Few can lay claim to living the American Dream of fame and financial success, but hotelier and casino mogul Donald Trump can—though prosperity is not without its consequences. Trump, or "The Donald" as he’s been dubbed by ex-wife Ivana, has mastered the art of deal making, starting with utilizing his inherent ruthlessness and cunning. A success in the business world first and foremost, Trump also managed to become famous for his brazen and unabashed personality, allowing him to be both darling and dupe of the media. Never one to be upstaged by anything, including the reality television trend, Trump starred and produced the series "The Apprentice" (Abc 2004- ), a surprise hit that forever etched Trump in the cultural lexicon with his infamous catchphrase, “You’re fired.”

A native of New York City, Trump represented the third generation of businessmen in his family. His father, Fred Trump, turned to real estate when his own father died young in order to support his family. Trump tagged along with his father and assisted with various business ventures while young, learning the skill of recognizing a good deal. After graduating from New York Military Academy in 1964, Trump studied finance at the Wharton School at the University of Pennsylvania, the first business school ever established in the United States. Upon returning to New York, Trump wormed his way through the upper crest by joining an exclusive club on condition that he not try to steal the wives of older members. Trump used his membership as a means to an end—making contacts, and from whence his empire was born.

Trump became the one of the premier real estate tycoons in the early 1980’s by amassing properties in New York City, including Trump Tower, Trump Plaza and the world-renowned Fifth Avenue skyscraper. Trump also delved into the casino business, where his name was blazoned on the only three casino/hotels in Atlantic City to be five star, five diamond rated. Throughout the 1980’s, Trump also had his name splashed across every tabloid newspaper and TV show due to his rocky divorce with first wife Ivana, and subsequent relationship with second ex-wife, Marla Maples. However, Trump continued to score financial success with the publication of his first autobiography, The Art of the Deal, which sold in excess of 3 million copies and settled in on the best-seller list for a comfortable thirty-two weeks. Three more books soon followed, though none were as successful as the first: Surviving at the Top, The Art of the Comeback and his first political manifesto, The America We Deserve. Also on Trump’s plate was his role as Executive Producer for the Miss Universe, Miss USA and Miss Teen USA Pageants, airing on CBS.

Despite a long-string of daring successes and a life at the top of the real estate world, Trump’s fortunes came crashing down in 1990 when he was forced to file bankruptcy after a loss of over two-thirds of his net worth, or $1.5 billion. True to his hard-edged style, Trump fought back and returned his net worth to a more relaxing $3 billion. But for most of the later-nineties and into the 21st century, Trump remained largely out of the public eye, so his comeback wasn’t complete until “The Apprentice” captured the public’s attention. On the show, sixteen contestants—eight men, eight women—compete against each other to become the president of one of Trump’s companies, complete with an annual salary of $250,000. Each episode contained tasks for the contestants to follow, like selling lemonade on the streets of New York, running a rickshaw company in Central Park or renting swanky apartment buildings for $20,000 a night. After each episode, The Donald brings all the contestants to the board room where he summarily “fires” one in business-like fashion. The surprise hit become one of the leading lights of the dimming reality series trend and a tentpole property for NBC, which launched a spin-off version starring Martha Stewart. Meanwhile, "The Donald's" public profile was reestablished and he reveled in limelight, using his TV popularity and pop cultural cachet to fuel projects big and small, from merchandising tie-ins to major corporate undertakings.

Not to be without his controversies, Trump found himself in financial trouble yet again. The threat of bankruptcy loomed over Trump once more, this time for his ailing casinos in Atlantic City which were swamped by $1.8 billion of debt. The entrepreneur found himself fighting to stave off bankruptcy proceedings by seeking a $400 million cash infusion. His personal life also remained colorful, with his opulent, over-the-top 2005 marriage to model Melania Knauss.