A look at MLB’s offseason calendar: Free agents, awards, Rule 5 draft, non-tenders, arbitration and more

Congratulations to the Washington Nationals on their World Series championship, the first ever where all seven games were won by the visiting team. That puts the 2019 MLB season in the books and we’re a few months out from spring training and the 2020 regular season.

But that doesn’t mean we don’t have baseball things to think about and keep track of over the rest of the autumn and winter.

Here are some dates to remember over the next few months.

The day after the conclusion of the World Series (today): All players with at least six years of service time who are not under contract for the 2020 season will become free agents. Minor league players with six years of service will also become free agents if not added to a 40-man roster. One of the toughest decisions the Cubs will have to make will be about Colin Rea, who had a solid year at Triple-A Iowa. He’ll have to be added to the 40-man or he becomes a free agent. For the first five days after the World Series there is a “quiet period” when clubs can talk to free agents but can’t sign them.

At the same time, teams are required to move all players on the 60-day injured list to the active roster. Currently, Xavier Cedeno, Kendall Graveman, Brandon Morrow and Allen Webster are on the Cubs’ 60-day injured list. I’d think Cedeno and Webster would be let go rather than take up space on the 40-man. Morrow has a $12 million option which will almost certainly be declined in favor of a $3 million buyout, making him a free agent. I wrote about the Cubs’ looming decision about Graveman earlier this month.

At the end of the quiet period, clubs must decide whether or not to extend one-year qualifying offers to their free agents. The qualifying offer for 2020 will be $17.8 million, down slightly from $17.9 million in 2019. The only Cubs free agent who might receive a qualifying offer is Cole Hamels. (This article says Hamels won’t get one, FWIW.) Any player receiving a qualifying offer has 10 days to consider those offers and can negotiate with other clubs during that 10-day window. After that deadline, all free agents can begin negotiating with all teams.

The end of the five-day quiet period is also the deadline for teams to pick up player options for the 2020 season. In addition to Morrow, Anthony Rizzo, David Phelps, Jose Quintana, Derek Holland and Tony Barnette have team options for 2020. Rizzo’s and Quintana’s will surely be exercised. Phelps, at $5 million, might not be, and Holland and Barnette (who is currently on the restricted list) are almost certainly gone. Also, players who have opt-outs have to decide by this deadline. Yu Darvish and Jason Heyward have opt-outs available to them this winter; per this article neither is likely to do so. Both would likely get qualifying offers if they did opt out.

The other Cubs free agents are Nicholas Castellanos, Brandon Kintzler, Steve Cishek, Jonathan Lucroy, Pedro Strop and Ben Zobrist. It seems likely the Cubs will enter the free-agent period (after the “quiet period”) with 31 players on the 40-man roster, with those six plus Hamels, Phelps and Holland removed, or 32 if they decide to keep Graveman.

November 3: Rawlings Gold Glove winners announced on ESPN2 at 6 p.m. CT.

November 4: BBWAA award “finalists” announced. They’re not really “finalists” as no further voting is taking place. These are simply the top three vote-getters for each award.

November 7: Silver Slugger awards announced.

November 11-14: General manager meetings take place in Scottsdale, Arizona. There could be discussions about the upcoming rule changes for 2020.

November 11: Jackie Robinson Rookies of the Year announced.

November 12: Managers of the Year announced.

November 13: Cy Young Awards announced.

November 14: MVP awards announced.

November 18: Comeback Players of the Year announced.

November 19: Designated Hitter of the Year announced.

November 19-21: Owners meetings in Arlington, Texas.

November 20: Deadline for clubs to turn in their 40-man reserve lists with the names of players who will be protected for the Rule 5 draft. Every player added will need a spot on the 40-man roster. Teams also need an open spot on their 40-man roster if they are planning on selecting a player in the Rule 5 draft. The Rule 5 draft will take place on the final day of the Winter Meetings, December 12.

December 2: Clubs must tender contract offers to players on their rosters who are not under contract for the 2020 season or they will become free agents. This is commonly referred to as the “non-tender deadline.” The Cubs might have a non-tender or two this winter. The most likely candidates are Addison Russell and Tony Kemp.

December 9-12: Baseball’s annual Winter Meetings. This year they will take place in San Diego. As noted above, the Rule 5 Draft takes place on the 12th, the final event of the winter meetings.

January 10, 2020: The deadline for clubs and arbitration-eligible players to exchange salary figures, if they have not settled on a contract by then. Cubs arbitration-eligible players for 2020 are Albert Almora Jr., Javier Baez, Kris Bryant, Willson Contreras, Kyle Ryan, Addison Russell and Kyle Schwarber.

January 17-19, 2020: Cubs Convention at the Sheraton Grand Chicago. Convention passes go on sale tomorrow, Friday, November 1. More details here.

January 21, 2020: Hall of Fame voting results will be announced by the BBWAA. This year’s induction ceremony in Cooperstown will take place Sunday, July 26.

February 3-21, 2020: Arbitration hearings will be held for those eligible players who do not come to terms with their clubs before their hearing date.

Mid-February, 2020: Pitchers and catchers report to spring training. The exact date for Cubs pitchers and catchers has not yet been announced, but figure it’ll be around February 10 or thereabouts.

February 22, 2020: Spring training games begin with the Cubs hosting the Athletics at Sloan Park in Mesa, Arizona. Here is the Cubs’ entire 2020 spring training schedule.

March 26, 2020: Play ball! The regular season begins. The Cubs open with a three-game series against the Brewers at Milwaukee. Also, rumor has it that the Brewers will be debuting their new/old logo on Opening Day.

March 30, 2020: The Cubs’ home opener at Wrigley Field against the Pirates.