2021-2022 MLB Offseason Schedule

The Boston Red Sox season is over, and now begins the long winter ahead of what we’re all hoping is another step in the right direction in 2022. The World Series is still going on, kicking off Tuesday night in Houston, but the offseason is not too far away now. Below are some key dates for the winter, along with some Red Sox-specific notes where applicable. We’ll keep this pinned on the front page for reference all winter.

Day after World Series: Free Agents File

The latest the World Series can go this year is November 3, which means the latest free agents will file is November 4, and it will likely be earlier than that. The following players from the Red Sox roster will enter the open market:

• Eduardo Rodriguez
• Adam Ottavino
• Hansel Robles
• Travis Shaw
• José Iglesias
• Danny Santana

Five Days After World Series: Start of free agency, plus more

When free agents hit the open market, they can’t actually sign with other teams for at least five days, leaving it as something of an exclusive negotiation window for former teams. Five days after the World Series wins, the frenzy can begin. (Though it’s not likely to begin this year due to the CBA situation.)

In addition to free agency starting, five days after the World Series also marks the deadline for option decisions to be made. The Red Sox have a few of those decisions that are going to be made this year. J.D. Martinez has a player option for $19.35 million, and right now it seems more likely he’ll stick in Boston. Kyle Schwarber has an $11 million mutual option, and it’s all but certain that will not be executed on both sides. The Red Sox have team options for Christian Vázquez, Garrett Richards, and Martín Pérez. The two latter options are unlikely to be picked up, but the $7 million option for Vázquez will be one of the most interesting early-offseason decisions.

And then finally, five days after the World Series is the deadline for teams to extend qualifying offers to impending free agents. Schwarber is ineligible as he was traded midseason. Rodriguez is unlikely to get one, leaving Martinez as the only possible Red Sox free agent to get the deal. He would certainly get it if he did decline his option as the qualifying offer is for less than his option, but as we said right now it seems more likely he will not opt out.

11/2: Gold Glove winners announced

The Red Sox could have candidates with Christian Vázquez, Enrique Hernández, and Hunter Renfroe.

11/4: Silver Slugger winners announced

As we learned on Monday, Boston does have three finalists in Xander Bogaerts, Rafael Devers, and Renfroe.

11/8: Rookie of the Year announced

Bobby Dalbec came on strong in the second half, but probably didn’t do quite enough to get this one. Randy Arozarena is the favorite.

11/9: Manager of the Year announced

Alex Cora will certainly get some consideration here, but it will be interesting to see exactly how much given his history with the Astros.

11/10: Cy Young announced

Nathan Eovaldi will appear on ballots, but it would be a big surprise if he won. It’ll likely come down to Robbie Ray and Gerrit Cole on the AL side.

11/11: MVP announced

Both Rafael Devers and Xander Bogaerts should get some mid- or down-ballot love, and Eovaldi could get a vote or two as well. But this is almost certainly going to Shohei Ohtani.

15 days after World Series: Deadline to decide on qualifying offer

Players have 10 days after receiving the qualifying offer to make a decision as to whether or not they will accept it. As we said above, more than likely the Red Sox will not hand out any offers.

11/19: Rule 5 Protection Deadline

Teams have until this date to place Rule 5-eligible minor leaguers on the 40-man roster to protect them from the Rule 5 Draft. The Red Sox have some interesting decisions to make this year. Sox Prospects has the full list of eligible prospects here. Notable names who are eligible this year, in no particular order, are:

• Jeter Downs, IF
• Gilberto Jimenez, OF
• Brayan Bello, RHP
• Josh Winckowski, RHP
• Thad Ward, RHP
• Kutter Crawford, RHP
• Kaleb Ort, RHP
• Durbin Feltman, RHP
• Tyler Dearden, OF
• Pedro Castellanos, 1B/LF
• Ceddanne Rafaela, UTIL
• Joan Martinez, RHP

12/1: Non-Tender Deadline

Teams have until this date to non-tender their arbitration-eligible players, who would then hit the open market as a free agent. The following players are arbitration-eligible for the Red Sox this winter, along with their 2021 salaries and their projected 2022 salaries from MLB Trade Rumors.

• Rafael Devers ($4.575M; $11.1M)
• Hunter Renfroe ($3.1M; $7.6M)
• Alex Verdugo ($649K; $3.2M)
• Nick Pivetta ($613K; $3.2M)
• Kevin Plawecki ($1.6M; $2.0M)
• Ryan Brasier ($1.25M; $1.4M)
• Christian Arroyo ($581K; $1.1M)
• Josh Taylor ($580K; $1.1M)

The only potential non-tender candidate I see here is Plawecki. I think the Red Sox like him, but if they think either Connor Wong or Ronaldo Hernández is ready for backup duties, they could free up a roster spot. Otherwise, some players like Renfroe could be a trade candidate, but the salaries seem reasonable enough to tender them contracts.

12/2: CBA expires

And here is the big key date for the coming offseason. Everything prior to this point will continue as normal, but if no deal is completed by this point the owners will lock out the players and a freeze will go into place for the winter. All eyes are on this date around the league.

12/5-12/9: Winter Meetings*

*Pending CBA

After a virtual Winter Meetings last year, things are supposed to be back in-person in San Diego. If there is no CBA, though, there won’t be a Winter Meetings, at least as we’re used to it. If it does take place, it is a big time in the winter for trades and other hot stove action.

12/9: Rule 5 Draft*

*Pending CBA

Again, this won’t happen at this point without a CBA, but if things are running normally the Rule 5 Draft will take place on this date. Chaim Bloom’s Red Sox have had a lot of success in this draft, both in the major-league and minor-league portions, the last couple of years. Garrett Whitlock and Jonathan Araúz both remain in the organization after being selected the last couple of drafts.

1/14: Arbitration figures exchanged*

*Pending CBA

As the years have gone on, this has become more and more important of a date on the offseason calendar as more and more teams have taken a file and trial approach. That means that once arbitration figures are exchanged teams stop negotiating and go straight to an arbitration hearing.