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A look at the Yankees’ offseason calendar

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The Yankees’ 2019 season has come to an end, so let’s take a look at what’s ahead of them as the offseason gets underway.

MLB: New York Yankees-Workout Brad Penner-USA TODAY Sports

After a long regular season full of dominating play and great stories, Yankee baseball in 2019 has come to an end. Unfortunately, they will not hoist any trophy or pop any champagne bottles. Nonetheless, they will get right back to work.

The two or three months after the season ends is a time for the players to rest, recuperate, and work on their games. The team’s brass, however, will have no time to step back. Now is when Brian Cashman and his team get their pens and pencils out. Here’s an outlook at what the Yankees and their higher-ups have ahead of them for the next few months.

October 31: MLB Postseason Concludes

If necessary, Game Seven of the World Series will be held in Houston on October 30. After that, several things will immediately take place. First, 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. In the Yankees’ case, the players most likely be added are Jonathan Holder, Miguel Andujar and possibly Greg Bird and/or Jacoby Ellsbury.

On top of that, you also will have to look at players that will immediately become free agents. There is a long list for the Yankees including players in arbitration and players completing the final year of their contract. These players consist of Edwin Encarnacion, Didi Gregorius, Brett Gardner, Dellin Betances, Austin Romine, Cameron Maybin, and a few others.

In the five days after the World Series ends, teams will have the option to exercise club options or to make qualifying offers to players. To start, the Yankees could bring back Encarnacion for $20 million in 2020 or pay him a $5 million buyout.

November 3-21: MLB 2019 Awards, General Manager’s Meetings, Owner’s Meetings

Beginning in November, the Baseball Writers Association of America (BBWAA) will announce their votes for awards such as MVP, CY Young, Rookie of the Year, Gold Glove, and Manager of the Year. DJ LeMahieu and Aaron Boone stand out as potential candidates to appear on ballots. LeMahieu is already a nominee for Gold Glove at second base, could receive some down-ballot MVP support, and Boone will be a prime candidate for AL Manager of the Year.

Starting on November 11, the General Manager’s meetings will take place in Scottsdale, Arizona and will last until November 14. Then from November 19-21, the Owner’s meetings will take place in Arlington, Texas. This is where anything regarding the 2021 CBA will likley be discussed.

On November 20, teams will have to submit a 40-man roster, thereby making any players not on that roster eligible for the Rule 5 Draft.

Yankees players that will most likely be protected from that are Deivi Garcia and Nick Nelson. Estevan Florial could be protected as well. He has been a huge potential trade piece over the past two to three years and the Yankees have decided to hold onto him.

December 9-12: Winter Meetings and the Rule 5 Draft

The Winter Meetings will begin on December 9 and will run until December 12. The Rule 5 Draft will take place on the last day, where eligible players that remain unprotected and not on 40-man rosters will be available for selection. To be clear, players eligible for the draft this year must have been signed at age 19 or older in 2016, or signed at age 18 or under in 2015.

January 10 - February 20: Arbitration and Hall of Fame Voting

January 10 is when teams can begin to discuss arbitration deals with their players currently under arbitration. For the Yankees, those players consist of James Paxton, Aaron Judge, Gary Sanchez, Tommy Kahnle, Chad Green, and Tyler Lyons.

On January 21, Hall of Fame voting results will be announced.

Beginning on February 1, arbitration hearings will begin for players who could not come to terms with their teams. The Yankees have notably struggled with Betances at times in the past.

Mid-February - March 26: Pitcher and Catchers, Spring Training and the Regular Season

Pitcher and catchers will begin to report to spring training on February 12. On February 17, position players will slowly trickle in as spring training games will begin on February 21. The Yankees’ first game of the spring will be on February 22 against the Blue Jays.

Then on March 26, the MLB 2020 Regular Season will begin as the Yankees take on the Orioles at Camden Yards. After two three-game series on the road against the Orioles and the Rays, the Yankees will play in their home-opener on April 2 against the Blue Jays.