Trump had made sure he could get out at a low cost. If the marriage proved to be brief, the prenuptial contract strictly limited the amount Maples could collect. She received $5 million or less. Trump, Goldberg observed, “had his eye on the clock.” He also had his eyes on other options.
• • •
ALMOST AS SOON AS he had crossed the bridge into Manhattan after college, Trump found ways to deploy beautiful women in service of his financial success. In Trump’s vocabulary, a superlative man is successful; a superlative woman is beautiful. He joined Le Club because it was, he said, “the hottest club in the city and . . . its membership included some of the most successful men and the most beautiful women in the world.” He started attending high-voltage parties, accompanied by photogenic women whose company he obtained by calling modeling agencies and asking for help filling out his guest list. He became a regular in the front rows of New York fashion shows, showing up in tabloid and fashion publications, surrounded by statuesque women with leonine hair and plenty of lip gloss.
In 1985, Trump found a way to create his own clubhouse, featuring the blend of success and beauty that he wanted his brand to embody. He bought Mar-a-Lago, a historic Palm Beach estate built in 1927 by one of the world’s richest women, Marjorie Merriweather Post. She had donated the 128-room mansion to the US government in 1973 for use as the winter White House. But President Jimmy Carter’s administration turned the property, just off the Atlantic Ocean on perhaps the ritziest stretch of beachfront in Florida, over to the private Post Foundation, saying it was too expensive to maintain. Trump wanted it and offered $28 million. Not enough, the foundation said. Trump didn’t raise his offer; he lowered it. He decided to play hardball. Through a third party, he bought the beachfront property directly in front of Mar-a-Lago and threatened to erect a hideous home to block the Post estate’s ocean view. “That drove everybody nuts,” Trump said. “They couldn’t sell the big house because I owned the beach, so the price kept going down and down.”
In the end, Trump bought the landmark for a bargain $5 million for the house, plus $3 million for Post’s antiques and lavish furnishings. He converted the estate of more than seventeen acres into a private club (in 2015, new members paid a $100,000 initiation fee plus annual dues of $14,000), available to rent for weddings and events. In Palm Beach, a tiny village of cloistered estates and private beaches where blue bloods and billionaires relished their privacy, Bentleys and Rolls-Royces slipped off South Ocean Boulevard and into estates hidden behind high hedges. At Mar-a-Lago, Trump had the hedges chopped down to give passersby a clear view of his castle. And he invited celebrity guests such as Michael Jackson to stay overnight, drawing paparazzi. The local newspapers took Trump to task for floating rumors that Princess Diana, Madonna, and other big names were joining his club, all part of his effort to build buzz around Mar-a-Lago. Trump also added a Louis XIV–style ballroom with forty-foot ceilings and $7 million worth of gold leaf on the walls (actually, Ivana was in charge of the redesign). Trump spent $100,000 on four gold-plated bathroom sinks near the ballroom.
Appalled by Trump’s ostentatious behavior, the Palm Beach town council handed him a list of restrictions it was imposing on membership, traffic, party attendance, even photography. But Trump refused to be hemmed in. He took his battle to the court of public opinion. His lawyer sent every member of the town council copies of two classic movies about discrimination—Gentleman’s Agreement, about a journalist who pretends to be Jewish to expose anti-Semitism, and Guess Who’s Coming to Dinner, about a white couple’s reaction to their daughter’s bringing home a black fiancé. The point was clear and painful: the town’s political leaders for decades had condoned rules by which the established private clubs in town excluded Jews and blacks, and now they wanted to slap Trump with tough rules on his club, which was open to anyone who could afford the steep fees. Council members insisted that their only concern was that Trump was turning a quiet, demure stretch of beachfront into a noisy party attracting a lot of outsiders. No matter: Trump’s tactic worked. Over time, he got most of the restrictions lifted.
The parties Trump hosted were designed to draw exactly the attention that the town council abhorred. Many of the guests were models from Miami, who floated around the patio and pool. Trump insisted on at least a three-to-two ratio of women to men at his bashes. “There’s a hundred beautiful women and ten guys,” recalled Roger Stone, his longtime adviser. “ ‘Look, how cool are we?’ I mean, it was great.”
