Our Trump Dump

Our Trump Dump
New York​​ Magazine’s look back on the GOP prince’s days as an NYC clown.

Last April, when President Obama delivered his annual roast at the White House Correspondents’ Dinner, he homed in on a familiar target for ridicule. “And Donald Trump is here,” the president said. “Still!”

He still is! Nine months later, the New York developer has transformed himself into a heartland populist, a nativist fearmonger, and a surprisingly skilled politician with a commanding lead in the Republican primary campaign. One piece of collateral damage: New York City has lost one of its great tabloid characters. Yes, journalists still enjoy writing about Trump (many more than ever before) but it’s easy to forget that he was once a figure of local absurdist fun — the city’s very own billionaire circus clown with a short temper and shorter fingers.

Trump went into business in 1968, the same year New York came into being. “The first time anyone heard much about Donald Trump was about five years ago,” contributing editor Marie Brenner wrote in a 1980 profile. “And it all sounded very fishy.” But over the succeeding years, this magazine got to know Trump intimately, chronicling his deals, his bankruptcies, his marriages, his affairs, his casinos, his yacht, his children, his vendettas, his television show, his marketing schemes, and his presidential campaigns. He occasioned and survived multiple bans by editors skeptical that there was anything about Trump left to say. He graced the magazine’s cover numerous times, most recently in September, when he was digitally placed in the guise of George Washington.

And so, as hordes of Iowan Republicans race to declare Donald Trump their pick to be the nation’s next president, we went into New York’s archives to find our favorite Trump moments. Perhaps you remember the day the Post put Trump’s smirking face on its front page, next to the headline “Best Sex I’ve Ever Had,” plugging a rave review that came from his newly discovered mistress, Marla Maples. But how about the time he floated a fake rumor that he was sleeping with Carla Bruni to make Maples jealous? Or the time he exchanged expressions of mutual admiration with Richard Nixon, or the time Puff Daddy ran around naked at the beach of his Palm Beach compound, or the time Mayor Ed Koch called him “Piggy, piggy, piggy”? Trump has trespassed on the historical stage with surprising regularity: He was at Studio 54 on opening night, in Moscow at the dawn of perestroika, in Tyson’s corner before his knockout of Michael Spinks. And so we complemented our own archival material with a review of some of the biographies and autobiographies (there are many!) and got a few people on the phone to recall their encounters from decades past. Below, you’ll find our favorite moments of Trump’s career to date — a portrait of a man charging shamelessly into the future, leaving victories and disasters in the dust, shifting personas the way other men change ties, but never, ever, evolving.

Trump’s first appearance in this magazine was in 1976, a few months after President Ford told New York to drop dead, as an unknown real-estate developer with a plan to build a new convention center on Manhattan’s West Side. Never mind that the city was broke, that its subways were busted up and its streets full of muggers, or that Trump was just 29 and brought little to the table besides a land-development option purchased from a bankrupt railroad company with no money down. Trump had an idea of where New York was headed: up. He feuded over his proposal with Bob Tisch, the hotelier who chaired the city’s Convention and Visitors Bureau. “I don’t think we should put up a convention center,” Tisch groused, “that someone is trying to build as a monument to himself.” If only he knew.

Chapter 1: Faking It, Making It

He Stole His Brother’s Toys

July 14, 1946 Donald Trump is born.

Donald Trump: My brother Robert likes to tell the story of the time when it became clear to him where I was headed. Robert is two years younger than I am, and we have always been very close, although he is much quieter and more easygoing than I am. One day we were in the playroom of our house, building with blocks. I wanted to build a very tall building, but it turned out that I didn’t have enough blocks. I asked Robert if I could borrow some of his, and he said, ‘Okay, but you have to give them back when you’re done.’ I ended up using all of my blocks, and then all of his, and when I was done, I’d created a beautiful building. I liked it so much that I glued the whole thing together. And that was the end of Robert’s blocks. —Trump: The Art of the Deal

He Picked His First Development Fight

April 1976 Trump fights to develop the Penn Central properties.

Immediately after business school, Trump started working for his father, Fred, a major Brooklyn builder. Fred was wary of Manhattan, but as soon as he could, Donald moved to “a small studio on Third Avenue and 75th Street” and referred to the family business as the “Trump Organization.” Trump began pushing to develop Penn Central’s rail yards on the Hudson River at 34th Street, where he wanted to build his convention center, and the Commodore Hotel, a rundown turn-of-the-century property that the company owned near Grand Central Terminal. But he ran into opposition both from city elders, like Bob Tisch, and political bosses who favored other convention-center sites. Eventually, however, the city decided to build the center on Trump’s parcel — without Trump. The brash young developer made himself into an obstacle, claiming his contract with Penn Central entitled him to a $4.4 million commission if the land was sold to the city. He magnanimously offered to forgo the fee if the convention center were named for Fred Trump. When city officials finally examined the contract, however, they discovered the younger Trump had exaggerated: the amount he was entitled to was more like $500,000. The center was built without Trump and named for Senator Jacob Javits.

Louise Sunshine, a longtime Trump employee: In the early 1970s, I was finance chairman for Governor Hugh Carey and a director of his fund-raising activities. Donald wanted this license plate with “DJT” on it, and I was able to obtain it for him. He thought I was some sort of miracle-worker. But he hired me, and we worked together approximately 16 years. For a while, the company was just the two of us in a small office on Lexington Avenue. He worked about 18 hours a day. His staff grew a lot after the first two or three years, but he was always involved in every single facet: the construction, the financing, the deal-making, the site acquisition, the hiring, the firing, the check-signing, the marketing, the sales. What really motivated him was a desire to be even more successful than his father. Fred Trump was like a bulldozer. Donald Trump is like three bulldozers.

—As told to Nick Tabor

He Seduced Ivana

July 1976 Trump meets Ivana Zelníčková at the Montreal Olympics.

Zelníčková was a sultry Czech model who later published a thinly veiled autobiographical novel entitled, For Love Alone, which described the attraction between “Katrinka” and “Adam”:

His extravagance both delighted Katrinka and made her uneasy. Until Adam’s appearance in her life, she had lived frugally, working hard for every necessity, and even harder for the luxuries … [nothing had] shaken her belief that what she wanted she must earn, what she got she must pay for. But she had done nothing to earn this flood of presents from Adam, and their cost was so clearly colossal that the idea of repayment of any kind was ridiculous.

“I only want you,” she said.

“You have me,” he replied, laughing. “Why not take the mink as well? Come on, Katrinka,” he coaxed, “don’t spoil my fun.”

She slipped her arms into the sleeves of the coat, turned again to look into the mirror, and thought how warm she would be in it next winter. “You are completely crazy,” she said, “to buy me a mink coat in June.”

“I didn’t mean to buy it. I just happened to be walking past a store on Fifty-seventh Street, and there it was in the window. I couldn’t resist.”

“You do never resist.”

“Not you,” he said, turning her around to face him, slipping his arms under the coat and around her bare waist … He took a nipple between his lips, flicked it with his tongue, and felt Katrinka’s arms tighten around his neck, her body arch in pleasure. In a moment, they were on the floor, on top of the mink coat, Katrinka’s legs gripping his waist as he moved deeper and deeper into her. Finally, after a long time, they finished and lay quiet, each one trying to come to terms with the depth of feeling the other inspired, so much stronger, more compelling than anything either had experienced with other lovers, sometimes bewildering in its intensity, producing alternately joy and terror.

As Adam pulled away from her, his cock fell for a moment into the valley between her legs, leaving a smear of semen on the dark silk. He smiled with satisfaction. “Now you have to keep the coat,” he said.

He Loved Studio 54: “First of All, You Didn’t Have AIDS”

April 1977 Trump attends Studio 54’s opening night.

Trump’s new relationship didn’t keep him from enjoying himself as a wealthy young man in the city. "What went on in Studio 54 will never, ever happen again," Trump said years later to Timothy O’Brien, the author of a well-researched and entertaining biography, TrumpNation. "First of all, you didn’t have AIDS. You didn’t have the problems you do have now. I saw things happening there that to this day I have never seen again. I would watch supermodels getting screwed, well-known supermodels getting screwed on a bench in the middle of the room. There were seven of them and each one was getting screwed by a different guy. This was in the middle of the room. Stuff that couldn’t happen today because of problems of death.”

