Everyone on this topic seems to be under the mistaken impression that a real businessman is some kind of educated intelligent individual.

While that might be true for middle management, it may not be true for the actual CEOs.

I remember hearing a statistic that most CEOs of American corporations had low GPAs in college, if they went to college at all.

Here's a random quote pulled off the internet in an attempt to track down the source of that stat:

"In “Talent is Never Enough”, leadership researcher and guru, John C. Maxwell, states “that more than 50% of all CEOs of Fortune 500 companies had a C or C- average in college and more than 50% of all millionaire entrepreneurs never finished college.” So why are most CEO’s “C” students? Does CEO stand for the “C” Entitled Officer?"

So in light of the this topic, which is the assumption that good businessmen are somehow more intelligent than a wiseguy, I would say that if a wiseguy could run an illegitimate business successfully, no it is not a sign of intelligence, but he also is probably just as smart as the majority of CEOs.