The MLB offseason is almost here, bringing a mixed bag of emotions for baseball fans. Some fans are excited to see who their favorite team will sign or trade for, others excited about the MLB draft and others, especially in the Florida and Wisconsin areas, are stoked to see if their team can finally capture their first World Series title.
Other fans are less excited -- potentially facing the realities of a closed competitive window and an incoming rebuild, others worried about another year of under-market spending. But I think it's clear that all baseball fans are starting to acknowledge that a lockout of the national pasttime, and a potential change to the structure of the game as we know it, is coming. Soon.
It's October 24. Game 2 of the World Series tonight. And while we all will enjoy the fall classic and watch a champion be crowned, it's also about that time to look forward to the deadlines and due dates that will put the 2026-27 offseason in the front of our minds, and the baseball history books.
Here are the deadlines you need to know for the 2026-27 MLB offseason.
1. The Day After The World Series Ends (Oct. 28-Nov.1)
MLB doesn't waste much time after a champion is crowned to return to business. On this date, which, depending on the amount of games played in the World Series, will fall between October 28 and November 1, is when players with expiring contracts officially become free agents. Expiring contracts come off the books, and the league enters into a 5-day exclusive negotiation window -- during this time, players can only talk with their "current" team. Teams can call players' agents to express interest in signing a player, but no official contract offer or discussion of terms can be had -- that's tampering.
During this time, don't expect anything more than players re-signing with their current team. I also wouldn't expect many fireworks here, unless Tarik Skubal decides to re-sign with the Dodgers without hearing any offers from other teams.
For the Nationals: According to Spotrac, the only player that is even eligible to do this is Miles Mikolas -- and we know that's not happening.
2. Rawlings Gold Glove Awards (Nov. 1)
Not to be overshadowed by what could also be happening on November 1 (depending on World Series results), the Gold Glove awards ceremony will be broadcast on ESPN, officially crowning baseball's best defenders from the 2026 season.
For the Nationals, Daylen Lile is a finalist for left-field, alongside Chicago's Ian Happ, and Milwaukee's Jackson Chourio.
3. Five Days After World Series Ends (Nov. 1 - Nov. 5)
This is probably the second biggest day of the entire offseason. At 5pm on this day, the exclusive negotiating window ends, and unrestricted free agents are allowed to negotiate with any team in baseball. This is where the big names like Tarik Skubal, Freddy Peralta, and Jazz Chisholm Jr., among a host of others can officially sign with another team.
This year's free agency class is considered to be somewhat weaker, but there are a few names that could find themselves hitting the open market if situations change with their current franchises. Opt-outs for the Mets' Bo Bichette, Padres' Michael King, and club or mutual options for Rays' Drew Rasmussen, Twins' Joe Ryan, and even Braves' Ronald Acuna Jr could add even more fireworks to winter that will already put baseball in national headlines.
Also on this date: The deadline for option decisions (club, player, mutual, vesting) and qualifying offers (valued at roughly $23 million). Players have 10 days to make a decision.
This date is the proverbial "play ball" to player movement this winter.
4. GM Meetings (Las Vegas, Nov. 9-12)
A typical catalyst for the hot stove and player movement, GM meetings this year could certainly carry a new echo, with a work stoppage and lockout looming on the horizon. No official league lockout business will happen here, the only deals getting struck will be between teams and free agents.
5. Silver Slugger Awards (Nov. 17)
Again, this event could likely be the lesser news of the day, but baseball's best bats (say that five times fast) will be recognized at this event. Finalists will be announced on November 2 -- it's fair to expect that James Wood (candidate last year) and CJ Abrams will likely be nominated after All-Star campaigns in DC.
6. MLB Owners Meetings (New York City, Nov. 17-19)
This is where the stove really gets hot. Every baseball fan in America now knows that the clock is ticking on baseball's current CBA, and that the financial structure of the game could look very different this time next year. Who knows, there might not even be baseball happening this time next year -- this lockout could get ugly.
No direct negotiation can happen with the MLBPA during these Owner's Meetings -- I predict this will be one final concerted effort from the owners to solidify their stance in favor of a salary cap.
Typically, conversations like the above can happen at MLB's Winter Meetings in early December. But again, with a lockout looming, don't hold your breath on that happening.
This could get ugly.
7. Non-Tender Deadline (Nov. 20)
This deadline is important -- here, teams are required to tender contracts to arbitration eligible players. Here's how it works.
If a team tenders a contract, that means that player will receive a contract from that team for the following season. Teams and players would then typically (if a lockout wasn't happening) take the time to try and agree on the salary for a 1-year deal. If the team and player do not agree, it goes to an arbitration hearing, where the contract value is decided by a panel of independent arbitrators.
If a team does not tender a contract to a player, that player immediately becomes an un-restricted free agent.
For the Nationals: CJ Abrams, Jake Irvin, Jacob Young, Richard Lovelady, Josiah Gray, Jake Bird, Mitchell Parker, and Ken Waldichuk are all eligible.
I'd certainly expect Abrams and Young to be tendered, likely Gray too. Arguments can be made for or against the others.
Again, thanks to the circumstances surrounding the following, final date, don't expect this process to happen any time soon.
8. Expiration of current MLB Collective Bargaining Agreement (CBA) -- (Dec. 1)
This is the grand-daddy of them all.
At 11:59pm on December 1, 2026, unless a deal between baseball's owners and the MLBPA is miraculously reached, the owners of all 30 franchises will lock out their players. Work will stop, and will not continue until an agreement for a new collective bargaining agreement is reached.
If you are not aware, baseball needs a collective bargaining agreement (CBA) to ensure that the players, alongside the owners of the teams, are in agreement about how revenue is shared, and how the game is played -- both on the field and off.
In short, baseball's owners want a salary cap -- to limit the spending power of big market teams, and to raise valuations on their franchises. Their argument is based on the concept of "a level playing field", debate that as you like.
Baseball's players think that is completely unfair and unacceptable, as the earnings of their clients (the players) would be severely hindered by enforcing a finite number to each teams payroll through a salary cap.
We won't spend more time debating this now, I, along with an increasing majority of baseball fans, believe that we will have ample time to debate this in the early months of the 2027 calendar year. But as it stands now, major doubt circles around Spring Training, and even Opening Day.
All that's left to do now is to enjoy the rest of what is shaping up to be a fantastic World Series matchup between the Rays and Brewers, then enjoy the fireworks of free agency...
... and then prepare for a long, nasty winter.
As usual, comment your thoughts below, or on X (@andrewpindc).
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