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With perhaps one of the most pivotal off-seasons in recent memory in store for the Cubs, I thought it might be worth laying out the time line for what will happen over the next few months.

October 26 – Theo Epstein’s first non-media-dominated day as President of Baseball Operations for the Cubs. Among his first tasks will be discussing the compensation the Cubs owe the Red Sox for his services, as well as the compensation the Cubs will owe the San Diego Padres for Jed Hoyer and Jason McLeod. The compensation decisions are expected to be made within a week. With respect to Epstein compensation, Commissioner Selig says he’ll decide the matter if the two sides can’t agree by November 1.

Approximately October 27/28 - The Cubs are expected to name Jed Hoyer as the team’s General Manager, coming over from San Diego with Assistant General Manager Jason McLeod. (Note: Because of tonight’s delayed World Series game (just happened), this could be pushed back to next Monday, October 31).

October 27 to November 1 – Theo Epstein will meet with current manager Mike Quade and make a decision on his future with the team. Presumably, Quade will be dismissed, and Epstein, with input from Hoyer, will search for a managerial replacement. The Cubs will also have to make decisions on current coaches – only hitting coach Rudy Jaramillo and bench coach Pat Listach are under contract for 2012. The new manager will also have input on the coaches.

Approximately October 27 to November 1 – As soon as the World Series ends, the five-day period of exclusive negotiating rights with a team’s own free agents occurs. Similarly, this marks the period in which the Cubs will have to make a decision on Aramis Ramirez’s $16 million option for 2012 (which can be bought out for $2 million, and which can be voided by Ramirez). This is also the period in which Ryan Dempster will make a decision on his $14 million player option for 2012. Of the Cubs’ free agents, none are expected to be re-signed in this period.

Approximately November 1 to November 30 – The month of November will probably include a great deal of “getting their feet wet” for the new front office staff. Further, that staff will be searching for additions – more scouts, assistants, etc. – and the managerial search may yet be ongoing. There will also be an organizational review during this period (and beyond), where Epstein and Hoyer, among others, will go over each level of the Cubs’ organization, making decisions about minor league coaches, philosophies, players, promotions, etc. Indeed, a great deal of this decision-making process will carry forward over the next couple of years.

Approximately November 2 to March 2012 – 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. We’ll find out who is – and, perhaps more importantly this year, who isn’t – a Cubs for 2012.

November 7 to November 11 – The Chicago Cubs’ Organizational Meetings will take place were going to take place at this time. Theo Epstein has, according to reports this morning, moved the meetings to the second week of February. Whenever they happen, the meetings will be, among other things, a time for the organization to conduct a hyper-focused version of the preceding two entries. Given the new front office, it’s understandable that they are pushing the meeting back.

November 14 to November 22 – The various MLB awards are announced. I don’t think you’ll have to concern yourself with these dates too closely this year.

November 23 – The deadline for offering arbitration to free agents in order to secure compensation if that player leaves the team. In other words, if the Cubs want to get compensation for their Type A/B free agents who walk, this is the date by which they have to offer arbitration (a one-year contract for a to-be-determined amount, which the player may accept or reject). The primary guy on whom the Cubs will have to decide here is Carlos Pena. Depending on how the option decisions shake out, this could also include Ryan Dempster and Aramis Ramirez.

December 5 – The deadline for having the team’s 40-man roster set for purposes of the Rule Five Draft (about which, more below). Thus, you could see some roster moves being made in the week or two leading up to this date.

December 5 to December 8 – 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, the groundwork for those moves is frequently laid at the Meetings. 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. (No, I will not be having a 96-hour blogathon.)

December 7 – The deadline for free agents to accept offers of arbitration from their 2011 team.

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.

December 12 – 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 guys like Matt Garza, Geovany Soto, Jeff Baker, Randy Wells, Jeff Samardzija, and … Koyie Hill. Note that tendering a contract to these players is optional.

