Congratulations to the Los Angeles Dodgers on winning the 2025 World Series, the ninth title in their franchise history. They’re the first team to win two straight since the Yankees won three in a row from 1998-2000.
With that, baseball’s offseason commences. Here’s a handy calendar to help you fill your fall and winter until Opening Day 2026.
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 2026 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 (Thursday, Nov. 6 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 2026 is $22.025 million, up from $21.05 million last year. The Cubs will certainly give Kyle Tucker a qualifying offer. No other Cubs are likely to get a QO this year. Other Cubs free agents: Ryan Brasier, Willi Castro, Aaron Civale, Brad Keller, Drew Pomeranz, Taylor Rogers, Carlos Santana, Michael Soroka and Caleb Thielbar. In addition, there are four Cubs with options/buyouts, noted below.
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.
The end of the five-day quiet period is also the deadline to settle 2025 contracts with opt-out clauses, player options, club options and mutual options. Here are the Cubs players with those clauses/options.
Andrew Kittredge has a $9 million club option or $1 million buyout. Colin Rea has a $6 million club option or $1 million buyout. Justin Turner has a $10 million mutual option or $2 million buyout.
Turner will certainly be paid the buyout. I’d expect the Cubs to keep Rea for $6 million. Kittredge — that’s a bit more complicated. He made $9 million this year and was productive. But he will be 36 in March — do the Cubs want to keep him another year at the same price? As always, we await developments.
Lastly, Shōta Imanaga has a complicated deal where the team and player both have options. Here’s a complete list of players who are in those contract situations heading into 2026, including this description of Imanaga’s choices:
Imanaga’s situation is one of the most complex of the offseason. The four-year, $53 million deal he signed prior to the 2024 season can go in a number of directions. First, the Cubs can trigger a three-year, $57 million club option that would pay Imanaga $20 million in 2026 and 2027, then $17 million in 2028. If Chicago declines that, Imanaga can exercise a $15 million player option for 2026; if that happens, the Cubs can add two more years and $42 million to his deal for 2027-28, or Imanaga would have another $15 million player option for 2027. It’s likely that he’ll be back with the Cubs next season, though exactly what his contract looks like at that point is anybody’s guess.
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 just one player currently listed on the 60-day IL: Justin Steele. He’ll be placed back on the active roster for now; since Steele might not pitch until mid-season, he could go back on the 60-day in March. As you can see on that roster link, there are 41 players listed, so someone will have to be removed to make room for Steele.
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. 2: Rawlings Gold Glove winners will be announced live on ESPN at 7:30 p.m. CT.
Monday, Nov. 3: The National Baseball Hall of Fame announces an eight-person Contemporary Baseball Era Players ballot.
Monday, Nov. 3: BBWAA award finalists announced on MLB Network at 5 p.m. CT.
Thursday, Nov. 6: National League Louisville Silver Slugger Awards will be announced for each position.
Friday, Nov. 7: American League Louisville Silver Slugger Awards will be announced for each position.
Friday, Nov. 7: Rawlings Gold Glove Dinner in New York and announcement of Platinum Gloves.
Monday-Wednesday, Nov. 10-13: General managers meetings in Las Vegas.
Monday, Nov. 10: 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. 11: 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. 12: AL and NL Cy Young awards will be announced live on MLB Network at 6 p.m. CT.
Thursday, Nov. 13: MVP awards for the NL and AL will be announced live on MLB Network at 6 p.m. CT.
Thursday, Nov. 13: 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 and selections for the All-MLB First and Second Teams will all be announced live from Las Vegas on MLB Network.
Monday, Nov. 17: The 2026 BBWAA Hall of Fame ballot will be released, with voting taking place through December 31.
Tuesday-Thursday, Nov. 18-20: Owners meetings in New York.
Tuesday, Nov. 18: 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, 12 players received the $21.05 million QO, but only one accepted, Nick Martinez.
Tuesday, Nov. 18: 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 2022 and players 18 or older drafted no later than 2021 are Rule 5 Draft eligible this year, as well as players signed internationally no later than 2021.
Friday, Nov. 21: The MLB non-tender deadline (7 p.m. CT). All teams must offer their pre-arbitration and arbitration-eligible players a contract for 2026 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 new CBA. The following four Cubs are arb-eligible this year (projected salary estimates here): Javier Assad, Reese McGuire, Eli Morgan and Justin Steele. As I noted a few weeks ago, the Cubs seem likely to non-tender McGuire and Morgan.
Sunday, Dec. 7: The Contemporary Baseball Era Committee of the Hall of Fame will meet, with the results of their vote announced live on MLB Network. Anyone elected will be inducted in Cooperstown Sunday, July 26.
Sunday-Thursday, Dec. 7-11: MLB’s annual Winter Meetings in Orlando.
Tuesday, Dec. 9: The winner of the Hall of Fame’s 2025 BBWAA Career Excellence Award (for writers) will be announced.
Tuesday, Dec. 9: 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 2025, the Cubs aren’t part of the lottery and will pick 24th. 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. 10: The winner of the Hall of Fame’s 2025 Frick Award (for broadcasters) will be announced.
Wednesday, Dec. 10: 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 2025 international signing period closes at 4 p.m. CT. The 2026 signing period opens next month (see below).
Thursday, 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.
Thursday, Jan. 15: The 2026 international signing period begins at 8 a.m. CT. Since MLB and the MLBPA couldn’t agree on an international draft for the current CBA, amateur players from countries outside the US, Canada and Puerto Rico can still sign with any team. This system will remain in place through at least Dec. 1, 2026, when the current CBA expires.
Friday-Sunday, Jan. 16-18: The Cubs Convention. Hotel room packages are on sale here and you can get weekend passes without the hotel stay here.
Tuesday, Jan. 20: The Hall of Fame announces its 2026 class in a live MLB Network broadcast at 5 p.m. CT. Any players elected will be inducted in a ceremony in Cooperstown on Sunday, July 26.
Late January/early February: Arbitration hearings for eligible players who have not reached agreement on contracts with their teams.
Wednesday, Feb. 11: Pitchers and catchers report to Spring Training.
Thursday, Feb. 19 or Friday, Feb. 20: The Cubs open their 2026 Spring Training schedule. The schedule has not been released yet and this post will be updated after that release.
Thursday, March 5: The 2026 World Baseball Classic begins in Tokyo, Houston, San Juan and Miami. The tournament runs 12 days and wraps with the championship game March 17 in Miami.
March, date TBD: MLB Spring Breakout. This post will be updated when details are announced.
Wednesday, March 25: Opening Day for MLB’s 2026 season in San Francisco with the Giants hosting the Yankees. This will be the only game that day and will be streamed exclusively on Netflix.
Thursday, March 26: The Cubs open their 2026 season at Wrigley Field against the Nationals, time TBD (but likely 1:20 p.m. CT). The Giants and Yankees will take the day off while the 28 other teams all open their seasons.
