Some people, like Ayn Rand, thought that a successful and ethical businessman was something to look up to.

Not sure where the heck you get the idea that a successful person is always someone who is "a poweful person steamrollering the weak."

That bias, built up from many inputs, is part of the problem, isn't it? It sure shows on you.

As far as "identification," not many people are cowboys or space heroes either. But that doesn't keep people from liking those movies.

Between us, we came up with two examples of a successful businessman that wasn't a villain. Thinking hard, I think "Working Girl" was like that, too. That leaves how many others?

In literature, Horatio Alger-type stories used to be big sellers. Many Heinlein novels are about some small fry who learns the ropes and becomes successful. Not always in business, but at something.

I'm sorry I live in a society that has deemed success to be something suspicious and an obvious sign that the successful person has done something wrong.

Oddly, literary intelligencia seem fascinated by portraits of wealthy and powerful people who didn't earn it. Not sure why.