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

Congratulations to the Los Angeles Dodgers on their World Series championship, the team’s first in 32 years. Baseball managed to get through the 60-game pandemic-reduced season with minimal interruption, though that was somewhat tainted during Game 6 with the announcement that Justin Turner had tested positive for COVID-19.

In any case, baseball will (presumably) return next spring, but in the meantime here are the key dates to remember this winter.

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 2021 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. 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, Daniel Descalso, James Norwood, Manuel Rodriguez and Brad Wieck are on the Cubs’ 60-day injured list. Descalso has an option with a buyout figure (see below) and almost certainly will be bought out and not be added back; the others will be, though Norwood is a potential non-tender this offseason.

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 2021 will be $18.9 million, up quite a bit from $17.8 million in 2020. Of the Cubs’ 12 free agents or potential free agents, there isn’t anyone who will receive a qualifying offer this year.

The end of the five-day quiet period is also the deadline for teams to pick up player options for the 2020 season. The Cubs have three players with options for 2021: Descalso, Jon Lester and Anthony Rizzo. Descalso ($1 million buyout, $2.5 million buyout) and Lester ($10 million buyout, $25 million option) will almost certainly be bought out. Rizzo’s $16.5 million option, the final one on his deal before he reaches free agency after 2021, will almost certainly be exercised.

The other Cubs free agents this winter are Andrew Chafin, Tyler Chatwood, Billy Hamilton, Jeremy Jeffress, Jason Kipnis, Cameron Maybin, Josh Phegley and Jose Quintana. I’ve already written an article about Quintana and another about Jeffress and whether they should be retained and will have articles on some of the others listed above in the coming days.

Here are some other dates to note this fall and winter:

Monday, November 2: The finalists for the annual awards from the Baseball Writers’ Association of America will be announced on MLB Network at 5 p.m. CT.

Tuesday, November 3: The winners of the 2020 Rawlings Gold Glove will be announced on ESPN at 6 p.m. CT. The Cubs have seven finalists, including Willson Contreras and Kyle Hendricks.

Thursday, November 5: The Silver Slugger Awards presented by Louisville Slugger will be announced on MLB Network.

Friday, November 6: The announcement of the Rawlings Platinum Glove Winners and the Gold Glove Team will be announced on MLB Network at 5 p.m. CT.

Monday, November 9: The winners of the AL and NL Jackie Robinson Rookie of the Year Awards will be announced on MLB Network.

Tuesday, November 10: The winners of the AL and NL Manager of the Year awards will be announced on MLB Network.

Wednesday, November 11: The winners of the AL and NL Cy Young Awards will be announced on MLB Network.

Thursday, November 12: The winners of the AL and NL Most Valuable Player Awards will be announced on MLB Network.

Friday, November 20: This is the deadline for teams to place players who are eligible for the Rule 5 draft on the 40-man roster. Those players must be added by 7 p.m. CT on this day to protect them from being selected in the Rule 5 draft.

Players who signed professional contracts at age 18 or younger must be added to the 40-man roster within five seasons or they’ll become eligible. Players who signed at 19 or older must be put on the 40-man roster within four seasons after signing a contract.

Wednesday, December 2: Teams must decide on whether to tender contracts to club controlled players on their 40-man roster. This is commonly known as the “non-tender deadline” and it happens on this day at 7 p.m. CT.

Albert Almora Jr., Rex Brothers and Jose Martinez are likely non-tenders from the current Cubs 40-man roster. Others on the bubble include Duane Underwood Jr. and Dillon Maples as well as James Norwood, noted above. If the Cubs are really looking for cost savings, they could even non-tender Kyle Schwarber, though it’s more likely Schwarber could be traded.

Monday, December 6 through Thursday, December 10: The MLB Winter Meetings are scheduled for these dates at the Omni Hotel in Dallas. It is very likely that these will not be held at that location due to the pandemic and instead will be conducted in some sort of remote fashion, though nothing has been announced as of now.

Friday, January 15, 2021: This is the deadline for arbitration-eligible players and teams to agree to contract terms, at 12 noon CT. If they don’t, each will submit a salary figure for 2021 and an arbitration hearing will be scheduled for sometime in February, though agreements between players and teams can still be made up to the hearing date. Cubs arbitration-eligible players for 2021 are Albert Almora Jr., Javier Baez, Kris Bryant, Victor Caratini, Willson Contreras, Ian Happ, Jose Martinez, Colin Rea, Kyle Ryan, Kyle Schwarber, Ryan Tepera and Dan Winkler. As noted above, Almora and Martinez are likely non-tenders for next season.

January 15-17, 2021: These would have been the dates of the annual Cubs Convention at the Sheraton Chicago, but as another nod to COVID-19, the convention was cancelled last July.

Monday, February 15, 2021 (approximate date): Cubs pitchers and catchers report to Spring Training at Sloan Park in Mesa, Arizona, with position players reporting a day after that. In reality, most players wind up in camp well before these deadlines.

Saturday, February 27, 2021: Cubs open the Cactus League season against the World Series champion Dodgers at Sloan Park.

Thursday, April 1, 2021: The Cubs host the Pirates at Wrigley Field to open the 2021 season.