Trump almost filed for bankruptcy in 1990 (5/13)

Due to massive personal and business debts. A significant amount of debt was garnered from financing the Taj Mahal, one of Trump’s casinos acquired in 1988, through high-interest junk bonds. However, he ceded 50 percent ownership of the casino to the original bondholders, who lowered Trump’s interest rates and extended the loan so Trump had more time to pay off the debt. Today, Trump owns more than 100 companies and his net worth is approximately $4 billion. – NewsWeek.com

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Even if he hadn’t gone into real estate, he would still be rich

He tried to sue an author for $5M for calling a Millionaire