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What Kind Of Compensation Can Boston Expect For Theo?

This isn't a sly announcement to tell you that Theo Epstein is on his way to Chicago, but, were the Red Sox to give him permission to speak -- something that is highly likely given the Cubs asked -- there would be compensation involved if he agreed to a deal. Now, it's easy to say, "The Cubs need to hand over their top prospects," or, "Send Starlin Castro back to Boston, and we're good," or, "Extort the Cubs for everything they are worth!" but reality is a little different from that.

The thing is, Epstein would be taking over the roster that is giving away players, prospects, or money for his services. The Red Sox won't be able to gut the Cubs, as much as we might want their shiniest baubles, in exchange for Theo, as the chances Epstein would want to run a team without its most promising parts are, well, less than if the roster were to still have them. The Red Sox need to get something in exchange for Theo, though, so what fits the bill?

Prospects: This is an area where the Cubs can deal from in one sense because their prospects aren't that great. On the other hand, Epstein, who will essentially be trading for himself, might not want to give up what little upside he has in the system before his flight even lands. Keith Law's midseason top 50 prospects list, posted in July, didn't have a single Cub on it, and neither did Kevin Goldstein's list. There were two-and-a-half-months of minor league baseball played after those were published, but none of their major prospects did much to give you the idea they would crack the next top 50 from those two.

Josh Vitters hit .283/.322/.448 on the season at Double-A as a 21-year-old, but the Red Sox already have a third baseman with plate discipline issues in their system, and Will Middlebrooks has (1) shown more power and (2) is one of the best defenders at the hot corner in the minors, whereas Vitters is considered good enough to stick at third. That's not to say they wouldn't take him in a trade, but it's hard to see him being considered as a piece, especially since Vitters, assuming his development continues, is the likely replacement for Aramis Ramirez at third in much the same way Middlebrooks is the eventual Kevin Youkilis replacement in Boston.

Brett Jackson is the intriguing name, as he doesn't have Vitters' ceiling, but is still a five-tool player who has performed admirably in the minors. The 22-year-old started out slow at Double-A, hitting .256/.373/.443 in 246 plate appearances, but picked things up in Triple-A, where he hit .297/.388/.551. Of course, that latter performance was in the PCL, where the average hitter put up a line of .286/.358/.448, but it's still impressive work for a player of his age at that level. 

The Cubs might be loathe to give up this prospect, but Boston could use the outfield depth with J.D. Drew departing, Ryan Kalish losing all of 2011 to injury after a 2010 that told us he wasn't quite ready for the majors yet, and Josh Reddick bouncing back-and-forth between being the answer and a question. Problem is, as my Baseball Nation colleague and Bleed Cubbie Blue czar Al Yellon points out to me, Jackson likely won't go anywhere for the exact reasons that Boston would want him. So, you'll just have to pine for him from afar. 

The last name worth inquiring about is Andrew Cashner, who to this point has thrown just 65 innings in the majors as a reliever, but is actually a starting prospect. The 24-year-old has just 23 innings at Triple-A on his resume, but he's struck out 7.4 batters per nine at the level, and has pitched well at Double-A (89 strikeouts against 40 walks in 97 innings). The limited innings in his professional career are partially due to his being a former closer that the Cubs slowly brought along. 

Whether he's a starter or a reliever, Boston could use him. And while his name isn't as sexy as, say, Brett Jackson, that's more likely the kind of player the Red Sox would get in exchange for Theo talking to Chicago (though, given Cashner's limited prospect-dom compared to the other two names, he might come with someone else attached, too).

Package Deal: Maybe we've been thinking about this the wrong way. Maybe the Red Sox shouldn't be taking a player back, but should be getting all BoGo on the Cubs and sending along a contract or a player they would like to be rid of. Sure, Epstein might not want to have someone tag along if they aren't performing well, but there are legitimate reasons to consider it for both sides.

Of course, I'm talking about John Lackey and the remaining three years and $48 million on his deal. While removing him from Boston would mean they need to acquire another starter for 2012 -- and in a year where they are already missing a fifth hurler -- it would also free up the money to do something like acquire Wandy Rodriguez and his contract from the Astros, should the free agent market prove unsatisfactory. Lackey just finished putting up the worst season in Red Sox history by ERA+ and ERA, so "missing" him might be an odd way of thinking about it, too.

The Cubs' rotation is currently in even worse shape than Boston's, and the switch to the NL Central could do a lot of good for Lackey. While Matt Garza is a better pitcher than Lackey, he went from averaging 7.1 strikeouts and 3.1 walks per nine in the AL East for the Rays to striking out a batter per inning for the Cubs. Were Lackey to make the switch out of the AL East, he still wouldn't be worth his contract -- without a move to a park with stronger-than-Earth gravity, he never will be -- but he would likely look more like a three or a four, rather than someone who gets decimated in half of their appearances. 

Is that realistic? Maybe not. But this isn't a situation with a whole lot of precedent behind it, so new ground needs to be broken. We still have to wait-and-see if this is even something that needs to be discussed, but these are my thoughts on the matter -- what do you think, in terms of realistic transactions, Theo should be worth in a trade with the Cubs?