9

LUCK RUNS OUT

Well, I loved women. But I was never a drinker. I was never a drug guy, and I was never a cigarette guy.

—DONALD TRUMP

Like Donald Trump, Marla Maples was officially sexy. Her bona fides were established in the beauty pageant circuit, which included an event where she had almost captured the title of Miss Hawaiian Tropic International 1985. Sponsored by a tanning-lotion company, the contest required the competitors to smile brightly as they paraded in bikinis. On her pageant application Maples wrote, “I hope to become successful as a screen actress and some day do Broadway.”

Some young women had found wealth, fame, and celebrity through pageants, which serve a screening function for industries that saw commercial value in young women who were approachably sexy. In the media age, the demand was great, but so was the supply. The vast number of hopefuls suppressed market values and worsened the odds of financial success, even for those who won the most coveted pageant titles. Countless Shirley Cothrans (Miss America) and Christiane Fichtners (Miss USA) captured crowns and little else. Contestants also had to consider the possible pitfalls associated with pageants in the era of media excess. Vanessa Williams, Miss America 1984, was forced to resign when photos of her nude, which were made before she won the pageant, were published in Penthouse magazine. In time, the public would become almost inured to this kind of incident, as nude photos of celebrities were published with such frequency that it seemed as if every young woman in America had chosen, at one time or another, to be photographed or filmed in the altogether and no one could be trusted to keep these images private.

Williams, Cothran, and Fichtner provided cautionary examples, but dreamers could always focus on Lee Meriwether, who went from Miss America 1955 to a career in television and film, and Bess Myerson, who had won the same tiara in 1945 and became a successful celebrity who helped make Ed Koch mayor of New York. Marla Maples had them in mind as she competed in her last pageant and made plans to move to New York City. Although she had been an honors student in high school and was doing well at the University of Georgia, she left before completing her degree. She had been to the city just once before, with her parents. The family had stayed at the Waldorf-Astoria.1

In Manhattan, Maples would be fortunate to find an inexpensive apartment, which she decorated with images of that icon of tragic beauty Marilyn Monroe. Like Monroe, Maples’s power resided in the kind of wholesome sexiness that one writer would say made her “a 13-year-old boy’s ideal woman. Pretty and sexy, yet safe, somehow. The centerfold next door.”

Although this kind of allure conferred some power, Maples found it could also be dangerous, especially when less-than-mature men regarded her as an object they might control. From a young age Maples seemed to attract men who became possessive and even obsessed. Her very first romantic relationship was with a handsome and engaging young man who could behave in frightening ways. Once, a disagreement led to a shove, and then Maples’s hand went through a glass table top. She went to the hospital for stitches. Years later she would say she wished she had learned more from this incident, but at the time she was quite naïve and all-too trusting

As she poured herself into her career Maples attended auditions and casting calls and took acting classes at HB Studios where many prominent performers—Jason Robards, Al Pacino, Barbra Streisand, Anne Bancroft, Robert De Niro—had learned the craft. She accepted some requests for dates but in a city filled with appealing men she was selective. In August 1985 she was introduced to Donald Trump, by Jerry Argovitz, who had been a Hawaiian Tropic pageant judge. He took her to Trump’s office where she appreciated the view of Central Park and admired the framed magazine covers on the wall. In the months to come Maples would run into Trump at a tennis tournament and on the sidewalk on Madison Avenue. She also saw him at a charity event she attended with Argovitz.

Although Argovitz and Maples saw each other off and on, no romance developed between them. Amid casting calls and meetings with agents, she met a former police officer named Thomas Fitzsimmons, who was trying to become an actor and writer and had a project that might include a part for her. Though an aspiring star Fitzsimmons was mainly a security man for the rich and famous. Licensed to carry a gun, he carried it often. After Maples was mugged she appreciated his toughness and the way he made her feel safe. He often accompanied her when she went out, saying she needed to be protected. The two became romantically involved.

Well-muscled and ruggedly handsome, Fitzsimmons had the physical attributes to match his ambitions. His pet project was a film script—called Blue Gemini—which was about twin brothers who were officers in the New York Police Department. Instead of just pitching his script to producers and directors, Fitzsimmons decided to create a few minutes of film, which would serve as a sample, or “trailer,” to show potential backers. Fitzsimmons relied on friends to serve as cast and crew for his trailer. Marla Maples got an on-camera role. A veteran New York press agent named Chuck Jones served as unpaid publicist.

A Marine Corps veteran who had worked as a combat reporter in Vietnam, Jones had come to New York after being discharged. He landed with an industrial paper called FilmTV Daily. When the paper went out of business in 1970, Jones used his experience and many contacts to become a press agent. Representing entertainers such as Lionel Hampton and Jack Lemmon, Jones arranged for interviews and kept reporters and gossip columnists supplied with items that reflected well on his clients. Jones was so well connected to photographers, writers, and editors, who felt indebted because of the access he provided, that he could almost guarantee a client favorable treatment in the New York media. Much like politicians and donors, these journalists played a continuous game, trading tips and favors without keeping score in any serious way. It was enough that everyone except the public was in on the action and eager to keep things going.

Outgoing and reliable, Jones had developed so many credits in various favor banks that he often used them to help friends who couldn’t pay his fees. When Tom Fitzsimmons asked him to help with Blue Gemini, Jones was able to get him attention. The tabloid press reported on the film shoot as if it were a feature-length movie beginning production in the city. Other than providing him a moment of excitement, the publicity didn’t do much for Fitzsimmons, whose script never found backers. Marla Maples, however, discovered in Jones someone who seemed eager to help her advance her career.

*   *   *

At the time when he met Marla Maples, Donald Trump’s fame was approaching a peak, thanks in part to a tussle with Mayor Koch over the ice-skating rink in Central Park. Named for the Wollman family, which had donated the funds to establish it, the rink had opened in 1949 and operated every winter until it was closed in 1980 for rehabilitation work that was supposed to be finished in 1982. The job had been complicated when city officials decided the rink should double as a pond in the summer and should employ a new type of refrigeration technology using Freon gas. More difficult to install than an old-fashioned brine-based system, a Freon setup would be less expensive to operate and was expected to save taxpayers money over the long run. But problems plagued the project and the rink remained closed. In May of 1986 Trump wrote Koch a letter in which he offered to rescue the mayor from “the greatest embarrassment” of his administration by building and then operating the rink. The mayor released the letter to the press along with his own letter, which accepted Trump’s offer to build the rink but declined his request to run it because the city intended to keep admission fees low. Koch concluded snidely, “With bated breath, I await your reply.”

Koch considered Trump’s “Dear Ed” letter to be excessively self-promoting, especially the part that noted Trump’s own accomplishments and promised to finish the job before winter. Koch thought New Yorkers would agree. However, the mayor miscalculated. Editorial writers at three local papers said that Trump was right. Koch wound up giving Trump what he asked for, and the developer relied on HRH Construction to fulfill his promise with the help of no-interest financing from his friends at Chase Manhattan Bank. Managers at HRH would say that they renovated the rink at cost because Trump promised the firm a great deal of work in the event that he got to develop the old Penn Central rail yards on the Upper West Side, which he still controlled.

Trump would claim that he found a Canadian company, Cimco, to design the rink, but the firm had been brought into the picture well before he wrote to the mayor. Trump added a bit of insult to Koch’s injury by hiring a city official named Tony Gliedman to oversee the rink. Gliedman had been the housing commissioner who opposed the tax abatement for Trump Tower. During that disagreement, Gliedman reported that Trump had threatened and berated him. Now, as his employee, Gliedman made Trump look good, shepherding the rink renovation to completion sooner than expected.2

As Gliedman showed, Trump had an eye for talent and was happy to recruit people who had shown their abilities by opposing him. Inside his organization they were paid well and enjoyed a level of autonomy equal to the pressure he placed on them. Success depended, at least in part, upon showing dedication and toughness the boss could respect. As Louise Sunshine told Harry Berkowitz of the Washington Post, “He finds talented people, and he brings out the best in them and also the worst. You become very single-minded. All the rest of your life falls away. He totally absorbs you.”3

Although many New Yorkers gave Donald Trump credit for the renovation of Wollman Rink, Mayor Koch rejected his request to have the facility named in his honor. This decision was, in part, the product of the terrible relationship between these two men. In his memoir, Citizen Koch, the mayor called Trump a “blowhard” and a “supreme egotistical lightweight.” The feelings were mutual. Evaluating the mayor many years later, Trump said that Koch was “a cheerleader his first term. After that he became a very angry man. He had many scandals and much corruption. Ed Koch was a highly overrated mayor, and his last term was a disaster, and he left a very angry person.”

