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Breaking down the Yankees offseason calendar

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The key dates for a long winter are here.

New York Yankees v Washington Nationals Photo by Michael Reaves/Getty Images

There may be no more baseball being played, but MLB certainly isn’t sitting around waiting for spring. The winter is full of important dates and two sets of meetings that will shape the landscape of the league for 2021.

October 28th

This was yesterday. Immediately after the conclusion of the World Series, the Yankees and all teams in baseball will have to activate all players on the 60-day IL and add them to their 40-man roster or release them. Additionally, yesterday marked the first day of team’s exclusive five-day negotiating window.

Teams get five days to negotiate with free agents before any other teams can enter the bidding. Although it’s rare for teams and FAs to actually come to an agreement in this time, it allows the building of common ground between the camps. Conversely, it also signals to the free agent what the lowest bound of offers should be, giving them a number to work with on the open market.

This is also the time period where the team will have to decide on the players who have options — Brett Gardner and JA Happ both have club options, with Gardner carrying a $2.5 million buyout. Meanwhile, Zack Britton’s option for 2022 must be picked up, or he can opt out of his deal immediately. The next few days are going to be really, really big for the club’s 2021 roster.

November 1st

The deadline for extending qualifying offers to free agents comes on Nov. 1. The QO is a one-year contract worth the average of the top 125 salaries, or $18.9 million, and can only be extended to players that spent the entire year with the club. The Yankees can expect to extend the QO to DJ LeMahieu, likely to Masahiro Tanaka, and James Paxton remains a mystery.

November 2nd-12th

The BBWAA Awards are announced over this time period. LeMahieu will be in the AL MVP mix, and two Yankees — Clint Frazier and Gio Urshela — are up for Gold Gloves.

December 6th-10th

The MLB Winter Meetings are scheduled to be held in Dallas, although given the continuing COVID-19 pandemic, expect these to be shifted to a digital experience. These are the big moments of the winter, where we can expect some major free agent signings — Gerrit Cole inked his deal last year on the final day of the meetings. The Winter Meetings will give us our best look at the economic landscape of baseball in 2021 — you can expect free agents to have a soft offseason, but just how soft remains to be seen.

The final day of the meetings will include the Rule 5 Draft.

January 15th

This is the final day for teams and players to submit their arbitration figures ahead of hearings. The Yankees will see a huge rise in salaries this year based on arbitration, although the shortened season may introduce uncertainty into just what players are worth headed into next season.

February 27th

The Yankees are scheduled for their first spring training matchup against the Tigers, although like so much else this year, this is subject to change based on the COVID-19 situation. Only 121 days to go, Yankee fans.