He Learned His Positive Thinking From the Master

April 1977 Trump marries Ivana in a ceremony conducted by his family’s spiritual guide, the Reverend Norman Vincent Peale.

Did you know Trump grew up attending Peale’s church and drew inspiration from his famous self-help sermons? “My father was friends with [Peale], and I had read his famous book, The Power of Positive Thinking,” Trump told Psychology Today in 2009. “I refused to be sucked into negative thinking on any level, even when the indications weren't great. That was a good lesson because I emerged on a very victorious level.” Peale once predicted that Trump would become “the greatest builder of our time.” Just as positively, if less perceptively, Peale told the Times in 1983 that Trump is ''kindly and courteous in certain business negotiations and has a profound streak of honest humility.''

He Tried to Manipulate a Village Voice Reporter

January 1979 The Village Voice publishes the first extensive investigation into Trump.

Wayne Barrett, then a 33-year-old reporter at the Voice, was the first of many investigative journalists to dig into Trump — and to contend with his unique approach to press management. In the late 1970s, his reporting on Trump’s political connections spawned a grand-jury investigation — though no charges were ever filed — and he would later go on to write the definitive account of Trump’s first chapter in public life, Trump: The Deals and the Downfall. Early on in his research, Barrett was going through files at a government office, where Trump, tipped off, reached him by phone.

Wayne Barrett: I was very early in the process, just looking at public records, when he called me and said, “Let's get together, Wayne!” As if we were old buddies. We had never spoken before in our lives. “Wayne! Let's get together!”

So I agreed to a meeting with him that was totally premature. He came on very strong. I tell you, I didn’t have my best ammunition yet—I had jumped the gun. I just remember he told me something like, “You know, you don’t have to live in Brownsville.” He said he had “plenty of apartments.” It was incomprehensible to him that I actually chose to live in Brownsville.

My memory is that he didn’t explicitly threaten me. What he did is tell me how he had broken some other journalist with a lawsuit.

—As told to Andrew Rice

He Built Trump Tower

October 1980 Trump secures financing for his Trump Tower development.

In 1979, he had purchased the Bonwit Teller building on Fifth Avenue with the intention of constructing a luxury condominium project. He immediately made himself into a villain of preservationists by demolishing the Art Deco department store and its famous limestone reliefs, which he had initially promised to give to the Metropolitan Museum of Art.

Trump used some clever manipulation of the zoning code to replace the department store with a gold-clad skyscraper that rose far above its neighbors, to 56 stories — although Trump used some fuzzy numbering to claim it went up to 68. “The Trump Tower will be the greatest building in New York, Trump told New York’s Marie Brenner. “There will never be another skyscraper built like it. Because of me they’ve changed the midtown zoning, and it’s kind of sad really, because there is nothing I can do that will be greater after this.” Trump promised that the building, then under construction, would be replete with gilded ornamentation — “real art, not like the junk I destroyed at Bonwit Teller.” And he said the negative press only made him stronger. “You know, the morning after that story hit the front pages of the Times, I must have gotten two dozen calls from people who wanted apartments in Trump Tower.”

Chapter 2: The Heyday

His Tower Defined the Decade

February 1983 Trump Tower is completed.

Once completed, Trump Tower would become a symbol of New York’s resurgence during the Reagan era. (Years later, when this magazine asked him to name New York’s greatest decade, Trump replied: “I built Trump Tower in 1983, so I’m fond of the eighties.”) It also made Trump’s name a luxury brand. Trump himself still lives and works in the building, which serves as the headquarters of both his business and his campaign. A handful of other residents have been there since the beginning:

Estelle Cohen, 41st-floor resident: I was one of the first people that moved into the building. There’s no better location in all the city. What could be better than living next to Tiffany and across the street from Bergdorf Goodman? What’s better than that?

It’s a fine building; it looks as new as it did when it was built. It’s always kept in perfect condition. In fact, there have been people who have moved back to the building. One widow I heard of, she remarried and moved to somewhere on Park Avenue. And after her husband unfortunately died, she came back into the building, because she said there was no better home than in Trump Tower.

Years back, I met Mr. Trump quite a few times. He speaks well. To the point. And he’s just very nice. I have nothing but praise for him — and especially the family. Those are the nicest children you would ever want to meet. I never saw them come through the lobby ill-mannered. And all the wives were very nice as well, frankly. From Ivana to the second wife to the third — Melania.

There has been a continuous change in the residents over the years. They come and go frequently. Most people that live there are foreigners who have it as their second or third homes. They have dignitaries, and they have ambassadors. A lot of nobility. Like Michael Jackson. Very few people knew he lived there until there was an announcement in the paper. But the same employees have been there for years and years. They do like working there. You wouldn’t think so, but that’s the way it is.

—As told to Nick Tabor

He Tried to Topple the NFL

September 1983 Trump buys the New Jersey Generals.

Trump Tower begat a litter of Trump-branded condo buildings — Trump Parc, Trump Plaza, Trump Palace — but Trump himself was not content to remain a mere real-estate developer. He expanded into Atlantic City casinos, bought the Eastern Airlines shuttle (which he renamed Trump Air), sponsored a professional cycling event called the Tour de Trump. But perhaps his most audacious move came in taking on the entire National Football League.

After Trump purchased the Generals, a franchise in the fledgling USFL, he immediately began spending lavishly on big-name college players, like Heisman Trophy winner Doug Flutie, and otherwise tried to pump up the team’s star power. He invited a panel of celebrities, including Andy Warhol, to judge cheerleader auditions. (“Ivana voted for any of the girls who looked like her,” Warhol recorded in his diary.) The USFL played in the spring, so as to avoid direct competition with the NFL on television, but Trump pushed the rest of the owners to move their season to the fall. The Hail Mary play backfired, and the league was soon out of business. Trump was savaged over his role in the demise of the league in the 2013 ESPN documentary, Small Potatoes: Who Killed the USFL?

Keith Jackson (USFL broadcaster): You just can’t say, all of a sudden, “We’re going to be on the same par as the NFL.” That was, to me, the silliest thing I’d ever heard.

Burt Reynolds (actor, part owner of the Tampa Bay Bandits): To go head-to-head with them was insane.

Chuck Pitcock (offensive lineman for the Tampa Bay Buccaneers): He manipulated [the other owners]. Because at that point, there were four or five owners that were broke, that didn’t have the power or the money. And they figured if they rode with Donald, they might end up with some. You ain’t gonna end up with none! He gonna throw your ass to the street too.

Chet Simmons (first USFL commissioner): He couldn’t care less about these other guys if it came down to it. He’d kill ’em all. Leave ’em in blood on the street.

He Blew Up Palm Beach

October 1985 Trump buys the Mar-a-Lago estate in Palm Beach, Florida.

Trump snapped up the 17-acre estate for the bargain price of $8 million, setting off 30 years of feuds between Trump and the aristocratic redoubt of Palm Beach. Trump initially didn’t care much for the house: In 1990, he wrote that he had visited it “no more than two dozen times in the years I’ve owned it.” But it has been a steady revenue generator since Trump turned it into a private club. (The fee to join is $100,000.) He generated publicity for the club by inviting celebrity guests, like Michael Jackson, to the house and by staging lavish parties, which were especially wild during his bachelor period. (Puff Daddy was reportedly once caught in flagrante with a friend on the beach.) Trump would invite the local press to cover events from the driveway to create the appearance of clamor. He also entertained biographer Timothy O’Brien:

When I return, Wild Cherry’s “Play That Funky Music White Boy” is cranking into the night. Donald, wearing a navy Brioni suit and a baby-blue tie, is biting his lower lip, doing his own halting version of a suburban disco dance. He’s happy. He turns to me and leans in toward my ear.

“I bet they can hear this fucking music up and down Palm Beach,” he shouts. “And I bet it’s driving them nuts, the stuffy cocksuckers. And you know what? I don’t care.”

He Retained Joe McCarthy’s Favorite Lawyer

June 1986 Roy Cohn, Trump’s attorney, is disbarred.

Trump met Cohn during the 1970s, at Le Club, an exclusive nightspot they both frequented. Cohn was infamous for prosecuting the Rosenbergs and acting as Senator Joe McCarthy’s chief inquisitor during the Red Scare of the 1950s, but by this time, he was operating an ethically malleable law practice, representing political power brokers, mobsters, and various creatures of the night. (Studio 54 was a client; so was Andy Warhol.) Trump convinced Cohn to represent his family company in a federal racial-discrimination suit related to his father’s rental properties. Cohn would become one of Trump’s most important advisers during the early part of his career.