The spectacle that was Trump versus Koch was an almost-endless source of entertainment for newspaper readers in New York. They were well-matched when it came to ego. Trump desired to reshape the city’s skyline and make his name a widely recognized emblem of success and power. Koch was one of only three mayors in city history to be elected to three full terms and so craved the public’s approval that he habitually shouted to people on the street, “How’m I doin’?” Both men loved the gamesmanship of politics, but as a private businessman Trump was not accountable to the public. Koch was expected to meet a certain standard of decorum, which made him more vulnerable to public opinion. When Koch called Trump a “lightweight,” Trump, true to his punch-back-harder style, declared the mayor “a piece of garbage.”4

As he fought with Trump, Koch suffered repeated scandals as officials in his administration were either subjected to criminal charges or forced to resign after abusing their offices. The scandals were so numerous that when the City Hall press corps held its annual charity roast, the musical program was titled Greedlock, a play on the term gridlock. In one of the more biting numbers, a reporter who played the mayor sang, “I’m not indicted! And I’m so delighted!”5

The most famous of Koch’s fallen allies was Bess Myerson, who was indicted for attempting to influence a judge by hiring her daughter. Myerson would eventually be acquitted at trial, but the scandal was just one indicator of the decay in the Koch administration. Donald Trump would make much of the mayor’s problems, and in a book he wrote he called attention to the sins of individuals such as Myerson. Conspicuously absent from Trump’s litany, however, was Stanley Friedman, who was convicted and imprisoned for his role in a kickback scheme at the city’s parking bureau. Friedman was, of course, Roy Cohn’s law partner and had worked furiously in the last days of the Beame regime to finalize the sweet deal Trump got when he turned the old Commodore into the Grand Hyatt. Friedman’s relationship with Trump was raised at his trial by federal prosecutor Rudolph Giuliani, himself a future mayor.6

Trump, Cohn, Koch, Giuliani: these were men so ever present in city affairs one could be forgiven for thinking that New York was like a small town where the same few people held sway over all local business, finance, development, and politics. This was hardly true. Among developers, Trump was just one of many who were putting up grand new projects in Manhattan. The Cohn law practice was overshadowed by dozens of bigger and more powerful legal firms. And a host of political figures often bested the likes of Giuliani and Koch. However, in the competition for the public’s attention, no one surpassed Trump. In 1987 alone, his name appeared in the local papers more than a thousand times. Radio and TV programs added to his fame, and then there was the book.

In the summer of 1987, Random House prepared to publish Trump: The Art of the Deal, which he produced with such considerable aid from the professional writer Tony Schwartz that Trump gave his collaborator credit on the cover. The title reflected Trump’s belief that clever negotiation, in the pursuit of profit, should be recognized as a creative endeavor equivalent to the efforts of a painter or a poet. The “deal,” as he put it, involved persuading someone to sell him a property, hiring the right architect to design a new development, obtaining government approvals, and then contracting with the builder who would make the thing real. If this was art, then it was a kind of performance art that depended on his ability to manipulate, schmooze, and cajole. It was also, by implication, a talent that millions of other people could also claim. The salesperson who got you to add rustproofing to your order for a new car or the waiter who talked you into purchasing an appetizer were practicing the art of the deal. Granted, their art would not benefit others in the way that a great artist’s may, but it was a kind of creativity.

Knowing the book would require massive amounts of publicity to satisfy his desire for sales, Trump planned to exploit his many contacts in the press, especially those at various TV networks. He also raised his own profile by dabbling in politics. In early July he met with Roger Stone, a longtime friend of Roy Cohn’s, to discuss Stone’s proposal for a challenge to New York Governor Mario Cuomo. Stone, who worked in the shadowy corners of right-wing politics, got his start in the Nixon campaign of 1972. In that race he made campaign contributions to GOP representative Pete McCloskey under the false name “Jason Rainier” and the “Young Socialist Alliance.” McCloskey was challenging Nixon in the New Hampshire primary. Stone alerted the press to the donation as proof that McCloskey was linked to the wrong kind of supporters. In 1987 Trump wasn’t interested in running for office, but he did like Stone’s proposal for an “open letter” kind of newspaper ad to attract attention.7

In early September, Trump spent more than $90,000 to purchase full-page advertisements in The Times, The Boston Globe, and The Washington Post. The headline of the ad announced, “There’s nothing wrong with America’s Foreign Defense policy that a little backbone can’t cure.” In the text, which was addressed “To the American people,” Trump questioned America’s defense commitments in Europe and Asia and argued that the United States “should stop paying to defend countries that can afford to defend themselves.” He added, “Make Japan, Saudi Arabia and others pay for the protection we extend as allies. Let’s help our farmers, our sick, our homeless…” His closing was a rallying call: “Let’s not let our great country be laughed at anymore.” Trump did not speak to the first reporters who phoned after the ad appeared, but then he changed his mind. He told them that he had no intention of running for office but had paid to spread his message because “I’m tired of watching the United States get ripped off by other countries.”8

Considering that Trump’s criticism constituted an attack on their beloved Ronald Reagan, the ad would have drawn howls of protest if Republican partisans believed Trump were a serious political figure. None did, and so none responded. His comments did spur press attention worth far more than $90,000 to someone about to publish a book. After the ads ran, newspapers across the country published items about the flamboyant New York businessman’s political interests. Then Trump’s executive assistant, Norma Foerderer, received a phone call from Michael Dunbar, a Republican activist in Portsmouth, New Hampshire. He said he wanted to meet “Mr. Trump” to talk politics.

Home to the first party primaries in the nation, New Hampshire played such an outsize role in presidential politics that a minor figure such as Michael Dunbar wielded remarkable influence. Days after he made his phone inquiry, Dunbar was at Trump Tower, where he was pleased to discover that his favorite noncandidate “didn’t treat me like I was a rube from New Hampshire at all.” Although he forgot to ask if Trump might want to run for president, Dunbar went back to the Granite State and ordered some new stationery with Draft Trump printed in red at the top. He collected donations and went to the leaders of the local Rotary Club to propose they invite his man to speak. They agreed and arranged to have him visit before Thanksgiving.9

Trump flew to New Hampshire in October, landing in his black helicopter at an airstrip in the seaside town of Hampton. Dunbar was waiting with a rented limousine, which sped north on US Route 1 to a roadside restaurant called Yoken’s. Marked by a kitschy neon sign depicting a spouting whale and the words Thar she blows!, Yoken’s provided the space and the food for the Rotary Club’s regular meetings. Hundreds of Rotarians and their friends packed the place along with several reporters. More than one would describe Trump’s forty-minute performance as more comedy than policy. President Reagan’s budget deficit should be addressed through a kind of tax levied on the nation’s allies, he said. “We’re being ripped off and decimated by many foreign nations who are supposedly our allies. Why can’t we have a share of their money? I don’t mean you demand it. But I tell you what, folks, we can ask in such a way that they’re going to give it to us—if the right person’s asking.” America’s trade imbalance with Japan should be approached with a tougher negotiating stance, continued Trump. “The Japanese, when they negotiate with us, they have long faces. But when the negotiations are over, it is my belief—I’ve never seen this—they laugh like hell.”

Without rimshots from a drummer, some of Trump’s lines missed their mark, but he kept on delivering them. The White House needed a tough guy, he said, because the world was filled with difficult adversaries. “You think [Soviet leader Mikhail] Gorbachev is tough? Think of this character Khomeini,” he said of Ayatollah Ruhollah Khomeini of Iran. “I mean this son of a bitch is something like nobody’s ever seen. He makes Gorbachev look like a baby. And Gorbachev is one tough cookie.” Then Trump turned sober, even a bit apocalyptic, adding, “If the right man doesn’t get into office, you’re going to see a catastrophe in this country in the next four years like you’re never going to believe, and then you’ll be begging for the right man.” The crowd greeted Trump enthusiastically. One woman told a New York Times reporter that he possessed the “aphrodisiac” that is power. Another noted that he had drawn a far bigger crowd than real politicians, including Senator Robert Dole and Congressman Jack Kemp.10

Anyone who listened closely would have concluded that Trump was not a real candidate. “I’m not here because I’m running for president,” he said. “I’m here because I’m tired of our country being kicked around and I want to get my ideas across.” He was also there, at the Portsmouth Rotary Club meeting, to give a camera crew from the ABC TV program 20/20 something exciting to film. (The title of the program referred to perfect eyesight, not insight, and the program was known for offering little more than glimpses into the lives of its celebrity subjects.) Weeks later 20/20 host Barbara Walters, who moved in Trump’s social circle, gave him the Judy Klemesrud treatment before a national audience of about a million people. Her narration began, “Look, up in the sky! It’s a bird! It’s a plane! No, it’s superbuilder Donald Trump’s ten-million-dollar French Aérospatiale helicopter, heading for the Sixtieth Street heliport to pick up the brash forty-one-year-old billionaire businessman and whisk us off to check up on part of his ever-expanding empire.”11

Walters’s homage, which was titled “The Man Who Has Everything,” was wealth pornography that titillated viewers with images of valuable real estate and a cooing narration that explained that “the Trumps are treated like American royalty” wherever they go. The display of the family’s gilded lifestyle was an advertisement for a man who was becoming a human brand. His residences, yacht, aircraft, and limousines were billboards that urged people to buy whatever he was selling, from swanky apartments to hardcover books, and join him in luxury. Though he often said he related best to “the construction workers and the cab rivers,” Trump understood what Barbara Walters meant by “American royalty.” The country may have been founded in rebellion against the crown, but the people still needed princes and princesses, kings and queens, if only for aspirational entertainment. In the United States, where money had replaced inherited titles as the pathway to aristocracy, everyday citizens could thrill to the possibility that they might grow rich and join the elite. This hope made it easier for people to admire Trump, even when he said obnoxious things. He was, by virtue of his money, entitled, and anyone who achieved as much would be entitled too.

