Theo Epstein Morning Update: Any Reasons for Concern?

Confidence in a Theo Epstein deal has waned ever-so-slightly as the Chicago Cubs and Boston Red Sox were unable to reach an agreement on compensation yesterday. I’m not panicking yet, but I’m a little nervous. I’m a Cubs fan, after all.

  • Last night, WEEI – who has been ahead of everything on this story – reported that yesterday’s compensation talks did not go well, with the Cubs looking to pay only cash for Epstein, and the Red Sox wanting prospects. Many are seizing on this story to raise some fear that things will fall through, but, given Bruce Levine’s report yesterday that the Cubs have a list of prospects they’re considering trading to the Red Sox, it sounds like the talks are still progressing.
  • For what it’s worth, I’ve been listening to WEEI all morning, and I’ve not heard them express any particular concern that the Epstein deal will not get done.
  • Gordon Edes cites sources who say Epstein has been conducting business as usual in Boston these last few days, still participating in the managerial search, for example. Those sources also say Epstein hasn’t yet told his colleagues that he’s leaving for the Cubs. Shrug. That’s the kind of story that, at first blush, sounds awful and concerning, but let’s step back. How else would this play out? Epstein may have agreed in principle to a deal with the Cubs, but he’s still a Red Sox employee, and, theoretically, things could still fall through with the Cubs during the compensation talks. So, naturally, his instinct would be to keep head down and working, out of an abundance of caution (he is, you’ll remember, an attorney).
  • If you’re at all skeptical and cynical, you have to start to wonder why all of the leaks are coming from the Boston side. A cynical reader would figure that the Sawx are trying to manipulate the discussion – perhaps, for example, work Cubs fans up into a frenzy (“OMG! WE’RE GOING TO LOSE THEO! JUST GET IT DONE, TOM!!! GIVE THEM WHAT THEY WANT!!! ROAAAR!!!!”), to pressure Cubs ownership to making a deal on favorable terms to the Red Sox. As their ownership has demonstrated in recent days, they have no problem using the media to nefarious ends.
  • The leverage question. Some people, as we have here, say the leverage lies with the Cubs – the Red Sox have all but named Ben Cherington the GM, they’ve trashed their own team, and they’ve started the “we’re ok without Theo” narrative among their fans. Their only option right now to kill the deal is to cut off negotiations with the Cubs, and then pay Theo to sit at home for the 2012 season. Would they really do that, and become the greatest villains in all of sports?
  • Others, on the leverage question, say the Red Sox have it. The Cubs clearly are desperate for Theo, and don’t want to have to come to the fans, hat in hand, saying things fell apart at the zero hour.
  • Where does the truth lie? As it usually does, somewhere in the middle. I think there is no leverage on either side with respect to employing Epstein, himself. My guess is that all sides recognize he’s coming to the Cubs, and the rest is just posturing for the compensation. In that regard, the Red Sox have no leverage at all, except one thing: Epstein wants to take some Sawx employees with him. I still suspect now what you’ll see is the Cubs sending cash and a couple good prospects for Epstein and a couple of his choice Boston employees (NOT guys like Cherington, mind you – probably lower level staffers we’ve not heard of).
  • So, bottom-lining it: how worried am I? Not terribly, but I have a little heartburn. If things fall through at this point, I can assure you it won’t be because the two sides couldn’t agree on compensation. Both sides want to get the deal done, and it will get done. If things fall through, it will instead be because Epstein has had a change of heart (which is hard to predict, not knowing him personally). And, in that case, it will suck, but it’s hard to be angry at the Cubs.

Brett Taylor is the editor and lead writer at Bleacher Nation, and can also be found as Bleacher Nation on Twitter and on Facebook.

100 responses to “Theo Epstein Morning Update: Any Reasons for Concern?”

  1. StockholmSyndrome

    I’m hoping the delay is not due to a request to get Starlin Castro in return.
    But if we’re just talking about a couple of minor leaguers…. I don’t get the issue.

  2. johnbres2

    Brett–beautiful summary, including the slight heartburn. I have a feeling the deal will get done today.

