Tom, I don't want this to come across as argumentative, but Michael Jackson did. Which, according to the news reports, was why he was planning to go on tour again. He was broke.
ESPN did a 30 for 30 show called Broke. It's about all of the athletes who made millions and blew it all. It was largely because of the hangers on who brought them down. Some of those athletes, Bernie Kosar in particular, said the best day was when he filed for bankruptcy. He didn't have anymore money so everyone left him alone. I think people really underestimate this and how hard it is to say "no". As another person posted, this is why many lottery winners wind up in the same monetary state within a few years of winning the lottery as they were before they won.
On a much smaller scale, I see this about every 18 months. We have a neighbor who has a 19 - 20 year old daughter. The daughter has gone through 3 - 4 cars in the 5 years they have lived in the neighborhood. Why? Because some relative always buys her another car after she has destroyed the old one. This kid has a sense of entitlement and the relative can't say "no".