The Chicago Cubs have a whole lot of turnover coming for their roster this offseason, but they nevertheless have a core that could compete just as well as the 2025 squad, if not better. You know, depending on what they do this offseason …
To that end, 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 …
This Weekend – The day after the World Series ends – so, either Saturday or Sunday – 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.
Approximately November 1 to November 5 – 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 Approximately November 5 – 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).
The Cubs have a number of options decisions to make, including Shōta Imanaga’s complex web.
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.
Approximately November 5 – 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 $22.025 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 2026 Draft, and pool space in IFA.
The Cubs will obviously make a Qualifying Offer to Kyle Tucker, 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 next year, as well as $500K in IFA money (this is the penalty for large-market clubs that are not over the luxury tax).
Approximately November 6 through March 2026 – 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 signing of the new CBA, the Ohtani free agency, etc. There always seems to be some significant externality each year, and the looming CBA fight – plus the reluctance of some teams to sign massive long-term deals right now – could be this year’s.
November 10 to November 13 – The GM Meetings and Owners Meetings in Las Vegas present an opportunity to conduct important league business, and also 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 21 – The various MLB awards are spread out, announced by various entities at various times within a three-week period. The Cubs are not likely to be super well-represented this year, though they do have some very good Gold Glove chances, and Cade Horton has a shot at the NL Rookie of the Year.
November 18 – 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.
November 18 – 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 (about which, more below; and also more soon).
November 21 – The deadline for tendering contracts to players under team control but not signed for 2026 – 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, the decisions this year are generally pretty straightforward, and not particularly extensive.
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 8 to December 11 – The Winter Meetings in Orlando, Florida. Let’s dance.
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.
December 9 – The MLB Draft Lottery. The Cubs made the playoffs, which means they aren’t in the lottery this year. But there is at least one potential pick impact that could affect them.
December 10 – 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 18 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. 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.
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, 2026 – This is about the time that the Cubs will be sending out non-roster invitations to 2026 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 2026 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. I mean, Brad Keller was one of these dudes.
January 8, 2026 – 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.
January 15, 2026 – The next International Free Agency period opens up. Many deals that were totally-not-already-agreed-to will be made official on this date.
January 16 to January 18, 2026 – The Cubs Convention! Here’s hoping, in addition to being a fun time, the Cubs also have some fresh faces to introduce.
February 2026 – It all starts again with a 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 2026 season …
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