    1. Jason

      ^ This – great work, as always. I agree that the only thing de-railing this deal at this point is Theo himself having a change of heart. After the original euphoria, I’m now back to cautiously optimistic. Even if this falls through, it won’t bother me because I still believe that there are a number of candidates qualified to lead the Cubs.

  3. Andrew

    “They’re only option right now to kill the deal is to cut off negotiations with the Cubs, ”

    The way I read that, it looks like the Red Sox themselves are the only option to kill the deal. :)

  4. Fishin Phil

    My gut tells me the majority of this is ego driven by the Red Sawx top brass, which would explain why all the leaks come out of Boston.  Ricketts is one tight-lipped son of a gun, and the Boston boys leak like an old rowboat.

  5. LouCub

    There is no way Starlin goes anywhere…that’s been a Boston pipedream from Day 1, him or Garza and it ain’t happening….

    1. Fishin Phil

      Even if the Cubs wanted it to happen, I don’t see MLB approving that deal.

  6. Sayueri

    Yeah, I’m thinking along the same lines. It’s a lot of posturing and the compensation issue has more to do with the others Epstein might want to take with him. If it’s just Epstein leaving, I think the Sox take cash from the Cubs and be done with it. If he wants to raid their front office, they’re not going to simply take cash in return.

  7. jstraw

    Any legal talent around here? How likely is it that Theo’s contract allows him to be paid to sit? It seems as unlikely to me as the Cubs being able to send a veteran to the minors to free up a roster spot.

    1. Internet Random

      Nearly 100%.

      1. jstraw

        You think it’s nearly 100% likely that the contract allows the Red Sox to pay Theo to sit at home? I don’t. There’s more than money at stake. I’d wager that the contract has a buyout in it but that it allows him to continue to advance his career if the Red Sox no longer require him to perform the services or which he was contracted.

        1. Internet Random

          You think it’s nearly 100% likely that the contract allows the Red Sox to pay Theo to sit at home?

          Yep. And what the contract “allows” the Red Sox to do, and what it binds them to do are two different things.

          And I agree that there is more than money at stake: There’s having a disgruntled GM on your hands.

  8. jstraw

    On the compensation question…it puts Theo in a very odd position. He’s still an employee of the Sox and has to due diligence in that capacity. He WANTS to be an employee of the Cubs and has the interests of the organization that he wants to be running in mind? Who’s side is he on in the negotiation? Is he a participant in the negotiation? If not, who’s doing it, Cherington? And doesn’t that strengthen the Cubs’ hand…if Theo is already being supplanted? It’s rather ironic.

  9. hansman1982

    The fact that they are far apart is a non-starter for me.  It is good that the Cubs weren’t willing to drop trou on day 1 and right now I am 60% certain that this deal gets done every time.

  10. Ari Gold

    Just give them Vitters and be done with that. He’s not going to be anything anyways.

    1. Ron Swanson

      Which is why the Sox probably aren’t intested in him either.

      1. JulioZuleta

        The Cubs would not offer Vitters. He has been playing pretty well lately and is still young, just turned 22 and was getiing really hot at AA. At this point, I would guess he would be with the Cubs at sometime during 2013, at 23 years old.

  11. Toosh

    Henry’s got balls, I’ll give him that. When he wanted Beane, the Red Sox were willing to give up Youkiliis, who, at that time, was 2 years away from the Majors and a marginal prospect, at best. Now, for Epstein, the Red Sox want more than a marginal prospect? Good luck.

  12. Edwin

    I heard the main problem with negotiations was when Tom took out his prospect list and it read something like this:

    Zookeeper on Blue Ray

  13. LouCub

    I’d bet he has nothing to do with the negotiations it was reported it was between Randy Bush and Cherington/Lucky Larry Luccino the prick…I remember when the Cubs hired Andy MacMuffin from the Twins, they gave up compensation for him, AFTER the deal was announced..Later that month, the Cubs hired away Jim Riggleman from the Padres and gave them compensation AFTER the deal was done…When Dallas Green was hired I was like 10 years old so i’m not 100% sure on this but I don’t think the Cubs gave up any compensation and Dallas took lots of people with him: Lee Elia, John Vukovich, Gordon Goldsberry, Hugh Alexander etc, etc, etc..This is rotten and hopefully it doesn’t drag on too much longer.

