Congratulations to the Milwaukee Brewers on winning the 2026 World Series, the first World Series title in their 58-year franchise history.
With that, baseball’s offseason commences. Here’s a handy calendar to help you fill your fall and winter until Opening Day 2027.
Presuming, that is, that there’s no interruption in the 2027 season due to a likely lockout by MLB team owners of MLBPA members when their collective bargaining agreement expires Dec. 1. How long that lockout goes will determine whether
and/or when some of the things listed in this calendar will actually happen. I’m listing dates as scheduled as of the date of this post, October 29, 2026. As always, we await developments.
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 2027 season will automatically become free agents (in fact, officially were as of earlier this morning, 8 a.m. CT). 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, although players can re-sign with their original team during this period.
At the end of the quiet period (Monday, Nov. 2 at 4 p.m. CT), clubs must decide whether or not to extend one-year qualifying offers to their free agents. The qualifying offer for 2027 is $23,15 million, up 5.1 percent from $22.025 million last year. The Cubs will certainly give Seiya Suzuki a qualifying offer. Two other Cubs, Ian Happ and Matthew Boyd (who has a mutual option that will likely be declined), might get a QO as noted in this article here last month. Players who receive a QO then have to decide whether or not to take it — note the deadline below. If they don’t, they are immediately eligible to sign with another team. Last year, 13 players were given a QO and four accepted, including, as you know, Cubs left-hander Shōta Imanaga, who is now a free agent. Players can only get a QO once, so Imanaga is now an unrestricted free agent.
Other Cubs who are unrestricted free agents: Kevin Gausman, David Peterson, Aaron Civale, Tyrone Taylor, Michael Conforto, Tyler Austin and Trent Thornton.
The end of the five-day quiet period is also the deadline to settle 2026 contracts with opt-out clauses, player options, club options and mutual options.
Here are the Cubs players with those clauses/options.
Besides Boyd, three other Cubs have mutual options for 2027: Hunter Harvey, Carson Kelly and Caleb Thielbar. Mutual options are almost always declined by the player; in Harvey’s case the Cubs will likely decline and they almost certainly will decline with Thielbar as well. With Kelly, I’d like to see the Cubs work out a deal for another year.
Two Cubs have team options: Colin Rea ($7.5 million) and Jacob Webb ($2.5 million). I’m not sure what the team will do with Rea, but they’ll almost certainly pick up Webb’s inexpensive option.
One Cub has a player option: Clay Holmes ($12 million). We discussed that here a few weeks ago.
At the same time, teams are required to move all players on the 60-day injured list back to the active roster. The Cubs have quite a few players currently listed on the 60-day IL (in addition to Austin and Harvey, mentioned above): Ben Brown, Porter Hodge, Cade Horton, Riley Martin, Phil Maton, Shelby Miller and Justin Steele. With all the free-agent departures noted above, there will be plenty of room to add back all those players.
Here are all the players who officially became free agents this morning, listed by position. There could be others after various contract clauses are exercised, or not.
Here are some other dates to note this fall and winter.
Sunday, Nov. 1: Rawlings Gold Glove winners will be announced live on ESPN at 8 p.m. CT.
Monday, Nov. 2: The National Baseball Hall of Fame announces its eight-person Contemporary Baseball Era Players ballot for managers, executives and umpires.
Monday, Nov. 2: BBWAA award finalists announced on MLB Network at 5 p.m. CT.
Thursday, Nov. 5: Silver Slugger finalists announced at 10 a.m. CT by Louisville Slugger.
Friday, Nov. 6: MLB Players Alumni Association (MLBPAA) announces its Heart & Hustle Award winner live on MLB Network.
Friday, Nov. 6: Rawlings Gold Glove Dinner in NYC and announcement of Platinum Glove winners.
Sunday, Nov. 8: Arizona Fall League Fall Stars Game on MLB Network at 7 p.m. CT.
Monday-Wednesday, Nov. 9-12: General managers meetings in Las Vegas.
Monday, Nov. 9: The Jackie Robinson Rookie of the Year Award winners will be announced for the National and American Leagues live on MLB Network at 6 p.m. CT.
Tuesday, Nov. 10: Manager of the Year awards will be announced for the National League and American Leagues live on MLB Network at 6 p.m. CT.
Wednesday, Nov. 11: AL and NL Cy Young awards will be announced live on MLB Network at 6 p.m. CT.
Wednesday, Nov. 11: The Hank Aaron Award winners, Comeback Players of the Year, Mariano Rivera & Trevor Hoffman Relievers of the Year, Edgar Martinez Outstanding Designated Hitter of the Year, selections for the All-MLB First and Second Teams, the MLB Executive of the Year Award, and several AUSL (Athletes Unlimited Softball League) awards will all be announced live from Las Vegas on MLB Network at 8 p.m. CT.
Thursday, Nov. 12: MVP awards for the NL and AL will be announced live on MLB Network at 6 p.m. CT.
Saturday, Nov. 14: Arizona Fall League Championship Game on MLB Network at 7 p.m. CT
Monday, Nov. 16: The 2026 BBWAA Hall of Fame ballot will be released, with voting taking place through December 31.
