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This evening, Buster Olney reports that the Cubs and Red Sox are talking about a Ryan Dempster trade right now, and the Red Sox are “aggressive” in their pursuit. Olney adds that the Cubs are “going through their process” on Dempster, which suggests they’re making the rounds to the interested teams, and probably asking for best and final offers, to the extent that’s a reasonable request.

(Say what you will about East Coast bias, but Olney’s sources within the Yankees and Red Sox are unquestionably good. So, when he reports something like this, which might otherwise seem a bit innocuous, I’m led to believe these talks are serious.)

But Olney tosses out a wrinkle in these trade talks, one which we’ve seen before, but from another perspective. A hurdle to a trade, Olney says, is the fact that Theo Epstein, now the President of Baseball Operations for the Cubs, “knows [the Red Sox] farm system very well.”

In other words, the Red Sox are afraid they’re going to get fleeced.

You can see why this might seem like a reasonable fear. Theo was in charge of the Red Sox for almost a decade, and he personally oversaw a great deal of the drafting and development in the farm system (together with Jed Hoyer and Jason McLeod, also now with the Cubs). If anyone knows how to find a diamond in the rough in the Red Sox system – or which erstwhile top prospects to avoid – it’s Theo. And the Red Sox didn’t exactly come out well the last two times the Cubs and Red Sox dealt. In Marlon Byrd, the Red Sox got underwhelming performance and a release (before a PED suspension came down), and in the Theo Epstein deal, the Red Sox’s major piece almost immediately had to have elbow surgery.

So should the Red Sox avoid dealing with the Cubs, even if they really want Dempster?

Ultimately, here’s why I think the Red Sox’s concern, such as they have one, is unfounded: sure, Theo (and Jed, and Jason) knows the Red Sox’s system as well as anyone not currently working for the Sox. But you know who else knows it well? All the guys who are STILL working for the Red Sox, who worked there when Theo did. Do you think Theo kept his prospect evaluations secret? Of course not. Everything Theo ever thought about a Red Sox prospect while he worked there is in a database somewhere. It’s also in Ben Cherington’s head. And every other executive still in the organization. And now they’ve got an extra 9 months on Theo.*

Frankly, the Red Sox wouldn’t be “aggressively” pursuing Dempster if they were too wigged out about what’s rattling around in Theo’s head. Yes, he knows their system well, but so do they. Better even. So all that means is the two sides might actually have an easier time putting together a win/win deal than would be the case with any other team.

Query whether you want the Cubs to put together a win/win deal with the Red Sox, of course, but that’s another conversation entirely …

*Aisle424 from ObstructedView makes a good point in the comments that, in addition to (or separate from) a fear about being fleeced, the Red Sox might be concerned that they can’t be the ones doing the fleecing, since Theo knows which guys in the system the Red Sox aren’t high on. That’s a great point, though it’s harder to see a source telling Olney that that’s why the two sides can’t get a deal done (“the Red Sox feel like they can’t rip the Cubs off enough”), as opposed to their fear that Theo’s got a leg up on which prospects the Cubs should affirmatively want.

  • Nick Nesler

    No link but on MLBTR in the comments of the demp article someone said that New York sports talk radio was reporting that the demp sweepstakes was down to Yankees and Braves and a decision would be made by tomorrow.

    • Carew

      Interesting. But its kinda hard to believe commenters on that. They are so hate-filled or bias

      • Nick Nesler

        For sure, just throwin it out there.

    • http://bleachernation.com someday…2015?

      Someone earlier brought up a Dempster for Minor and Delgado trade… I think if the Braves throw in one low level high upside prospect that deal would get done… The Yankees… How about Dempster and LaHair for Betances, Sanchez and Marshall?

      • http://www.bleachernation.com Luke

        Dempster for Minor and Delgado? Just Dempster?

        That would be huge. Despite their numbers this season, both those guys have No 2 starter ceilings. That would be a fantastic return for Dempster.