Approximately December 15 to January 31, 2012 – This is about the time that the Cubs will be sending out non-roster invitations to 2012 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 2012 job, but have to “prove it.”

January 13 to January 15, 2012 – 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, 2012 – Pitchers and catchers report to Spring Training, and our irrational excitement builds.

  • Cedlandrum

    man you are a busy guy today.

    • http://www.bleachernation.com Brett

      Only way to be successful in something like this, Ced. I’m learning from Theo: gotta work harder than anyone else…

      • CubFan Paul

        nice

      • JulioZuleta

        Theo would do a 96-hour-blogathon.

        • http://www.michigangoat.blogspot.com MichiganGoat

          Theo doesn’t sleep

      • montellew

        If baseball had a Chuck Norris, Theo would be it!

        • http://www.michigangoat.blogspot.com MichiganGoat

          There is no theory of evolution only a list of animals that Chuck Norris has allowed to live.

          • EQ76

            Chuck Norris once got bit by a rattlesnake.. after 3 days of agonizing pain.. the rattlesnake finally died.

            • Matt Murton

              When in rome, they do as Theo does

  • matt

    LOOKING FORWARD TO THE CUBS CONVENTION!!!!!!! You need to sell some Bleacher Nation t-shirts! I love the website, thanks for all the information.

    • montellew

      I’d buy one and wear it proudly!

    • Ian Afterbirth

      I’ll buy a shirt!
      As long it’s 100% cotton and not powder or royal blue, or yellow, or pink, or light green.
      Dark colors are good.
      Or white.
      And remember – it’s against the US flag code, adopted by Congress in 1942 for it to be “used for advertising purposes in any manner whatsoever” so I’d leave it out of the design if you were considering it.

    • Mom’s A Cubs Fan

      I will buy a shirt as well. Bleacher Nation needs to seen at the Convention. Can someone start waiting in line so we get good seats to the Theo panel?

    • http://www.bleachernation.com Brett

      Thanks, Matt.

  • Cliffy

    I cant recall where i read this but im sure i heard that Theo has moved the organizational meetings from November to the week before Spring Training starts in February. I will try and locate that source.

    • Fishin Phil

      I read the same thing somewhere just this morning Cliffy.  I can’t remember where I saw it, I was all over the interwebz this morning.

      • JulioZuleta

        Weird, that would make very little to no sense. The organizational meetings are important to set your course for the off season. This year, it would be especially important for everyone to get together under one roof and get on the same page. Can’t think of a reason why you would wait until February to do it.

        • Fishin Phil

          That’s what I thought too.

        • http://www.bleachernation.com Brett

          Strange yes, but it’s not like they won’t be meeting and making decisions over the next few weeks. I guess they want to dig into the org first before meeting top to bottom.

      • http://www.bleachernation.com Brett

        Ah, thanks guys. I’ll root around and update.

  • Kerf

    I tensed up when I read the deadline for tendering contracts to arb eligible players and saw Koyie Hill…but then I realized Jim Hendry is no longer the GM and calmed myself down.

    I’m still undecided how I feel about offering arb to Pena – how do you feel about the chance of him turning it down to pursue a long term deal via free agency? I’m leaning towards not offering.

    • http://cubbiescrib.com Luke

      I’d offer it. I think he does turn it down to pursue the longer deal, but even if he doesn’t it doesn’t hurt the Cubs. Pena could be traded at the deadline instead of resulting in a draft pick if he turns arbitration down. By the deadline the Cubs might have a bat ready to step into first base from the minors anyway (LaHair, Vitters, and Ridling come to mind. LaHair may be starting in left by then).

    • http://www.bleachernation.com Brett

      It’s going to be a tough decision, because he’s indicated that he loves it in Chicago. The Cubs would have to make the offer before seeing how the rest of the 1B market is shaping up. If they don’t offer, we’ll know it’s because they wanted to see who else was available before risking a commitment to Pena.

  • die hard

    Lackey would be nice addition if Tommy John works. Could trade Zambrano for him now and would be worth waiting a year for Lackey to recover.

