I always come back to the Schiavo issue because back then I had *some* backchannels to influential DC people and I was just begging them to understand that there was a big difference between "Michael Schiavo should not pull the plug" and "Tom DeLay should be in charge of these decisions. It shouldn't be too hard to get that people were capable of having both opinions.
A big problem with our glorious pundit class is they are disproportionately made up of people who don't think anything affects them, and they are mostly right. Another big problem is they assume the great masses of unwashed losers who went to, at best, state universities, are just intellectual and moral cretins. However bigoted and racist these pundits are, personally, they believe, very deeply, that they are the smartest and most tolerant people. Nobody who went to Yale could be bad, and nobody who went to Ohio State could be any better.
Sure a lot of people are assholes, but a lot of people aren't, and even more people are able to understand that "this could be me and my kid."