30. In Happier Times
This photo shows Donald and Fred Trump with then-New York city Mayor Ed Koch in July 1982. The trio looked delighted, but in just a few years, Trump would be seeing red thanks to his attempts to get into the casino business in New Jersey. After acquiring several properties, it soon became clear the ventures weren’t going to turn a profit.
As Trump was acquiring properties in Atlantic City, poor financial performances began to mount and Trump was forced to restructure debt and sell off his money-losing airline, Trump Shuttle, as well as his mega-yacht, Trump Princess. By 1995, Trump consolidated all of his casino properties in N.J. (as well as one in Indiana) under Trump Hotels & Casino Resorts. THCR underwent bankruptcy restructuring in 2004 and 2009.