Entitled American royals possessed no power to govern directly, but their wealth allowed them to buy the lawyers, lobbyists, politicians, and other functionaries who would help them impose their will on others. They also enjoyed the attention of various courtiers, who fluffed their egos with a chorus of assent. In Trump’s case, many of the most important voices of support emanated from the mass media, and they often assured readers, listeners, and viewers that they could have faith in the superior qualities of leading executives, entrepreneurs, and investors. This superiority justified the growing gap between the super-rich and everyone else.

The distraction provided by reports on the lifestyles of the rich and famous helped divert attention from how the middle class as it was known in the fifties and sixties was rapidly disappearing. Stabilized for thirty years, income inequality began to increase sharply in 1980 as the richest Americans seized more of the wealth generated by the economy and workers barely kept up with inflation. Tax rates levied on capital gains from investments were slashed, and salaries of chief executive officers in American corporations rose from forty-two times the average worker’s pay in 1980 to a multiple of eighty-five in 1990. In the same decade the ranks of American billionaires would increase from about a dozen to almost one hundred. The number of Americans with fortunes greater than $100 million more than tripled, to twelve hundred. For these richest Americans, investments in stocks, bonds, and high-end real estate, Trump’s specialty, were the surest source of wealth. In New York, where Wall Street millionaires competed with the global rich to buy choice apartments, prices rose and Trump reaped the profits.12

A mere millionaire, Barbara Walters was nevertheless a media queen who wielded the imprimatur of ABC News as she asked Trump, in all apparent seriousness, “If you could be appointed president, and you didn’t have to run, would you like to be president?” He coyly replied that to be appointed leader of the free world might not be so appealing because he would be deprived of the satisfaction of winning an election. He concluded, “It’s the hunt that I believe I love.”

The 20/20 profile presented was aired on the day Trump’s book went on sale. The timing was no doubt arranged as a condition of Walter’s access to her glamorous subject. Other networks presumably sought this “get,” as exclusive interviews were called, but Walters enjoyed real advantages in such competitions. The daughter of a showbiz impresario, her stock-in-trade was the personality profile that offered a view of the famous that was mostly celebration. She might get a subject to cry with a deft play to emotion, but as a shrewd player in the celebrity economy, she was unlikely to expose too much of the people she interviewed. No sense in risking future valuable access.

Four days after the 20/20 program aired, Phil Donahue presented Trump to the millions who watched his afternoon TV talk show. One viewer, in Saddle River, New Jersey, was so impressed by what she saw that she made sure to mention Trump’s performance to her husband. A week later he signed a typed note, which was dispatched directly to Trump Tower:

Dear Donald

I did not see the program, but Mrs. Nixon told me you were Great on the Donahue show.

As you can imagine, she is an expert on politics and she predicts that whenever you decide to run for office you will be a winner!

With warm regards,

Sincerely

RMN13

When it was reviewed, the Trump book was generally found to be readable and charming. Framed as a “week in the life” story, it was also, in the words of Christopher Lehmann-Haupt, “a display of the author’s not inconsiderable ego.” In its pages Trump pointed to the personal qualities that had allowed him to become wealthy beyond anyone’s dreams, and he portrayed himself as a deal-maker without equal. He even tried to sell his readers on the notion that money wasn’t important to him. “I don’t do it for the money” was the opening line of the text. “I’ve got enough, much more than I’ll ever need.” It was an implausible, if not impossible, claim. But as Lehmann-Haupt would also note, in most of the book Trump managed to blow his own horn without sounding too many sour notes. Yes, he bragged, but he also copped to many of his flaws (he selected the ones that were essentially harmless) and charmed with heartfelt passages about his family and business associates. The result was, the reviewer noted, “like a fairy tale,” but also a book that entertained and inspired.

Trump: The Art of the Deal would spend months on various bestseller lists and reveal its putative author as a champion promoter. In the book he wrote, “A little hyperbole never hurts. I call it truthful hyperbole. It’s an innocent form of exaggeration and a very effective form of promotion.” In his effort to sell his memoir Trump’s hype included so many exaggerated claims that tracking them was almost impossible. But he did not have to hype the party he threw for himself at Trump Tower. Thousands of people streamed through the lobby of the building as twenty violinists played and boxing promoter Don King, clad in a floor-length mink, repeatedly shouted, as Donald and Ivana circulated, “Here’s the king and the queen!” In his remarks Trump was generous in praising his publisher and his collaborator, Tony Schwartz, and in pledging his royalties to charity. Schwartz said he would hold on to his share.

Schwartz and Trump represented the top end of an emerging genre of professionally aided autobiographies. Begun with auto executive Lee Iacocca’s 1984 bestseller, Iacocca, these books were of limited value to the public record and rarely offered much insight. Of his work for Trump, Schwartz would say, “There was nothing I wrote that on its face was false. But there’s a lot open to interpretation.” This was a kind way to describe the mythmaking in a book that reiterated the claim that Ivana Trump was an Olympic skier and inflated the cost of saving the Bonwit Teller friezes, which Trump had chosen to destroy, to hundreds of thousands of dollars. But like society-page reporters, reviewers are not fact-checkers, and celebrity memoirs are not intended to present unvarnished truth, but a glossy version of reality. This is best done with carefully crafted revelations about flaws and foibles that are either inconsequential or have been overcome.

Missing from the personal revelations in the Art of the Deal was any indication that Donald Trump was vulnerable to the allure of beautiful women, though he truly was. Eventually he would admit this weakness, and to the trouble it caused him. But he wouldn’t have to correct anything he wrote about his family attachments. Trump was a genuinely loving father who often conducted business while his children played on the floor of his office. He also valued the stability of marriage as it was represented in his parents’ lives. As Fred Trump had demonstrated the workings of power to his son, he had also shown him that the support of a wife and family—through illness, loss, achievements, and scandals—was essential to his success.14

*   *   *

Almost unnoticed in the crush of people at the Trump book party were Tom Fitzsimmons and Marla Maples, who attended at the insistence of her publicist Chuck Jones. In his version of the story, he did his best to introduce Maples to people who might help her find work as an actress and even took her to California for the Daytime Emmy Awards show, where the people in soap operas, talk programs, and game shows competed for recognition. He hoped she might attract some attention and, perhaps, some work. He also pressured her to attend the book event and a party celebrating the reopening of the famous Rainbow Room five floors below the top of the RCA Building at Rockefeller Center.15

Closed for two years while restorers worked on everything from the floor to the colored lights, the Rainbow Room had been a cherished part of New York since it opened in 1934 as a supper-and-dancing club for the rich. Over the years it had evolved from a formal and exclusive setting where Astors might bump into Roosevelts, into a place where anybody who could pay was welcomed. The guest list for the party that marked the reopening reflected the shifting social scene. The great doyenne Brooke Astor was in attendance, but so were many whose celebrity came as the result of their talents as politicians, entertainers, and businesspeople. As the party buzzed, Mayor Koch lectured the wandering cigarette sellers, who were dressed in pink pillbox hats, on the evils of smoking. Leona Helmsley gazed out the window and asked, “How do you like my husband’s buildings?” Donald Trump swanned into the room with Ivana at his side, scanned the renovated space, and said, to no one in particular, “Nice job.”16

Standing to the side of the stage, where Lionel Hampton conducted his orchestra, Jones and Maples eyed the crowd. Jones took notice when the Trumps entered and made sure that Maples noticed too. (Later she would wonder if Jones hoped she would give him access to Trump.) The scene was an elegant blur of men in tuxedos and women in gowns. At a long buffet table the guests selected from boneless quail on watercress, scallops in their shells, and striped bass with lobster mousse.

As Maples would recall it, Trump’s longtime aide Norma Foerderer telephoned her after the Rainbow Room event to say that her boss, a married man with three children, was inviting her to lunch at the St. Regis Hotel. After several more phone calls, she accepted. The date was set for December 19.

Lunch lasted five hours. In that time Maples and Trump would discuss, among other topics, his business, his family, her family, and their views on religion. Although she felt as comfortable as if she were sitting with a longtime friend, Maples continued to call him “Mr. Trump.” He introduced her to people who happened by their table and, in the most important part of their conversation, insisted that his marriage was all but over.

