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.

  • cubfanbob

    When does the bidding for Tanaka start ?

  • cubzfan23

    “Walking” up, I assuming is waking up lol.

  • cubzfan23

    “Am”, lol

  • Patrick G

    Just read a NY Mets blog mentioning the Cubs are making Castro available and the Mets should be interested since they need a SS and they have a good pitching system the Cubs would need. I don’t buy into the Cubs trading Castro, but if so, what would be a good return from NY? I would think it would have to be Wheeler and Syndergaard. Is this too much or am I overvaluing Castro?

    • When the Music’s Over

      Pretty sure they’d give a hard no to that one.

    • YourResidentJag

      Also heard about this with respect to the Cards through MLBRadio via reports on CubsDen.

    • Frank

      The Lou Brock trade all over again.

  • Jamie

    “MLB Offseason 101 for Dummies.” I admittedly needed this, Brett. Thanks for explaining a lot that I have trouble, at times, explaining to my kids.

  • Jono

    This is an amazing write-up. It’s an example of why BN is my #1 source for Cubs news, information, rumors, and stupid arguments!

  • Randy

    I would be happy if barney wasn’t offered anything . He is strictly a backup only….

    • ssckelley

      I find it highly unlikely Barney will be non tendered.

  • Norm

    The problem with trading Castro is that the Cubs will price him based on his potential, where teams will price him based on 2013.

    That gap is too wide, a trade won’t happen.

    • SH

      The issue is, of course, that if he continues to play poorly he’s worth much less. It’s hard to dream on potential when you’ve seen back-to-back bad seasons and he’s a year older. But, if he improves, we keep a young and cost-controlled SS.

      So really, now’s the time to sell it: barely older than rookie phenom Michael Wacha, already three good seasons under his belt, we f-cked with his mechanics last year but he’s really still the same .775 OPS player, we have a crunch of IFs and don’t have the space for yet another young IF with upside, etc.

      • Voice of Reason

        back to back bad seasons?

        2012 wasn’t a bad year.

        2013 could be described as bad because we expected more. BUT, when compared to other shortstops in the league, it wasn’t bad.

        • SH

          The Voice of Not-Read-son

      • SH

        (or, now’s the time to *not* sell it — depending on what we think of the upside, others’ view of the upside, and our chances of actually filling our IF with talent going forward)

      • ETS

        I don’t think I disagree with your general idea, but “barely older than rookie phenom Michael Wacha” – it’s not a good idea to compare position players and pitchers by age. Pitchers usually peak much later in their careers.

        • SH

          Fair point. Go with Wil Myers — whoever. I listed, somewhere around here(…), four big rookies from this year who are all <1 year younger than Castro.

    • Voice of Reason

      No, the Cubs and any team they talk to about trading Castro will look at:

      1. His contract (very friendly contract for teams to take on)
      2. His age (he’s 23)
      3. His past (numbers in first thee years comparable to Robby Alomar, Derek Jeter and Edgar Renteria)
      4. His future potential

      A trade could happen. He is making peanuts for a starting shortstop with his past and potential.

    • JB88

      Given the price that Arizona paid for Gregorius, I think the Cubs could find a trade partner and could get a killing to make that trade.

      • Kevin


      • Norm

        What price did they pay? Trevor Bauer, who they couldn’t wait to get rid of?

      • AB

        Gregorius has a $60 million dollar contract??

  • Curt

    Hey Brett is there an obsessive managerial search coming soon just wondering .

  • JM

    A little too early to give up on Castro. One more year and I feel like a better determinan can be made. Has been way too good a hitter over three years to give up on him in a year where everybody will be evaluated.

  • itzscott

    Can’t see Castro being traded until the 2014 trade deadline to see if he can rebuild his value and at which time they’d be able to slide Baez into ss

    • On The Farm

      But if he returns to form to be traded at the 2014 deadline, will the Cubs really want to trade him? If he returns to All Star form (or even close to it) he is worth keeping based on his contract. They will either cut bait or hope he becomes 200 Hits Castro again.

      • http://deleted cub2014

        on the farm, i agree the cubs arent going to want to
        trade castro after his worst year. That would be silly,
        if he was part of a deal for wacha then yes he would
        be traded instantly (no chance though). If they trade
        him (which they wont) it will be in june or july after
        he gets off to a good start.

