If the 2021 World Series goes a full seven games, the latest it can end is Wednesday, November 3.
The day after a champion is crowned, players set to become free agents officially hit the market.
For the first five days after the World Series ends, teams have an exclusive window to negotiate new contracts with their own free agents. Once that five-day period ends, players are free to sign anywhere, though we rarely see immediate huge signings as is custom in the NBA or NFL.
Here is a list of all of the key dates this MLB offseason pertaining to the Nationals and the league in general. Keep in mind that the Collective Bargaining Agreement expires on December 1, so absent an agreement, the pace of this offseason could slow considerably.
November 1: Awards finalists
The three finalists in each league for MVP, Cy Young, Rookie of the Year and Manager of the Year are announced on MLB Network at 6 p.m.
November 2: Gold Glove
Gold Glove award-winners at each position in both leagues are revealed.
November 3: DPOY
Defensive Players of the Year are revealed. Unlike the Gold Glove, this award is based on advanced stats rather than a poll of managers and coaches. One player at each position is selected for each league, along with the No. 1 overall defensive player at any position, and the best overall defensive team.
November 4: Silver Slugger
Silver Slugger awards announced.
November 8: Rookie of the Year
Rookies of the Year announced. Reds second baseman Jonathan India, who led off and hit .269/.376/.459 with 34 doubles, 21 home runs, 98 runs scored and 12 stolen bases, is the heavy favorite in the National League.
November 9: Manager of the Year
Manager of the Year awards are presented. Former Phillies and current Giants manager Gabe Kapler is a lock to win the award in the NL. It might be unanimous.
November 10: Cy Young
Cy Young award-winners revealed. Zack Wheeler is very much in the running. His main competitors appear to be Corbin Burnes and Max Scherzer.
If workload matters, Wheeler will win. This is a regular-season award, and in the regular season he pitched 34 more innings than Scherzer and 46 more than Burnes.
November 10: Qualifying offer deadline
Players who were extended the one-year qualifying offer from their team must officially decide whether to accept or reject. The QO for 2022 is actually down from 2021. It was $18.9 million last year and projects to be $18.4 million this winter.
If a player accepts the qualifying offer, the team has him for $18.4 million in 2022. If he rejects, the former team receives draft pick compensation if he signs elsewhere.
November 11: MVP
MVP awards announced on MLB Network. Bryce Harper's top competition is Juan Soto, Fernando Tatis Jr. and Austin Riley. Again, only three will be finalists. This will be an extremely close race. There are cases to be made for all four, thought Tatis' case may be the weakest since his second half did not come close to Soto's or Harper's and his team was among the worst in baseball the final two months.
November 15: Hall of Fame ballot
The HOF ballot for 2022 is released. Voting takes place on New Year's Eve.
November 19: Rule 5 cut-off
College players drafted in 2018 or prior, and high school players drafted in 2017 or prior must be added to their team's 40-man roster or they will be susceptible in the upcoming Rule 5 draft.
December 1: Non-tenders
The deadline for teams to non-tender their pre-arbitration and arbitration-eligible players. Non-tendered players immediately become free agents.
December 5-9: Winter meetings
MLB's annual Winter Meetings take place in San Diego, culminating with the Rule 5 draft.
January 14: Arbitration exchanges
The deadline for teams to exchange figures with arbitration-eligible players. If the team and player cannot find common ground and reach an agreement, they have an arbitration hearing. Those hearings take place in the middle of February.
February 26: Spring training opener
Pitchers and catchers officially report the prior week.
March 31: Regular season begin