Donald Trump: I don’t kid myself about Roy. He was no Boy Scout. He once told me he’d spent more than two thirds of his adult life under indictment on one charge or another. That amazed me. “Roy, just tell me one thing. Did you really do all that stuff?” He looked at me and smiled. “What the hell do you think?” he said. —Trump: The Art of the Deal

He Didn’t Pay Retail

November 1986 Trump is named a sales-tax dodger.

Although Trump likes to show off his lavish expenses — he put gold-plated faucets in the bathrooms of his Trump Air planes — the documentary record is replete with evidence that he is a secret miser. For instance: The state attorney general named him in an investigation into a Manhattan jewelry store, saying he had avoided sales taxes on $65,000 worth of merchandise by having it sent to Cohn’s house in Connecticut. (Only the store was charged, not Trump.) John O’Donnell, a former executive at his casino company, wrote in his memoir, Trumped!, that his boss would often raid his gift shops for snacks, scoop up handfuls of chocolate candy and stuff them in his pockets to eat later.

He Tried to Build the World’s Tallest Skyscraper — And Lost

May 1987 Mayor Ed Koch torpedoes Trump’s plan for Television City.

Trump’s ambitions were only rising. He was no longer content to simply develop condos; he wanted to build the tallest skyscraper in the world. First, he proposed to build a 150-story building at South Street Seaport. When that idea went nowhere, he shifted his attention to developing 150 acres of Upper West Side waterfront land. “It’s the hottest property in the world,” he told New York writer Tony Schwartz, after he secured the development rights. Trump’s 150-story skyscraper would now be the centerpiece of a project called Television City.

Trump hoped to lure NBC as a tenant. But Koch, with whom Trump had previously clashed, refused to give the developer a $700 million tax break, killing the potential deal. In a series of highly publicized attacks, Trump called Koch a “moron,” the city “a cesspool of corruption and incompetence,” and demanded the mayor’s immediate resignation.

“Piggy, piggy, piggy,” Koch retorted.

He Began to Consider Himself Presidential Material

October 1987 Trump stages a campaign event in New Hampshire.

As Ronald Reagan’s second term wound down, Trump flirted — as only Trump flirts — with the idea of running for president. In 1987, he traveled to Moscow and afterward started speaking out on foreign policy, buying newspaper ads calling for protectionist tariffs. A Draft Trump movement sprang up, and Trump flew to New Hampshire in his helicopter to address a meeting of the Portsmouth Rotary Club. The speech was well received, but Trump backed out of running — a teasing act he would perform during several subsequent election cycles. Each time, he would pull out before things got serious, then deny he had ever truly been interested.

Donald Trump: People have always asked me if I’ll ever be involved in politics. It seems every so often there’s some unfounded rumor that I’m considering seeking office — sometimes even the presidency! The problem is, I think I’m too honest, and perhaps too controversial, to be a politician. I always say it like it is, and I’m not sure that a politician can do that, although I might just be able to get away with it because people tend to like me. Honesty causes controversy, and therefore, despite all the polls that say I should run, I would probably not be a very successful politician. —Trump: The Art of the Comeback

He Became a Best-Selling Author

November 1987 Trump’s first book, The Art of the Deal, becomes a best seller.

Cynics pointed out that the abortive presidential campaign provided a bounty of free publicity for Trump’s autobiography, which was also excerpted as a cover story in New York. It was a huge hit, selling 835,000 copies in hardcover alone. Afterward, Random House reportedly paid Trump a $2.4 million advance for a sequel. Trump — who collaborated with Tony Schwartz on the first book—hired a new ghostwriter, Charles Leerhsen. In a feature timed to coincide with the release of Trump: Surviving at the Top, Leerhsen described the developer’s extremely hands-on approach to the writing process (as quoted in another New York story):

As anyone who has ever written about him knows, Trump tries to stay in control of his image; it’s a more than full-time job for him, and critical to his business operations. Trump exerted total control over the book. “He dictates, with the punctuation marks put in,” Leerhsen says, only half-kidding. Trump edited Leerhsen’s first drafts with a blue felt pen, and Leerhsen claims he could see microscopic pieces of felt left on the page as an emphatic Trump crossed out words and sentences. “At the beginning, drafting the first chapter, I was groping around to find his voice,” Leerhsen says. “He called me at home on a Sunday night very upset and bawled me out. I had dropped in a joke that he said didn’t sound like him.” Leerhsen adds, “I can talk about it now, but it was painful then.”

He Won Nixon’s Endorsement

December 1987 Richard Nixon writes a letter to Trump predicting, “Whenever you decide to run for office, you will be a winner!”

He Bought the Plaza

March 1988 Trump buys the Plaza Hotel for $390 million.

Donald Trump: “I thought owning the Plaza would be extremely cool, which is sort of my investment policy in life and it seems to work.”

Even at the time, Trump publicly admitted that the economics of the Plaza Hotel couldn’t justify the purchase price he paid. He just wanted it. Seven years later, facing ruinous debts, Trump’s lenders forced him to sell the hotel for just $325 million, all of which went to the banks.

Over the years, many of Trump’s investments have succeeded, many have failed, but it’s notoriously difficult to assess his overall performance as a businessman. Most of his assets remain privately held and are subject to Trump’s own assessments of value, which are … elastic. Trump claims his net worth surpasses $10 billion, while the Bloomberg Billionaires Index says it’s more like $2.9 billion. Timothy O’Brien, who conducted a thorough inquiry into the question in the mid-aughts, came up with a far lower figure once issues like his debt burden were taken into account—and Trump sued him for saying it. (See below.) A few financial commentators, including S.V. Dáte of National Journal and Matt Levine of Bloomberg View, have questioned whether Trump might have done better as an investor by simply putting his inheritance into an index fund. But what fun would that have been?

He Advised Mike Tyson on His Fights

June 1988 Trump sits ringside, next to the Reverend Jesse Jackson, as Mike Tyson knocks out Michael Spinks.

Tyson fought at Trump Plaza, the then-brand-new Atlantic City casino, as an unknown 19-year-old shortly after he turned pro. And as Tyson pummeled his way ferociously up the ranks, Trump’s interest in boxing increased: he knew a superstar when he saw one. The pinnacle of Trump’s career as a boxing promoter was Tyson’s fight against Spinks, where the champion dispatched the previously undefeated challenger in just 91 seconds. “Although it was not a masterpiece of athletic competition,” Trump later wrote, “the Tyson-Spinks bout was one of the great events of the eighties.” Many of the era’s biggest celebrities were in attendance: Warren Beatty, Paul Simon, Jack Nicholson, Sean Penn and Madonna. A New York columnist described the scene as Trump played master of ceremonies at a party at Trump Plaza before the fight:

Ivana and Donald posed standing above young Donny, who shook his head and made a face into his cheesecake when the lights went on.

“Bigger than ever! You should see who just walked in the door!” said Donald and took a sip from the ice tea held by his iced-tea bearer.

[Malcolm] Forbes went over to compliment Jackie Mason, who was having dinner with Milton Berle.

Then Jesse Jackson came in with the Secret Service, the guys of Trump, and three of his sons. Donald brought Malcolm Forbes over. The swarm swelled and churned. Jesse Jackson whipped out a dollar bill and gave it to Malcolm Forbes. “I always wanted to do that,” said Jackson.

When Forbes came back, his plate was gone. Then, just as I was beginning to miss him, Norman Mailer appeared with his son.

“Anything the Trumps do …” Jack Kemp said to Fred Trump.

He Advised Mike Tyson on His Marriage

October 1988 Tyson’s wife, Robin Givens, files for divorce.

As Tyson’s focus on boxing began to waver, in part due to his tumultuous relationship with Givens, an actress, Trump insinuated himself into the boxer’s inner circle, offering him advice about his finances and marriage.

Donald Trump: Suffice it to say that Mike, who is normally a picture of mental toughness, completely came apart at the seams during his marriage. One night, at a point when things were happening fast and furiously, Mike called me at home. “Listen, Mike,” I said, “you’ve got to ask yourself how you really feel about this woman.

