There's a pretty big difference between how a lottery winner behaves and how someone who grew up rich, with a successful family business behaves once they get the money.
Sure, maybe the blind squirrel would have lost Trump's daddy's money, but I'm thinking it's unlikely since the blind squirrel wouldn't have been able to spend it. He would have had to just stick it into an account and let it sit. If he had chosen a low cost index fund, he'd be richer than Trump.