        • Carew

          Somebody from the Cubs would have to be added. But who?

          • Whiteflag

            Cardenas?

            • Carew

              What happens to Cardenas probably depends on what happens to Barney

        • Dumpgobbler

          I’d do a dance if we could get Minor and Gilmartin for Dempster let alone Minor and Delgado. I still think its Minor or Gilmartin and a lower arm for Dempster deal.

      • Nick Nesler

        LaHair would make alot of sense for the Yankees. He could provide some of the pop they lose if they don’t re sign Swisher. He could play OF, 1st, and DH, and help them get under the tax threshold.

        • http://bleachernation.com someday…2015?

          Could you imagine LaHairs power in Yankee stadium??… He could hit 40 if he got enough at bats in that stadium.

          • http://bleachernation.com RicoSanto

            LaHair is not even a good pull hitter.He could not hit 40 in any park.He is going to finish the year with 20 -22 that is it. e hit the first 10 very fast

            • gutshot5820

              Who made you the fortuneteller on BN?

              • WhiteSox Nation

                Lehair couldn’t hit 40 homers any where the guy is right

      • EB

        Yes, I’d be very happy with just one of Minor or Delgado plus a low level guy or 2

        • WhiteSox Nation

          If they can make that happen one of them would be great both woohoo!!

      • Whiteflag

        I’d like Minor, Delgado, and T.Harrison (3B)

        • Whiteflag

          This is actually a trade possibility a braves fan offered up for Dempster. I played it cool like maybe I’d take take that but really I want to scream *#!% yeah.

  • http://bleachernation.com grace17

    Bautista may be hurt maybe we can finally dump soriano?

  • http://bleachernation.com lou brock lives

    If Barnes not part of deal then LHP Owens & 3B Cechinni would get the deal done. We may have to throw in Camp or a low level minor leaguer like Watkins or DeVoss.

    • Steve

      Logan Watkins goes nowhere.

      So shall it be written, so shall it be done!

      Just kidding…I just love saying that.

      • Leroy K.

        Ours is not to reason why, ours is but to do or die….

  • AD

    Anthony Gose (#2 Ranked Prospect of the Blue Jays) was just pulled early from his game at Triple-A. Just speculation, but a move to watch.

    • AD

      Probably to replace Bautista.

  • Robert

    I don’t see how dempster doesn’t have tremendous value.. yeah, he’s old. BUT he leads the majors in ERA he’s a clubhouse leader, he’s throwin like a cy young this year. We should get MORE than just a “b” prospect. hell i think we should get the teams number 2 prospect. AND another B (7-10)

    • Dumpgobbler

      Hes got value, but probably not that much. Lets face it, teams know hes going to regress a bit. Hes a 35 year old rental that wont net any kind of compensation. If we can get 2 pieces that have a chance to be soemthing, we should pull the trigger.

  • Twiz

    David Ortiz injured his right achilles, having MRI on Tues. Never wish an injury…but
    Soriano is just a phone call away

    • CUBS

      I hear Bautista from the Blue Jays just got hurt as well.

      The line starts here for Soriano!!!

      • http://bleachernation.com someday…2015?

        Anthony Gose, Jays top prospect was pulled early in his game… Either he got moved in a deal(not likely) or he was moved up as soon as the Jays saw an x-ray with little cracks in Bautista’s wrist.

        • http://bleachernation.com someday…2015?

          Sorry Gose is not the Jays top prospect. Darnaud is still at the top. Forgot him since he got injured.

      • bbmoney

        Bautista’s injury could just convince the Blue Jays to wait for next year, if its serious at least,…..might hurt in the Garza sweepstakes.

        • http://bleachernation.com someday…2015?

          Yeah I completely agree. If the Jays are out on Garza that would hurt big time.

        • BN Virgin

          Very easily could…one thing to keep in mind, however, is that they would still have Garza next year, too, when they are wanting to go for it. Not saying you’re wrong. There’s no way of knowing that right now. Just saying Garza is a different situation than Dempster- who is strictly a 3 month rental.