“Mr. Trump,” he replied, sounding as confused as ever, “I just love that fucking bitch.” —Trump: Surviving at the Top

Trump says he advised Givens, too, and rumors circulated that the two were having an affair. Tyson once came to his apartment to angrily confront him. Trump recalled the ensuing conversation to Timothy O’Brien:

“Everyone’s telling me that you’re fucking my wife and I think you’re fucking my wife,” Tyson said.

“Mike, let me tell you something: I’ve never even thought about it. And I heard those rumors and they’re disgusting … She’s your wife, she’s with you, she’s loyal to you, and it’s total bullshit.”

(Donald told me years later that his life flashed in front of his eyes during the encounter. “That was a scary moment, you understand … Here’s the heavyweight champion of the world sitting there and he’s a solid piece of fucking armor.”)

“Mike, it’s absolutely bullshit, it’s false,” Donald reiterated. “I give you my word.”

“Could I lie down on your couch?” asked Tyson.


“Because I’m so tired I just want to nap.”

Last October, Tyson endorsed Donald Trump for president.

He Called for the Execution of Black Teens (Who Were Innocent)

May 1, 1989 Trump buys ad advocating “Bring Back the Death Penalty.”

Even as his involvement in the boxing world brought him in contact with civil-rights activists like Jackson and the Reverend Al Sharpton, Trump’s demagogic attitudes about race were already very much in evidence. After five black teenagers from Harlem were accused of brutally raping a Central Park jogger, a crime that horrified the city, Trump took out a full-page ad in the Daily News. “Mayor Koch has stated that hate and rancor should be removed from our hearts. I do not think so,” he wrote. “How can our society tolerate the continued brutalization of our citizens by crazed misfits? Criminals must be told their CIVIL LIBERTIES END WHEN AN ATTACK ON OUR SAFETY BEGINS!” After many years of imprisonment, the Central Park Five were ultimately exonerated by DNA evidence and received $40 million in compensation in a 2014 legal settlement. Trump called the payment “a disgrace.”

The Reverend Al Sharpton: We first met when I was leading picket lines against him about his ads on the Central Park Five. I marched on him and the Plaza Hotel, which he owned at the time. He and I got into a back-and-forth in front of his office. He said these kids were thugs, and I was telling him they were innocent until proven guilty, and the language of his ads was racist. I won’t say it was a shouting match, but it was a very passionate debate.

So then, fast forward, he wants to get the Tyson fights down to Atlantic City. And Don King tells him that he has these lasting feelings in the black community over Central Park, and Don was a big supporter of mine and the National Action Network. He said, “Mike Tyson grew up in Al Sharpton’s old neighborhood and knew Sharpton since he was a kid, and you need to calm that down.” And Trump said, “Sharpton’s a demagogue. He’s not going to talk to me.” And Don said, “I’m going to bring you guys together.” Then he told me that Trump may have conservative views, but he’s a great American.

So I ended up flying with Don King and Donald Trump to Atlantic City on Trump’s helicopter. And it was like 45 minutes of two guys talking nonstop, in a helicopter, not listening to each other, not coming up for air. Don was selling the fight to Trump, and Trump was selling to Don what he was going to do to Atlantic City. I can’t remember the content, other than they both were convinced they were the smartest, wealthiest guys on the planet.

As told to Nick Tabor

He Buried a Documentary That Ultimately Screened Just Twice

July 1989 Production on the investigative documentary Trump: What’s the Deal? is halted.

Leonard Stern, a competing real-estate developer, was a constant source of aggravation to Trump during this period. Stern owned The Village Voice, which had been investigating Trump’s dealings since the 1970s. Another Stern publication, 7 Days, questioned the quality and design of Trump Tower and other Trump buildings. Stern had also reportedly tried to lure NBC, Trump’s envisioned Television City tenant, to a competing development he was involved with in Secaucus, New Jersey. But when Stern financed a documentary titled Trump: What’s the Deal?, Trump got really nasty, spreading a rumor that Stern’s wife of 18 months, Allison, had repeatedly phoned his office “asking for a date.” Allison Stern called it “absurd,” “the product of a juvenile mind,” but Trump told a reporter, “We spoke. I wasn’t interested.”

In a New York cover story about the whole imbroglio, Stern alleged that Trump offered to disavow the rumor if he called off the documentary. “He had a representative call and say, ‘We’ll retract if you drop the program,’” Stern told writer Edwin Diamond. “They tried to initiate meetings to ‘bury our hatchets.’ I told them, ‘Drop dead.’”

Trump found another way to stifle the film, though, threatening lawsuits and using business connections to block the producer’s effort to find a TV outlet. Trump: What’s the Deal? was screened only twice at a small theater in Bridgehampton. But in September 2015, producer Libby Handros posted it for streaming at www.trumpthemovie.com.

His Womanizing Caught Up to Him

December 1989 Ivana Trump confronts Marla Maples in Aspen.

As the 1980s ended, Trump’s world began to implode. Gossip about Trump’s womanizing had circulated for years. But Trump’s marriage truly began to unravel when he began his affair with Maples. He shamelessly put her up in a suite at his St. Mortiz Hotel, even as he had Ivana running the Plaza Hotel next door. Finally, Marla and Ivana found themselves in Aspen at the same time, and they had a confrontation at Bonnie’s, a restaurant on the slopes of Ajax Mountain. In 1998, Maples reflected on the event in this magazine’s 30th anniversary issue:

Marla Maples: When we saw each other in Colorado, Ivana and I, it was just a moment of both of us wanting to know the truth. It was good that the truth became known, but that was also when the real pain began. I realized that we had both been deceived. You’re left in a very uncomfortable position — and the world knows about it ... Donald and I still really wanted to be together, but I was fighting to keep what we had privately, and once the world gets involved in your life, little by little it breaks it down until you forget what it was in the first place. What was a really private and nice relationship was judged and made to be something ugly.

I loved this man. Yes, I was young, but it was my choice. I was romanced, I had Mister Charm all over me, and it was very hard to say no. When that man wants something, he’ll stop at nothing to get it. And I also believed in the good of him.

Chapter 3: Debts and Defiance

He Began to Lose His Mojo

February 1990 Donald and Ivana Trump announce their formal separation.

As the 1980s ended, Trump was drifting into financial peril. All his expansion had burdened him with billions in debt at the very moment the economy in general — and New York real estate in particular — was headed for a deep recession. At the same time, his personal life was unraveling. While Trump was in Japan, watching his prizefighter Mike Tyson get knocked out by Buster Douglas, Ivana announced their separation, igniting one of the great tabloid frenzies in the history of the city. Trump claimed the breakup had nothing to do with his affair:

Donald Trump: My big mistake with Ivana was taking her out of the role of wife and allowing her to run one of my casinos in Atlantic City, then the Plaza Hotel. While she did an excellent job at both, I could have hired a manager who also would’ve done a very good job. The problem was, work was all she wanted to talk about. When I got home at night, rather than talking about the softer subjects of life, she wanted to tell me how well the Plaza was doing, or what a great day the casino had. It was just too much … I soon began to realize that I was married to a businessperson rather than a wife. It wasn’t her fault, but I really believe it wasn’t my fault either. It was just something that happened. —Trump: The Art of the Comeback

He Rebounded!

February 1990 The Post publishes the front-page headline “Best Sex I’ve Ever Had.”

The day the Post published Marla’s famous rave performance review, Trump sat down with New York writer John Taylor to do some damage control. “The Post headline today,” he said. “Well, you could take it as a great compliment.” Trump tried to counter the tabloid rumors the only way he knew how: by slandering others. “Famous women — I can’t give you their names — but famous women have now been calling the newspapers, their agents have been calling, saying they were with me, trying to get their pictures in as one of the so-called conquests.”

Trump has always served as his own PR man, to the frequent aggravation of the people he actually employs as publicists. In the 1980s, the New York tabloids were at the height of their power, and he skillfully traded tidbits with gossip columnists who helped to build his myth. (“It definitely helped create his first level of celebrity hell,” the former “Page Six” reporter Susan Mulcahy said in a 2004 oral history in Vanity Fair.) When Trump wanted to maintain a degree of distance from his leaks, he would sometimes call up the press using an alias: “John Baron.” Unsurprisingly, Trump was often an unreliable source. Later on, during a rocky period in his relationship with Maples, a Trump spokesman named “John Miller” — who sounded just like Trump himself — called up People magazine to spread the word that he was sleeping with the Italian model Carla Bruni. (Bruni denied it, calling Trump a “lunatic.”)

