Even if you never met him, you know this guy. He's the guy at the country club with the beautiful date, holding a martini and a cigarette that stands against the wall and makes snide comments about everyone who passes by.
Of course, the country clubs Rove hangs out at wouldn't let a guy with Obama's complexion in without a court order. Karl Rove is trying to paint Obama as a sarcastic elitist, yet he uses a country club metaphor. Sounds to me like Rove has had a fair amount of snide comments directed his way by kids who were cooler than he was, and he hasn't quite gotten over it.