In time, much of America would study the details of Donald Trump’s romantic life, thanks to the tabloid press. But Maples would say their long lunch at the St. Regis marked a moment when her relationship with Trump was entirely private and not well defined. She said that she had told him she would not enter into a relationship with a man whose marriage might be saved. According to Maples, he replied that a divorce was inevitable. In fact, a couple of years would pass before Donald and Ivana’s relationship would end. The pages of Maples’ datebook, which Jones took and copied, include a note that declares, “I don’t want to be only something that keeps the boredom away!”

Considering the frenzied quality of Donald Trump’s activities, it would be difficult to imagine the man was ever bored. While he operated high-profile commercial buildings and hotels, he was also laboring to develop new projects. In addition, he was having trouble digesting the deals he had made to acquire the Taj Mahal and the Plaza Hotel, where he had put Ivana in charge. Nevertheless, he soon began to pursue the purchase of Eastern Airline’s shuttle, which linked New York City to both Washington and Boston. He was keenly interested in the shuttle’s cash flow, which would be substantial considering that many flights were packed full of travelers paying the maximum walk-up fare.

After years of losses—the deficit was more than $180 million in 1987—in the airline’s overall operations, which spanned the nation and included routes to the Caribbean and South America, Eastern’s managers needed cash, The one part of the company that made money, the shuttle possessed valuable gates at three busy airports, where airlines had great difficulty adding flights because of the lack of spaces to dock more arriving planes. Although he knew so little about airlines that he had considered his deceased brother’s work as a pilot comparable to driving a bus, Trump did see that the gates were like coveted bits of real estate. LaGuardia, Logan, and National Airports were unlikely to build any more of them, so their value would only increase over time.

Negotiating directly with Frank Lorenzo, the chief of the holding company that owned Eastern, Trump quickly accepted that the price for the shuttle would be in excess of $300 million. The price, and the prospect of her husband’s managing an airline in addition to his other businesses, bothered Ivana Trump. She had noticed that her husband was having trouble sleeping at night and couldn’t imagine how he would handle the additional burden. Ivana was also concerned that profits from the Trump gambling operations, which she helped to manage, were going to be wasted on the purchase. But as she raised her concerns, the negotiations went forward, and the deal was eventually completed for $365 million.

When his purchase was announced at a press conference at the Plaza Hotel, Trump also revealed that he would call the service the Trump Shuttle. Soon all the planes were painted with the name TRUMP in gold, and the interiors were outfitted with wood veneers, leather seats, and gold-colored restroom fixtures. All of this was done with portions of $380 million in debt ($365 for the Eastern assets, $15 million to revamp the equipment), which was arranged by Citibank and then divided among some twenty banks. To cover the obligation, let alone generate positive cash flow, Trump would need to capture at least 60 percent of the Boston–New York–Washington business, which meant thrashing the rival Pan Am shuttle.17

*   *   *

With an airline, casinos, real estate, and hotels, Donald Trump had no need for distractions, but he continued to have one in Marla Maples. He also saw certain elements of the press turn against him in ways that would have wounded almost anyone. A new magazine called Spy, which was founded by Graydon Carter, Thomas Phillips, and Kurt Andersen, targeted him regularly. Spy was comparable to Tom Wolfe’s landmark novel Bonfire of the Vanities in the way that it skewered New York society and the financial elite. Wolfe’s book viewed the greed and narcissism of the age with an unblinking eye. Its main character was a wealthy, self-described “Master of the Universe” who could have been modeled after Donald Trump. For its part, Spy was a monthly accounting of the poseurs, the pretenders, and the naked emperors of 1980s New York.

In early 1988, the editors of Spy commissioned an article about Ivana Trump, which prompted a letter from Trump attorneys who threatened “rapid and major” litigation in the event of an inaccurate or defamatory piece. In October 1988, the magazine’s Joe Queenan made Donald Trump one of several case studies in a column that asked, “Why do good things happen to bad people?” Seeking answers, Queenan phoned Rabbi Harold Kushner, author of When Bad Things Happen to Good People, who said that Trump was either an honest, driven businessman or an “evil person” who will “trip himself up at some point.” On the following page readers were treated to a photo essay titled “The Unglamorous World of Mr. Trump.”

In response to Spy and later articles that Carter published in other magazines, Trump took to attaching the word sleazebag to Graydon Carter’s name every time he uttered it. He also told gossip columnist Liz Smith of the Daily News that he believed the magazine was in financial trouble. Smith reported to her readers that she had chided the “handsome mogul, of whom I am very fond,” for speaking ill of others. In the circular way that comments can become newsworthy when they relate to the press, Spy’s editors then recycled the item in their own pages. Thus, idle chatter at a party became fodder for public consumption in not one publication but two. This was the risk anyone takes with the press. A stray comment gets published, then republished, and pretty soon you find yourself in a conflict with people who use ink by the barrel.

Trump was not afraid to splash some ink around when he thought the moment demanded it. He had happily invested in the big print ads that announced his purchase of the Plaza and his views on foreign policy. He was so skilled at obtaining free publicity that he could command press attention almost at will. In early 1989 journalists from Time spent hours with him to produce a cover story that was filled with cringe-worthy quotes from the man himself. Writer Otto Friedrich began with Trump’s claim that Britain’s Queen Elizabeth, who was last in America in 1983, asked to use his helicopter when she “is over in this country” because it is the safest to fly. Trump further asserted, “No one has done more in New York than me,” and that the Eastern shuttle was “the single greatest franchise in the world.”

Along with his more outlandish claims, Trump offered pithy explanations for his business success and explained how his approach to real estate differed from his father’s: “It’s much easier to sell an apartment to Johnny Carson or Steven Spielberg for four million dollars than it is to collect a couple of dollars of rent in Brooklyn.” (He didn’t mention that Carson had recently sold his apartment and was angry that he had lost money on his investment.)18

Friedrich quoted Trump as he confessed that he possessed something like a con man’s talent for persuasion. “I can sit down with the most sophisticated people in the arts in New York and get along fabulously with them. If I want to, I can convince them that I know as much about something as they do, and I don’t.” Asked how he managed this trick, Trump said, “It’s a feeling, an aura that you create.” In another bit of reflection Trump revealed himself to be defended even against self-evaluation: “When you start studying yourself too deeply, you start seeing things that maybe you don’t want to see. And if there’s a rhyme and reason, people can figure you out, and once they can figure you out, you’re in big trouble.”

Born in Boston and educated at Harvard, the Time writer Friedrich was a New Englander with an old-fashioned moral sense that obviously guided his consideration of Donald Trump. His profile included a complaint from a designer who said Trump took two years to pay his fees and an anecdote from Der Scutt about an awful display of temper. As he recalled it, Trump ruined his expensive shoes when he kicked a chair across a conference room after being informed that a project was behind schedule. “He always has to have his way,” said Scutt. Friedrich concluded that Trump could become his generation’s Howard Hughes, “living alone in a single room.”

The Hughes reference may have stung Trump (even though he admired the reclusive billionaire), but it did not deflect him from the overarching project of his lifetime—the construction of his public image. In a subsequent interview with the Chicago Tribune, he and Ivana offered a version of him that was warmer and more sympathetic. “He’s the people’s billionaire,” she insisted. He confessed, “I have a feeling of guilt about my living so well. I don’t need three hundred rooms. I’m not even interested in boats.” But even as he strained to strike a populist note, the man who demanded and won tens of millions of dollars in tax breaks had to complain about the rent-control program that made it possible for thousands of less-than-rich people to live in Manhattan: “The rent-control laws are incorrect, and the big losers are the people of New York, because the city is getting such a tiny tax revenue.”19

In April 1989, Trump saw another opportunity to speak his mind when a young woman who was white and an investment banker was raped and beaten until she became unconscious while out for a jog in Central Park. As media reports shocked the city and the victim struggled for survival, police mounted an intense investigation that ended with the apprehension of five black youths between the ages of fourteen and sixteen who were then interrogated for many hours. The five implicated themselves, but would later recant, saying they had been pressured into making false statements. Editorial writers at the tabloid Post urged readers to “channel your outrage” by demanding lawmakers reinstate the death penalty. Donald Trump bought full-page advertisements in the city’s four big daily papers to proclaim, BRING BACK THE DEATH PENALTY. BRING BACK OUR POLICE!

Although he avoided naming the accused in the jogger case, Trump’s reference to “roving bands of wild criminals” left no doubt about why he had paid for the ads. Newspaper accounts had described “wolf pack” gangs marauding in the park. (The press reported, erroneously, that the slang term for this kind of spree was wilding.) Trump also took a swipe at his nemesis Mayor Koch, who had said that New Yorkers should not indulge in hatred and rancor as they considered the attack. “I don’t think so,” wrote Trump. “I want to hate these muggers and murderers. They should be forced to suffer and when they kill they should be executed for their crimes.”