Trump’s hands-on publicity strategy has been a key element of his presidential campaign, winning him countless hours of free airtime. He’s also cultivated a friendship with the CEO of the National Enquirer, which has given him fawning coverage while savaging his rivals.

He Gambled on Atlantic City

April 1990 The Trump Taj Mahal casino opens.

Trump was already operating two Atlantic City casinos when he opened the Taj Mahal, which cost $1.1 billion. He offered New York a tour of the floor:

One of Trump’s hype techniques is to get people to agree with him that his casino or his yacht or his condo or his girlfriend is fantastic or incredible or fabulous or the best … “There are so many people who want to see this place,” he explained. “In a way, we’d like to keep them out, but what can we do? They want to see it. Because it’s such an incredible place. It’s the Eighth Wonder of the World.”

A year later, the Taj Mahal would file for bankruptcy.

He Owed the Banks Billions

April 1990 Trump is $3.4 billion in debt.

Around this time, Trump was walking down the street with Maples one day and pointed to a homeless man. “Right now,” Trump said, “he's worth $900 million more than me.” Trump had guaranteed about that much of his various companies’ debts, meaning he was at the mercy of the banks, who could easily force him into personal bankruptcy. But his lenders decided he was more valuable alive than dead. Trump gradually negotiated deals to sell off many of his prized assets — the airline, the yacht, the Plaza — at bargain prices. He didn’t do it agreeably, though. A recent Wall Street Journal article described how he fought his lenders at every turn. The largest of them was Citibank. “I drove [Citibank] nuts,” Trump told the Journal. “I did a number on them that you wouldn’t believe.”

One Citibank executive, Patricia Goldstein, felt particular wrath. Goldstein and Trump had once been close. When her husband was terminally ill, Trump asked for Cardinal John O’Connor’s help in getting him into a good hospice. But when Trump tried to call in the favor, when Citibank was attempting to force him to liquidate the Plaza Hotel, Goldstein rebuffed him. “I said, ‘No one has ever spoken to me in that way. See what I do to you,’” Trump recalled telling her in the Journal. He maligned her all over the real-estate industry. “I would see her at functions at various ballrooms throughout the city and I would say such things that some people were shocked.” Goldstein died in a bicycle accident last year.

“I didn’t send flowers,” Trump said.

He Fell Off the Billionaire List — Loudly and Homophobically

May 1990 Forbes says Trump is no longer a billionaire.

After Forbes published an article that revised its estimate of Trump’s fortune downward by 70 percent to a mere $500 million, an outraged Trump called his ghostwriter to dictate last-minute revisions. His book Trump: Surviving at the Top, published shortly afterward, included a rambling attack on his former chum Malcolm Forbes, the magazine’s founder, who had only recently died. Trump attributed Forbes’s hostility to his jealousy over the size of Trump’s yacht, the Trump Princess. “I also saw a double standard in the way he lived openly as a homosexual — which he had every right to do — but expected the media and his famous friends to cover for him,” Trump wrote. (Forbes had only been publicly outed after his death.) Trump claimed that shortly before the Forbes article was assigned, he had ordered Malcolm Forbes and “a couple of his young male companions” removed from the Oak Room Bar at the Plaza Hotel. “This wasn’t journalism, I thought to myself,” Trump wrote, “this was Malcolm finally getting back at me from the grave, with the help of his family, especially his son Steve.”

His Father Bought Him $3.5 Million in Chips at His Own Casino

December 1990 Fred Trump gives Donald an under-the-radar cash infusion.

As one of Trump’s Atlantic City casinos faced imminent bankruptcy, his ailing father bought $3.5 million worth of chips at the Trump Castle casino, allowing Donald to make an interest payment on his bonds. The New Jersey Casino Commission investigated whether the purchase amounted to an illegal loan but ultimately took no action.

He Ran Into Macaulay Culkin

November 1992 Trump makes a cameo in Home Alone 2: Lost in New York. Location: the Plaza.

He Blew Up at Barbara Corcoran

January 1994 Barbara Corcoran introduces Trump to Chinese investors.

Post-bankruptcy, Trump retained his public swagger, but he adopted a cautious business strategy. Though he still put his names on buildings, most of the capital — and the risk that went with investment—in his projects would come from deep-pocketed investors. In 1994, Barbara Corcoran — then a real-estate broker, now a star of the television show Shark Tank — brought some wealthy developers from Hong Kong to meet with Trump. He convinced them to pay $82 million for his Television City site, while assuming around $250 million of his debt. The Chinese investors would entirely finance a residential development called Riverside South, while Trump kept his name on the project and retained a minority stake. Craig Horowitz wrote a cover story for this magazine about the Riverside South deal, headlined: “Trump’s Near-Death Experience.” Trump was furious with Corcoran for talking to Horowitz and sued to withhold her commission, claiming (among other things) that she had exposed confidential information. Trump ultimately was rebuked by a judge and ended up paying Corcoran millions in fees.

Barbara Corcoran: I really expected a thank-you note. I did not expect a lawsuit. But my impression was that he did not like the cover drawing. He saw the word death. I think his little fingers were hanging on a wall, as I recall, and he was sweating and he looked like he was about to drop off. It didn’t make him look powerful.

I was emotionally drained. I didn’t sleep for months on end and was not very effective in my day-to-day business. The lawsuit hung over me like an ax—an ax that was being wielded by someone who was so much more powerful than me. The wrath was everywhere. I mean, every opportunity he had to speak on the press or on TV, he bad-mouthed me or my company. What helped tremendously is when I remembered my mother’s words as a kid: You need a bully to beat a bully. I went out and found an attorney who was ferocious in court.

It is funny, Donald continued to say negative things for it seemed like forever, but somehow it wound down. I met him when I was at the Today show, where I was a real-estate contributor. He came over to the show to promote The Apprentice, and when he walked in he looked so happy to see me, “oh, Barbara this and Barbara that,” [and] bragged about me. And I was like, Whoa, it feels better to be on the sunny side of Donald.

—As told to Andrew Rice

He Picked a Fight With the Cuomo Family

November 1994 Governor Mario Cuomo is defeated by George Pataki.

Trump claims that shortly after Cuomo lost reelection, he asked him to intercede with his son Andrew—then U.S. secretary of Housing and Urban Development—to ask for a “perfectly legal and appropriate favor involving attention to a detail.” When Mario said it would be inappropriate, Trump reminded him of his many campaign contributions:

Donald Trump: I did the only thing that felt right to me. I began screaming. “You son of a bitch! For years I’ve helped you and never asked for a thing, and when I finally need something, and a totally proper thing at that, you aren’t there for me. You’re no good. You’re one of the most disloyal people I’ve known and as far as I’m concerned, you can go to hell.”

My screaming was so loud that two or three people came in from adjoining offices and asked who I was screaming at. I told them it was Mario Cuomo, a total stiff, a lousy governor, and a disloyal former friend. Now whenever I see Mario at a dinner, I refuse to acknowledge him, talk to him, or even look at him. —Trump: How to Get Rich

Trump apparently made peace with Mario’s son, Andrew, who later became governor himself. He has donated more than $60,000 to Andrew Cuomo over the years.

He Had a Thing for Princess Di

January 1995 Trump claims Prince Charles and Princess Di have joined his new club Mar-a-Lago; a palace spokesman calls it “complete and utter rubbish.”

Politically, Trump poses as a populist, but the evidence suggests he may harbor monarchist tendencies. The doorman uniforms at Trump Tower were designed to make them look like palace guards, with towering black bearskin hats. Trump once proposed a Madison Avenue apartment building, Trump Castle, that would have had a drawbridge and a medieval-style moat. (The idea died, and he later recycled the name for a casino.) He named one of his sons Barron. But the strangest manifestation of his royal obsession involved Princess Diana. Trump repeatedly leaked rumors to the press associating Diana with his properties. After her divorce from Prince Charles, Trump reportedly went courting. “He bombarded Diana at Kensington Palace with massive bouquets, each worth hundreds of pounds,” former BBC television personality Selina Scott, a friend of the princess, claimed in a newspaper column last year. "Trump clearly saw Diana as the ultimate trophy wife. As the roses and orchids piled up at her apartment she became increasingly concerned about what she should do. it had begun to feel as if Trump was stalking her." Two months after Diana's death in a car crash, Trump said in an interview with NBC's Stone Phillips that he regretted never asking her for a date. Did Trump think she would have accepted? Phillips asked. "I think so, yeah," Trump said. "I always have a shot."

