I think he may have tried to become more controversial and broached controversial issues in an effort to boost ratings. Don't these types of shows thrive on rants, arguing, controversy, etc.? The biggies -- O'Reilly, Beck, Olbermann, etc. all seem to be opinionated ranters who thrive on debate and aren't afraid to be viewed as controversial. It seemed like he was trying to generate some of that vim and vigor and move into that mold. That endears him to some and alienates him from others.
My understanding is his background is in business -- he was a business reporter originally, I believe.