• • •
BEFORE AND BETWEEN HIS marriages, Trump played up his image as a ladies’ man. He arranged to be photographed with beauty queens in skimpy outfits, in limos with models, visiting Hugh Hefner’s Playboy mansion. Trump blended his interest in certified beautiful women with his expanding empire, diving into the beauty-pageant and modeling businesses. “What I do is successful because of the aesthetics,” Trump said. “People love my buildings and my pageants.” The pageant industry raised Trump’s international profile, taking him around the globe, to countries large and small where he would pose with Miss Wherever at his side at ribbon cuttings or announcements of Trump real estate and hotel projects. Foreign political and business leaders were eager to join him at events that featured beauty queens as well as a little commerce. Trump saw pageants as a welcome diversion from blueprints and environmental impact meetings, a chance to “mix it up” in his investment portfolio, as well as entrée to a large national and international television audience.
Trump’s investment in pageants began with the American Dream Calendar Girl Model Search contest, which had started in 1966 as a joint venture between a men’s toiletries company and a motor-sports-calendar business that wanted to add scantily clad women to its pages. In 1992, Trump entered into a partnership with the Florida couple who owned American Dream. George Houraney and Jill Harth hoped the Trump brand would lend buzz to their contests and calendars featuring women posing in bathing suits next to fast cars. The relationship did not last long. After the 1993 pageant at Trump Castle, Houraney and Harth sued for breach of contract, claiming that the venture lost them $250,000 and as much as $5 million in future revenue.
In a tangled legal battle that stretched on for years, Harth accused Trump of groping her. She sought $125 million in damages, alleging in a deposition that Trump made aggressive and unwanted sexual advances at a 1993 party at Mar-a-Lago. “When we got to the dinner table, Donald started right in on the groping under the table,” she said. Later that same night, by Harth’s telling, Trump brought her to a bedroom ordinarily used by his then eleven-year-old daughter, Ivanka. There, Trump “kissed, fondled, and restrained” Harth from leaving the room, she alleged. Harth and Houraney left the estate in the small of the night. Trump vehemently denied that any of that happened. Rather, he cited a 1997 National Enquirer account of the incident that quoted an unnamed Trump friend saying it was Harth who was obsessed with Trump. Harth said, however, in a deposition that Trump had been going after her ever since she and Houraney first met with him, even after Houraney made it clear that he and Harth were married. “Basically, Donald Trump stared at me throughout that meeting,” she recalled under oath. “He stared at me even while George was giving his presentation.”
Harth also alleged that Trump “directed that any black female contestants be excluded” from his Mar-a-Lago parties; Houraney said Trump systematically eliminated black women from the pile of photos he was sent to choose contestants for the finals of the calendar competition. Trump consistently denied the couple’s claims; his attorneys called Harth “delusional” and said her allegations were “clear evidence of mental instability.” Years later, an attorney for Trump said, “There is no truth to the story at all,” and that Harth “was a pawn in a lawsuit that was created by her ex-husband.” In 1997, Trump settled the breach-of-contract case with American Dream; Harth at the same time dropped the suit in which she alleged the sexual misconduct. Houraney told the Boston Globe that he received a payment from Trump but w
as not allowed to reveal its amount. Harth said she dropped her case as a condition for settlement of Houraney’s suit, but she said her allegations were accurate.
Around the time he was dealing with those lawsuits, Trump had already stepped up to a grander stage in pageantry, to what he called “the triple crown of beauty.” In 1996, he bought a controlling share of the Miss Universe pageants, which included the Miss USA and Miss Teen USA competitions. At the time, he said he paid $10 million for his stake in the organization; years later, he said he had spent only $2 million. Miss Universe started out in 1952 in Catalina, California, as a swimsuit competition, without the academic component that the Miss America contest boasted of. Miss Universe had a reputation as the racier of the two popular pageants, and Trump set out to make it sexier. As a result of his leadership, he said, “The bathing suits got smaller and the heels got higher and the ratings went up.” (Actually, the ratings sank over time. When Trump bought the pageant in 1996, Miss Universe’s Nielsen ratings had already declined, from about 35 million viewers in 1984 to about 12 million. The pageant never regained those higher numbers, and in 2013, two years before Trump sold it, fewer than 4 million people tuned in.) Trump’s management of pageants became a family affair: his daughter, Ivanka, hosted Miss Teen USA one year; his second wife, Marla, herself a former beauty contestant, cohosted Miss Universe and Miss USA; and his third wife, Melania, would serve as a judge at the Miss USA pageant. Although pageant executives traditionally tended to be men, Trump promoted women, including Maureen Reidy, an accountant in the Trump Organization whom he named the first female president of the Miss Universe organization in 1997, when she was twenty-seven.
