You have a man who was not part of the elite establishment and yet has managed to get wealthy by breaking the law and avoid getting caught, then managed to become president against all odds, twice.
Sure, he came from wealth, but plenty of other people came from even more wealth and had way more political connections and failed to become presidents.
Hate him all you want, but if achieving all that is not a form of intelligence and system knowledge, I don't know what is.