The 2015/2016 Offseason: Dates, Deadlines, What and When to Expect Things

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The 2015/2016 Offseason: Dates, Deadlines, What and When to Expect Things

Chicago Cubs

roadmap and compassThe World Series ended last night, which means the offseason has begun in earnest. Obviously expectations are high for excitement this offseason – I’d caution against having any specific hopes, but it should be exciting – and folks want to get rolling.

But what exactly is “the offseason”? What does it include? What happens when? When do I 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 2 – Today, the day after the World Series ended, players eligible for free agency become free agents. The Cubs have eight free agents:

Trevor Cahill
Chris Denorfia
Dexter Fowler
Dan Haren (has said he will retire)
Tommy Hunter
Austin Jackson
Jason Motte
Fernando Rodney

And there could be more if the Cubs wind up releasing or non-tendering others. Here’s your early discussion of the 40-man roster and how it’ll shake out, minus Jacob Turner, who’s already been waived and claimed by the White Sox. (And, sure enough, the Cubs already moved three other guys out from the 40-man roster today.)

November 2 to November 6 – 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 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 $15.8 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 its first round pick in the 2016 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.

Options decisions will also be due by November 6. The Cubs have no options decisions to make this year, nor do any Cubs players. But, depending on decisions around baseball (for example, Alex Gordon holds a player option for 2016 that he’s likely to decline), 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. We’ll look at this a little more closely later in the week.

November 6 to March 2015 – 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.

November 13 – 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. We’re still waiting for the first time a player actually accepts a qualifying offer. My guess is we see it happen for the first time this year, and I also expect we’re going to see an enormous number of qualified free agents.

November 9 to November 12 – The General Manager Meetings take place in Boca Raton, 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.

November 16 to November 19 – The various MLB awards are announced. The three obvious ones for Cubs fans to follow: Rookie of the Year on November 16, Manager of the Year on November 17, and Cy Young on November 18.

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 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, Chris Coghlan, Justin Grimm, Clayton Richard, Hector Rondon, Pedro Strop, and Travis Wood, if they’re still around at that time. Note that tendering a contract to these players is optional. I’ve discussed the tender decisions on these guys here and here. Jonathan Herrera and Taylor Teagarden would have been on this list, but the Cubs already made those decisions.

December 7 to December 10 – The Winter Meetings in Nashville, Tennessee. 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 signed Jon Lester, Jason Hammel, and traded for Miguel Montero. 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 10 – 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 lefty reliever Andrew McKirahan in the Rule 5, after which he was suspended for PEDs, and then put up a terrible year by ERA, but a very solid year by peripherals. There was also some activity on the minor league side of the Rule 5 Draft last year for the Cubs.

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, 2016 – This is about the time that the Cubs will be sending out non-roster invitations to 2014 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 2015 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. Jonathan Herrera fell into that category last year, for a less exciting, but more helmet-rubbing example.

Approximately January 12 to January 15, 2016 – 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 15 to January 17, 2016 – 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. The thing sold out weeks ago, which tells you just how excited Cubs fans are. 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 18, 2016 – 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.


A small sample of miscellaneous dates from last offseason for context:

  • The Russell Martin drama played out between November 5 and November 17.
  • He signed at virtually the same time as the Cardinals traded for Jason Heyward on November 17.
  • News of the Cubs signing Jason Hammel broke on December 8.
  • News of the Cubs trading for Miguel Montero broke on December 9.
  • News of the Cubs signing Jon Lester broke on December 10.
  • The Cubs traded for Dexter Fowler on January 19.
  • News of the Nationals signing Max Scherzer broke on January 21.
  • The James Shields drama played out between February 2 and February 9.

Obviously there was a great deal going on around baseball throughout that period, and with the Cubs before and after that period. The point is just to underscore that the offseason often kicks off quickly, and then spans a relatively long period of time where things are still happening.

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.