Not one of the accused was linked to DNA evidence discovered by investigators, but all five would be convicted and begin their prison terms in less than eighteen months. The crime would remain one of the most notorious in generations. Trump’s expression of outrage, which echoed the feelings of many, would reinforce his status as a figure who occupied a unique place in the public arena. His instincts were populist and generally conservative. With the exception of his frequent references to his own Ivy League education, he almost always favored a stubbornly anti-intellectual type of common sense that played to the grievances of the kind of white men represented by the TV character Archie Bunker, who, like Trump, came from Queens and offered his opinions with chin-jutting pride.

Donald displayed his inner Archie in the summer of 1989 when he told TV interviewer Bryant Gumbel, “A well-educated black has a tremendous advantage over a well-educated white in terms of the job market. I’ve said on one occasion, even about myself, if I were starting off today, I would love to be a well-educated black because I believe they have an actual advantage.” In the universe of “well-educated black” men, some had gained from affirmative action programs, but only the most superficial view of the landscape would lead someone to agree with Trump. On the program, filmmaker Spike Lee called Trump’s statement “garbage” because it reeked of racial ignorance. But it sounded like tell-it-like-it-is honesty to many who would insist that they were decent people who were not at all racist because, like Archie, they could be respectful to all sorts of individual people. To them, Trump and his wealth—which was supposedly the product of bold entrepreneurial effort and not book learning—represented what was good about America, and they welcomed his frank talk.20

The Trump approach was consistent with a long/tradition of divisive and extreme rhetoric in American politics. Trump’s provocative statements invariably attracted the attention of the news media, especially the tabloid press, where his style was tailor-made for headline writers. Of course, on rare occasions Trump would have preferred to be left alone. One of those arose when Spy finally produced its article about Ivana. The magazine’s cover that month featured a more-or-less life-size photo of her cropped to show her eyes, nose, teeth, and painted lips in a garish light. Though factually accurate, the article was by turns mocking, hilarious, and cruel. It was illustrated with images of Ivana as a Barbie doll and filled with damning anecdotes and quotes. (“She would scream at the top of her lungs and really lose her temper big-time,” said one source.) Writer Jonathan Van Meter also dissected the distortions in accounts of Ivana’s past and asserted she was as ambitious and controlling as her husband.21

Spy’s withering portrait of Ivana hit the newsstands at a moment when both she and her husband were especially vulnerable. So many rumors of infidelity swirled around Donald Trump, who made no secret of his interest in beautiful women, that one gossip columnist published a barely veiled hint about his relationship with Marla Maples. When Ivana’s friends suggested her husband was betraying her, she turned them away. After he complained about her appearance, she flew to the West Coast for plastic surgery. She returned looking younger, but so surgically altered that she was almost unrecognizable. For Donald, the stress at home was substantial, but it was one of many problems of his own making. As he acquired the Eastern shuttle and devoted extra millions to give it the gilded Trump brand, he also added expensive upgrades to the Taj Mahal, which he had wrested from Merv Griffin at a cost of more than $270 million. To pay for the pricey construction of the casino, Trump turned to Merrill Lynch to sell $675 million in junk bonds. The high interest rate on the bonds would further burden the casino operation.22

With so much of his corporate borrowing done at high rates of interest, Trump needed everything to go right, especially with his airline and his giant new casino. Under Eastern, the shuttle routes were profitable. However Trump had burdened the operation with so much debt in acquiring it, he had to do better than the previous owner. With upgraded airplanes, better service, and splashy promotions, he did attract more passengers than Eastern, but he failed to break even in revenue.

As the airline racked up losses, Trump faced self-inflicted problems at the Taj construction site, where upgrades that he ordered helped push the cost of the project past $1 billion. The casino became a mishmash of minarets, striped domes, and flashing signs. The entrance was guarded by life-size statues of Indian elephants. Inside awaited more than one hundred gaming tables and three thousand slot machines. Given his debt-driven operating costs, Trump needed these tables and one-armed bandits to produce more than $1 million per day. The odds of this happening were not good.

Long before the Taj was even finished, an industry analyst named Marvin Roffman had warned that Atlantic City already had too many gambling halls and revenues were not keeping up with inflation. Seven of the city’s twelve casinos lost money in 1988. The troubles continued in 1989, with Merv Griffin putting Resorts International into bankruptcy and the Atlantic casino closing. Atlantic City’s mayor and more than a dozen of his associates were arrested on corruption charges. Unemployment and blight continued to plague most of the city as outsiders took most of the casino jobs and profits were delivered to distant investors. “Atlantic City used to be a dump,” Roffman told the Los Angeles Times. “Now it’s a dump with casinos.” Six months later Roffman would describe the whole Atlantic City gambling business as a “house of cards.”

Roffman spoke as the local casino operators reeled from the effects of a fatal helicopter crash that killed three of the top executives in the Trump gambling empire. Stephen F. Hyde, Mark Estess, and Jonathan Benanav had been in Manhattan on business and were returning to Atlantic City. Witnesses said that the helicopter’s tail rotor broke off before the copter plunged into woods along the Garden State Parkway. The pilot, Robert Kent, and copilot, Lawrence Diener, also died. As chief operating officer for all of Trump’s gambling businesses, “Hyde was the most important ingredient in Donald Trump’s success in Atlantic City,” said Roffman. Hyde’s death, devastating to family, friends, and colleagues, was also a loss for the companies he served. No one else in the organization could match his experience, or talent.23

Within the Trump organization talk circulated of possible sabotage, which seemed plausible to those who knew that the boss received the occasional death threat. John O’Donnell, another Trump casino executive, would report this concern and take issue with Trump’s claim that he had considered taking the flight but changed his mind. In O’Donnell’s tell-all book—titled Trumped!—he also recounted the effort made to prevent a face-to-face meeting of Marla Maples and Ivana Trump when they attended the funeral services. Maples had become a regular presence at the Trump casino hotels and often showed up with friends or family. O’Donnell would describe her as a charming woman who became accustomed to first-class treatment. In his telling, many Trump employees were aware of her status, but she and Donald would take pains to avoid flaunting their relationship. They did not sit together at shows, and when he left her messages, he told desk clerks to tell Marla that “the Baron” had called.

With turmoil in his personal life and the loss of three key executives, Trump was more embattled than ever. Investors rendered their verdict on the condition of his Taj Mahal casino, pushing the value of its bonds down by 70 percent. Trump could take some comfort in that this downgrade was, at least in part, a reflection of a larger market trend. Nearly all the undersecured, high-interest junk bonds issued in the go-go 1980s dropped in value during this time. This included the debt issued in takeover actions such as the Kohlberg Kravis Roberts acquisition of RJR Nabisco for $25 billion. The enormous RJR Nabisco deal, accomplished with just $15 million of the buyers’ own cash, became the iconic example of a practice that allowed financial engineers to earn hundreds of millions of dollars by loading debt onto a company before selling its parts. It was all a matter of paperwork, accomplished in KKR’s case by a firm with just eighty-five employees and twenty partners. KKR’s owners, who were relatively anonymous, made vastly more money than world-famous actors, athletes, and artists. “Henry Kravis would make $400 Million! Without lifting anything heavy!” wrote financial journalist Adam Smith.24

In dollar terms, Donald Trump’s bonds represented a tiny fraction of the vast pool of junk-bond debt that frightened many investment experts, but he had made himself such a visible figure that reporters invariably threw him into their stories about troubled companies. Similarly, when they considered Trump, they quoted Marvin Roffman, who was the man to call for critical analysis of gambling in Atlantic City.

Roffman was so respected on Wall Street that Donald Trump sought to win him over. He invited the analyst to come to Atlantic City for a tour, to be conducted by his brother Robert. But on the day Roffman arrived, Neil Barsky of The Wall Street Journal published an article in which financial analyst Kaye Handley predicted, “Somebody will probably lose money on the Taj Mahal, but it might not be Donald Trump.” Roffman’s quote in the same article was more biting and more specific: “When this property opens, [Mr. Trump] will have had so much free publicity he will break every record in the books in April, June and July. But once the cold winds blow from October to February, it won’t make it. The market just isn’t there.”

With his words preceding him, Roffman encountered an infuriated Robert Trump at the door of the Taj. In a burst of temper, Robert shouted, “You’re no fucking good,” and barred Roffman from the property. Coming from the more reserved Robert, this angry display revealed the pressure that accompanied the debut of the Taj at a moment when the Atlantic City casino market was going sour. It was also consistent with Donald Trump’s way of speaking when he was unhappy, and it suggested a family trait that may have been handed down by their tough-talking father. Donald Trump saw a world inhabited by winners and losers, allies and enemies. When displeased, he would indulge in tirades spiced with expletives. Employees, rivals, critics, and associates would become, in his words, “stupid,” “dumb,” “losers,” or “wimps.”25

On the day when his brother kept Roffman away from the Taj, Donald Trump wrote to the analyst’s employer, Janney Montgomery Scott, to say, “I am now planning to institute a major lawsuit against your firm unless Mr. Roffman makes a major public apology or is dismissed.” The letter began one of the strangest episodes in the annals of finance. Roffman’s boss curtailed his duties, demanded the return of a bonus, and then asked Trump for input on the wording of an apology. Roffman then signed a letter that said, among other things, “Unquestionably, the Taj’s opening will be the grandest and most successful the city has ever seen.” Immediately regretting his decision, Roffman sent another letter stating, “I retract the [previous] letter and direct that you not use it for any purpose.” When he went to work the next day, he was dismissed.