Trump was actively involved in the pageants. After Miss Universe Alicia Machado, a Venezuelan, gained considerable weight in 1996, Trump publicly excoriated her. He staged a photo op to show Machado exercising at a Manhattan gym. In front of about eighty reporters and photographers, Trump said, “When you win a beauty pageant, people don’t think you’re going to go from 118 to 160 in less than a year, and you really have an obligation to stay in a perfect physical state.” Machado called the photo op an ambush designed to humiliate her. “He had his triumphant entry,” she recalled, “and I got to feel like a hamster on a wheel for an hour. I was his first Miss Universe when he just bought the company. Unfortunately, this also meant that I experienced, firsthand, his rage and racism and all the misogyny a person can demonstrate.” Trump wrote years later that he did what he did to protect her from being fired: “God, what problems I had with this woman. First, she wins. Second, she gains fifty pounds. Third, I urge the committee not to fire her.”
Trump kept close tabs on pageant contestants. Carrie Prejean, who was Miss California in 2009 and first runner-up in that year’s Miss USA contest, said Trump “inspected us closer than any general ever inspected a platoon.” In front of fellow competitors, Prejean recalled, Trump asked Miss Alabama who was the most beautiful contestant. When Miss Alabama suggested that Miss Arkansas was “sweet,” Trump responded, “I don’t care if she’s sweet. Is she hot?” Trump posed the same question to several contestants, and then, Prejean said, “motioned those girls he liked over to one side, leaving the discards to one side of the stage.” Trump said he had to step in because “the judges didn’t know what they were doing. . . . They wouldn’t pick the women that should’ve been in the finals. . . . So I developed a system where everybody would be on stage . . . with numerous people from CBS. . . . I’d be on stage and I’d talk. We would pick the top fifteen smartest, most beautiful women. Once I got involved . . . it became very successful. . . . Look, it is a beauty pageant, okay? It’s about beauty. We can’t be ashamed of it.”
A few years after investing in Miss Universe, Trump branched out into another aspect of the beauty business—modeling. His new agency, originally conceived as Trump Models Inc., ended up with the name T Management after protracted negotiations between Trump and a veteran of the industry, Annie Veltri, a part-owner of the company. Known for its “legends”—older models—T Management was otherwise an “inconsequential agency,” said James Scully, a prominent casting director in the fashion industry. T’s models were generally not household names. It was “a way to funnel beauty-pageant contestants somewhere,” Scully said. Some of the bookers at Trump’s modeling business were also pageant judges, and favored pageant contestants would score modeling contracts with the agency. Although Trump wasn’t involved in day-to-day management of the modeling business, he approved major decisions, and some models said they got their contract offers directly from Trump.
The modeling business introduced a different culture to Trump’s empire. Initially housed in Trump Tower, the model bookers eschewed the uniform of suits and dresses that was the rule in the Trump Organization’s offices. The modeling culture was far less formal than what the boss generally enforced. “They were all, ‘Mr. Trump,’ ‘Mr. Trump,’ ‘Mr. Trump,’ ” said John Bassignani, who worked at the agency. “And we were, ‘Hey, Donald,’ ‘Hey, Donald,’ ‘Hey, Donald.’ ”
• • •
THE SUBJECT WAS MARIAH CAREY, the singer. “Would you bang her?” Howard Stern asked on his nationally broadcast radio show. Trump replied, “I would do it without hesitation.” On another morning, the host of the daily raunch-fest asked the same question, this time about Princess Diana, then one of the most famous and most admired women in the world. “Without hesitation,” Trump said. “She had the height, she had the beauty, she had the skin. . . . She was crazy, but these are minor details.”
Starting in the nineties, Trump appeared about two dozen times on Stern’s popular morning talk show, which grew ever more explicit through the years. Stern and Trump developed a rollicking patter on the air, rating women’s tops and bottoms, debating the merits of oral sex, and egging each other on about whether they would like to go to bed with famous women from Cindy Crawford to Diane Sawyer. Trump seemed to love the game. On one show, the shock jock asked, “Is oral sex important to you? Man to man, and I’ve had this discussion with many men.” Trump replied, “No, it’s not important to me.”
