The 2026-27 Offseason Begins

The Brewers finished off a dominant postseason with a 4-1 victory over the Rays last night. Now that Milwaukee’s first championship is in the books, Major League Baseball pivots to offseason mode. Unfortunately, the specter of a lockout looms over the horizon. The current collective bargaining agreement between Major League Baseball and the MLB Players Association expires at 11:59 pm Eastern on December 1. Negotiations on a new CBA are ongoing but there hasn’t been anything to suggest significant progress has been made. It won’t be a surprise if December 2 arrives with no deal in place. Virtually everyone in the industry expects the league will lock out the players at that time, to prevent them from having the leverage of calling a strike during the 2027 season. That is the way things played out when the last CBA expired in 2021. There are no guarantees that this winter will play out in the same way but it could be similar, so it’s worth going over the details of the 2021-22 offseason to provide a rough outline of what to expect. In 2021, the lockout and transaction freeze were anticipated. That led to a frenzy of activity in the weeks leading up to the deadline as teams, players and agents tried to get business done before the darkness arrived. Between the end of the 2021 World Series and the lockout, nine-figure free agent deals were signed by Corey Seager, Marcus Semien, Javier Báez, Max Scherzer, Robbie Ray and Kevin Gausman. Nine-figure extensions were signed by Wander Franco, José Berríos and Byron Buxton. Trades involving Junior Caminero, Adam Frazier, Jacob Stallings, Joey Wendle, Hunter Renfroe and others took place. The lockout put major league transactions on pause and threw other things out of whack. The Winter Meetings were cancelled. The Rule 5 draft, which normally takes place at the Winter Meetings, was postponed. The minor league portion of the draft still took place. The major league portion was in a limbo state until March, when it was officially canceled. The arbitration filing deadline, normally in January, was in March after a deal was in place. Arbitration hearings, which normally take place in February, were pushed into the 2022 season. The start of spring training and the regular season were both delayed, though a full 162-game season did take place. Once a new deal was in place on March 10 of 2022, transactions resumed. To make up for lost time, there was another flurry of activity in the weeks following the new agreement. Kris Bryant, Freddie Freeman, Trevor Story, Carlos Correa and Nick Castellanos signed nine-figure free agent deals. Matt Olson was traded to Atlanta and signed a nine-figure extension. Other trades involved Josh Donaldson, Mitch Garver, Chris Bassitt, Sonny Gray, Eugenio Suárez, Matt Chapman, Craig Kimbrel, AJ Pollock, Sean Manaea, Isaac Paredes and more. Below, you will find scheduled dates of importance for the upcoming winter. But given the aforementioned history, some of them are in flux more than usual. It’s possible the Rule 5 draft will eventually be cancelled again, though the players would like it to take place before the lockout. The MLBPA has already proposed moving the draft up to November in years where a CBA is expiring but the league has not agreed to that as of yet. With the Rule 5 protection deadline occuring in November, teams may have to make some tough calls about how to respond to the uncertainty. No team is going to take a risk on leaving a top prospect unexposed but the possibility of a canceled draft might push more borderline players into being left unprotected. The Winter Meetings may be canceled again. It’s unclear how that would impact the draft lottery, which was only implemented with the current CBA. The lottery has taken place at the Winter Meetings in the past few years. The typical offseason arbitration schedule will likely be delayed again. Time will tell if the pre-lockout activity is as frenzied as five years ago. This year’s free agent class is far weaker than the 2021 group. Apart from Tarik Skubal, there’s no slam-dunk candidate for a nine-figure free agent deal. It’s possible some teams will be more willing to wait for a new CBA before leaping into action. Here at MLBTR, the impending lockout doesn’t change our usual coverage plans. We will be publishing a list of the game’s Top 40 trade candidates later today. We’ve already released projected arbitration salaries from MLBTR contributor Matt Swartz and taken a position-by-position look at the upcoming free agent class while previewing the qualifying offer decisions for pitchers and position players. MLBTR’s Offseason Outlook series for Front Office subscribers is also nearly complete. Our Top 50 Free Agents post will be published on Monday evening after the finalization of option and QO calls. OCTOBER 29: Free agency begins for eligible players, but they aren’t permitted to sign with other teams for at least five days. Free agents no longer count against their previous teams’ 40-man rosters. Trades of players who were on the 40-man roster reopen for the first time since the deadline. NOVEMBER 1: Gold Glove winners announced. NOVEMBER 2: Free agents become eligible to sign with any team at 4:00 pm Central. All players or teams with contractual options/opt-out clauses must make their decisions before then. Teams have until the same time to decide whether to issue qualifying offers to eligible free agents. Teams must reinstate all players from the injured list and get their 40-man rosters in compliance. NOVEMBER 9: Rookie of the Year award winners announced. NOVEMBER 10-12: General managers meetings in Las