The 2016/2017 Offseason: Dates, Deadlines, What and When to Expect Things

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The 2016/2017 Offseason: Dates, Deadlines, What and When to Expect Things

Chicago Cubs

roadmap and compassThe World Series ended last week, which means the offseason has begun in earnest. Eh hem. Let me amend that.



But now the business of the offseason is upon us. Although it’s entirely possible this offseason will be much less dramatic for the Cubs than the last two, I’d argue it could be an even more enjoyable offseason, because we are all fairly well relieved of the stress of feeling like the Cubs *have* to do this or *have* to do that in order to build the team that finally does it. We still want to see the Cubs competitive in 2017, though, so the offseason remains very important.

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

So, let me lay out a road map of the important dates, deadlines, and time lines on things over the next few months.

November 3 – It already happened: the day after the World Series ended, players eligible for free agency became free agents. The Cubs have as many as nine free agents:

Trevor Cahill
Aroldis Chapman
Chris Coghlan
Jason Hammel (Cubs tentatively expected to pick up team option) (UPDATE: Nope. He’s a free agent.)
Dexter Fowler (will decline mutual option and become free agent)
Munenori Kawasaki
David Ross (expected to retire)
Joe Smith
Travis Wood

And there could be more if the Cubs wind up releasing or non-tendering others in the coming weeks.

November 3 through November 7 – Although players are immediately free agents, 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 7 – 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 $17.2 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 its first round pick in the 2017 Draft (unless their first pick is in the first 10 selections, unlike the Cubs, in which case they lose their second round pick). The obvious guy for the Cubs here is Dexter Fowler, but it’s important to follow all qualifying offer decisions, since it impacts the free agent market dramatically.

(This all assumes, by the way, that the qualifying offer system will remain in place for this offseason. The current Collective Bargaining Agreement is set to expire after this month, and the system could be overhauled significantly. There has been at least one report, though, that the current free agent system will stay in place for this offseason, regardless of the rest of the CBA.)

Options decisions will also be due by November 7. 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).

For the Cubs, as noted above, the options decisions will concern Dexter Fowler (he is going to be a free agent) and Jason Hammel (the Cubs will probably pick up their club option).

November 7 to March 2017 – 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 8 to November 10 – 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.

November 14 – Players must decide whether to accept the qualifying offer by this date. Big-time free agency won’t really get going until after this date, and that’s on the early side.

November 14 to November 17 – The various MLB awards are announced. The three obvious ones for Cubs fans to follow: Manager of the Year on November 15, Cy Young on November 16, and MVP on November 17.

November 18 – 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 days, 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 arbitration-eligible players (i.e., generally-speaking, players with three or more  years of service time, but fewer than six years of service time). This decision will include Jake Arrieta, Justin Grimm, Munenori Kawasaki (per his contract, apparently Kawasaki becomes a free agent, even though he’s not at six years of service time), Hector Rondon, and Pedro Strop, if they’re still around at that time. Note that tendering a contract to these players is optional.

December 5 to December 8 – The Winter Meetings in Washington, DC. 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 Starlin Castro, signed Ben Zobrist, finalized their John Lackey deal, and laid the groundwork for finalizing the Jason Heyward signing. The rest of baseball was crazy active, too.

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 I do find myself waking up at 3am to quickly check in and make sure nothing is breaking.

December 8 – 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 few years ago, and they’ve also lost some players along the way. Last year, the Cubs lost a whole bunch of players in the minor league phase.

With a significant number of intriguing players eligible for the Rule 5 Draft this year, it could be a nervous day for Cubs fans. You can see the full list of eligible players over at TCR. The Cubs should be able to protect as many as four or five or six, if they so choose.

Approximately December 15 to January 31, 2017 – This is about the time that the Cubs will be sending out non-roster invitations to 2017 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 2017 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. Chris Coghlan was a minor league free agent non-roster invitee before the 2014 season, thankyouverymuch. Munenori Kawasaki was one of the Cubs’ minor league signings last year.

Approximately January 11 to January 14, 2017 – This is approximately 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. The Cubs did not require any hearings last year.

January 13 to January 15, 2017 – 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 busy event, to say the least. Maybe not quite 5 million, but there will be a whole lot of attendees. Fortunately, even if you’re not able to attend, there’s usually quite a bit of interesting information rolling out throughout the weekend.

Approximately February 16, 2017 – 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.

Buckle up.

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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.