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.

  • Corey

    My worry is that Theo may think too highly of their prospects, much like we Cubs fans think very highly of our own prospects, even if it isn’t warranted..

    • Brett

      I can empathize, given that the previous management seemed to do that a lot. Now, though, I feel like: if Theo thinks highly of a kid, I reckon he’s got a good reason for it.

      • Richard Nose

        See: Rizzostalking. True, he hasn’t put together a career yet, but he creates squeals and pee.

        • Carew

          “creates squeals and pee” You sir just made me laugh out loud

        • Tony

          Yeah, I’m stealing squeal and pee for my own evil deeds.

          • Jeff

            Some people are in to S&M, Brett is into S&P!

            • ferrets_bueller

              You know…you don’t necessarily have to remove the M, lmao. Could be S&M&P…

    • Aisle 424

      Also, Theo looks at players as assets when he is assessing trade value. He has traded prospects that he’s loved (that ended up doing quite well, like Hanley Ramirez) for pieces that he felt helped him more at the time. He’s not a robot, but I don’t think his FEELINGS play into his deals as much as someone like Hendry, who seemed to develop bromances with some of his top prospects.

  • Aisle 424

    I would say it’s not that they fear getting fleeced, but know they can’t pull one over on Theo. They can’t trot out some middle-of-the-road prospect having a good couple of months and sell Theo on him as easily, because Theo will readily know which guys are playing to their true talent levels and which may be over-performing (and thus the Red Sox try to sell them high).

    • Brett

      That’s another way to frame it, and very fair. I’ll add a note.

      • Cheryl

        Another aspect is what Dempster thinks of the current management of the Red Sox. He wants a manager he can live with and have confidence in and he may know the people and managers on either teams better than the Red Sox.

        • Aisle 424

          I could see Dempster not wanting any part of the Boston mess right now. It’s not like they are guaranteed going to the playoffs or anything. But if Theo and Jed are talking seriously with Boston, chances are pretty good they’ve at least given Dempster a heads-up about it and he’s given his approval.

          • Noah

            That’s a decent point, but I do think that if the Red Sox go on a run that will fix a fair amount of their clubhouse problems. And that division is definitely close enough to do so and get in the postseason.

          • Mysterious4th

            Yes that’s a good point but ryan dempster is willing to help this team in more then one way, even if it means pitching somewhere else for the remainder of the season to bring in some young talent and he knows he is a FA at season ends and the cubs would re-sign him in a quick second. So he’d help the team this year and the future and 98% sure he can return on a team friendly deal. So, its a win-win-WIN deal for everybody….even if it includes theo’s ex-wife aka the red sox

    • rcleven

      I really hope this is not the case. I hope they are all grown ups in assessing there wants and finding a fair price. Boston has to go in and figure out what they are willing to pay for three months of Dempster’s service. Theo should ask for what he wants. If Boston thinks the price is too high then move on. It is after all a sellers market.

  • AD

    The way Demp has pitched do you think Matt Barnes (Red Sox #4 Ranked Prospect) out of UCONN is out of the picture?

    • Aisle 424

      Yes. I’d be shocked. And thrilled.


      I hope not. Lavernway and Barnes. Is that enough?

      I know we have lots a very good potential in prospects in the low minors but is Bogaerts and Barnes asking too much?

      • Richard Nose

        Still talking about Dempster??? yes, too much for sure.

      • Noah

        Bogaerts alone is too much for Dempster. Barnes very well might be. Quite honestly, if you’re getting Barnes for Dempster, you take Barnes as the only return piece and jump up and down in joy. You’re talking about a guy who in his first professional season is striking out more than a hitter an inning and not allowing any walks or home runs.

        Lavarnaway doesn’t do anything for the Cubs. He’s a bad defensive catcher who should only be used there as a backup. Since the Cubs already have a young stud 1B and can’t play a DH, they don’t really have a spot for Lavarnaway that would allow him to play more than 50 games a year or so.

  • AD

    The thing I like about him is that he was drafted just last year by Theo and has a pretty high ceiling.

  • cubzforlife

    Having watched Dempster these past nine years I believe he’s due for a slump. There’s no doubt he’s been lights out but he is a 35 year old who barely cracks 90. I’m sure all the GM’s are thinking the same thing. What is he really worth? What someone will pay.

  • CUBS

    2 of Barnes, Lavernway and Bogaerts???

  • Cubs Dude

    I can see how it would be hard to trade with the Red Sox now. Brett, why don’t we just avoid them for awhile until the whole thing with Theo leaving cools off? We didn’t exactly make out in the Byrd deal and Theo compensation either (even though Carpenter is hurt now). I just don’t see them handing over what it would take to get Demp or Garza.