    • montellew

      I’ll bring the beer and chicken for him! LOL

    • Dave H

      Too many other pitchers are available better than Lackey. Stop getting the walking wounded from all the other MLB teams. That’s a Hendry move not a Theo move.

      • Ian Afterbirth

        And thus a philosophy for life is born….

        • JulioZuleta

          Plus, and I thought this would have been addressed by now, Lackey won’t be available to pitch again until after Zambrano’s contract is up. Why take on 3 years of an overpaid player’s salary, when the one you are trading away will be up in 12 months?

          • Dave H

            Amen.

    • ron

      I would actually consider the idea if the Sox are willing to through in some cash to offset the expense for 3 years, Maybe 4-5 mil a year. I think Lackey’s wife was going through breast cancer or something and there were reports that this was effecting his performance. I think he could bounce back once that is resolved, a year of rehab and a change to the national league.

  • Diego

    I’m not sure if I’m supposed to know this but I’ll ask anyway…..where does the Cubs Convention take place?

    • EQ76

      It’s mentioned above in Brett’s bullet points… Go Diego Go!

    • http://www.bleachernation.com Brett

      I should have linked in the post (it’s there now). It’s at the Hilton in Chicago.

  • EQ76

    Can’t wait to be irrationally excited!

    • Dave H

      Already there!

  • Cubsglyph

    Regarding the five day negotiating period that begins when the World Series ends – Joe Nathan of the Twins recently said his agent told him that it is now a three day period. Is Nathan wrong?

    • Cliffy

      That is the window in which the original teams for potential free agents have to try to resign their players. MLB shortened that window from 15 to five days last September. However, original teams can still negotiate with their players after that time.

    • http://www.bleachernation.com Brett

      Yeah, it’s five. It used to be 10, and it shrunk to 5 this year. Not sure where the three is coming from, but maybe there’s something particular about his situation.

  • Cliffy

    About being a newfound Chicago celebrity (yes, he does have some humor): “I should probably have another (news conference) to resign because my popularity is definitely going to be at an all-time high right now. It has peaked and it’s only going to go downhill.

    “In baseball, when you make moves, you do a great job and you’re right about 55 percent of the time. The other 45 percent of the time you’re going to tick some people off, and I understand that. I’ve come to grow more comfortable with the realities that, unlike 20 years ago, general managers now are sort of the public face of the franchise.”

    From the there’s-so

  • vegascubfan

    you forgot: January 23-28 Randy Hundley’s Cubs Fantasy Camp. This will be the 30th year that the camp will be held.

  • mac

    I find it amazing how much more exciting/interesting this off season has been/will be in comparison to the actual 2011 season. It is so nice to be engaged in the Cubs again.

    • Hawkeye

      Of course the off season is going to be great.   We can’t lose any games in the off season.   Over the past few years, the offseason is the best time of year to be a Cubs fan.

  • Hawkeye

    World Series Game 6 Officially Postponed.   Today is now considered an off day.   Let’s get a press conference scheduled and announce Hoyer and McLeod.

    • http://www.bleachernation.com Brett

      I hadn’t thought about trying to sneak the announcement in now – probably not possible, given the lack of planning, and flights necessary.

  • http://TheoWaiting Cheryl

    OK. Any predictions on the Cubs making it to the World Series? I say 2015.
    If we make the playoffs in 2013, maybe I shpuld move the World Series up to 2014.

    • http://www.bleachernation.com Brett

      I’ll start at the playoffs: 2013.

      • Internet Random

        That’s what I’ve been saying too.  I hope we’re wrong (2012 would be nice), but that’s obviously not where I think the smart money is.

      • Lou

        I’d say more like playoffs 2014. Theo and his staff have got lots of holes to fill on the MLB roster.

  • Mike Foster

    Great summary Brett, this what I want in a blog. Plus “irrational excitement” hardly covers it, can’t wait till Spring Training, wife and I have been talking about going for years, I think 2012 will be it.

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