One of the tricks to being a good pundit is the ability to be clever. Being clever allows a pundit to put unique spins on the ordinary, and to describe things in ways that make them tasty and easily digestible. On the whole, this is a good thing. But part of the risk with being clever is that you have a tendency to over think things – (I do this a lot) – and when you over think things you sometimes find that even though you were sure you were almost to Vegas, you’re somehow just pulling into Amarillo. This is why Obama confuses so many pundits on the right and the left, despite the fact that there’s just not a lot of mystery there.I'd drink to that, except perhaps that last where he talks about why Obama confuses so many pundits. I suspect it it why any object of punditry confuses the pundits, and I will generalize: specialist always differ from amateurs. That's why so many Booker Prize novels are unreadable, why nobody much loves modern opera, and why architectural prizewinners are leaky and drafty.
You'll say I'm just catering to the vulgar masses as if I want to transform the whole of the art world into Thomas Kinkade (or as his friends call him, Thomas "no sales tax" Kinkade) but that's not my point at all. My point is that the very process of becoming a (pundit/critic) redefines your horizon; it leaves you bored with a lot of things that others do not find boring and opens you up to a range of possibilities that no amateur (including your former self) is likely to comprehend. And in the particular case of punditry, it means the very process that qualifies you to speak as a specialist--that same process probably disables you from understanding the very subject on which you hope to pundicize.