He's consistently wrong because he is a classic limousine liberal.
He lives a very sheltered and fragile little bubble and he gets off on wiggling the skin of said bubble but never popping it.
He's always been a mediocre comedian, and his smarmy shtick got old in the mid 90s.
Now he's playing at deep-thinking political discussion but he has a very limited view of things, as one would expect someone with millions in the bank and assistants to fetch coffee, dry cleaning and food for him.