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Tucker Carlson's Theory of Obama

This afternoon, for no particular reason, I swung by a conference in downtown DC at which an association of conservative state legislators was presenting its annual journalism award to Tucker Carlson. Carlson, in turn, had a few thoughts on current events, including a theory for why Obama--as he claimed--has so drastically overreached in his domestic agenda.

Obama's problem is not that he's not smart, it's not that he's some kind of crazy Marxist. His problem is that he's never failed, actually. That's his problem. Because with failure comes wisdom.
And I don't mean just kind of failed, like 'Oh, i didn't live up to my expectations today.' Or 'I was rude to the Maitre d’!' I mean real, humiliating, public disgrace. I mean failure so profound that neighbors avert their gaze when you pull into their driveway.
It's only when you're smacked down, in the face, by life, and really put on your butt for a minute, in public, that you are forced to rethink what you're doing, and to ask yourself basic questions about your life and its trajectory, like what do I want at the end of this journey, am I doing the things I need to do to get there. Is it worth it? Are my priorities in order? Success prevents us from asking those questions. Because as long as you're kind of succeeding, success is self-justifying. What you're doing is obviously working. Why tamper with it? Go with the formula, it's Coca-Cola! And that's what Obama is. And that's not an attack on Obama, it's an observation, that I think gets to the root of why he's about to make a real mistake. I mean a real mistake. Because he doesn't know what it's like to be smacked around in the political arena. And I think you could imagine your powers to be a lot greater than they are, if you haven't had that experience.

Well, the first refutation of Carlson's theory that jumps to mind is Obama's failed campaign for U.S. House in 2000, which he lost by a 2-1 margin against Bobby Rush. Then there are his nights spent on the street after transferring from Occidental to Columbia. And then there's the year out of college when he couldn't find work doing anything he wanted to do. And then the fact that most of his community organizing campaigns didn’t really work out, as John Judis chronicled last year.
Anyone got any others? Or, perhaps, you think there's some truth in Carlson's theory?