The 2017/2018 Offseason: Dates, Deadlines, What and When to Expect Things

The 2017 season may be over for the Chicago Cubs, but now the business of the offseason is upon us (well, it’ll start in earnest after the World Series ends, but, hey, we’re pretty close).

And unlike last offseason (in plenty of ways), this winter feels like an especially critical one for the Chicago Cubs, who figure to be the NL Central favorites once again, but have far more holes to fill than they did over the past two winters. And it’ll ll be especially challenging for the front office as they try to plug multiple holes, while saving powder for the huge 2018-2019 offseason (which features none other than Bryce Harper). We may even see a big-time trade or two.

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

Let’s lay out a road map of the important dates, deadlines, and time lines on things over the next few months. (Note: we have to use some approximations for dates not yet announced, or dates tied to the undetermined end of the World Series.)

Approximately November 2 – The day after the World Series ends (if it needs seven games), players eligible for free agency became free agents. The Cubs have as many as eight free agents:

  • Alex Avila, C
  • Rene Rivera, C
  • Jon Jay, OF
  • Jake Arrieta, SP
  • John Lackey, SP
  • Wade Davis, RP
  • Koji Uehara, RP
  • Brian Duensing, RP
  • And there could be more if the Cubs wind up releasing or non-tendering others in the coming weeks.

    Approximately November 2 through November 6 – 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.

    Approximately November 6 – At the end of that five-day window, teams must also 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 $18.1 million this year. (UPDATE: The final number came in at $17.4 million.) 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 in the 2018 Draft.

    The Cubs will almost certainly extend qualifying offers to Jake Arrieta and Wade Davis, and that’s it.

    Options decisions will also be 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 don’t have any options to worry about this time around, so the focus will be on players with options on other teams.

    Approximately November 7 to March 2018 – 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 pretty hot well into February.

    November 13 to November 16 – The General Manager Meetings take place in Orlando, Florida. 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.

    Approximately November 16 – 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 13 to November 17 – The various MLB awards are announced. The Cubs don’t have a lot of obvious candidates this year.

    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 2018 – 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 Justin Wilson, Hector Rondon, Justin Grimm, Leonys Martin, Kyle Hendricks, Tommy La Stella, Kris Bryant, and Addison Russell. 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 2 falls on a Saturday this year, which could push this deadline up to Friday, December 1, or back to Monday, December 4. I haven’t seen the official announcement yet, but often these deadlines are moved off of the weekend.)

    December 10 to December 14 – The Winter Meetings in Orlando, Florida. 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). For example, during last year’s meetings, the Cubs traded Jorge Soler to the Royals for Wade Davis.

    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 14 – The Rule Five 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. This is how the Cubs got Hector Rondon a many years ago, and they’ve also lost some players along the way.

    You can see the full list Cubs players eligible for the Rule 5 Draft over at TCR. The Cubs should be able to protect as many as five or six, if they so choose.

    Approximately December 15 to January 31, 2018 – 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 2018 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.

    Approximately January 12, 2018 – 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 12 to January 14, 2018 – 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 16, 2018 – Pitchers and catchers report to Spring Training, and your heart climbs up into your throat once again, not to depart for another eight and a half months.

    The OFFSEASON. Boom. There it is.

    Brett Taylor contributed to this post.

    written by

    Michael Cerami began covering the Chicago Cubs for Bleacher Nation as a part-time contributor in 2015. One year later, he joined Bleacher Nation full-time, covering the Chicago Cubs and Major League Baseball. Today, Michael runs Bleacher Nation, contributing as a writer (Cubs, MLB) and an editor for all sections of the site, including the Chicago Bears, Bulls, and Blackhawks, as well as MLB, NBA, NHL, and NFL. In 2019, Michael was the co-host of NBC Sports Chicago's Cubs Post-Game Show Outside the Ivy. You can find him on Twitter/X @Michael_Cerami

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