The Offseason Calendar and Its Impact on the Chicago Cubs 40-Man Crunch

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The Offseason Calendar and Its Impact on the Chicago Cubs 40-Man Crunch

Chicago Cubs

The big topic around the Cubs right now, internally and amongst roster nerds, is the Cubs’ pending 40-man crunch. Jed Hoyer discussed it the other day, and it’s shaping a lot of the decisions we see at every level above A-ball right now. The Cubs are not unique in having this problem, mind you. I imagine at least two-thirds of MLB teams are staring at more than 40 organizational names they like, and debating how best to allocate their spots.

As we continue to debate which players are best to keep, which players are best to let go, and which players are appropriate to risk losing, it strikes me that a review of five dates on the offseason calendar are especially important to keep in mind. (One of my favorite BN posts of every year is when Brett reviews the full offseason calendar, and have no fear that post will still happen. I’m talking about this specific set of dates now because I think it will help inform how we talk about the roster crunch.)

Day After the World Series

Two 40-man-roster-related things happen the day after the World Series ends. First, free agents earn that official designation, meaning they are dropped from the 40-man roster. Second, players on the 60-day IL and Restricted List that are under team control come back onto the 40-man roster.

The interesting thing about this for the 2022 Chicago Cubs? They have more players on the 60-day IL than they have pending free agents.

Number of players on 40-man roster right now: 40.

Number of players due for free agency: 3 (Miley, Smyly, Contreras)

Number of players on 60-day IL or Restricted List right now: 8.

Therefore, the day after the World Series, the Cubs will have to say goodbye to five players just to stay at a compliant 40-man roster. I think we know that Jason Heyward is going to be one of those players. Alexander Vizcaino is probably going to be forced to a decision about his playing future, and we could see a hint at the decision he’d made on this day.

Five Days After the World Series (And then 10 days after that, as it relates to one specific player)

For five days, the Cubs will have an exclusive negotiating window with their free agents. By the fifth day, the Cubs and Drew Smyly will have to decide on his mutual option (or a contract of a different structure (or is it a club option?)). He has indicated very much liking Chicago.

Or perhaps the Cubs will look to continue their relationship with Wade Miley? He is beloved in the clubhouse and has been effective when he’s been able to take the mound (which unfortunately hasn’t been often this year).

I’ll also note that minor league free agents hit the open market on this day, so if the Cubs want to prevent anyone from reaching free agency, they could do so by adding them to the 40-man roster. In my opinion, the only player likely to receive real consideration on this front is outfielder Yonathan Perlaza, who has a 120 wRC+ and 23 home runs in Double-A this year.

But the player we’re all going to be talking about during this time is Willson Contreras. Five days into the offseason, the Cubs must either agree to an extension with Contreras, or make a decision on whether to extend a qualifying offer to their star catcher. Contreras will then have 10 days to decide whether to accept it. As we know, a qualifying offer has previously served as a limiting factor in a player’s free agent earning potential (given that it requires the signing team to forfeit a draft pick, associated bonus pool space, and IFA bonus pool space).

I believe the Cubs are likely to extend Contreras a qualifying offer, and while I would guess Contreras is unlikely to accept it, I’m far less convinced on that piece given the potential impact on his market, and the signals we may have seen from the market on his perceived value at the trade deadline.

Ultimately, should any of the four players discussed in this section return to the Cubs around this time, a simultaneous 40-man roster-clearing will have to take place.

November 18: Protection Day

This is the date by which the Cubs will have to add the Rule 5 eligible players to the 40-man roster, thereby removing them from the Rule 5 Draft player pool (more on this here). When we’ve talked about the roster crunch before, this is the moment where we’ll really feel it, for at least two reasons.

The first reason is: it’s likely the Cubs will go into this week with a pretty full 40-man roster. So, in deciding how many players to protect, they will also have to decide which players to risk losing, or, in some cases, to let go (if additional 40-man space is needed). Players on the bubble – and there are so many of them – will likely have their futures decided on this day, or in the days leading up to it.

And then there’s the decision about whom to protect. At this moment, I see only three unequivocal locks (this list was five before Jeremiah Estrada and Hayden Wesneski were called up): Brennen Davis, Ben Brown, and Kevin Alcántara.

From there, it’s a game of chicken, as an organization has to figure out who other teams might poach in the Rule 5 if available to them, and then, what the likelihood might be of that player then sticking on a Major League roster for an entire season. I’ll spend much of the months of October and November going through individual player cases, so we’ll save that, but Brett recently wrote out the relevant names in this post.

I’ve also heard it suggested in a number of places that the Cubs should pull off a consolidation trade to alleviate their crunch. The issue I see is this: you can count on two hands the number of big, meaningful trades that happen in MLB before November 18. It’s just not common. A trade, or even a couple of them, are definitely possible for the Cubs, but I think it would be more like trading your Rule 5 eligible prospect for someone else’s slightly worse non-Rule 5 eligible prospect. Far less exciting.

In the end, I’m expecting the Cubs to protect about 4-7 players, which means that, in the days leading up to November 18, they will have to make another 4-7 subtractions.

December 2: The Tender Deadline

For players who don’t have guaranteed multi-year contracts, the tender deadline is a big one. This is when the Cubs have the option of not offering a 2023 contract to anyone under team control, both arbitration-eligible players and pre-arbitration players.

Here’s the catch: you can subsequently re-sign players that you non-tender (the Cubs did with Michael Hermosillo last year, for instance). But players you let go before the tender deadline (the guys to help fit in players on November 18 and the day after the season), those players can’t be added back to the 40-man until May 15.

So if there’s a player on the bubble that you’d love to keep under a different contract format (like on a minor league deal), keeping that player until the tender deadline is important. Perhaps this is relevant for a Tommy John surgery guy like Brad Wieck (or even Ethan Roberts), who you might want to keep rehabbing in the organization, but not have to carry them on the 40-man roster for the entire winter. Maybe this is why the Cubs being patient with Sean Newcomb, as they view him as someone to retain on a minor league deal, should he agree. If so, they might have to wait to actually non-tender him until December 2.

Given that the Cubs will go into December 2 with a full 40-man roster, their non-tenders on this date will also help allow them to sign players in free agency.

December 7: The Rule 5 Draft

This is when the Cubs are likely to experience a bit of pain. My expectation, these three months away, is that the Cubs do not select anyone in the Major League phase of the Rule 5 Draft, but that they likely lose a player or two or three. These things happen, it’s part of the game, and the Cubs have been on the other side of that coin before (with the results as good as Hector Rondon).

Heck, the Cubs have so much system depth that they might feel pain in the minor league phase of the Rule 5 Draft, too.

I’ll also note that any minor league contract signings that happen prior to December 7 leave those players eligible for the Rule 5 Draft. So you’ll often see teams reach agreements with players, but ask that the deal is not finalized until December 8.


I wanted to write this out so we can see that the reductions from the Cubs roster will mostly come in three batches: at the end of the playoffs, around the protection deadline, and at the tender deadline. There will be a strategy involved with what players go at what times, and it’s going to be fascinating to watch. We’ll have much more on these pending decisions in the weeks to come, I promise you that.

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Author: Bryan Smith

Bryan Smith is a Minor League Writer at Bleacher Nation, and you can find him on Twitter at @cubprospects.