With securities firms laying off thousands of employees amid a market downturn, Roffman’s employment prospects were dim, and he felt besieged as Trump criticized him in the press. Trump described Roffman as “a mediocre man with no talent” and even claimed to have intervened to save Roffman’s job when his bosses considered dismissing him months earlier. Incensed, Roffman said, “He’s a liar.” Clearly David to Trump’s Goliath, Roffman enjoyed a few moments as a cause célèbre as financial industry watchdogs sided with him. But it would take nearly a year for him to win his arbitration case against his employer and receive a $750,000 judgment. His suit against Trump would take even longer to resolve and resulted in a confidential settlement.26

Amid the furor over Trump’s battle with Marvin Roffman, the Taj Mahal opened in April 1990 with a smiling Donald Trump touching a magic lamp like the one of Arabian (not Indian) legend to prompt a light show and fireworks display. The most famous celebrity guest at the gala was, ironically enough, Merv Griffin. As Marvin Roffman had predicted, the Taj did well and then it did poorly. Forbes cut its estimate of Trump’s worth to $500 million and speculated that his businesses were losing $3 million every month. Although Trump argued with the Forbes account, it was affirmed in an independent audit, which said that if he sold his assets in an orderly way, he might net half a billion dollars. In an immediate fire sale, the report added, he could wind up almost $300 million in the hole.

The raw numbers explained why construction contractors were complaining about unpaid bills totaling more than $30 million. Trump said they were attempting to overcharge him. When Neil Barsky came to interview him for The Wall Street Journal, Trump made a show out of displaying a collection of Barksy’s articles and complained that he was spreading rumors about Trump’s cash-flow problems. He threatened to sue. Then he confirmed that he was intending to sell the Trump Shuttle.

On June 4, Barsky published a stunning report on Trump’s debt problems, layoffs at the Taj Mahal and Trump Shuttle, and his failed attempts to raise cash through the sale of properties or refinancing. (One offer, which lenders rejected, included stakes in the Grant Hyatt and the Plaza.) Barsky noted that much of the trouble stemmed from lenders’ having accepted Trump’s assertion that by adding his name to a casino, hotel, or airline he could raise its inherent value. This wasn’t true for the shuttle, which had lost $85 million under the Trump name, and it wasn’t true of the Taj, which was also losing money. Many of his possessions, including a yacht called the Trump Princess and a Boeing 727, had also declined in value. Publicly Trump disputed bankers who said his net worth might be zero. Privately he admitted they were right, telling Marla as they passed a homeless man on the street that the poor fellow enjoyed a higher net worth than his own. He would later make much of the fact that Marla supported him during this time.

The anxieties Trump shared in private were not shared in public. Instead, he expressed great confidence in his abilities and shifted blame to others. He criticized the casino executives who had perished in the helicopter crash, blaming them for much of his troubles in Atlantic City. While one source told The Times, “People are hiding under their desks,” to avoid becoming Trump’s targets, he insisted that his team was functioning well: “People want to work for me. Trump does well with management.” The same article noted that he had promptly fired a casino executive who was hospitalized for exhaustion after the chaotic opening of the gambling floor at the Taj Mahal.27

Trump’s detractors savored his struggles. Late Show host David Letterman made Trump the subject of the his nightly, satirical Top 10 list, which was titled “Top Ten Signs That Trump Is in Trouble.” Among the “signs” was that Trump had “asked his advisers how they thought a ‘battling billionaire’ character would go over on the pro wrestling circuit.” After years of drama and stress, John O’Donnell would leave Trump’s employ in 1990. When the onetime president of the Trump Plaza Hotel published his tell-all book about his former boss, he presented a picture of an imperious and possibly prejudiced man who seemed indifferent to others. In Trumped!, O’Donnell wrote that his former boss had said, “I’ve got black accountants at Trump Castle and at Trump Plaza. Black guys counting my money! I hate it. The only kind of people I want counting my money are short guys that wear yarmulkes every day.” O’Donnell also reported on a race horse named Alibi, which Trump had promised to purchase and rename D. J. Trump. Impatient for an account of Alibi’s performance, Trump supposedly pressured trainers to run him even though they were worried he might have caught a virus. The horse ran and, as the trainer feared, got sick. Veterinarians had to amputate Alibi’s front hooves to save his life. The hooves would grow back, but Alibi, whose bloodline included the famous Native Dancer, would never be fit to race. According to O’Donnell, when the weeping trainer called with the sad news, the purchase was canceled.

Drawn from his years spent working for the man, many of O’Donnell’s anecdotes about Trump were repeated in the press. O’Donnell admitted that Trump considered him a “disgruntled former employee.” When interviewed by Mark Bowden for Playboy after the book came out, Trump called O’Donnell “a fucking loser.” He said that he had only met with him a handful of times, but also allowed that “The stuff O’Donnell wrote about me is probably true.”

Although Trump would say that O’Donnell “needs the money, so he uses my name to sell some books,” in fact the former head of Trump Plaza landed a top job with Merv Griffin Resorts. (In his first year as chief operating officer, O’Donnell would help the Resorts Casino Hotel achieve the greatest revenue gains in Atlantic City) During this time Trump lost other key personnel at his casino. In New York his chief counsel and his leading real estate sales executive resigned. He would also lose his chief financial adviser, engineer Barbara Res, and Tony Gliedman, who had been instrumental in the Central Park skating-rink project.28

*   *   *

The Taj Mahal went bankrupt in January 1991. Under an agreement with creditors Trump gave up a substantial portion of the casino’s ownership, but he would be allowed to net a bit more than $1 million per year in exchange for leaving his name on the building. Soon he would give up control of the Trump Shuttle to his lender, Citibank. The planes would be operated by USAir, which showed no interest in keeping the Trump name. According to the arrangement made between the bank and the airline, USAir would be permitted to top any bid for the shuttle when it came up for sale. The airline would purchase the operation in its entirety in 1997.

As USAir relieved him of responsibility for the shuttle, Trump and his lenders, including dozens of banks, undertook complex negotiations to salvage what they could from his companies and avoid bankruptcy court. This course only made sense to those who knew that under US bankruptcy laws a debtor who owed billions was a greater threat to his lenders than they were to him. If Trump used the courts, he could tie up his assets for years and escape most, if not all, of the debt. If his creditors stayed in business with him, they stood a chance of receiving more of what they were owed, while avoiding the enormous legal fees that accompany such bankruptcy cases. This reality exasperated some of those who held Trump casino bonds. In one creditors’ conference call, bondholder Randolph Goodman challenged the idea that the courts would leave Trump in charge of a bankrupted casino: “We would be stuck with the worst guy in town?” The answer came from a lawyer who worked for all the bondholders: “If it were possible to throw the bums out on the basis of their past performance, the standard in bankruptcy would be the immediate appointment of a trustee. But in virtually every case that goes to bankruptcy court, management is left in place.”29

Trump grasped the power in his position after the lender who held the mortgage on his yacht not only accepted that Trump had stopped making payments, but took responsibility for the vessel’s upkeep and insurance, at a cost of $500,000 per month. In time Trump was able to reduce his obligations by $750 million and hold on to many of his properties, including the West Side rail yards and Mar-a-Lago. Others had used the peculiar dynamics of bankruptcy to similar effect, preserving substantial fortunes while escaping the stigma of personal bankruptcy, but few considered it a great accomplishment. Ever the showman, and an optimist, Trump saw in this outcome a public relations advantage. “If I had filed a personal bankruptcy, I don’t feel that my comeback story would have been nearly as good a story,” Trump said. “It would have been always a tarnished story.”

Spinning the tale like a gifted advertising man, Trump said that bankers “love me because I’m good and I’m honest,” and “through cooperation rather than conflict, everybody has come out much better.” This assessment was true from the perspective of the various bank officers. They had been paid well as they approved Trump’s borrowing and would remain well employed because Trump would be responsible if things didn’t work out. One former member of Trump’s executive team told writer Harry Hurt, “We had all these assets but we never had any money in hand. That’s why we had to keep doing more deals.” The deals, which typically included extra money for operating or upgrading a new property, provided the cash fuel that kept the juggernaut rolling.30

Not everyone felt so sanguine. Lawrence Lambert, speaking for the investors who held Trump bonds, said, “I think it’s morally reprehensible what he gets away with.” No one spoke for the millions of depositors and stockholders whose investments in various banks were diminished by the losses these firms accepted to square their accounts with Trump. Likewise, no one could place a value on the loss of public confidence caused by the spectacle of a tycoon walking away from obligations totaling more than half a billion dollars when ordinary American householders were ruined because they couldn’t repay consumer debts of a few thousand dollars. In time, the phenomenon that spared Trump would be understood by the general public as “too big to fail.” However many ordinary Americans would forever be puzzled when lenders gave troubled borrowers more money.