  14. Sam

    It’s as good as done. If the Red Sox back out now then they will be stuck with a pissed off GM who will be in the last year of his contract. Not to mention the fact the Red Sox have named Ben Cherington as Theo’s successor. The Red Sox dropped the ball on these negotiations when they allowed Theo to take the Cubs job, when they did that they lost all leverage, and the Cubs gained it. Like I said what are they going to do, hold onto a lame duck Theo Epstein, lets be real if the Sox back out Theo would probably leave as soon as his contract with the Sox ended at the end of next season. I think the holdup is over who Theo is trying to bring with him, and its completely plausible that the Red Sox are asking for prospects in exchange for other members of their front office.

    1. Toosh

      I echo your last sentence.

    2. Wilbur

      This is what I’m thinking …

  15. Ron

    If this falls through, which I don’t think it will, the Cubs already have a built in reason to save face. Because the Cubs have been so tight lipped and the Sox the titanic for leaks, TR can say they were asking for Castro and Garza. A price no one would pay. What I am saying is, advantage Cubs and good on ya Tom!

  16. Hawkeye

    How long should it take for Wilkins, Fleita, and Bush to evaluate the list of prospects.   It’s not like the are looking at this list of names and talent for the first time.   One would hope that these names and talent are discussed in periodic progress reports.   We discuss the successes and failures and the Cubs prospects on a daily basis, and it is not our job to do so.

  17. CubFan Paul

    in that Gordon Edes piece he points out that Boston has twice allowed leaving execs to take front office staffers with them

    “Josh Byrnes to the Arizona Diamondbacks and Jed Hoyer to the San Diego Padres. In both instances, they were allowed to take two Red Sox staffers with them, one apiece in terms of major staff positions. In 2005, Byrnes took Peter Woodfork, the team’s director of baseball operations, with him to Arizona, along with a highly regarded stats guru named Shiraz Rehman, who had been a Red Sox intern. In 2009, Hoyer was permitted to take scouting director Jason McLeod and Sam Ray”

    “Epstein’s inner circle, besides Cherington, includes Mike Hazen, vice president of player development and amateur scouting; scouting director Amiel Sawdaye; Brian O’Halloran, vice president of baseball operations; Allard Baird, vice president of player personnel; Dave Finley, special assistant to the GM; and Craig Shipley, the senior VP of player personnel and international scouting”

  18. Mikey

    so there is a possibility were theo doesn’t come ay all? ):

    1. Wilbur

      It’s always a possibility, but if he hasn’t burned his bridges in Boston by not going public with a “I’m putting my toe in the water to check the temp” statement he’s standing in a kerosene soaked, covered bridge with a flame thrower in his hands …

  19. die hard

    Wouldnt have had this mess with Dick Tidrow….I tried to warn you …lets hope it turns out for the best

  20. oswego chris

    Okay…I saw side-arming Dick Tidrow play…but where is all of this love coming from?…granted I find it very funny…I just must have missed something


    1. TWC

      Uh, “Chris”… you new around here?

    2. MichiganGoat

      Well, Artist Formely Known as Philoe, Mr. Tidrow has been the troll known as die hard’s number 1 pick for GM (because he’s “tough”) so then Chuck Norris was suggested by me and it’s just taken on a fun life from there.

      I’ve come to enjoy die hard’s comments because they are irrational but lead to fun

  21. Hawkeye

    Had to post this one as well.   Couldn’t help myself.

    Rick Ankiel gave up pitching and moved to the outfield just to get further away from Dick Tidrow.

  22. steve

    Who do you think is a reasonable proespect(s) to give up for theo?

