They shouldn't have been handling his money in the first place. I'm not sure why that's so hard for people to pick up on. Do any of you have a joint bank account with your parents? Do any of you let your parents buy things in your name, or with your money? When was the last time you looked at your bank account and thought "hmmm, mom didn't spend as much as I thought she would?". Never? That's because only stupid people let others (including their parents) spend their money.
You are assuming he expected them to make the financial transactions themselves, versus them being the ones to go out and find financial advisors to handle his money.
He was a 25 year old who just signed a contract for 30 million dollars, which isn't quite the same situation as having your parents on your checking account. It's a tremendous amount of money and people start coming out of the woodwork to get a piece of it. So he put it in the hands of people he trusted while he went out and earned it. I'd venture to guess he's not the only pro athlete who's done this and most of the time it works out.
I'm not sure why that's so hard for you to pick up on.