1) Castro to Boston is a pipe dream, but it shouldn't be. As I mentioned above, the problem is that there is no standard and MLB doesn't necessary have the initiative to start paying front office talent like their on the field talent (though they're headed there whether they like it or not). But if we think about what Epstein will mean to the Cubs, an organization that is operating on outdated philosophies and has struggled in recent years in all facets of player acquisition, you can't argue that he isn't worth. I can't say it better than a piece I read early today
Imagine, for a moment, if you transformed Epstein into a player on the Red Sox Who would he be? Would he be backup outfielder Darnell McDonald? Or would he be first baseman Adrian Gonzalez, who will pull down an average annual salary north of $20 million?
The Red Sox gave up the top two prospects within their farm system from Gonzalez - though admittedly, neither player is a sure thing. If Epstein is Gonzalez, isn't a similar return reasonable? If I was Lucchino, I'd start with Castro and work my way down. If I was Ricketts, I'd keep Castro off the table knowing that GM's are not currently valued appropriately, but I'd absolutely be willing to go to a package of either two solid prospects and low A throw in, or a major leaguer, a solid prospect, and a low A guy. Epstein is absolutely worth that much to them.
2) I've read what's been posted about Jackson, and might try to find more on the other guys. Don't know much about them but would love to hear more if anyone has anything.
3) Baker isn't acceptable unless as a throw in. The more you look at him, the uglier it gets. Sure he's still got another year of arbitration and can do everything but pitch and catch, but the only thing he actually does well is play defense at 2B. No power, no patience, strikes out a lot, below average defense at all other infield spots.
4) A player I'd love to get in return - Sean Marshall - a great strikeout/groundball pitcher lefty out of the pen. Still has another year of arbitration. Would give the Red Sox their first trustworthy lefty out of the pen since Okie's good years. If Bard is actually moved into the rotation, could slide right in as the set up man. Chicago should have no problem parting with him as the centerpiece of a trade. Relief pitchers are volatile and on a team years away from winning, they're also the least valuable players.
5) Lackey - if I were the Cubs, if the Red Sox were willing to pay a significant chuck of his salary, I would absolutely take him on as part of the deal. While Lackey is clearly no longer the pitcher that he was in '05/'06, a move to the NL Central (though the least pitcher friendly division in the NL) and possibly free of the personal problems that plagued him throughout the season could result in a turnaround. Lackey could absolutely get back to being the pitcher he was in '09/'10, assuming that his problems lie more in mechanics and the AL East, and less in any long-term physical ailments .