  23. die hard

    we have to stop thinking about what to give up for him…he cant hit, throw, or run….we have to think about what Boston will pay us to assume last yr of his contract cause he was going to be fired anyway…cant anyone but me see this?…yeeesh!!!

    1. TWC

      Sometimes I sneak a cookie or two before I finish my lunch.

      1. Hawkeye

        You kidding me…you guys are multiplying now? 

        I don’t know what I like more, diehards comments, or the follow up cookie comment from TWC.  


    2. die hard 2- the airport one, sometimes know as Die Harder

      yeah man, they should give us Ellsbury and Pedroia along with Tom Brady and Rajon Rondo. Thats where negotiations start. I hear ya die hard

      1. T C

        edit: didnt get that this certainly isn’t another die hard/totally missed point….

  24. JulioZuleta

    That Mnookin article says the Red Sox might ask for Jay Jackson and Alberto Cabrera. If that’s the case, do it and move on.

  25. Hawkeye

    ESPN now reporting that the hold up is most likely the Red Sox’s demands that no other front office personal be allowed to leave with Theo.   I think I read that somewhere on this site yesterday?

  26. Katie

    I’ve been lurking for awhile and thought I’d say hi to everyone. Personally, I love the updates here regarding the Theo Epstein mini drama. Plus I love a man who uses ‘nefarious’ in a sentence. Grrrrr!

    Oh, and Hawkeye, while I do love Hawkeye from MASH I was raised on the Hawks and Cubs!

  27. Katie

    Mine autocorrects in the wrong direction too.
    I am picking up on the “interesting” qualities of die hards comments. I doubt I’ll ever be one of the cool kids here but I appreciate the welcome!

    1. Dave

      Don’t worry, even the cool kids around here are pretty uncool.  Just check out some of the stuff on the message boards.

      As far as die hard goes, I imagine he comments a lot on YouTube.

      1. MichiganGoat

        Especially on Cookie Monster videos

    2. MichiganGoat

      Trust me we’re not that cool. We’re a bunch of passionate Cub fans who actively check this site like a junkie looking for a fix mixed with an occasional troll who loves cookies

      1. Dave

        Sad but true: BN is the most visited site on both my laptop and my phone.  Somehow its ahead of Facebook.  And

        1. kansas cubs fan

          “”, and to think I thought I was the only one who went there!


      2. hardtop

        speak for yourself, i’m fucking cool man.

        :insert quote from adult cartoon or start wars here:

  28. Katie

    Oh yes, I’m definitely a Cubs junkie. isn’t cutting it and hasn’t really ever cut it for news, to be honest. As for the message board, I haven’t been brave enough to wade in there quite yet.

    1. MichiganGoat

      Oh join us on the dark side that is the BN Message Board

      1. Katie

        Eeeeek! I did and I even posted. Now if I could figure out how to give myself an avatar via my iPhone I’ll be set.

        1. MichiganGoat

          Can’t do via iPhone got to go to and set up an account

  29. Katie

    Good to know Michigan Goat! Thank you!

  30. Hawkeye


    Glad to see a new face as well as a fellow Hawkeye/Cubbie.   Sorry I hadn’t responded to you earlier as family time takes away from BN time on the weekends.  It will be nice to get back to work tomorrow so that I can get my priorities back in line and focus on BN.   Again, welcome to this little slice of heaven that Brett has created for us all.

    1. Katie

      Oh I totally understand! How ’bout those Hawks this weekend?!

      Thank you for the welcome. It IS a little slice of heaven.

      1. Hawkeye

        Hawks looked real good this weekend.   Though I love my Cubbies in Chicago, my love does not stray down the road to Northwestern.  They have been a thorn in the Hawks side over the past few years and it was nice to take them down.

        1. Katie

          Most definitely! I kept waiting for the 2nd half choke routine we normally see! I live in Iowa so it Iowa or Iowa State from birth. Still can’t believe they lost to State. Shameful.

          1. Hawkeye

            I live in Iowa as well.  Originally from the eastern part of the state.   Loosing to ISU did suck, but at least  we will win more games this year.  Can’t say I think ISU has another win in them.