He Swore He Was a Really Good Dad

February 1996 “Is my girl growing up?” Trump asks his daughter Ivanka, as they discuss a photo shoot to promote his acquisition of the Mar-a-Lago resort.

Despite the messiness of his divorce from Ivana, Trump has maintained good relations with their three children, all of whom now work for the Trump Organization. In 2004, Trump told Jonathan van Meter: “I’m a really good father, but not a really good husband. You’ve probably figured out my children really like me — love me — a lot. It’s hard when somebody walks into the living room of Mar-a-Lago in Palm Beach and this is supposed to be, like, a normal life. But they’re very grounded and very solid. The hardest thing for me about raising kids has been finding the time. I know friends who leave their business so they can spend more time with their children, and I say, ‘Gimme a break!’ My children could not love me more if I spent fifteen times more time with them.”

He Bought the GM Building, Predicting the Apple Store

May 1998 Trump leads the $878 million purchase of the GM Building.

When Trump heard that the General Motors Building might be for sale, he called up Steve Hilbert, the similarly flamboyant CEO of the Indiana insurance company Conseco. 

Steve Hilbert: I met Donald in mid-’90s, and it was brief. He was working on a project in Indiana, and we were working on a different project in Indiana, and we talked about, “Maybe there's something we can do together.” Then he asked if I knew the Simon family — that's the Simon Property Group — and they were dear friends. They were doing an acquisition of a big commercial company, and one of its assets was the General Motors Building. Donald said, “I think this is without a doubt maybe the greatest building in the world.” And you know, it turned out to be an unbelievable deal.

He put in $12.5 million, and we put in $12.5 million. And then we provided some debt financing. Lehman Brothers provided the bulk of it, which was $700 million. And we were 50-50 partners.

When we acquired that building, a lot of people thought we were out of our minds. There were articles written that we had paid more than anyone else had paid per square foot. And Donald had said from the beginning he had a vision. If you look at where the Apple Store is, his vision was to have retail right there. That was all Donald's idea. Virgin Records was trying to get in there in the worst way, so was the Cheesecake Factory. Everything he told us he was going to do with the GM Building, he did. And you know, everybody made a lot of money on that transaction.

—As told to Andrew Rice

He Started Selling Models

December 1998 Trump launches Trump Model Management.

Trump has always had a thing for them, and in 1998, he went into the agency business (in partnership with an Italian businessman who was later indicted on federal fraud charges). He also co-owned the Miss Universe Pageant with NBC, before the relationship dissolved in controversy related to his campaign last year. Before he married Melania Knauss, a Slovenian model, Trump was romantically linked to many others.

Donald Trump: Women have one of the great acts of all time. The smart ones act very feminine and needy, but inside they are real killers. The person who came up with the expression “the weaker sex” was either very naïve or had to be kidding. I have seen women manipulate men with just the twitch of an eye — or perhaps another body part. I have seen some of the roughest, toughest guys on earth, guys who rant and rave at other tough guys and make them cry, and yet they’re afraid of their 120-pound girlfriends or wives. There’s nothing I love more than women but they’re really a lot different than portrayed. They are far worse than men, far more aggressive, and boy, can they be smart. —Trump: The Art of the Comeback

He Became a Rap Icon

May 1999 “White guy in the middle,” Trump says, as he joins Russell Simmons at his table at Jean Georges.

A partial compendium of hip-hop lyrics mentioning Trump, compiled from Rap Genius:


Yo, the new Mike Tyson's Roy Jones

Bill Clinton’s the new JFK, without the hole in his dome

The new Don Trump is Bill Gates

Not because his occupation, it’s cause we respect his cake

A Tribe Called Quest (Phife)

Beeper’s goin’ off like Don Trump gets checks

Keep my bases loaded like the New York Mets

50 Cent

Real niggas snatch Glocks, and run up in spots

We can talk Trump talk, real estate, stocks, and bonds

Fat Joe

We into real estate

We fuckin with Donald Trump now


I’m fucked worse than Donald Trump

On Lexapro in Mexico across from a Texaco in McDonald's drunk

Mac Miller (on his song “Donald Trump”)

Take over the world when I’m on my Donald Trump shit

Look at all this money, ain'’ that some shit

Gucci Mane

Donald Trump

I made Forbes list this month!

Donald Trump

I made Forbes list this month!

Donald Trump

I made Forbes list this month!

Donald Trump

I made Forbes list this month!

Kendrick Lamar

I’m the son of the pioneer that got you niggas on

Play with him, bitch you better off voting for Donald Trump

I’m yelling Mr. Kanye West for president

The Game

This is doomsday, I can have Guadalupe

Come through and knock Donald Trump out his toupee

Kanye West

I’m so appalled, Spalding ball

Balding, Donald Trump taking dollars from y’all

Baby, you’re fired, your girlfriend hired

But if you don’t mind, I’mma keep you on call

Tyler the Creator

The tooth fairy blow me, swallow don't shit this

With my Donald Trump hair piece you’re an apprentice

You’re fired and tired, you can’t stay up like a limp dick

If you think you can spit then I am the fuckin’ dentist

Frank Ocean

Donald Trump said buy an apartment wit’ her (uh)

Buying an apartment wit’ ya

Greenspan said the rate was good

My pastor says that your faith is major

Bun B

Fuck Black Caesar niggaz call me Black Trump


Now I ain't talkin’ ’bout no bullshit ass flippin’ z's

I'm talkin’ Trump-type access, they comin’ off a gang of keys


I buy cars wit’ straight cash, have meetings with Donald Trump

Y’all meet wit Honda, no payments for 12 months

Snoop Dogg

Twenty-seven cars and a twelve-bedroom house

Now they call me Snoopy Trump

P. Diddy

I spend absurd money, private bird money

That Bill Gates, Donald Trump, Bloomberg money

Kendrick Lamar

My name ’til they strain the veins in they vocal cords

Give me fame and fortune, me and Trump on golf courses


I push one button, the roof gon’ go into the trunk

I’m John Gotti paid, now I’m going Donald Trump

Lil Wayne

Throw my weight like Sherman Klump

I gotta hold up my estate like Donald Trump


Used to want dough like JC but now I’m thinking Donald Trump

Bob Johnson, Warren Buffett, fuck it, it ain’t that tough

Lil B

Call me Donald Trump how I fire losers

How Donald Trump fire workers, I fire Rugers

Lin-Manuel Miranda (From “In the Heights”)

I’ll be a businessman, richer than Nina’s daddy!

Donald Trump and I on the links and he’s my caddy!

He Impressed At Least One Architecture Critic

December 19, 1999 Herbert Muschamp sizes up Trump.

Even as pop culture embraced him, Trump was receiving a degree of appreciation from New York’s aesthetic elite. Herbert Muschamp, the Times’ lively and idiosyncratic architecture critic, led the critical reassessment. Originally, Muschamp panned the Trump International Tower and Hotel on Columbus Circle, and Trump was enraged. The critic asked Trump’s architect, Philip Johnson, to propose a meeting at the Museum of Modern Art in front of Warhol’s Gold Marilyn Monroe.

Herbert Muschamp: I don’t share Mr. Trump’s taste, but I love his style. I far prefer it to the style of those who buy their ideas off the peg at Ralph Lauren. And I’m curious to know how he will deal with that.

A Wednesday morning before the museum is open. Winter, very cold. Mr. Johnson and I are waiting in the lobby. He's wearing his famous Astrakhan fur hat. Limousine pulls up, very black. Mr. Trump gets out with three associates. Gray and blond. Great color combination. But a terrible expression on his face: pursed mouth, no smile, I’m going to get this guy.

We head upstairs and clip through the galleries. When we reach the room where the Marilyn is hanging, I point it out. “Philip gave that. Isn’t it great?” There’s a large sculpture in the middle of the room, a brass floor piece by Donald Judd. Evidently Mr. Trump mistakes it for a coffee table, for he uses it as one, tossing his overcoat and some binders full of pictures on top of it as we walk over to the painting. Mr. Trump barely glances at the Marilyn, but this doesn’t matter. My goal is to capture them together in the same frame. He’s a work of art himself, as well as a piece of work, a living self-portrait with a trademark signature sought by foreign banks, condo dwellers, autograph hounds, advertisers and publishers. Warhol’s dream was to live off putting his signature on soup cans. Mr. Trump has more or less fulfilled it.

