A classic case of the Dunning-Kruger effect. People with money are constantly receiving reinforcement from everyone around them, the media, and pop culture that the fact they have a lot of money is proof of expertise. They come to believe that buying their way to third base means they hit a never-ending stream of home runs.
I often use this to my advantage as an organizer and shit-disturber. I look, dress, and smell like a bum. The people I fight – cops, lawyers, politicians, and business lobbyists – believe that the same way wealth indicates expertise, lack of it indicates incompetence. For some of them the prejudice is so strong that even when I’ve beaten them in the courts, in the media, and on the streets, they still can’t bring themselves to believe they’ve been hustled and continue to hand me easy victories by underestimating me. This is significant because you look at someone like Donald Trump, who is a terrible businessman, the exact opposite effect occurs: no matter how many poor decisions he makes or how much money he loses, the fact that he’s rich is enough to convince people he’s successful and infallible.