Tuesday-Thursday, Nov. 17-19: Owners meetings in New York.
Tuesday, Nov. 17: Players who have received qualifying offers must accept or reject them by 3 p.m. CT. Players accepting the offer, obviously, remain with their previous team. Players who reject the offer become free agents attached to draft pick compensation. Last year, 13 players received the $22.025 million QO, andfour accepted: Imanaga, Gleyber Torres, Brandon Woodruff and Trent Grisham.
Tuesday, Nov. 17: Teams must add eligible minor leaguers to their 40-man rosters by 5 p.m. CT or risk losing them in the Rule 5 Draft. Players 19 or older drafted or signed no later than 2023 and players 18 or older drafted no later than 2022 are Rule 5 Draft eligible this year, as well as players signed internationally no later than 2022.
Tuesday, Nov. 17: Silver Slugger Awards will be announced for each position by Louisville Slugger.
Friday, Nov. 20: The MLB non-tender deadline (7 p.m. CT). All teams must offer their pre-arbitration and arbitration-eligible players a contract for 2027 by this date. Players who do not receive a contract offer are considered “non-tendered” and become free agents. This date was moved up from early December to the Friday immediately before Thanksgiving in the current CBA. The following 12 Cubs are arb-eligible this year (projected salary estimates here): Justin Steele, Edward Cabrera, Braxton Garrett, Javier Assad, Tyler Austin, Miguel Amaya, Gabriel Arias, Ryan Rolison, Ethan Roberts, Michael Busch, Ben Brown and Daniel Palencia. Here’s how I see all those players resolving their arb deals for 2027; it’s possible that Arias and Roberts could be non-tendered.
This brings us to Dec. 1 and the likely lockout. Some of the events listed below might not happen, or be rescheduled. The Hall of Fame announcements should proceed regardless of the lockout.
Sunday, Dec. 6: The Contemporary Baseball Era Committee of the Hall of Fame will meet, with the results of their vote announced live on MLB Network at 7 p.m. CT. Anyone elected will be inducted in Cooperstown Sunday, July 27, 2027.
Monday-Wednesday, Dec. 7-9: MLB’s annual Winter Meetings in San Diego.
Tuesday, Dec. 8: The winner of the Hall of Fame’s 2025 BBWAA Career Excellence Award (for writers) will be announced.
Tuesday, Dec. 8: The MLB Draft lottery will take place. The 18 teams that did not make the postseason all have a shot at the No. 1 pick, though the worst teams have the highest odds. As a postseason team in 2026, the Cubs aren’t part of the lottery and will pick 22nd. The lottery will be held at 3 p.m. CT and the results will be televised on MLB Network at 4:30 p.m. CT.
Wednesday, Dec. 9: The winner of the Hall of Fame’s 2025 Frick Award (for broadcasters) will be announced.
Wednesday, Dec. 9: The Rule 5 Draft is the final event of the Winter Meetings. It will begin at 1 p.m. CT. Players taken in the Rule 5 Draft must remain on their new team’s major league roster all season or be offered back to their original team, although sometimes trades are arranged so teams can keep the player in their minor-league system. The Rule 5 Draft is usually streamed live on MLB.com.
Monday, Dec. 15: The 2026 international signing period closes at 4 p.m. CT. The 2027 signing period opens next month (see below).
Friday, Jan. 8: Teams must exchange salary figures with arbitration-eligible players by this deadline. The two parties can avoid arbitration by reaching an agreement any time prior to the beginning of an arb hearing. In many cases, players and teams agree to a contract before filing salary figures.
Friday, Jan. 15: The 2027 international signing period begins at 8 a.m. CT. Since MLB and the MLBPA couldn’t agree on an international draft for the CBA that expired in December, amateur players from countries outside the US, Canada and Puerto Rico can still sign with any team.
Friday-Sunday, Jan. 15-17: The Cubs Convention. Hotel room packages are on sale here and you can get weekend passes without the hotel stay here.
Tuesday, Jan. 19: The Hall of Fame announces its 2027 class in a live MLB Network broadcast at 5 p.m. CT. Any players elected from the BBWAA ballot will be inducted in a ceremony in Cooperstown on Sunday, July 25.
Late January-early February, dates TBD: Arbitration hearings for eligible players who have not reached agreement on contracts with their teams.
Wednesday, Feb. 10: Pitchers and catchers report to Spring Training.
Friday, Feb. 19: The Cubs open their 2027 Spring Training schedule against the A’s at HoHoKam Stadium in Mesa, Arizona. The next day, they will play their first 2027 spring home game at Sloan Park against the Reds.
Friday, March 19-Monday, March 22: MLB Spring Breakout tournament at various spring parks in both Arizona and Florida. Minor leaguers not on 40-man rosters can participate. Details will be announced later. This tournament will take place regardless of the status of any lockout.
Thursday, March 25: The Cubs open their 2026 season at Wrigley Field against the Cleveland Guardians, time TBD (but likely 1:20 p.m. CT). All 30 teams are scheduled to play that day.
