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MLB Offseason Key Dates



With the Atlanta Braves defeating the Houston Astros in game six of the 2021 World Series, the offseason is officially underway. With the uncertainty surrounding the collective bargaining talks, it is sure to be a unique winter around Major League Baseball. With that being said, here are some important dates to keep in mind.

Nov. 3: Players Officially Become Free Agents

Though free agency doesn’t start this day, players who are heading for free agency officially become free agents and are removed from the team’s roster. For the Pirates, Yoshi Tsutsugo, Trevor Cahill and Shelby Miller will all become free agents. The Pirates are free to talk to all three of their free agents about the possibility of re-signing during this time.

Nov. 7: Gold Glove Award winners announced/Qualifying Offer Deadline

The Pirates have Jacob Stallings, Kevin Newman and Bryan Reynolds as potential winners as all were named finalists at their positions. 

This is also the last day for teams to extend qualifying offers to impending free agents – though no Pirate will be receiving one. The qualifying offer is set at $18.4M this offseason.

Nov. 8: Free Agency Begins

Free agency officially opens as players can sign with any team and discussions between teams and players can officially begin. Additionally, decisions on option years are due. The Pirates can finally decline the $10M team option on Felipe Vazquez in favor of a $1M and rid themselves of his contract. Teams will also have to activate players currently on the 60-day injured list by this day. The Pirates will have to make room on the roster for Steven Brault, Blake Cederlind, Chase De Jong, Dillon Peters, Jose Soriano, Duane Underwood Jr. and Bryse Wilson or remove them from their roster. Cahill is also on the 60-day IL, but is a free agent.

Nov. 8-11: General Manager’s Meetings

This is where a lot of preliminary discussions for free agent signings and trades take place.

Nov. 11: Silver Slugger winners announced 

Reynolds is one of the finalists for National League outfielders to win the award – the Pirates lone finalist.

Nov. 15-18: American and National League Award Winners Announced

Award winners begin with Rookie of the Year winners on the 15th, followed by Manager of the Year, Cy Young and MVP.

Nov. 19: Deadline for Protection from Rule 5 Draft

Teams have to add Rule 5 eligible prospects to their 40-man roster in order to protect them from being selected. Some of the notable names the Pirates will need to protect or risk losing to another team include – Travis Swaggerty, Mason Martin, Liover Peguero, Diego Castillo, Cal Mitchell, Canaan Smith-Njigba and others.

Dec. 2 : Non-Tender Deadline

This is the final day that teams can non-tender their players including those who are arbitration-eligible. The Pirates in jeopardy of being non-tendered include: Chasen Shreve, Chad Kuhl, Wilmer Difo, Colin Moran, Kevin Newman and Michael Perez

Dec. 2: CBA Expires

The current collective bargaining agreement will expire on this day and unless a deal is reached beforehand, could freeze the rest of the offseason.

*All of the following dates are contingent on a deal getting done prior to the expiration date

Dec. 6-9: Winter Meetings

The busiest week of the offseason, the Winter Meetings are back in person in Orlando, Florida. All 30 Major League front offices, agents and players will convene to one location and discuss signings, trades, extensions, etc.

Dec. 9: Rule 5 Draft

The Rule 5 draft is always set for the final day of the Winter Meetings and that is the case again this year. Last year, the Pirates selected Jose Soriano with the first pick and acquired Luis Oviedo from the Mets during the Rule 5 Draft. The Pirates will have the fourth selection in this year’s.

Jan. 14: Arbitration Exchange Deadline

This is the deadline for teams and players to exchange arbitration figures and if no agreement is reached, they will go to an arbitration hearing (sometime in February) to settle the dispute. The Pirates have 11 arbitration-eligible players. 

Jan. 15: International Signing Period Begins

The 2021-2022 international signing period opens and runs through Dec. 15.

Head Beat Writer at Pittsburgh Baseball Now. Covering all things Pittsburgh Pirates.

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