He Began to Mull the White House Again

January 2000 Trump publishes The America We Deserve.

As the end of the (first?) Clinton administration approached, Trump once again publicly considered a run for the presidency — this time as the candidate of the Reform Party, which had been established by his populist billionaire forerunner Ross Perot. Trump wrote his first explicitly political book, in which he attacked Pat Buchanan, citing “egregious examples of intolerance” toward “Blacks, Mexicans, and Gays.” (When he pulled out of the race that February, he would call Buchanan, who ultimately won the nomination, a “neo-Nazi.”

In an epilogue titled “Roll Call,” Trump listed his dream Cabinet roster. It included:

Oprah Winfrey

Jack Welch

Governor Jesse Ventura

Senator Robert Torricelli

Teamster leader James Hoffa Jr.

Governor Jeb Bush

He Buried His Face in Rudy Giuliani’s Bosom

March 2000 Appears in an Inner Circle sketch and gropes New York’s mayor, who is in drag.

He Lost the GM Building

August 2003 Trump is forced to sell the GM Building.

After Conseco’s stock crashed, Steve Hilbert was ousted from his job, and the GM Building was put up for sale. Trump had an opportunity to buy out the insurance company’s stake at a discount price but was unable to close the deal, and it sold instead to developer Harry Macklowe for a then-record price of $1.4 billion. “He should have kept it, in hindsight,” Hilbert says. “I mean, that building is worth, what, four or five billion today?”

Chapter 4: Celebrity Grotesque

He Had an Idea for a Reality Show You’re Gonna Love …

January 2004 The Apprentice premieres on NBC.

By the end of the century, Trump the business celebrity had molted into Trump the celebrity businessman. Though he was once again developing buildings — Trump World Tower, a black monolith next to the United Nations, caused a great neighborhood stir — much of his business activity revolved around selling his persona. Condominium developers from around the world were coming to him, offering him stakes in their profits for the simple privilege of allowing the Trump name to grace their buildings. Trump claimed such arrangements were “better than ownership, because it’s a licensing. You don’t put up money. You don’t put up anything.”

Then, reality-show producer Mark Burnett approached Trump with an idea for a TV show where contestants would compete for the approval of a business mogul. In his book Jump In!, Burnett wrote that Trump immediately jumped at the opportunity.

Mark Burnett: I called his office to set up a meeting during the car ride from La Guardia to Manhattan. Much to my surprise, his executive assistant, Norma Foerderer, immediately put Trump himself on the phone. “How are you doing, my man? I see your Survivor ratings are still on top. Isn’t it great being No. 1? Where are you?” he asked.

I told him I was in the car, on my way into the city.

“Come here right now,” Donald said. “You’ll be here in 20 minutes. Come straight up. Tell the doorman you’re here to see me.”

He One-Upped Monopoly (Or at Least Tried)

August 2004 Trump rereleases Trump: The Game.

In the late 1980s, during Trump’s initial heyday, he attempted to capitalize by releasing his answer to Monopoly. The instruction book promised: “Live the Fantasy! Feel the Power! Make the Deals!” But the rules were bewilderingly complex—perhaps a bit too reminiscent of Trump’s real-life business dealing — and the game flopped. But after the success of The Apprentice, he introduced a revised version to capitalize on his reality-show fame. The game was simplified and given a sharpened slogan: “I’m Back and You’re Fired!” Flanked by silver-clad models, Trump unveiled it at a Trump Tower press conference, as play money bearing his picture fell from the ceiling. “The game is about winning, losing, and coming out on top,” Trump said, as "We're in the Money" played over loudspeakers. "I also play in real life."

He Dominated the Ratings (At Least by His Telling)

May 2005 The Apprentice’s ratings skid, creating problems for PR man Jim Dowd.

Jim Dowd: There were times when Mr. Trump would say things about the show ratings that were, let’s say, creative. And working at the time for NBC, obviously, I had to play both roles. So if he’s out there saying, “The Apprentice is the No. 1 show on television,” and at that time we might have been the No. 32 show on television. I would be told by my superiors, “You need to get him on the phone, and you need to tell him that’s not accurate.” And that was difficult for me, because he did not want to hear that, and he would not listen to that advice.

After I opened my own publicity firm and made a deal to work with Mr. Trump, I asked [his secretary and confidante] Norma Foerderer, “All right, what advice do you have for me?” She said, “Well, get ready. He’s going to want his pound of flesh.”

—As told to Nick Tabor

He Was Skewered by Muppets

September 2005 Sesame Street airs a sketch titled “Grouch Apprentice,” featuring an orange-haired character named “Donald Grump.”

“Grump,” sung by Oscar the Grouch

Who’s got more trash than anyone does?

Grump, Grump, Grump

Who’s got the best rubbish and scuzz?

Grump, Grump, Grump

He Swore He Was a Billionaire

January 2006 Trump sues Timothy O’Brien for libel.

Over the years, Trump has provided fanciful estimates of his wealth to journalists, and he’s gone as far as to personally lobby the journalists who prepare lists like the Forbes 400. (He’s currently listed at No. 121, with an estimated fortune of $4.5 billion, though Trump claims he’s really worth twice that.) In TrumpNation, though, Timothy O’Brien cited sources familiar with Trump’s finances who estimated he was really worth around $150 million to $250 million. Trump responded by suing O’Brien for $5 billion in damages. In a deposition taken in connection with the case, Trump explained his accounting method:

Trump: My net worth fluctuates, and it goes up and down with markets and with attitudes and with feelings, even my own feelings … as to where the world is, where the world is going, and that can change rapidly from day to day. Then you have a September 11, you don’t feel so good about the world and you don’t feel so good about New York City. Then you have a year later, and the city is as hot as a pistol. Even months after that, it was a different feeling.

So yeah, even my own feelings affects my value to myself.

He Patented Himself

May 2006 Trump applies to trademark his ceremonial crest.

In an application to the U.S. Patent and Trademark Office, Trump sought to trademark a family crest as a commercial logo. It was described as “a heraldic coat of arms consisting of a shield and crest design, all in gold. A shield appears in the center of the design. The shield contains three lions, two chevrons made of repeating rectangles, and many small orbs with crosses. The shield is topped by a knight's helmet. Above the helmet, an extended arm raises a spear. An organic gold leaf or mantling design starts from the helmet and falls to frame the shield. Below the shield, there is a banner carrying the name TRUMP.”

Over the years, Trump and his family members have applied to trademark numerous other commercial applications of their name, including:

Trump Pak (packing materials, 1989)

Trumpnet (telecommunications, 1990)

Oysters Trump (restaurant services, 1990)

Trump (cologne, 1993)

Trump Card Interactive Marketing (online marketing, 1995)

Trump World Fair (casino, 1996)

Trump Style (magazine, 1997)

Trump’s Golden Lager /Trump’s American Pale Ale (beer, 1997)

Trump Super Speedway (sports, 1999)

Trump Touch (hotel concierge services, 1999)

Trump Ice (bottled water, 2003)

Trump World (magazine, 2003)

The Trump Card (credit card, 2003)

Donald J. Trump’s Victorian Garden (amusement park, 2003)

The Donald J. Trump World Open (golf wear, 2004)

Trumped (radio program, 2004)

Trump Class (real-estate services, 2004)

Trump Power/Trump Fire (carbonated beverages, 2004)

You’re Fired! Donald J. Trump (paper goods, housewares, toys, alcoholic beverages, 2004)

Donald J. Trump Signature Collection (manicure sets, shaving kits, cigar implements, 2004)

Donald Trump the Fragrance (perfume, 2004)

Trump University (education, 2004)

Trumptini (alcoholic beverage, 2005)

Go Trump.Com (online travel, 2005)

Trump Vodka (alcoholic beverage, 2005)

Ivana Las Vegas by Ivana Trump (real estate, 2005)

Trump Mortgage (lending, 2005)

Donald J. Trump Boardroom (business books, 2006)

The Trump Follies (variety show, 2006)

The Trump Art Collection (books, 2006)

Trump Tower (toy construction sets, 2006)

Ivanka Trump (jewelry, 2006)

Trump Gold Book (telephone directory, 2006)

DJT (watches and timepieces, 2006)

Trump Executive Office (furniture, 2006)

Donald J. Trump Home Collection (furniture and housewares, 2006)

Trump Attaché (personal valet services, 2007)

Trump Verdict (book and TV series about dispute resolution, 2007)

Trump Tycoon (video game, 2008)

Trump (breakfast cereals, 2008)

Trump Financial (mortgage brokerage, 2008)

Trump Home (fragrance diffusers, 2008)

Trump Home (toothbrush holders, shower curtains, bed linens, etc., 2010)

Trump D’elegance (auto shows, 2010)

Success by Trump (cologne, 2011)

Trump Hotel Collection (hospitality, 2011)

Melania Trump (cosmetics, 2012)

Ivanka Trump (gambling services, 2012)

Ivanka Trump (household goods, 2013)

Trump (limousine service, 2014)

Trump New World Reserve (wine, 2015)

Trump (political-action committee, 2015)


He Let Rosie O’Donnell Get Under His Skin

March 2007 Trump trades barbs with Rosie O’Donnell.

