It's more than bad investments. Dame would spend lavishly. He used to brag about never wearing the same shirt or socks twice. Didnt pay his taxes and owed over 4 million. Then child support.IDK bro. Seems like Dame blew his money on poor investments. You not suppose to take care of everybody. You suppose to put them in position to take care of themselves and that doesn't involve spending your money all the time.
The hardest truth a man has to learn is no one owes you anything. It doesn't matter what you did for them. If you are doing things for anyone and expect them to return the favor, you will always be disappointed eventually.
Solid business is solid business. From your post, Dame made a lot of risky business decisions.
With that said, I don't doubt he looked out for a lot of people and those people are long gone. It sucks but it's the oldest story in the book.