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.



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