Less opaque, thanks to Neil Barsky of The Wall Street Journal, was the maneuver Trump used to avoid defaulting on the bonds floated to support another of his casinos, Trump Castle. As Barsky reported in January 1991, Fred Trump had sent an attorney to the casino with a $3.5 million check, which was used to purchase gambling chips that were never used. Essentially a loan, from father to son, the money inflated the Castle’s balance sheet and helped the casino make its bond payment. Truly clever, this arrangement meant that the senior Trump could get back his money at any moment by simply redeeming the chips. None of his son’s other creditors could do the same.31

As Donald Trump’s creditors accepted losses, advanced him new loans, and permitted him to keep substantial assets, he escaped the humiliation of personal bankruptcy and put himself in a position to continue the deal-making game. However, he could not evade the shame that accompanied the slow-motion destruction of his marriage, which began when Jerry Argovitz brought Marla Maples to his office. Out of his first encounters with her—on the sidewalk, at the Rainbow Room, at the book party—he developed a relationship that doomed Donald Trump’s marriage and revealed the dreadful side of the business of celebrity.

*   *   *

Despite the rumors and the direct questions from friends such as the Post’s gossip columnist Cindy Adams, Ivana Trump had worked to keep her family together. For his part, Donald Trump vacillated between discretion and loose talk. While he relied on “the Baron” to hide his calls to Marla, he couldn’t help but brag about her beauty to those he wanted to impress. At age twenty-four, Marla was fourteen years younger than Ivana, the mother of three children who, while still beautiful, was approaching her forties and had endured all the stress of accompanying her husband through more than a decade of striving. Marla regarded Donald as the “king” his father had said he would be, and she was enchanted by all that she encountered in his realm. She did not dwell on the possibility that her dream could become a nightmare.

The incident that led to the cascade of scandal depended on such a mundane intervention—Ivana picked up an extension to listen to her husband on the phone—that Hollywood writers have abandoned it as a device to drive their plots. Ivana acted as a worried spouse, not as a character in a script. She heard a male voice on the call noting, in the crudest terms, that “Marla” was sexy. When the call ended, Ivana confronted her husband. He told her that Marla was a woman who had been pursuing him for two years, but he was not involved with her.

This tense exchange occurred in the lovely setting of a recently opened luxury hotel called the Little Nell, in Aspen, Colorado. The Trumps had arrived two days after Christmas, when Aspen was crawling with celebrities. (Among those who regularly spent time there were the actor Jack Nicholson, the singer Prince, and the ubiquitous Barbara Walters.) In the winter of 1989–90 the locals were debating a possible ban on the wearing of fur, which had been proposed by animal rights activists. The transient rich were engaged in their usual party-hopping, posing for the paparazzi, and displaying their elegant skiwear.

Two days after the telephone incident, Ivana confronted Marla at a slope-side lunch spot. As later reported in print, Ivana had noticed Marla and realized she was the woman mentioned in the phone call she had heard. According to People magazine, she said, “You bitch, leave my husband alone,” and then chased after her husband, who had put on his skis and taken off down the mountain. The magazine reported, “Fascinated observers swear they saw her whip in front of Donald and then ski backwards down the slopes, wagging her finger in his face.”

The confluence of events that brought Ivana, Donald, and Marla together in that moment was so remarkable that it would appear to have been planned. Marla would marvel at the many witnesses, including journalists, who happened to be present during the episode on the mountainside, which she thought was quite unusual and wondered if she was set up. She said nothing of this at the time. She also said nothing about the ring, a sign of commitment, that Donald had already given her.

Donald tried to smooth things over with Ivanna, but the weeks that followed the incident in Aspen were strained. It didn’t help that when he appeared in an article in the March issue of Playboy magazine—which was published in early February—he refused to answer when interviewer Glenn Plaskin asked, “What is marriage to you? Is it monogamous?” In the same question-and-answer session Trump observed that every successful person, including Mother Teresa and Jesus Christ, was driven by ego. “Far greater egos than you will ever understand.” He also acknowledged his publicity seeking: “The show is Trump, and it is sold-out performances everywhere.”

Trump’s ego, which depended on status and the attention of others, made it all but impossible for him to let go of a beautiful woman such as Marla who expressed so much interest in him. His makeup also made it difficult for him to recognize his vulnerability. He decided to travel to Tokyo to see heavyweight boxer Mike Tyson fight Buster Douglas and, perhaps, to sell some real estate to wealthy locals who presumably didn’t know or didn’t care that he had used Japanese businessmen as straw men in his speech before the Portsmouth Rotary Club. As Trump departed, Ivana spoke to the Daily News columnist Liz Smith about her marriage. Having heard many rumors about Donald and gotten wind of Ivana’s run-in with Marla in Aspen, Smith was not entirely surprised. (In 1988 the Post had reported that Marla was involved with “one of New York’s biggest business tycoons, a married man.” The paper subsequently reported that Maples “supposedly goes around to all the stores in Trump Tower saying, ‘Charge it to Donald.’”) Nevertheless, Smith was disappointed by what she heard from Ivana. Donald had always been, in Smith’s mind, a rambunctious boy whose sins could be forgiven because he was good at heart. Her article, “Love on the Rocks,” appeared in the Sunday, February 11, edition of the Daily News. It announced that the Trumps were separating and touched off a media frenzy that surprised even the man who collected newspaper clippings by the hundreds.

In the torrent of reports that followed the Liz Smith icebreaker, reporters rehashed all the rumors about actresses, models, and socialites Donald Trump supposedly knew in the carnal sense and speculated that he and Ivana were locked in a conflict over her work as manager of the Plaza. In the nation’s most competitive press market, the Trump breakup was irresistible to editors. Smith and the News generally stood by Ivana, while the competing Post, and its columnist Cindy Adams, gave a little more leeway to Donald and painted his wife as eager to fleece her husband in divorce proceedings. Generally more down-market, the Post was also the first to name Marla Maples and publish her photo.

Feeling as if she had been caught in a publicity meat grinder, Marla lodged protests with various reporters but they seemed uninterested in what she had to say and inured to her anguish. At the same time, Ivana Trump transformed herself from a symbol of aggressive ambition into the ultimate example of the middle-aged woman wronged by a her husband. Finally Maples escaped the city, and the press, for the Hamptons and then Guatemala where she stayed with a friend who was in the Peace Corps. Her former boyfriend Tom Fitzsimmons was hounded by reporters and, he later said, he turned down a six figure offer to tell all he knew to a national tabloid. Marla’s family in Georgia was hounded by reporters who, at various points, hid in ditches near their homes and walked into their kitchens. One media company even put a $1,000 reward in the Dalton (Ga.) Daily Citizen, the newspaper in Maples’s hometown, for any information locals might share. Many came forward, including some who didn’t know her at all.

On Valentine’s Day, photographers and TV news crews, tipped off by an item in Liz Smith’s column, crowded the sidewalk in front of La Grenouille, the posh Manhattan restaurant, as Ivana arrived for a long-planned lunch. For two hours, Ivana and a dozen women who were friends and family dined on lamb chops and shared conversation that occasionally brought tears to Ivana’s eyes. Among the attendees were her mother-in-law, two sisters in-law, and Georgette Mosbacher, whose husband was the US secretary of commerce. When the meal was finished, Liz Smith and Barbara Walters, would escort Ivana from the restaurant to her waiting car. “Take him for all he’s worth!” shouted one onlooker as the photographers jostled for position. Another yelled, “Get the money!”33

In time Hillary Clinton would widely be regarded as the most wronged woman in America, but in February 1990, Ivana attracted such enormous sympathy that Spy magazine’s portrait of her as temperamental, self-interested, and materialistic was all but erased. In its stead appeared the image of a woman who had supported her husband, even when others found him insufferable, and had been terribly wronged. She won the publicity war because her husband was painted as a cad, and because Liz Smith was the best ally anyone could hope to recruit in a battle of headlines.

Born in 1923, Smith had been raised in Fort Worth, Texas, where she learned about glamour at the Tivoli movie house, which was flanked by a hamburger joint playfully named Rockyfellers. Captivated by celluloid glimpses of glamour, she arrived in New York in 1949 as a “stage-struck out of towner” and found work as a writer at a movie fan magazine called Modern Screen. By 1990 she was one of the most powerful gossip columnists in the country, but she retained her out-of-towner charm, which no doubt felt reassuring to many of the people she interviewed. Her kindness showed when she declined to use tidbits that would harm those she considered innocent. On television Smith’s engaging smile and warm Texas accent inspired trust and confidence. She was the friend, sister, or aunt you could rely on.

