The Chicago Cubs have A LOT TO DO this offseason, with a boatload of departures, but also a roster that stands ready to compete in 2027. And with the World Series concluding last night, it’s time to lay out the roadmap for the offseason, giving you the dates and deadlines ahead. Get your calendar handy, because here are your MLB dates and deadlines, subject to the looming lockout …
October 29 – The day after the World Series ends, players eligible for free agency became free agents. The Cubs have a boatload of outgoing free agents this year, and the group could increase by way of options decisions, releases, and/or non-tenders.
October 29 to November 2 – Although players are immediately free agents after the World Series concludes, they cannot sign with a new team for five days. So, while teams can start reaching out to agents, no new contracts can be inked. This five-day period, then, serves as something of an exclusive negotiating window for teams with departing free agents. Usually you don’t see too many deals struck at this time, but it does happen very occasionally.
By November 2 – Contract options decisions are due around five days after the World Series (it’s actually specified in the player’s contract, but the maximum is five days). Depending on decisions around baseball, the free agent pool could be further increased. There is also sometimes trade activity in the days leading up to the option decision date (because, for example, Team X might have an option on Player A that they don’t want to pay, but Team Y definitely does want Player A at that option price – so the two teams consummate a trade at the last minute where Team X picks up the option, and then deals Player A to team Y).
Clubs also have to activate their 60-day IL players by this date and ensure their 40-man roster has no more than 40 players on it. That will not be an issue for the Cubs this year, due to the huge volume of free agents.
Eligible minor league free agents also hit free agency after this date.
November 2 – At the end of the five-day window following the World Series, teams must make decisions on whether make a “Qualifying Offer” to free agents – in short, in order to receive draft pick compensation should a free agent sign with a new team, his former team must first offer him a one-year deal worth the average of the top 125 salaries in MLB from the previous year. The qualifying offer amount is $23.15 million this year. If a player receives a Qualifying Offer, he can accept it, negotiate a different deal with his former team, or sign with another team, costing that team a pick (or picks) in the 2027 Draft, and pool space in IFA. (This entire system could change in the new CBA, of course, but teams have to operate for now with the system in place. From there, it’s up in the air exactly what would happen if the rules change midstream.)
The Cubs will obviously make a Qualifying Offer to Seiya Suzuki, and he’s probably the only one. Also, it’s worth watching other teams’ Qualifying Offer decisions, as any qualified free agent the Cubs sign would cost them their second rounder and fifth rounder next year, as well as $1 million IFA money (this is the penalty for large-market clubs that are over the luxury tax; again, this is subject to modification midstream by the CBA, but my guess is that, no matter what, the penalties will at least be in place for 2027).
Approximately November 2 through March 2027 – The “Offseason.” The “Hot Stove.” The “Lukewarm Stove.” Whatever you want to call it, this is the meaty period where a team’s roster is built for the subsequent year via free agency, trades, tender decisions, minor league decisions, etc. Historically speaking, the hottest period was always from about mid-November until mid-January, but there was always a ton of stuff that happened outside of that window, too.
In recent years, though, activity has been kind of bifurcated, with a ton of action happening from mid-November through mid-December, and then a lull, and then picking back up in late-January. We’ll see if this year follows course; it’s always hard to tell for sure, because sometimes the cycles are driven by external factors, like the pandemic, the lockout, the Ohtani free agency, orrrrrrr the expiration of the Collective Bargaining Agreement.
Yes, that’s the big story this offseason, and it makes all considerations of dates and deadlines a little wonky. The CBA expires December 1 at midnight, which is the biggest date of all. But its impact is going to be felt throughout November as teams and players plausibly rush to get deals complete before things shut down.
November 9 to November 12 – The GM Meetings in Las Vegas present an opportunity for teams and agents to start laying the very preliminary groundwork on deals. Teams often conduct organizational meetings around this time, too, so you might see more hiring/promotions/etc. announcements around this time or shortly thereafter.
November 2 to November 17 – The various MLB awards are spread out, announced by various entities at various times within a three-week period. The Cubs will mostly be represented by Pete Crow-Armstrong. Repeatedly.
November 17 – Players must decide whether to accept the Qualifying Offer by this date. It’s another bottleneck on free agency, because there are always some guys who are on the fence, and that can hold up other moves. I would not expect any significant free agents to sign before this date at the extreme earliest, though the impending lockout could plausibly move the urgency up a bit.
November 17 – This is also the deadline by which a team’s 40-man roster must be set for the purposes of the Rule 5 Draft (i.e., players already in the organization that the team would like to protect must be added by this date). It’s coming at the same time as the Qualifying Offer decision deadline this year, which means it’ll be a very busy day. In addition to the various QO and rostering decisions, there might also have to be a lot of transacting at the margins of the roster that day.
The Cubs will purge some names from the 40-man roster before this deadline, partly to open up spots for Rule 5 purposes. From there, the Cubs will decide on a few young players to add to the 40-man so that they cannot be selected in the Rule 5 Draft.
