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.
Josh Marshall detects a hidden racial message; Rove is implying that Obama is getting uppity. Matt Yglesias isn't so sure, but he sees a big honking class faux pas.
How many Americans have had the experience of being at a country club and watching some dude with a beautiful date hold a martini and smoke a cigarette? Certainly I haven't. Rove assumes that "you know this guy" but unless "you" are a wealthy person from the past, you probably don't know a guy like that.
Putting Obama in a country club was was meant to imply that Obama is an elite (eek), but assuming we know the types who hang out at country clubs much more firmly lands Rove in the dreaded elites than it does Obama. But then, we all know Rove's type. He's the pathetic guy who is still trying to get back at the kids in high school who wouldn't him join their clique. You don't have to be uppity or an elite to know--and avoid--that guy.