        • Kevin

          I believe Castro’s value is much higher than his performance last year. The Cubs are tanking on purpose (for better draft position) and allowing a losing attitude which brings performance down. You put Castro on a winning team and i believe you’ll get much better results.

          • Funn Dave

            Doubt it. It’s possible that a culture of losing may have contributed slightly to his decline last year, but if so it is just one small reason among many others.

    • ssckelley

      why not? Then the Cubs would have room to start Donnie Murphy.


  • Mr. Gonzo

    I would think that the FO would need to be absolutely face-melted Lost Ark-style by the awesomeness of an offer to move Castro this off-season. Based purely on buzz – and i’m not talking about your/my Halloween hangover – the focus seems to be extend or trade “Shawk” for a potential TOR + either one of SP/OF/C prospect, and make a serious play at Tanaka. Obviously no one in the Cubs’ FO can control the feverish pace of LA/NY’s checkbook…. I may or may not still be wearing my Captain Obvious outfit from last night.

    • Kyle

      Maybe they need to be face-melted. But I think about how little Castro meshes with their philosophies of OBP and defense, and how Epstein has a history of trading high-profile shortstops, and I just can’t help but wonder.

      • Betty Amie

        Did you not hear Theo say last season after they has messed up Castro and then told him to go back to his normal approach, that everyone didn’t need to comply? After all every individual is not the same, and these players are not the stepford husbands. Even using “The Cubs Way” you wouldn’t want it that way.

  • Spriggs

    Anyone know when the Cubs have their internal organization/strategy meetings? It has usually been right around this time of the year in Mesa, AZ.

  • kielovher

    105 Days until Pitchers/Catchers!

    • Dan Foote

      I, for one, am more excited about THIS, than the rest of the off season…………

  • CubbieBubba

    when is the spring training schedule released? My understanding is that it gets posted some time soon.

    • CubbieBubba

      and when do those tickets go on sale? (both important dates on my calendar)

      • Dan Foote

        Mine, too. I live to far away to make it to Wrigley, but I can get to Mesa in about 6 1/2 hrs, so I go as often as possible……

  • Die hard

    Time is of the essence– memo to Theo : sign Ozzie and get it over with

    • Jamie

      Don’t $&$#^)&! want $%#$#$%@ Ozzie %#@!&*) Guillen in any #@#!&^(#) Cubs dugout, any#$@#$@& time! Not #$@!&()% now! Not #!!(()$# ever!
      He can *$@()$@!go roll a (%%#@#! cigar with @#%^(_%Fidel!

    • Jamie

      Sorry. That was my fan rant about Ozzie through a Lee Elia filter.

  • Aaron


    Does going after Ubaldo Jimenez make any sense for the Cubs this offseason?

    • Norm

      I think Josh Johnson would better fit the Cubs expected target.

  • Funn Dave

    Cool idea for an article.

  • Ballgame

    I’d be extremely worried trading Castro could come back to bite us. He’s 23 and a hitting machine (note: not ’13). They tried to alter his approach this year and it didn’t work. He’ll be back to his original approach next season which will allow his avg. to get back above .300. Dude’s a natural hitter and this will be his 5th season. He has mental lapses in the field, but he’s admitted fault every one of those times which shows he’s holding himself accountable. I understand the right deal will make any player tradable, but trading Shark would make way more sense to me then trading Castro. Castro is locked up and Shark is gonna be due up, plus I think either player would yield same type of package…

  • Jason P

    Great stuff. Does anyone know exactly how the minor league phase of the rule 5 draft works? I can’t find much specific info on it anywhere. Players selected in the minor league phase don’t have to be kept on that team’s 25-man, correct? And are all the players eligible for the major league portion eligible for the minor league portion?

    I think the whole premise of the rule 5 draft is a bit ridiculous anyway. It’s main purpose is to prevent teams from keeping major league quality players in the minor leagues, but who would even do that? You’d think any team with usable players but no room in the majors at their position would trade them for a different player who does play a position of need.

    • Kyle

      In the AAA and AA phase, each team is allowed to protect a bunch more players. Anyone taken in those phases is full property of the new team, no rules about having to keep them on the roster for a year or anything. But because so many players can be protected, there’s not really anything worthwhile there.

      The rule 5 draft and it’s predecessors date back to the days before the amateur draft when the richest teams could just stockpile all the amateur talent in the world.

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