As the financial markets improved in the 1990s, Trump rebounded as well. But the comeback did not include his casinos for long. Stock in his casino company, once valued at $35 a share, bottomed out at a stunning 25 cents. Today all three casinos are once again facing bankruptcy.
"Anybody who took the ride for the long term has lost 99 percent of their money," Roffman said.
Who's The Best?
No one would dispute that Trump has had many successes, but that does not seem to be good enough for him. Trump says is not merely great, but the best.
His reality show boasts that he is the biggest developer in New York City, but top real estate developers contend that isn't true. An ABC News analysis of total units already built clearly shows other developers are ahead of him:
However, there is no official ranking, and several of Trump's friends and associates in real estate said that they do believe he is the biggest developer based on total value — a financial factor nearly impossible to prove.
It also turns out the Trump name on a building does not always mean what it suggests. Public records indicate that of the 15 Manhattan buildings that bear his moniker, Trump owns nearly none of them outright.
"When Donald says 'I own something,' take out a magnifying glass," said O'Brien. "A lot of the big things that he owned 10 years ago, he doesn't own outright now anymore."
In any case, Trump is a master of profiting from his name. "He will make no bones about creating that image in order to bring the value up in his products and bring the value up in everything that he touches," Maples said.
Learning from past mistakes, Trump often relies on partners to carry much of the financial load, but that means he gets a considerably smaller piece of the pie.
When the Master Was the Apprentice
Trump's late father was an example and inspiration to him, Maples said. "Even in his last days, he would get up and put on that suit, ready to go to work … A father that got dressed and went out into the battlefield."
The young Trump was raised to emulate his father, she said. "From early on … to be like dad, but to be even better … and to impress daddy. To show daddy what Donald can do. Always make daddy proud."
"He is a little boy who always wanted to be a star," Maples said of her ex-husband. "He just happened to become a businessman. He became an entrepreneur. So now this little boy who had the training of his father to become an incredible real estate developer and took it to the next level and the next level and the next level — can suddenly have it all."