Trump spent way too much building the Taj Mahal because everything had to be "the best" for his ego, and then when he was already overextended he also bought the Plaza Hotel in NYC. At the time this was all Trump's personal dealings, not public, and he personally guaranteed all the loans. 1995 was the year he took his casinos public to deflect some of the losses to the investors, but he couldn't cover it all. The reason it all went south was that a few years before Mississippi legalized gambling, and quickly became the preferred destination for everyone who lived south of the Carolinas. All the AC casinos took a hit from the new competition, but Trump was far too overextended to handle the contraction.