My thoughts about the award were triggered by Wales' decision to begin with a 1962 quote from Charles Van Doren on the need for radical rethinking of the concept of an encyclopedia. I grant that my reasoning is somewhat arcane, but part of the fun of these awards is that I can be playful with them from time to time.
I see that I have yet to give a Chutzpah of the Week award to either Wikipedia or Jimmy Wales and, while it is still early in the week, I was sufficiently 'inspired' by Wales' keynote address to ad:tech San Francisco this morning (entitled 'Wikipedia, Wikia and the Future of Consumer Generated Media') that I figured I would strike while the iron was hot.