cat calendarThe World Series ends tonight, which means, one way or another, the offseason begins in earnest tomorrow. 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 roadmap of the important dates, deadlines, and time lines on things over the next few months.

October 29 – As soon as the World Series ends, players eligible for free agency become free agents. The Cubs technically have just one impending free agent – Carlos Villanueva – but others may pop up eventually by way of releases or non-tenders. You’ll recall, the Cubs have a very crowded 40-man roster right now, and they need to clear some space.

October 30 to November 3 – 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. 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 $15.3 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 2015 Draft (unless their first pick is in the first 10 selections, like the Cubs, in which case they lose their second round pick).



Options decisions will also be due by November 3. The Cubs have a $5 million team option on Tsuhoshi Wada, which has been the subject of a great deal of discussion. Depending on decisions like the Cubs hold on Wada, 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 (it happened a couple years ago with Ervin Santana and the Royals, and it almost happened with the Cubs and Dan Haren/Carlos Marmol)).

November 4 to March 2014 – 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 10 – 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 10 to November 12 – The General Manager Meetings take place in Phoenix, 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 10 to November 13 – The various MLB awards are announced. I don’t think you’ll have to concern yourself with these dates too closely this year. Again.

Approximately 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). (I say “approximate” because this roster date is usually two weeks before the tender deadline, so that’s the date I’ve set for now.)

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 will include Wesley Wright, James McDonald, Chris Coghlan, Luis Valbuena, Justin Ruggiano, Travis Wood, Pedro Strop, Jake Arrieta, Felix Doubront, John Baker, and Welington Castillo, if they’re still around at that time. Note that tendering a contract to these players is optional. Baker and McDonald will be non-tendered for sure. Wright is a possibility, as are Wood and Ruggiano. I tend to think those three are ultimately tendered (if they haven’t already been traded), but a lot can change between now and then.

December 8 to December 11 – The Winter Meetings. The gist: MLB executives, agents, and players (as necessary) get together in San Diego 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 I do find myself waking up at 3am to quickly check in and make sure nothing is breaking.



December 11 – 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 couple years ago.

Approximately December 15 to January 31, 2015 – 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 last year, thankyouverymuch.

Approximately January 13 to January 16, 2015 – 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 16 to January 18, 2015 – 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. That might actually be a pretty big thing this year. The Convention will also be an opportunity to hang out with me, which I know is what you’re really excited about.

Approximately February 18, 2015 – Pitchers and catchers report to Spring Training, and our irrational excitement begins anew. Maybe slightly less irrational this year?




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