  • MightyBear

    If the Cubs get Matt Barnes, that’s a super squeal. I can see the Sox and Cubs making a deal because Theo knows they system so well, he can ask for lower level prospects that other teams may not know about and don’t want for the likes of Dempster. (ST rental). Also, while Byrd didn’t work out, the kid they got isn’t exactly lighting up AAA and Chris Carpenter could still be a star, so the jury is still out on the fleecing.

    • Tony

      Ummm…we stole Theo. Chris Carpenter will never be a star, nor will he even pitch 300 ML innings.

  • Pasadena Cub Fan

    What if Theo makes a major deal with the Red Sox, –a number of Cub players for a number of Red Sox prospects? Will people just say he just transplanted the Boston farm system to Chicago. Rizzo was a Boston prospect. (And wasn’t there a Boston connection with Sveum as well?) Would that sort of taint any future Cub success?

    • Noah

      Sveum was the third base coach for the Red Sox in 2004-2005.

      The deal you presented is utterly silly and just won’t happen. Who, aside from a pitcher, would the Red Sox want? Soto isn’t any better than the catching tandem they have. With Ellsbury and Crawford back in the line up and Ortiz playing DH, they have nowhere to put Soriano. They also don’t need back up outfielders, so Reed Johnson is out. They aren’t going to bench Middlebrooks, Pedroia or Gonzalez against LHPs, and you don’t have to pinch hit for the pitcher, so Baker isn’t of use to them.

      Could a veteran bullpen guy or two be added on? Possibly. But the only scenario I see for that is saying that they’ll do something like throw Camp in with Dempster if there is one prospect the Cubs really want but Dempster alone isn’t quite enough for.

  • Jeff

    I feel that whomever trades for Dempster will be trading from an area of depth and have surplus of good young arms. It is a gamble to trade for Dempster but much like the Colby Rasmus trade last year, if you get a pitcher that helps you in the playoffs and you win it all, it’s worth the loss of the young talent. Dempster needs to go to a team that can win it this year, not a team that might make the playoffs.

    • Noah

      But you do realize that when the Cardinals traded Rasmus for Jackson and Alphabet Soup, they were just a team that “might make the postseason.” Those are the sort of teams that make these trades, because once you’re in the postseason it’s a crapshoot.

      Beyond that, there’s only one team in the entire Major Leagues I look at right now and say that, for sure, barring massive injuries, they are 100% going to the postseason, and that’s the Texas Rangers. And Dempster doesn’t really help the Rangers.

  • Dan

    Theo isn’t stupid neither is Jed so if they are talking to teams about Dempster (which I’m sure they are) then you know that they have talked to Dempster about the teams he will not accept a trade.

    • Cheryl

      True. But he is probably more comfortable with some teams than others.

    • JoeyCollins

      But does that mean you don’t talk to the red sod if dempster has said no. It might be kinda underhanded but would the front office pubically eliminate any team even if dempster has privately? I think the more precieved bidders the better the offer is going to be, make he dodgers top the red sod best offer even if there’s no way demp goes to them.

      • Cheryl

        No. You would never eliminate them. But say Dempster has a choice beween A and B and he knows A better than B. He wouldn’t say no, but if he is given a choice between A and B, which I believe will take place. He may say A without any downing of B just because he knows them better. But if B’s offer is hands-down a better offer than A’s, being the pro he is, he’ll probably go with B.

  • Jackalope

    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.

    I think that just about sums it up for me. Not a big deal for the Cubs to trade with Boston.

    • coal

      As long as terms like “significant compensation” are well defined in advance :)

  • Pasadena Cub Fan

    LA papers are reporting Chad Billingsley of the Dodgers is going in for 2nd MRI today. First MRI showed inflamation. He missed his start on Saturday and has been pitching in pain for two weeks. Might this get the Dodgers moving on Dempster?

  • CUBS

    Different subject but Votto is out up to 4 weeks. Could they go after Soriano now?

    • Daniel

      Or Lahair…

      • CUBS


  • Mike S

    Dempster to an AL East team can only help Garza’s value. If Boston goes and gets Dempster, now the Yankees, Blue Jays, and Rays are all looking for pitching help with a little more sense of urgency, IMO.

    Hello Mr. Garza :)

  • Featherstone

    As much as I want to be an adult and say let’s get a fair trade for Dempster. I’d much rather be a child and say fleece the hell out of Boston Theo.

  • Master Gonzo

    If Dempster goes to Boston, I would love to see a package in return built around RHP Matt Barnes. Is that realistic?

  • Mike S

    Brett, who hangs up first (Theo or Ben)??

    Ryan Dempster
    Ryan Lavarnway, Matt Barnes, and Henry Owens

    I’d say Boston hangs up first, because I’d be happy with that return for Dempster.

