Because despite the 3 bankruptcies he still has more money than we ever will! Keep in mind that most of Don's money is in real estate not casinos. He probably made his money when the casino company first went public. Plus he is an active participant at what is probably an outrageous salary. Don is very good at taking money out of properties and sticking it into his personal pocket before anyone is the wiser. His casinos have to have been making serious money for the last several years. That the company is bankrupt just means he managed to bleed off the excess.