          • bbmoney

            Good point.

    • WhiteSox Nation

      I’ll pack his bags LOL

  • http://bleachernation.com someday…2015?

    I just read 6 teams are inquiring and are serious about Chase Headly. I have a feeling the Cubs are one of those teams seeing as in Hoyer has a lot of familiarity with him. They also haven’t been quiet in saying they want a future 3B man. I don’t know if this would be popular but I would be ecstatic if the Cubs could do a Garza for Headly and Padres top prospect Casey Kelly trade. I think that’s fair, not sure though…

    • http://www.worldseriesdreaming.com dabynsky

      Love Headly, but his value is pretty high right now. Buying high on a guy in his late 20s doesn’t seem like a move that the FO is keen on making at this point.

  • Cub Gone Wild

    Jays and Redsox wont come after Soriano as replacement for injured players. They continue to use their system as they have done all year. LaHair will be playing 1b in Cincinnati to replace Votto for remainder of July and most of August then LaHair plays LF and hits 3rd.

  • Cub Gone Wild

    Cechinni can play 3b for Cubs and Defensemen for the Black Hawks. Thats a hockey name.

  • Leroy K.

    “In other words, the Red Sox are afraid they’re going to get fleeced.”

    I literally laughed out loud in my office and got a couple weird looks.

  • Brady

    This is how I see trade talks going between Theo and Ben Cherington go (pretend I am doing a boston accent and it will be more fun):

    Ben: Hey Theo, what’s it gonna take to get this man Dempster on my team?

    Theo: Well I don’t know Ben let me think. Didn’t you guys have a young pitcher. A righty, um what was his name. Charlie Charpenter, nah that wasnt it but I know it started with a C.

    Ben: Screw you Theo. *click*

    • http://www.bleachernation.com Brett

      Chow-duh.

      • Brady

        Yup. I can’t even pretend to do a Boston accent. Was working with a russian national who moved to New York when he was 14 so I kinda have the Italian tough guy thing down now after working on it a bunch.

    • baldtaxguy

      “Let’s go…Demp-stah !!”

    • Carew

      pahk the cah in the hahvahd yahd

      • Sweetjamesjones

        “Fuck Buck Showaltah in the eaar”

  • Kevin

    Cubs should allow Mark Cuban a 47.5% ownership, this way they can afford to do things right and not be controlled by the City, State or Riensdorf anymore. Let’s make it happen.
    The Arlington Heights Cubs has a nice ring to it. No more Chicago politics. No more restrictions from the greedy residents of Wrigleyville. No more 12% amusement tax. Let’s not sink $500M into a 100 year old stadium. Let’s move forward, WTF? Wrigley really is showing it’s age and turning into a dump. 100 years of losing, that’s what I want to hold on to. Trade a early 20th century stadium in for a brand new state of the art retro looking 21st century stadium. It’s the only long term solution, period!

    • http://www.viewfromthebleachers.com Norm

      oy, this Mark Cuban stuff is about as tired as the Josh Hamilton stuff.

      • Kevin

        Let’s hear how you get this mess resolved.

  • Lou

    Dempster could go to the Nationals given that Strasburg is on a strict pitch count. I’d like to see Dempster and Reed Johnson to the Nats for Alex Meyer and Skole.

    • http://www.bleachernation.com Brett

      I like the thinking outside the box. Not sure it works, but it’s interesting.

  • http://bleachernation.com someday…2015?

    SBerthiaumeESPN Steve Berthiaume
    From #BlueJays RT/ Bautista Update: no break, tendon injury, will have an MRI tomorrow to determine extent of injury…. Good to here.

  • Pingback: Lukewarm Stove: Now the Nationals Want Ryan Dempster, and a Great Many Other Rumors | Bleacher Nation | Chicago Cubs News, Rumors, and Commentary

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