Rate Kenny Williams' 10 years of trades

I'm in the midst of writing a retrospective on Kenny Williams' first 10 years as general manager of the White Sox, which will be the central theme/essay in White Sox Outsider 2011. It's using up most of my analytical/organizational mojo, so I figure I'd foist today's post onto your collective brawny shoulders.
Below is a list of Kenny Williams' 55 significant trades since taking over in November of 2000. He made plenty more, but these are the trades that ultimately had a measurable major-league impact, either for or against the Sox.
The best example of where I drew the line: The first Roberto Alomar trade made the cut, because it cost Royce Ring and Alomar was brought in to make a difference. The second one didn't, because the Sox traded a player to be named later (Brad Murray), and Alomar had nothing left. No risk, no reward.
What I'd like you to do is rate them on a scale from 1-10, from "most embarrassing" to "most impressive," with the middle representing no net gain or loss. Warning: Them's a lot of trades, but 1) it's a fun walk down memory lane, and 2) you might not have much else to do.
A couple of quick definitions:
Most impressive: Weighing a large net gain while factoring in a high degree difficulty. The Sox got a good year out of Alex Cintron for nothing, but trading Brandon McCarthy for John Danks took serious balls. I would say the latter is better résumé fodder.
Most embarrassing: Flawed reasoning, flawed execution, zero redeeming value (I would call your typical salary dump a "3.")
So have at it. You have the option of leaving trades blank, although I imagine if they inspire zero emotion, you could just as easily call it a  "5."