Negative bias. We notice these anomalies more than we notice the ones that don't disappoint their mothers.

With people like him I'd say it's about a combination of being contrarían in general, being surrounded by yes men, and looking up to rich assholes.

More generally, we can all fall for reactionary crap if we don't see it for what it is and if it speaks to some grievance we have. We need to be smarter and look at historical patterns, the fascists never helped any workers, they just got countless people killed, and letting them rise to power eventually leads to someone, either you or someone you care about, being next.