Donald Trump: The Genius of Self-Promotion

With his gleaming financial empire and an unparalleled acumen for self-promotion, Donald Trump has emerged as America's business icon. But some say there's less to this image than meets the eye.

The boastful baron's name is on everything from skyscrapers to board games, and he is the centerpiece of a hit reality show that portrays him as a sort of Jedi financial master to his young apprentices. But is he really the financial and business guru he plays on TV?

In dozens of interviews, ABC News found many who say there is less to the Trump mystique than meets the eye. A review of thousands of documents and financial records, and scores of court cases, pointed to the same conclusion.

"Of all the things he's developed, the biggest thing he's developed is that image," said Jeffrey Sonnenfeld of the Yale School of Business Management.

Even Trump's ex-wife, Marla Maples, says that has long been one of Trump's strongest features.

"In the beginning, when he first started out, [and published his 1987 book] Art of the Deal, he always was exaggerating," Maples told ABC News' Chris Cuomo in an exclusive interview. "Being able to 'Trump' that up really helped put him on the map."

Building His Image

"If you look at him as a marketer, you have to say he's successful. I think if you look at him as an operator, he's had a number of failures that are out there, demonstrable, they exist," said Timothy O'Brien of The New York Times.

Critics often cite Trump's Atlantic City casinos as examples. When he first went into that market in the 1980s, he was a budding media darling — having purchased his first New York hotel at age 31, and then five years later, building the Trump Tower, a 68-story skyscraper in the heart of Manhattan.

When the casinos started making money, the buzz grew even louder. Bankers lined up to lend him billions of dollars, and Trump fed the circus by going on a spending spree and buying what he called his 'trophies'. Among them:

a $32 million yacht, the Trump Princess

a $365 million airline, the Trump shuttle

and New York's grandest hotel, the Plaza, for $407 million.

"He never was just a real estate genius. He was always a star," Maples said. "That's a whole part of how he worked his business and manipulates in the world in that way."

But then Trump built his third casino in Atlantic City, the Taj Mahal. It was his biggest deal ever, and some say, his biggest mistake.

The Big Mistake

The Trump Taj Mahal cost $1 billion, and it was built on junk bonds with the whopping interest rate of 14 percent. It put him $1.4 billion dollars in debt on his casinos alone.

"He borrowed too much money," said O'Brien. "And the casino couldn't throw off enough money to pay back the debt."

Soon Trump was facing failure. His debt grew to $3.4 billion, and the casinos that bore his name all went bankrupt, as did the Plaza hotel. Bankers who were throwing money at Trump just months before were now at his door.

But they faced a dilemma: they had lent Trump so much money that if he went down they might go down with him.

Casino analyst Marvin Roffman says he thinks Trump "convinced them that he was their best hope of getting their money back." The banks took control of some of Trump's prized assets, and put him on a financial leash.

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."