    • Patrick G

      I like the look of Owens. If Barnes is off the table, I’d like Ranaudo/Owens package. I’m dreamin tho

    • Brett

      Yeah, Boston would slam down the phone.

  • Patrick G

    I’m surprised the Nationals are not considering Dempster. They are in the playoff hunt, shutting down Strasburg, you would think he would be a perfect fit considering he would be a rental and they want to make a name for themselves never being in the postseason.

    • Richard Nose

      Thought of that too, makes perfect sense.

      • jungledrew

        Seems like the nationals would be more likely to drink the garza koolaid… They dont seem like a team to sell their future for a few months of player use, but if they’re getting more for their money (like with gonzalez) i could see them parting with some higher level prospects

        • Patrick G

          Their future is on the field now. They traded a lot for Gio, who is 24, Strasburg and Zimmerman are very young. Harper, Zimmerman, Desmond are all young and I’m sure they would want to try and win now. Don’t think they would want to sell a lot to get Gio then do the same to get Garza. Dempster would make sense since they want to shut down Strasburg in September, would become a free agent and they still have most of their top prospects, ones who would be needed for Garza.

  • Tony S

    Demp, BJax and ‘insert lower level prospect here’ for Barnes and Boegarts.
    I’d be more than happy to include BJax in a deal if it meant getting over the line on receiving a top pitching prospect back especially with our abundance of outfield prospects.

  • Mysterious4th

    Brett- that picture is as great as the throw in picture! Your cleverness is the cats pajamas!

  • TakingWrigleyToSaoPaulo

    Maybe Garin Cecchini (3rd base) and Anthony Ranaudo (pitcher)? Two top ten prospects in a top ten system? Would be pretty solid.

  • Jackalope

    It would be really interesting to hear how this type of conversation goes b/t Jed/Theo and Cherrington.

  • Norm

    Dempster won’t get you Barnes. Or Boegarts. And probably not Lavarnway either.

  • Jeff1969

    I just don’t think we should expect some huge haul for Dempster. I really think a lot of the reluctance to trade this year has been because of all the readjusting to the new rules & what it really means now to rent a guy like Dempster. It’s not the same at all anymore. I’m thinking Theo is looking at guys who were hugely regarded that he can buy low on right now, guys like Anthony Renaudo (currently hurt & sucking this year), & Jose Igelsias, former #1 Red Sox prospect who has fallen of the charts pretty much, though he’s 22, at AAA, and seems like he’s starting to hit & get on base a little bit better, and is still a possible gold glove candidate. Also, remember the talk of Ryan Sweeney, though I don’t know what we would do with him now. But I think we might be looking at something like those first two guys for Demp.

    • Jeff

      How does the idea of a package deal with Dempster and say LaHair sound? I think if a team knew they were getting more than just a few months rental with Dempste,r than they would be more likely to included better prospects. Garza can be traded by himself since he still has a year and a half and any team trading for him would get compensation if he left in free agency.

  • Jeff1969

    Oh, btw, I’ve been trolling the blogs, Red Sox fans want to send usguys like Darrell McDonald & that Nava guy for Dempster. Many of them say they don’t want a rent a player like Bedard was last year. If they were on this blog it’d be an all out curse fest if they saw names like Boegarts, Lavanway, Barnes, etc.

    • Tyler

      McDonald is on the Yankees

    • dudeski

      you should remind them that mcdonald is in the yankees organization now

    • EB

      Sounds like those sox fans are really on top of it since McDonald plays for the yankees now lol

    • EvenBetterNewsV2.0

      Ha, I think every team is like that outside of Oakland. Nobody knows they still have a Major League team.

    • Brett

      As with most things in life: the true tends to lie somewhere in the middle.

      • Jeff

        Amen to that!

  • nkniacc13

    Would Porcello be a fair return for Dempster/ I knowe its not the non 40 man return that most think they may get butis i fair, to much, not enough?

    • EvenBetterNewsV2.0

      If I were Detroit I would not give up Porcello when I could get him for my 3rd best LHP in the minors.

    • Brett

      Fair? Maybe. Interested? Eh. Porcello is arbitration eligible for three more years, and isn’t progressing. So you might end up paying him $5+ million next year, and he once again puts up a sub-100 ERA+.

  • Jeff

    Yankees Garnder could be out for the rest of the season, hey Mr. Cashman, Soriano would love to go out a Yankee!!

  • Drew7

    Off-topic, but Ha is a double short of hitting for the cycle in the 5th!

  • Dumpgobbler

    Red sox match up real well. Bogaerts, Barnes, Lavarnway and Middlebrooks are / should be off limits, but that doesnt mean we could find a combination. I’d LOVE Cecchini and Owens for Dempster deal.