The World Series is over, which means the 2013 season is over, which means we can officially start thinking about all those wonderful things the Chicago Cubs will do in the offseason. To that end, I thought it worth laying out a roadmap of the important dates, deadlines, and time lines on things over the next few months.

October 30 – As soon as the World Series ends, players eligible for free agency become free agents. The Cubs had four free agents – Scott Baker, Kevin Gregg, Dioner Navarro, Matt Guerrier – and it seems unlikely that any of the four will be re-signed within the next few days. Baker is possible, but he may want to see what’s out there in free agency first.

October 31 to November 4 – I say “next few days” because, 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 $14.1 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, which team would lose its first round pick in the 2014 Draft (unless their first pick is in the first 10 selections, in which case they lose their second round pick).

Approximately November 4 to March 2014 – The “Offseason.” The “Hot Stove.” The “Lukewarm Stove.” Whatever you want to call it, this is the period where a team’s roster is built for the subsequent year via free agency, trades, minor league decisions, etc.

November 11 – 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 11 to November 13 – 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.

November 11 to November 14 – The various MLB awards are announced. I don’t think you’ll have to concern yourself with these dates too closely this year. Again.

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 will include Jeff Samardzija, Luis Valbuena, James Russell, Travis Wood, Nate Schierholtz, Darwin Barney, Daniel Bard, Pedro Strop, and Donnie Murphy. Note that tendering a contract to these players is optional. All but Barney, Bard, and Murphy are locks to be tendered contracts, and I’d be shocked if Barney was non-tendered.

December 9 to December 12 – The Winter Meetings. The gist: MLB executives, agents, and players (as necessary) get together in Orlando 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 (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 I do find myself walking up at 3am to quickly check in and make sure nothing is breaking.

December 12 – 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. Last year, the Cubs took Hector Rondon in the Rule 5 Draft, and lost Starling Peralta (who was later returned by the Diamondbacks). The Cubs also lost a few minor leaguers in the minor league phase of the Rule 5, but none appear to have been of any consequence.

Approximately December 15 to January 31, 2014 – 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 2014 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.

Approximately January 2 to January 31, 2014 – This is approximately when teams and 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 17 to January 19, 2014 – 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 Convention will also be an opportunity to hang out with me, which I know is what you’re really excited about.

Approximately February 13, 2014 – Pitchers and catchers report to Spring Training, and our irrational excitement begins anew.



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