I think some of it is the Bizzaro American brand of "anti-elitism". Despite inheriting millions of dollars and never facing consequences, to chuds he's "one of us". All the mockery for his lack of diction, irrational hate, ignorance, failure, lowbrow diet, etc. is perceived as attacks on "us (chuds)". So the more he's attacked the more they feel the need to support him.

Or not, I'm just talking out my ass