Many voters seem to worry more about the threat of "liberal elites" looking down on them* than about authoritarian elites skewing the economy in favour of the rich, pursuing a reckless foreign policy agenda that is more about macho posturing than ensuring peace, etc.
Now, if this were a high school popularity contest, maybe it would be understandable to vote for the dumb jock over the aloof valedictorian. (I think that would betray poor taste, but of course I would say that, given my cultural sympathies.) But this is a contest with real and significant consequences. So to let petty cultural resentment get in the way of actually making the world -- and one's own life -- better, seems grossly irresponsible to the point of perversity.
We shouldn't want a 'regular Joe', someone who seems "like us", to be president. We should want someone better than us, who might actually do the job well. Yet people talk as though being a member of the 'educated elite' is somehow a disqualification for the presidency. How backward is that?
* For what it's worth, I'm not sure there's actually much evidence that Democratic politicians (as opposed to a small subset of rank-and-file liberals like myself) are actually contemptuous of 'ordinary folks'. Republican politicians, on the other hand, seem happy to lie and manipulate voters into supporting them against all reason, which seems pretty contemptuous to me. (And, when you get right down to it, a major reason some of us subsequently think poorly of republican voters is precisely because they're stupid enough to fall for it.)
But forget the 'elitism' charge. Get over it. At the end of the day, it shouldn't matter who esteems who (and who merely pretends to). What matters is what they'll actually achieve.