CK was a Dem, but somewhere, sometime he supposedly suffered a conversion to the right.
Interesting to listen to - the way he constructs sentences and so forth, but for analysis === just another talking head.
That he is perceived as "conservative" means that when he comes out with pro-Obama statements, it is demoralizing. You expect the liberals to praise Obama, but if a "conservative" does so, it looks like the situation is hopeless and there is no chance of defeating Obama.