The Post’s Cindy Adams, in contrast, was more like the mean girls everyone knew in high school. When offered a quip about how Donald feared that Ivana would become like Leona Helmsley, who had recently been convicted of tax fraud, Adams printed it. Cindy became Donald’s conduit to the public and a sympathetic ear. Although he was taken aback by the level of press attention his marriage troubles received, he remained faithful to his belief in the value of publicity and would tell Newsweek that the scandal had been “great for business.” Though his father complained that “it’s going to give me a stroke,” Donald fed fuel to the tabloid fire and contributed to the speculation about dalliances with beautiful, famous women. He even told a reporter for the News that his wife still loved him. “Ivana doesn’t want the money,” he insisted. “She wants Donald.” (Trump often referred to himself by name, a nickname such as The Trumpster, or by his own initials—DT—as if he were reporting on the activities of a separate person.)34

The storm in the press reached its howling worst when the front page of the Post screamed, “Marla Boast to Pals About Donald: ‘Best Sex I’ve Ever Had.’” The source for the story was a woman who claimed to have attended an acting class with Maples. A distressed Marla insisted the anonymous claim was false, and Chuck Jones, who became her spokesman during the scandal, would refute it. However nothing they said would save her acting career, which was being destroyed by the negative publicity. Playboy came with an offer of $2 million for her to pose nude, which she rejected. Maples also refused to lend her name to a brand of lingerie called The Other Woman but finally did agree to endorse a brand of jeans called No Excuses. The company’s previous high-profile model had been Donna Rice, who was the “other woman” in the scandal that ended presidential candidate Gary Hart’s political career. Maples would receive $500,000 and use half that sum to help her family financially and she required the company to match her donations to an environmental advocacy group. Later Maples would note that her charity work was mostly ignored by the press and she cringed at the memory of a TV commercial that was “sad and laughable because they focused on my body in the jeans and spoke over my speech about the environment.”

The No Excuses ad helped sell millions of dollars’ worth of jeans and confirmed the commercial power of tabloid fame. In the weeks when the scandal blazed hottest, that a woman who looked like Marla Maples found Donald Trump attractive confirmed that he possessed true sex appeal. Maples had the kind of wholesome, youthful good looks that Trump and most American men preferred. He definitely favored her over the gaunt and overly decorated women of high society, whom writer Tom Wolfe had dubbed “social X-Rays.”

In the most trenchant published analysis of the whole affair, New York magazine writer John Taylor reviewed the roles played by each of the participants. Taylor and his sources described Donald Trump as a remarkably buoyant man who could delight in headlines that would have made others distraught. In Taylor’s view Trump may have resented Ivana’s visibility and chafed at the restrictions imposed by his marriage vows. Although Taylor quoted Trump’s kind words for his wife, and his pledge to “always treat Ivana great,” these statements could not be accepted at face value because they came from a man who publicly justified his use of “truthful hyperbole.”

The Ivana Trump whom Taylor revealed sought and enjoyed the acceptance of high society, which her husband disdained, while striving to please him even to the point of undergoing plastic surgery. Her suffering was the suffering of every woman who approached midlife only to be thrown over by her husband for a younger woman. Her pain was exacerbated by a media circus that found even President George H. W. Bush using her marriage as a punch line. “I am here in New York where one of the great contests of 1990 will take place,” joked the president at a campaign rally. “But I’m not here to talk about the Trumps!” Ivana also had to endure nastiness from those who saw an opportunity to settle scores. Alfred Winklmayr, who had momentarily been married to Ivana when she sought to leave Czechoslovakia, surfaced to sell his story to a tabloid. He snidely commented, “I can’t help but think she’s finally getting what’s coming to her.”

In Taylor’s reporting, Marla Maples represented all the interlopers who possess the power that comes with beauty. She clearly served Donald Trump’s ego, and given his beliefs about publicity, she aided his bottom line. But based on the account in New York magazine, it was difficult to imagine things working out well for her. Sources quoted by Taylor insisted that Marla was not sufficiently “classy” (whatever that meant) to hold Trump’s interest, and Donald seemed so certain that as a woman aged a man might be justified in looking elsewhere that Maples had good reason to fear the clock and the calendar.

Marla dreaded dealing with the press, which, in its Murdochian form, had a voracious appetite for scandal. This was new in American journalism. For generations journalists had ignored the sexual transgressions of major public figures under a sort of gentleman’s agreement. The Gary Hart–Donna Rice scandal of 1987 ended this agreement and announced a new era in which salacious stories, expressed at sufficient volume, would find their way into mainstream media. Journalists would say this new practice revealed truths that should not be hidden and served some public purpose. This Taylor dismissed as a fig leaf that couldn’t obscure the real value of the story, which was the entertainment of the masses.35

As a married couple’s breakup became entertainment, the Trump children paid a price. Aged six, eight, and twelve, they had not asked for the life in the spotlight that their father and mother had cultivated. Their parents did try to shield them, but they could not put the children in a protective bubble. Ivana confessed to Liz Smith that her daughter and son were “wrecks.” She said that Donny had confronted his father with real anger, shouting, “You just love your money!” Ivanka had been crying, and Eric feared his mother would be exiled. Decades later, middle child Ivanka would readily recall how she felt when a classmate brought a tabloid to her school and how snide remarks circulated among her classmates. The Internet would forever be populated by accounts of her parents’ troubles.

The Trump kids were on Liz Smith’s mind when she paused in the midst of the blitz to say she regretted the fire she had started. “I want to let this go,” she told an interviewer from The New York Times. “But I have my bosses, two sets, editors at the newspaper and producers at the television station. They want this to go on.” The story was so big that it was picked up by the very untabloid Washington Post. As the international press began to report on the ongoing drama, it became clear that reconciliation would not be possible. Ivana’s lawyer hired a team of investigators to document his client’s contribution to the Trump fortune. Donald briefly barred his estranged wife from her office at the Plaza.36

The war of the Trumps continued for months, with the two sides trading leaks to the press. In one moment the Post reported that Donald was rejecting Marla for good. In another the News revealed that she had stayed at Trump Tower for almost six weeks. Ivana’s first legal move involved a challenge to the nuptial agreement that supposedly governed their divorce. The legal papers she filed quoted her husband’s praise, in his book, for all her work on his various projects. They also said that when she signed the agreement, in 1987, Donald intended to betray her. She followed the lawsuit with a cover story in Vanity Fair, complete with glamorous photos of her at Mar-a-Lago, and several public appearances where she seemed to be enjoying her independence. Donald briefly retreated from public view while his lenders worked out the agreement that would allow him to escape personal bankruptcy in exchange for accepting temporary supervision of most of his financial affairs.37

Confronted with Ivana’s demands, Trump hired a divorce lawyer named Jay Goldberg who had described himself as a “killer” who could “rip the skin off a body.” As Goldberg and Ivana’s lawyer Michael Kennedy dueled with subpoenas, Donald began to appear in public with Marla Maples and introduced her to his parents. When Vanity Fair offered Marla the opportunity to be photographed for the November issue, she agreed. After she was dressed and posed with her hair and makeup arranged just-so, the result was a series of pictures that resembled those of Ivana published in the magazine’s May issue. As any subscriber may have noticed, the spreads invited snide, side-by-side comparisons of the two women. Although Marla was a willing participant, she regretted the decision when she saw the result, which practically screamed “this is the other woman.”38

Given the game she had joined, Marla didn’t engender much public sympathy as she explained that Ivana “wants a billion, but we just don’t have it.” In fact, Donald Trump did not have anywhere near $1 billion to give his soon-to-be-ex-wife. He would insist he couldn’t pay her more than $1.5 million, let alone the many millions called for in their nuptial contract. When Ivana told the court she believed that her husband had been involved with other women, he reminded her that the most recent nuptial agreement, completed in 1987, did not require his “continuing love and affection.” Their previous agreements had included this term.39

When a judge finally granted Ivana Trump’s petition for divorce on the grounds of “cruel and inhuman treatment,” she mentioned Marla Maples by name. In the negotiations for the financial settlement Ivana’s lawyers concluded that once various loans and obligations were considered, he may not have been worth more than $100 million. Ivana accepted a $10 million check upfront plus $650,000 a year in support for herself and the three Trump children. Thirteen months had passed since Liz Smith announced the crisis in the marriage. In that time, Donald had been dealt a crushing defeat in Atlantic City, and his supposed great fortune had been revealed to be an illusion.

Years later Trump would explain, “Learning how to win is a very important thing. Very few people understand how to win, very few people.” But just as winning begat winning, defeats could cascade. “You can be tough and ruthless and all that stuff, and if you lose a lot, nobody’s going to follow you because you’re looked at as a loser.”

Having suffered some losses, Trump would set out to prove he was resilient. With all that he had attempted, and gained, and lost, he was still just forty-four years old. He remained one of the most recognized men in America, and few, if any, knew better how to transform recognition into cash.