 28: Teams and players have five days to decide whether to exercise or decline contract options and opt-out clauses for 2021.  All players eligible for free agency are now free agents, but cannot sign with any team other than the one they were with for the five days.

November 1: Teams have until 4pm CT to extend qualifying offers to eligible players, who then have 10 days to accept or decline. There was a little debate here and on social media way back in May when we wrote that the Cubs extending José Quintana a QO seemed like a longshot, but it would now be nothing short of shocking if they did it.

November 2: This is the official start of full-on free agency, five days after the World Series* concluded.

Sometime in early November: The GM Meetings, which took place from November 11-14 in Scottsdale last year, will be held remotely. No official dates have been announced. Though not nearly as robust as the Winter Meetings, this event did at least give some hints of activity in the past. That’s calmed in recent years and may offer nothing of substance for the rumor mill this time around as no in-person meetings will be held.

November 20: Teams must finalize 40-man rosters to prepare for the Rule 5 Draft on December 10.

December 2: This could be a very big day because it’s the deadline for teams to decide whether or not to tender contracts to arbitration-eligible players. The Cubs have several such decisions to make, including several core players who are set to make quite a bit of money in 2021. Though it’s more likely they’ll non-tender some fringe players, many speculate that some big names could be made free agents. That goes for the rest of the league as well.

December 6-10: The Winter Meetings are still scheduled to take place in Dallas, but heavy speculation is that they will be cancelled and replaced by some sort of virtual format. Much more than the GM Meetings, this is typically when the hot stove really gets stoked by various rumors from meetings between agents and execs. Scott Boras will have to come up with a new way to hold court if indeed the event goes online.

December 10: The Rule 5 Draft will take place remotely on the final day of the Winter Meetings.

January 15: The 2020-21 international signing period finally opens after being pushed back from July 2 due to the pandemic. It will run until December 15, 2021, then the 2021-22 international window will open on January 15, 2022. The Cubs are expected to sign shortstop Cristian Hernandez, one of the top five players in his class.

This is also the deadline for teams and arb-eligible players to submit their salary figures if a deal hasn’t already been reached. The idea of “file and trial” in which teams lowball players and essentially force arbitration has been discussed more over the past two years, but could really gain steam this winter as teams try to pinch pennies. Agreements can still be reached prior to arbitration hearings, which typically take place in February prior to the start of spring training.

For what it’s worth, the Cubs have only gone to the arbitration table one time under Theo Epstein and Jed Hoyer. That was with a disgruntled Justin Grimm and may have actually been a strategic move by the Cubs to lessen their salary obligations following his release.

Mid-February: Pitchers and catchers report and everything seems right with the world for like a day or two.

February 27: Spring training games start in Arizona and Florida.

April 1: Opening Day!

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