Howard Stern is a social liberal, who for years had enough money to disregard the customary democrat redistribution of wealth. He is smart enough to realize that they have been fleecing him and all the other high-earners for years. Sooner or later, his financial smarts will overrule his hedonism in voting. His perverted act is just an act. You don’t get to where he is without some brains. Maybe, he is starting to see that.
He was more worried about the FCC censoring him than the IRS robbing him.