If the White Sox do decide to trade Edwin Jackson in the next dozen days, chances are it'll be for pitching.
Jared Stegall at Over the Monster examined whether the Red Sox should trade for Jackson -- but, for me, the question is if they can trade for Jackson.
The caliber of prospect Stegall suggests is probably right -- a grade C+ guy, at best -- but the Sox have a dearth of pitching in their system that Kenny Williams likely would look to address if Jackson is dealt.
It's tough to see any of the prospects mentioned in the post working out -- Yamaico Navarro wouldn't be an ideal return, as he's blocked by Alexei Ramirez and Gordon Beckham up the middle and projects as a utilityman anyway. Even if Lars Anderson were hitting, he wouldn't have a spot in the organization behind Paul Konerko, Adam Dunn and Dayan Viciedo. And Tim Federowicz would seem to be a hedonistic acquisition, if you can consider having too many mediocre minor league catchers hedonistic.
The Sox are probably staring down a back-of-the-rotation starter, at best, in return for Jackson. Maybe they have another Don Cooper Reclamation Project™ in mind somewhere.
While it's a dangerous strategy, perhaps the best way to go about acquiring a starter would be to pluck a higher-ceiling guy out of Single-A. That's dangerous because, for pitchers, the path from Single-A to the majors is a minefield if injuries and ineffectiveness. But considering the Sox may not need a starter to graduate from the minors full-time until 2013 at the earliest, shooting for the lower levels may be better.
Or, the Sox could blow all this up and trade for a major-league hitter who, like Jackson, has a contract that's up after 2011. With Brent Morel apparently falling out of favor at third base, perhaps an upgrade there could be an option with Morel being optioned to Triple-A.
The best strategy for the White Sox remains to hang on to Jackson and keep the six-man rotation in place, though. With Jake Peavy's physical problems and Philip Humber's recent ineffectiveness, the Sox probably should do everything in their power to limit the innings load for both those pitchers.
Plus, as a Scott Boras client, that Jackson is a 99 percent chance to not return means the Sox could reap a sandwich pick between the second and third rounds of the draft after he declines arbitration sometime after Thanksgiving. That pick could ultimately provide more value than a mediocre prospect or two could in a mid-season trade involving Jackson.