ROFL! No, it's not. At some point he wasn't doing well financially on a personal level, but the bankruptcies were filed by companies that he owned. Basically he burdened his companies with a lot of debt hoping things would go great, and when they didn't, they had to file bankruptcy instead of repaying those loans. It's kind of like the recent financial crisis... a lot of people (including home buyers, banks, and even hedge funds and real estate firms) basically saw in the period before the financial crisis that there was this great payoff where either they made money hand over fist with very little personal investment, or if they did lose money, it was the lenders' money anyway. Like a trip to the casino using somebody else's credit card! Granted that somebody else was dumb enough to say "Hey, have my credit card. Please! I'm begging you!"