Editors Note: This article was originally published in the October 2004 issue of Playboy magazine.
Somehow it's fitting that the Friars Club, the venerable brotherhood of shtick men, has chosen to roast Donald Trump at its centennial celebration this month. Few billionaires have provided as many punch lines as the flamboyant real estate developer with the bombproof comb-over and inexcusable tastes. Even with the gold-plated success of The Apprentice, "the hottest reality show in the history of TV," as Trump likes to call it, it's hard not to laugh at the high-camp spectacle that is the Donald's life.
But if the current Trump renaissance has taught us anything, it's that the joke is on the rest of us. Even if you can't stand his pink ties or squinty I'm-so-great delivery, you have to admire Trump for staying on top as long as he has. He nearly went bankrupt during the early-1990s real estate slump, only to fight back with more cash than ever. He sucked it up through tacky marriages and public divorces, only to find romance with Slovenian model Melania Knauss, his fiancée. And in New York City, where Trump bashing had become as common as turbaned cabbies, he now outhits even the Yankees on the hometown popularity scale.
It's hard to say whether The Apprentice made him cool again or whether Trump finally brought cool to the hot-tubbing, spitswapping squalor of "unscripted" television. More than 20 million people watched the original series each week, with twice that many tuning in for at least part of the finale, when Trump hired cigar salesman Bill Rancic to help construct a 90-story Chicago tower. By the end, The Apprentice had become more than just a TV show. It was required viewing at such places as Harvard Business School and the Wharton school of business, and more than a million people applied to take part in round two, which airs this fall.
Not that being a Hollywood titan satisfies Trump, who just keeps moving and building, stamping his name in gold wherever he goes. His latest book, How to Get Rich, is his fifth national best-seller, and his latest real estate deals are bringing that special brand of Trump splendor to the Caribbean, Brazil and even Korea.
Born in Queens in 1946, Trump grew up learning to master the universe from his father, Fred, who accumulated millions by selling moderately priced housing to half of Brooklyn and Queens. Not long after Trump the younger crossed the bridge into Manhattan, his behind-the-scenes exploits rivaled the spectacle of his gleaming skyscrapers. His marriages to Ivana and Marla Maples fed a generation of gossip columnists. And even with his current popularity, tabloids love to find chinks in his armor: The casinos are failing! The stockholders are angry! The billions don't exist!
Trump met with journalist David Hochman over the course of a few days at Trump Tower in Manhattan, midway through the second Apprentice shoot. Hochman reports: "Carving big chunks of time out of his busy schedule isn't easy. During one two-hour interview, his executive assistant, Rhona Graff-Riccio, logged more than 50 phone messages. The only call Trump took was from his son Eric, one of his four children. Trump says he always takes his kids' calls. Despite a harried production schedule and a docket full of meetings, public events and charity functions—as well as various interruptions from Trump Organization honchos such as Carolyn Kepcher and other unwitting stars of The Apprentice—Trump was focused, enthusiastic, open and direct. He was even gracious enough to leave me with a lapel pin featuring the catchphrase of the year: 'You're fired!'"