Another morning, Trump considered the assets of Nicollette Sheridan, an actress on the nighttime TV soap opera Desperate Housewives: “A person who is very flat chested is very hard to be a ten.” Trump turned the tables and asked Stern about Sheridan’s costar: “Would you go out with Marcia Cross or would you turn gay, Howard?” The two guys traded barbs about all manner of female celebrities, mainly focusing on whether they’d be worth having sex with. Trump’s guest appearances, which stretched from 1990 to 2005, included his judgments on reality TV star Kim Kardashian: “Does she have a fat ass? Absolutely!” and “Her boob job is terrible. They look like two light posts coming out of a body.”
Trump talked on one show about how taken he was with Princess Diana. After her marriage to Prince Charles broke up in 1992, Trump began sending her flower arrangements. He seemed to believe they could have dated. “You could’ve gotten her, right?” Stern asked Trump soon after Diana was killed in a car crash in 1997. “You could’ve nailed her.”
Trump thought for a moment, then replied, “I think I could have.”
Trump’s comments about his sexual desires were not limited to theoretical cases. Calling in to the show in 2000, he talked about his girlfriend, Melania Knauss, then handed her the phone. “We have incredible sex once a day,” she told Stern’s listeners, “sometimes even more.” A few years later, when Donald and Melania were married, Stern asked if Trump would stay with his wife if she emerged from a car accident disfigured, with her arm and leg damaged, and with “one hundred stitches on her face.”
“How do the breasts look?” Trump asked.
“The breasts are okay,” Stern said.
“That’s important,” Trump said.
• • •
FOR ALL OF TRUMP’S salacious chatter on the radio and carefully staged appearances with models and other beautiful women, those who spent lots of time with him
through the 1990s described not an overheated Casanova, but rather a workaholic and something of a homebody, a savvy business operator who was keenly aware of the value of being perceived as a player. Goldberg, the attorney who was often by Trump’s side during those years, said many of his client’s much-ballyhooed associations with famous women and top models were mere moments, staged for the cameras. “Give him a Hershey bar and let him watch television,” Goldberg said. “I only remember him finishing the day [by] going home, not necessarily with a woman but with a bag of candy. . . . He planned his next project, read the blueprints, met with the lawyers, never raising his voice, never showing off, never nasty to anybody in the office, a gentleman. . . . I never heard him speak romantically about a woman. I mean, I heard him speak romantically about his work.”
Kate Bohner, who cowrote Trump: The Art of the Comeback, said the public perception of Trump as a serial womanizer and a glamorous night crawler was a calculated effort to add gloss to the brand, and nothing more. “There were times when I’d see him chatting up a bevy of gorgeous creations, and I can see how an outsider might think he was in it to win it, so to speak,” she said. “But never did I feel that it was anything other than part of his shtick to fuel the Trump brand. I saw Mr. Trump being more paternal toward women than playboy.”
Trump often said he wouldn’t have had time to breathe if he had truly consorted with all the women he was credited with dating. People “may be surprised that my life is much less glamorous than they thought, including every story about a supermodel,” he said. His wives were all good people, he recalled, “but I’m married to my business. It’s been a marriage of love. So, for a woman, frankly, it’s not that easy in terms of relationships.” In his book Trump: Think Like a Billionaire, Trump attributed his success, like that of “Jeff Bezos, Steve Jobs, and Ted Turner” to an “unrelenting focus [on] achieving their dreams, even if it’s sometimes at the expense of those around them. . . . Narcissism can be a useful quality if you’re trying to start a business. A narcissist does not hear the naysayers. At the Trump Organization, I listen to people, but my vision is my vision.” To think like a billionaire, Trump said, never take vacations (“I love relating to [my kids] just the way my father related to me—through a passion for work well done”), “have a short attention span,” “don’t depend on technology” (“I don’t even have an ATM card—I’ve never used one in my life” and “email is for wimps”), don’t overthink things (“The day I realized it can be smart to be shallow was, for me, a deep experience”), and “think of yourself as a one-man army. . . . You must plan and execute your plan alone.”
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