The 2026 MLB season is officially over after the Milwaukee Brewers were crowned World Series champions on Wednesday night. That would usually begin our transition into an offseason of 40-man roster decisions, free agent signings, trade rumors leading into spring training. However, this will not be a typical offseason.
Instead, the black cloud lingering over this offseason is an expiring collective bargaining agreement and a potential lockout over the discrepancies between Major League Baseball and the MLB Players Association over the need for, and implementation of, a salary cap and floor system. As a result, the normal process of projecting free agent deals and trade targets has been replaced with wondering how many games of the 2027 season might be missed and what the future salary structure of the league will look like.
Yet, we do still have an MLB offseason to navigate, and we’re here to give you the key dates you need to have circled as we head into an uncertain few months.
Before diving into the biggest questions surrounding an uncertain MLB offseason, here’s a quick look at the important dates and deadlines to know for 2026-27.
- October 29: Players become free agents, trades once again allowed for players on 40-man rosters
- November 1–17: Major MLB awards announced, including Rookie of the Year, Cy Young and MVP
- November 2: Deadline for teams to exercise contract options, extend qualifying offers
- November 2 at 5 p.m. ET: MLB free agents can begin signing with other teams
- November 10-12: General Manager Meetings
- November 17: Deadline for players to accept or reject qualifying offers
- November 17: Deadline to protect eligible players from the Rule 5 Draft
- November 17-19: MLB Owners Meetings
- November 20: Non-tender deadline
- December 1: Current MLB collective bargaining agreement expires at 11:59 p.m. ET
- December 2: Potential lockout begins
- February 19, 2027: Scheduled start of MLB spring training games (subject to CBA negotiations)
When will we know if there is an MLB lockout?
The current Collective Bargaining Agreement (CBA) expires at 11:59 p.m. ET on December 1st. If there has not been an agreement by then, team executives, coaches, training staff, everybody will be prohibited from communicating with any player on the 40-man roster. Yes, that does mean that minor leaguers not on the 40-man roster would be able to have a normal offseason and even to begin their minor league season on time.
At this rate, it seems all but certain that there will be a work stoppage and a lockout on December 2. The question is how long that lockout might last and whether it will impact the 2027 regular season.
What can happen before a potential MLB lockout?
Anything. Teams are free to make any normal moves they would during an offseason. In fact, the Red Sox and Athletics already made a trade on Thursday. It wasn’t a major trade, but it was part of the typical roster clean-up that we see each MLB offseason.
All MLB teams have five days from the end of the World Series to finalize their 40-man roster. Since there is no 60-day injured list in the off-season, that means every team will need to activate all the players who ended the season on the 60-day injured list and add them to the 40-man roster. They will then need to either waive, designate for assignment, or trade any remaining players until that total sits at 40 players. Players who are waived or designated for assignment can choose to stay in the organization at Triple-A if they clear waivers, or they can become free agents. This is why Boston traded Nate Eaton, who was on the 40-man roster, to the Athletics for a low-level minor league pitcher. You’ll see a bunch of teams make similar moves over the weekend.
When does 2026-27 MLB Free Agency start?
Technically, it already has. After the World Series ends, MLB teams have five days to negotiate with their own free agents. After that five-day period ends, players are allowed to sign with any team. That means that Monday will be the final day teams can negotiate with their own free agents. Starting at 5 p.m. ET on Monday, players can begin signing with other teams.
Since players and teams have no idea what the MLB’s salary structure and economic model will be in the new CBA, we should expect a flurry of signings in the month of November. The last time the CBA expired, in December 2021, there were plenty of moves before the deadline because players wanted to have financial security and teams wanted to have a roster in place just in case the negotiations lasted right up until the beginning of the season. Also, teams that sign players early in November can communicate with them for an entire month, bring them to their facilities, and create offseason training/workout plans before they are forced to go dark by the lockout.
What is the qualifying offer this season?
Teams can extend a qualifying offer to a player within the same five-day deadline that they can negotiate with their own free agents. The qualifying offer for 2027 is a one-year, $23.15 million deal.
How long is the 2026-27 MLB Offseason?
Unfortunately, there is no answer to that question this season. As of now, 2027 MLB Spring Training is officially set to begin games on February 19, with players reporting earlier that month. However, none of that will happen until a new CBA has been agreed upon. Back in 2021-22, there was a lockout in the offseason but no regular season games were missed. Perhaps that’s the case again this year.
This also means the annual Winter Meetings, which are set to be held in December, will surely be canceled. Instead, executives from all 30 teams will meet in Las Vegas in the middle of November (November 10-12) to negotiate the CBA in person as well as feel out other teams’ interest in trades.
What will happen to the Rule 5 Draft?
This part is less clear. The Rule 5 Draft is centered around a rule that players who signed with a team at 18 years old or younger must be added to the 40-man roster within five seasons of signing. Players who are signed at 19 years old or older need to be added within four years. If they are not, they are eligible to be selected by any other organization in the Rule 5 Draft. They must then remain on the active MLB roster (or the injured list) for the entirety of the season or be offered back to their original team. Teams must add players to the 40-man roster by November 17 to protect them from the Rule 5 Draft.
That draft is usually held during the Winter Meetings, and if those are canceled, it would stand to reason that the Rule 5 Draft might be too, as it was in 2021. There is a minor league portion of the Rule 5 Draft, and that would still proceed.
When are 2026 MLB Awards announced?
- November 1: Rawlings Gold Glove Awards
- November 6: Platinum Glove Awards
- November 9: BBWAA Rookie of the Year Awards
- November 10: BBWAA Manager of the Year Awards
- November 11: BBWAA Cy Young Awards
- November 11: All-MLB Teams, Reliever of the Year Awards, Comeback Player of the Year Awards, and Outstanding Designated Hitter Awards
- November 12: BBWAA MVP Awards
- November 17: Silver Slugger Awards
Why is the MLB set to face a lockout?
This is a more nuanced question, and The Athletic has a great breakdown of it here. The short answer is that the owners want a salary cap and floor with the argument of creating more parity. Owners are faced with rising costs of player salaries and operations, while local media money is no longer in such large supply in all markets, and they want to ensure their enterprises can stay profitable, which is made easier when you can prevent salaries from getting too large.
As a result, MLB wants teams to be limited to a $245.3 million payroll in 2027, with a minimum of $154.1 million. That would also require teams to meet a multi-year “floor” salary that would be assigned for each season. Many teams this season, including the Guardians, who made it to the ALCS, were below what the salary floor would be, while teams like the Mets, Dodgers, Yankees, etc. were all above the top of the cap.
The issue is that we just saw the smallest market team in the entire league win the World Series, which hurts the argument for increased parity. Additionally, the proposed cap would also deliver less overall money to players than they make today. It would also create a fixed set of money that can be distributed to the players that would be predefined and unchanged even if the labor market changes. There would be new limits on the lengths of contracts and the value of contracts, and many players are worried that star players would still make a sizable amount of money, and the result would be that the vast majority of players in the league would have to take a significant salary hit.
As it stands now, the two sides are extremely far apart, and a deal doesn’t seem likely by the December 1 deadline. However, MLB has not missed regular season games due to a work stoppage since the 1994-95 strike. In 2022, games were rescheduled when Opening Day was moved from March 31 to April 7, but no games were missed. When games are missed, both the players and owners lose money, and since the owners and the league are hoping to negotiate new TV rights deals after the CBA is agreed to, it would be detrimental to them to take current games away from these TV stations with a lockout.
So, could we miss games in the 2027 regular season? Yes, but both sides have plenty of reasons to avoid having that happen.
