The 2019/2020 Offseason: Dates, Deadlines, What and When to Expect Things for the Cubs

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The 2019/2020 Offseason: Dates, Deadlines, What and When to Expect Things for the Cubs

Chicago Cubs

The 2019 offseason, like the 2018 offseason before it, is colored by our relatively vague expectations for change.

We knew the manager was going to change, and we also were pretty sure it was going to wind up being David Ross. We also knew that the infrastructure in the organization, itself, was going to change. But what about the big league roster? You know, the most important part of the big league team’s success or failure? The part that needed significant change last year at this time, was talked about as if it were going to receive significant change at this time last year, and then wound up basically being the same group as the year before? And performing even worse?

I don’t mean to sound entirely cynical about what the Cubs will or will not do this offseason, as they have routinely alternated enormous offseasons with relatively quiet ones. I think the front office knows that deep changes are necessary this offseason.

But what exactly is “the offseason”? What does it include? What happens when? When do we expect what?

With the World Series ending as soon as tonight, the offseason could begin as soon as tomorrow. So now seemed a wise time to lay out a roadmap of the important dates, deadlines, and timelines on the things that will be taking place in the coming months of “the offseason.” (Note: we have to use some approximations for dates not yet announced, or dates tied to the undetermined end of the World Series.)

October 31 – The day after the World Series ends, players eligible for free agency become free agents. The Cubs will likely have at least ten free agents:

  • RHP Steve Cishek, 33
  • LHP Cole Hamels, 35
  • LHP Derek Holland, 33*
  • RHP Brandon Kintzler, 35
  • RHP Brandon Morrow, 35*
  • RHP David Phelps, 33*
  • RHP Pedro Strop, 34
  • C Jonathan Lucroy, 33
  • OF Nick Castellanos, 27
  • UTL Ben Zobrist, 38

*options decisions due

Note that this does not include Yu Darvish or Jason Heyward, who can opt out, but I reckon they will not (Heyward is obvious, Darvish is only slightly less obvious). It also does not include Kendall Graveman, on whom the Cubs hold a $3 million club option that I think the Cubs may well pick up. I did include David Phelps, on whom the Cubs have a $5 million option that I expect they’ll decline. Same for the obvious decisions to decline options on Derek Holland and Brandon Morrow.

For some player-specific looks at each of these free agent decisions, see our conversations here, here, here, here, and here. There could be additional free agents if the Cubs wind up releasing or non-tendering others in the coming weeks.

October 31 through November 4 – 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 occasionally.

November 4 – Options are due five days after the World Series. Depending on decisions around baseball, the free agent pool could be further increased. There is also sometimes crazy 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 several options decisions that will impact their free agents, as noted above. These players will not fully join free agency until the options decisions are made.

November 4 – At the end of that five-day window, 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 $17.8 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 2020 Draft, and pool space in IFA.

The Cubs will have to make a qualifying offer decision on Cole Hamels.

Approximately November 4 to March 2020 – 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, minor league decisions, etc. Generally speaking, the hottest period is from about mid-November until mid-January, but there’s always a ton of stuff that happens outside of that window, too. In fact, in recent years, activity has been pushed later and later, with more of the action in the December to March window than typical.

November 11 to November 14 – The General Manager Meetings take place in Scottsdale, Arizona. A precursor to the Winter Meetings, the GM Meetings are an initial opportunity for teams to lay some early offseason groundwork for the moves that could come later. Teams also often have organizational meetings around this time, and the league sometimes makes rules decisions.

Approximately November 14 – 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, and that’s on the early side.

November 3 to November 14 – The various MLB awards are announced, starting with the Gold Gloves and concluding with the MVPs. The Cubs don’t have a lot of obvious candidates this year, and some of their obvious candidates got screwed out of even being a finalist.

November 20 – 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). The Cubs will purge some names from the 40-man roster over the coming weeks, 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 – Deadline for tendering contracts to players under team control but not signed for 2020 – 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 Kris Bryant, Javy Baez, Addison Russell, Kyle Schwarber, Willson Contreras, Albert Almora, and Kyle Ryan. 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 9 to December 12 – The Winter Meetings in San Diego, California. 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 12 – The Rule 5 Draft. The gist: 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 25-man roster, and then kept for good if the player can stick on the 25-man roster for almost all of the subsequent season. Typically, in this draft, rebuilding clubs do some selecting, and competitive clubs do some sweating.

You can see the full list Cubs players eligible for the Rule 5 Draft over at TCR. The Cubs should be able to protect upwards of five or six, if they so choose, but historically you see about three or four prospects rostered before the draft. 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. (We dig in deeper on the prospects as the rostering deadline on November 20 approaches.)

Approximately December 12 to January 31, 2020 – This is about the time that the Cubs will be sending out non-roster invitations to 2018 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 2020 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 10, 2020 – 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 17 to January 19, 2020 – The Cubs Convention. Fans will get a chance to see, meet, and hear from Cubs players, coaches and management, and the Cubs frequently like to use the Convention as an opportunity to introduce a big offseason acquisition to the fans. You can keep tabs on passes here. It figures to be a fun and busy event, as always.

Approximately February 11, 2020 – 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.



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.