Trump’s feuds changed, too: Instead of combating mayors and journalists, he was taking on other celebrities. After O’Donnell criticized Trump on The View, Trump fired back by calling her a “fat slob” and a “degenerate.” He dragged his old sort-of friend Barbara Walters into fight. “Trump tried to drive a wedge between them,” Lloyd Grove wrote. “He sent out an ‘open letter’ to O’Donnell — ‘You have good reason to be angry’ — and quoted Walters in a phone call to him as saying ‘Working with [O’Donnell] is like living in hell.’”

When Fox News anchor Megyn Kelly brought up Trump’s sexist language in the first Republican debate, he smirked and interjected that it was in reference to “only Rosie O’Donnell,” to riotous cheers. O’Donnell recently called Trump’s campaign “a nightmare.”

He Almost Shaved His Head

April 2007 Trump body-slams Vince McMahon in wrestling’s Battle of the Billionaires.

Having won the title of America’s foremost sexist, Trump took his act to an appreciative audience: pro-wrestling fans. After months of intricate grudge-building—including a phony wrestling match pitting him against O’Donnell—Trump took on McMahon, the WWE’s villainous founder, in a pay-per-view extravaganza. The match was billed as “Hair Versus Hair.” Trump’s team won the fight and ended up ceremonially shaving McMahon’s head.

He Monetized His Appetites

May 2007 Trump launches Trump Steaks, briefly sold at the Sharper Image.

Interview with Timothy O’Brien, TrumpNation

Q: What’s your favorite food?

A: Meatloaf … Oreos … pastas … The Atkins Diet is a total fraud, but because of it I eat a lot of steak and I feel better about it. And hamburger and all of that. You know, Atkins, he did hit his head, but he was dead before he got to the ground. He exploded. You know that, right?

Q: When you’re sleeping, what’s your most frequent dream?

A: Always sexual. It’s always fucking.

He Dabbled in What Certainly Looked Like a Pyramid Scheme

May 2009 Trump purchases nutritional-supplement business Ideal Health.

Trump got into the dietary health business when he purchased a vitamin company and renamed it the Trump Network. “The name is hot!” Trump boasted to writer Jessica Pressler. “It’s on fire!” The company was a “network marketing” scheme, like Amway, with Trump sitting at the top of a pyramid of independent salespeople. Its signature product was a urine test that it would supposedly determine what nutritional supplements a customer needed. According to an investigation by the health website Stat, though, experts cast doubt on the test’s reliability. The Network soon ran into financial problems and was sold.

He Married Off His Daughter — To a Jew!

October 2009 Ivanka Trump marries Jared Kushner.

Trump’s first daughter is, by most accounts, the smartest and most business-savvy member of the next Trump generation, and in marrying Kushner, she picked a husband from a similar background of wealth and tabloid controversy. Jared’s father, Charlie, is a billionaire developer who was once a kingmaker in New Jersey politics. Charlie served time in prison in connection with election violations, witness tampering, and a scheme to take revenge on his own brother-in-law by making a tape of him having sex with a prostitute. The younger Kushner, who idolizes Trump, has a taste for big, risky real-estate deals (like buying 666 Fifth Avenue at the top of the real-estate bubble). He also has an interest in the press: He owns the New York Observer. Two years ago, the paper published a strange, 7,000-word attack on New York state attorney general Eric Schneiderman at a time when he was investigating Trump University. “It’s a shame that a once-great newspaper chose to use its front page to regurgitate a discredited complaint filed by the father-in-law of the paper’s publisher,” Schneiderman’s office replied. Although there have been reports that Ivanka is uncomfortable with her father’s xenophobic turn, she and Kushner have been visible on the campaign trail, showing up onstage with Trump after debates.

He Wouldn’t Let Oliver Stone Near His Hair

September 2010 Trump is edited out of Wall Street: Money Never Sleeps.

In the sequel to Stone’s tale of greed, there was supposed to be a scene where Trump met Gordon Gekko while he having his hair cut. But Trump reportedly made things complicated by refusing to allow the crew near his famously suspicious orange pompadour. “The scene wound up getting cut,” a source on the set told the Daily News, “probably because you had two guys in a barbershop and one couldn’t have his head touched.”

He Was the Most Entertaining of All the Birthers

April 2011 President Obama makes Trump the butt of his jokes at the White House Correspondents’ Dinner.

A few mainstream Republicans had dabbled in birtherism, but Trump was the first to fully embrace the lunacy, announcing that he was sending private investigators to Hawaii to hunt for Obama’s birth certificate. Shortly afterward, the state released Obama’s long-sought “long form” certificate, proving he was American-born. Trump attended that year’s White House Correspondents’ Dinner, and Obama took pleasure in ridiculing his stunt.

President Obama: Donald Trump is here tonight. Now I know that he’s taken some flak lately. But no one is happier—no one is prouder—to put this birth certificate matter to rest than The Donald. And that’s because he can finally get back to focusing on the issues that matter: Like, did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac? All kidding aside, obviously we all know about your credentials and breadth of experience. For example … no seriously, just recently, in an episode of Celebrity Apprentice, at the steakhouse, the men’s cooking team did not impress the judges from Omaha Steaks. And there was a lot of blame to go around, but you, Mr. Trump, recognized that the real problem was a lack of leadership, and so ultimately you didn’t blame Lil Jon or Meat Loaf, you fired Gary Busey. And these are the kinds of decisions that would keep me up at night. Well handled, sir. Well handled.

As he spoke, Obama had a real decision weighing on his mind: the raid on Abbottabad. The next night, he would announce the killing of Osama bin Laden.

He Hawked Sunscreen

April 2011 Steve Hilbert appears on Celebrity Apprentice.

After he was forced to sell the GM Building, Trump remained friendly with the former CEO of Conseco, Steve Hilbert. When Hilbert needed some cash, Trump bought his house in St. Maarten. When Hilbert and his wife — a former exotic dancer whom he met after she jumped out of a cake at a bachelor party — wanted to promote their new venture, a suntan lotion, he called up Trump.

Trump was happy to help his friend — in return for a fee of $100,000. Hilbert said it was worth it: All the big drug stores wanted to stock Donald Trump’s favorite sunscreen.

Steve Hilbert: The Celebrity Apprentice was a great way to get incredible distribution. There are a lot of rich people who, because of envy or whatever, don’t like Donald, but the average person loves Donald. Loves Donald. He once came to Indianapolis for a Pacer playoff game against the Knicks. There were literally a thousand people who came down to see Donald and to ask him to sign a $5 bill or a $10 bill, just to say hello to him. That’s why he is leading the polls. He's saying things that the average person has been saying for a long time. He first entered the race, I had some people say to me, “Oh well, he's not serious, he's not gonna win.” I said, “You know, you're missing something.”

—As told to Andrew Rice

He Entered the Republican Primary Race, Shot to the Top of the Pack, and Shows No Signs of Losing

June 2015 Trump announces his candidacy for the Republican presidential nomination.

Trump: You can’t con people, at least not for long. You can create excitement, you can do wonderful promotion and get all kinds of press, and you can throw in a little hyperbole. But if you don’t deliver the goods, people will eventually catch on.

—Trump: The Art of the Deal

Additional reporting by Katy Schneider, Reeves Wiedeman, and Nathan Pemberton.