Vegas, Nevada. The GM Meetings typically lay the groundwork for the offseason rather than spurring much roster movement in themselves. This winter’s GM Meetings could take on more significance than usual given the likelihood that the Winter Meetings will be canceled. NOVEMBER 10: Manager of the Year award winners announced. NOVEMBER 11: Cy Young award winners announced. NOVEMBER 11: Reliever of the Year, Comeback Player of the Year and Hank Aaron award winners announced. All-MLB teams revealed. NOVEMBER 12: MVP award winners announced. NOVEMBER 17: Players have until 3:00 pm Central to decide whether to accept the qualifying offer. If they accept, they’ll return to their previous team on a one-year, $23.15MM contract. Players who accept a QO, like all major league free agent signees, cannot be traded without their consent until June 15. Those who decline the QO are tied to draft compensation. MLBTR’s Mark Polishuk recently covered what each team would receive for losing a qualified free agent and the penalties that teams would pay to sign a player who declined a QO. NOVEMBER 17: Rule 5 protection deadline. Teams have until this date to add players who would otherwise be eligible for the Rule 5 draft to their 40-man roster to keep them out of the draft. NOVEMBER 17: Silver Slugger Award winners announced. NOVEMBER 17-19: Quarterly owners meetings in New York. Commissioner Rob Manfred typically speaks with reporters at this time. This will be an opportunity for league officials to discuss their strategy for CBA talks. NOVEMBER 20: Non-tender deadline at 7:00pm Central. Teams must decide whether to offer contracts to the arbitration-eligible and pre-arbitration players on their 40-man roster. They do not need to agree to salaries by this date, but there’ll be a flurry of salary agreements as players who might otherwise be non-tender candidates often lock in deals at slightly lesser than projected salaries to avoid being cut loose. Players who are non-tendered immediately become free agents without going through waivers. DECEMBER 1, 10:59 pm Central: Expiration of the 2022-26 collective bargaining agreement. Barring the extremely unlikely possibility that there’s a new CBA in place, Major League Baseball owners are expected to immediately implement a lockout to freeze all MLB activity. Teams will no longer be permitted to have any work-related contact with players who are on a 40-man roster, and all major league roster movement will cease until a new CBA is ratified. Note: MLB has technically scheduled a typical offseason post-lockout, though all league business after December 1 is highly unlikely to take place as scheduled. Those are marked with an asterisk. DECEMBER 6: Hall of Fame Contemporary Baseball Era Managers/Executives/Umpire Committee announcement. Formerly known as the Veterans Committee, the 16-person panel votes on eight candidates. Those under consideration are usually announced in early November; those who receive at least 12 votes on December 6 are elected to the Hall of Fame. This year’s committee will consider only managers/executives/umpires whose greatest contributions came in the 1980s or later. The Hall of Fame process is independent of the CBA and will take place as scheduled even during a lockout. * DECEMBER 7-9: Winter Meetings in San Diego, California. The Winter Meetings are usually the offseason’s busiest few days and annually feature ample free agent and trade activity. The major league portion of the Winter Meetings was canceled during the 2021 lockout and is expected to be scrapped this time as well. * DECEMBER 8: Amateur draft lottery. The lottery system was not yet in place during the last lockout, though one would presume this will be paused pending the ratification of a new CBA. * DECEMBER 9: Rule 5 draft. This typically concludes the Winter Meetings. It’s not likely to take place on December 9 this year. During the 2021 lockout, MLB canceled the big league portion of the Rule 5 draft. It’s possible the MLBPA will try to bargain with MLB to move this year’s Rule 5 draft up to the final few days of November to avoid that fate. The minor league portion of the Rule 5 draft, where selected players are not added to teams’ 40-man rosters, is not impacted by the lockout and will take place as scheduled. The vast majority of players selected in the minor league phase will not reach the majors with their new team. DECEMBER 15: Closing of the 2026 signing period for international amateurs. * JANUARY 8: Teams and arbitration-eligible players exchange salary filing figures. JANUARY 15: Opening of the 2027 signing period for international amateurs. The majority of the international signings for the year will be announced on this date, as virtually all the top prospects have reached handshake agreements by this point. Because these are minor league transactions, they progressed as scheduled during the 2021-22 lockout. JANUARY 19: Baseball Writers’ Association of America Hall of Fame announcement. * EARLY FEBRUARY: Arbitration hearings. These would not take place during a lockout. The filing exchange date would likely be set within a week or two of the ratification of a new CBA, and it’s possible that time limitations will push a few hearings into the regular season. * FEBRUARY 19: Spring Training games scheduled. *MARCH 24: Standalone Opening Night game; teams TBA if the season begins on time. * MARCH 25: Opening Day for the other 28 teams. MARCH 26: Triple-A Opening Day. The minor league baseball season will proceed as scheduled, though players on 40-man rosters would not be eligible to play in any affiliated games if there’s still a work stoppage.