The 2022-23 MLB Offseason: Dates, Deadlines, What and When to Expect Things

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The 2022-23 MLB Offseason: Dates, Deadlines, What and When to Expect Things

Chicago Cubs

For the first time since maybe the offseason after 2018, there are no real “yeah, but” statements you can make about the Chicago Cubs’ need to be aggressive. There is no massive payroll or long-term commitments. There is no freshly-arrived pandemic or looming lockout. There is no plan to tank and sell-off. Simply, the Cubs need to add impactful pieces to start competing. Sometimes it isn’t complicated.

This is a big offseason for the Cubs.

With the World Series now just a few games away from a resolution, I figured it was time to lay out the roadmap for the offseason, giving you the dates and deadlines ahead. Get your calendar handy.

Note where I say “approximately,” because those are dates that depend on when the World Series ends. That could come on November 5 or November 6. So, for purposes of those dates, I’m assuming the series goes the full seven games.

Approximately November 7 – The day after the World Series ends, players eligible for free agency become free agents. The Cubs have two-slash-three outgoing free agents:

C Willson Contreras, 30

LHP Wade Miley, 35

LHP Drew Smyly, 33

Why do I say “two-slash-three”? Well, technically, Smyly isn’t a free agent immediately after the season ends like Contreras and Miley, because his deal includes a mutual option. More on that in a moment.

Also, the Cubs are HIGHLY likely to have additional free agents in the weeks ahead, because there will be some non-tenders by the Cubs. Some could happen right away, and others might not come until the non-tender deadline on December 2.

Approximately November 7 through November 11 – 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.

Approximately November 11 – Contract options decisions are due around five days after the World Series (it’s actually specified in the player’s contract, but it’s usually right around here). 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).

As mentioned above, the option decision here is the mutual option between Drew Smyly and the Cubs, which I tend to think Smyly will not want to exercise (it is for $10 million with a $1 million buyout, so if he can do better than $9 million in free agency, he should not pick it up). There is mutual interest in a reunion, though, so it’s possible the sides work out a new deal in this period of time. Otherwise, Smyly will become a free agent.

Approximately November 11 – At the end of that 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 expected to be around $19.65 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 2023 Draft, and pool space in IFA.

The Cubs will make a Qualifying Offer to Willson Contreras, and he is highly likely to reject it. If so, and assume he then signs with a new team this offseason, the Cubs will get a compensatory draft pick after the second round of the 2023 Draft.

Meanwhile, 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 $500,000 in IFA money.

Approximately November 7 through March 2023– 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 pushed later and later, with more of the action in the January to March window than was previously typical.

November 7 to November 10 – 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.

November 14 to November 17 – The various MLB awards are announced, and the Cubs will not be represented.

November 21 – Players must decide whether to accept the Qualifying Offer by this date (they used to have just seven days after receiving a QO, but that’s since been increased to ten days). Big-time free agency won’t really get going until after this date, which makes for some funky timing because of the rostering deadline I’m about to mention. (UPDATE: This one has been mucked up, too. Per Jon Morosi, players now have only five days to decide on a QO, not tend days. So you’re looking at QO decisions due by November 16.)

November 18 – Yup, I just went backwards. I shouldn’t do that, because it’ll mess with you as you scroll, but I wanted to underscore how backwards this one is thanks to the way the season fell after the lockout. This is 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 BEFORE the Qualifying Offer decision deadline this year, and that’s just really weird. It means there might have to be a lot of transacting at the margins of the roster before that QO period is passed. I don’t think it’ll be a problem for the Cubs – because Willson Contreras is likely to reject his Qualifying Offer – but it’s definitely an extra layer of weirdness.

As for the 40-man projection decisions, Bryan talked about it last month, and we’ll hit it some more in the next couple weeks.

Meanwhile, 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).

December 2 – The deadline for tendering contracts to players under team control but not signed for 2023 – 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). This decision will include Ian Happ, Steven Brault, Franmil Reyes, Rowan Wick, Alec Mills, Brad Wieck, Nico Hoerner, Codi Heuer, Nick Madrigal, and Rafael Ortega. 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. (NOTE: There are MLB.com articles out there stating that the tender deadline this year is November 18, which would be the same date as the rostering deadline. That would be a substantial change from years past, and it’s possible they’re right – we still haven’t seen the full language of the new CBA. (UPDATE: This is now confirmed. The new tender deadline is November 18. They really made some substantial changes this year without really telling folks until now!))

December 4 to December 7 – The Winter Meetings in San Diego, California. Pacific Time. Get ready for some late nights.

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 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 7 – 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 extraordinary depth in your farm system (like the Cubs), 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 gonna need to protect at least five or six, but they might have to roll the dice on a few guys they really like, betting that some other team can’t realistically afford to use a 26-man roster spot on them. 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. More coming soon on the eligible prospects.

Approximately January 1 to January 31, 2023 – This is about the time that the Cubs will be sending out non-roster invitations to 2023 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 2023 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.

January 13, 2023 – 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 13 to January 15, 2023The Cubs Convention is finally back! Here’s hoping, in addition to being a fun time, the Cubs also have some fresh faces to introduce.

February 14, 2023 – It’s a day for love! Pitchers and catchers report to Spring Training, and your heart climbs up into your throat once again, not to depart for (hopefully) another eight and a half months. It’ll be nice to have a normal Spring Training for the first time since 2019. Woof.



Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.