Guess what? The caveat arrives again: with the lockout looming, there’s a chance the Rule 5 Draft gets cancelled (the big league phase, anyway), and it’s POSSIBLE teams will count on that when making rostering decisions.
November 17-19 – The Owner Meetings in New York. This is usually about league business, but with the CBA expiring just a couple weeks later, you can bet that’ll be the heavy focus. Probably less about coming to an agreement (just ain’t gonna happen for a while), and more about how to operate during the lockout.
November 20 – The deadline for tendering contracts to players under team control but not signed for 2027 – i.e., players in their first three years of service time who can be “renewed,” and arbitration-eligible players (players with three or more years of service time, but fewer than six years of service time).
For the Cubs, most of the decisions this year are generally pretty straightforward, though there are a couple lower-dollar close calls.
Note that tendering a contract to these players is optional. Players shy of arbitration level service time are also sometimes non-tendered by this date.
December 1 at midnight – The bell tolls for baseball. The CBA expires, and the owners will lock out the players. All operations related to players on the 40-man roster must cease. Teams will have laid out offseason plans for these players in advance, if they’re smart, but then that’s it. For players in your organization and for big league free agents you might want to target.
December 7 to December 10 – The Winter Meetings in San Diego. Maybe.
Historically, the gist: MLB executives, agents, and players (as necessary) get together for a week. The Winter Meetings are a notable source of rumors, signings, trades, etc. While not all of the big offseason moves go down at the Meetings, there’s always a ton to discuss (not only amongst ourselves, but also amongst those MLB executives, agents, and players). In short, it’s an exciting time for folks who love rumors – like a mini version of the Trade Deadline, but spread out over three to four days. It’s not quite a Blogathon around here, but it’s pretty close, and we do find ourselves waking up at 3am to quickly check in and make sure nothing is breaking.
BUT. Again. Lockout. If that happens, then the Winter Meetings will not. That’s the smart bet right now, which makes me deeply sad.
December 8 – The MLB Draft Lottery. The Cubs made the playoffs, which means they aren’t in the lottery this year. I think this will still happen even during the lockout?
December 9 – The Rule 5 Draft. Players who’ve been in an organization’s system for a while (several years) without yet reaching the 40-man roster are eligible to be selected by other teams for a small fee, placed on that team’s 26-man roster, and then kept for good if the player can stick on the 26-man roster for almost all of the subsequent season. Typically, in this draft, rebuilding clubs do some selecting, and competitive clubs do some sweating. Then again, if you’ve built up depth in your farm system, you might also do a little sweating.
You can see the full list Cubs players eligible for the Rule 5 Draft over at TCR. The Cubs are not going to have an enormous crunch this year, but there are probably at least a couple prospects who’ll get protected on the November 20 deadline. Otherwise, they’ll roll the dice that some other team can’t realistically afford to use a 26-man roster spot on the guys the Cubs do not protect (or they’ll roll the dice that the Rule 5 Draft won’t happen). It depends on talent, on which guys are likely to be selected, and on how much 40-man roster space you need for other moves.
If the lockout is ongoing, the big league phase of the Rule 5 Draft will likely be cancelled. The minor league phase could go on, though, albeit with players who are much easier to protect, and thus much less impactful.
December 15 – The International Free Agency period closes for the year. Any final signings to be made with whatever pool dollars you have left, you have to make them official by this date.
Approximately January 1 to January 31, 2027 – This is normally about the time that the Cubs will be sending out non-roster invitations to 2027 Spring Training. The invitations go to prospects and players in the Cubs’ system who’ve not yet been placed on the 40-man roster, as well as veterans who are looking for a 2027 job, but have to “prove it.” You will roll your eyes at most of the minor league free agent non-roster invitees, but it doesn’t hurt to grab as many of the best as possible – and sometimes it pays off. We’ve seen it many, many times before.
Of course, if Spring Training doesn’t look like it’s going to happen on time, then all of this changes.
January 8, 2027 – This is when teams and arbitration-eligible players will submit arbitration requests (each side picks a number – we’ll have more on those details when the dates approach), and then hearings will be set, if necessary, for early February. Yada yada lockout yada yada.
January 15, 2027 – The next International Free Agency period opens up. Many deals that were totally-not-already-agreed-to will be made official on this date. It is plausible that this will continue as normal during the lockout, which is what happened last time.
January 15 to January 17, 2027 – The Cubs Convention! Here’s hoping it actually happens.
February 2027 – The next season begins new Spring Training. Of course, there will still be some “offseason” business being transacted as Spring Training goes on, so we can’t quite call it the end of the offseason. But it certainly marks the official transition into the 2027 season …
… unless things are still shut down. Which is what happened last time. There was not a new agreement in place until March 10, with an abbreviated Spring Training kicking in soon thereafter and Opening Day punted to April 7.
Will history repeat itself? The sides seem even more dug in, and the next pain point might not come until late-May (when 60 games are lost, the national TV deals roll over for another year instead of coming to market when the owners would like, and thus that COULD be the range where the sides finally feel enough sting to get a deal done, sadly).
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