Business as a Formative Experience
While Trump has continuously portrayed himself as a successful businessman, his career has been a rollercoaster of successes and failures. While as a real estate tycoon Trump had numerous successes including the Grand Hyatt hotel, Trump Place, Trump Tower, 40 Wall Street, and Trump International Hotel and Tower in Chicago, a number of his other business ventures were failures. This includes Trump Airlines, Trump Vodka, Trump Magazine, GoTrump.com, Trump Steaks, Trump University, Trump Ice, Trump Mortgage, and his casinos. Trump Airlines, for which he took out a $245 million loan in 1988, focused on commuter flights between New York, Boston, and Washington, DC. The planes, which featured gold bathroom fixtures, were not successful and eventually he could not earn even enough profit to cover the monthly $1 million interest payments on his loan. He eventually defaulted on his loans and surrendered the business to his creditors. Trump University, which was open from 2005 to 2010, ended up with two federal class-action lawsuits: one against Trump himself and one against the university and its managers, plus an additional suit in New York State. The lawsuits alleged that Trump University engaged in such illegal business activities as false claims and racketeering. In 2016, Trump agreed to pay $25 million to settle all three cases. As for Trump’s casinos in Atlantic City, he filed for bankruptcy three separate times. The first time was in 1991 for the Trump Taj Mahal, which faced roughly $3 billion in debt after being open for only one year. Then in 2004, Trump filed bankruptcy not only for the Trump Taj Mahal, but for Trump Marina and Trump Plaza casinos, with debt of about $1.8 million. After this, Trump rebranded as Trump Entertainment Resorts, Inc., which eventually declared bankruptcy as well, following which Trump stepped down as chairman.
The Important Mentoring Influence of Roy Cohn1
Young Trump, within two years of graduating from the University of Pennsylvania and still living in Queens, was on the hunt for attractive women. He joined a private disco, “Le Club,” in Manhattan, which he described as a “hot” social club. There he met and developed a close relationship with Roy Cohn, who was infamous as Senator Joseph McCarthy’s right-hand man and lawyer during his notorious investigations for the House Un-American Activities Committee. Trump and Cohn instantly hit it off. As Cohn was later to reflect, both Trump and he were men of action, who preferred their deeds to speak for them, rather than speaking in portentous tones like the political class.
While it was his father, Fred Trump, who identified Donald as his successor, bringing him as “crown Prince” into the family real estate rental business in middle-class Brooklyn and Queens, it was Cohn who encouraged Donald Trump to transcend the cautionary boundaries his father had set and cross the river and enter the lists with the major Manhattan real estate entrepreneurs. Cohn introduced the ambitious young man to the social and political elite of Manhattan.
Cohn was an important mentor for Trump, teaching him always to fight back, never to settle. Cohn linked Trump to mob-owned construction companies. Trump described Cohn as someone who could be “vicious” for him and would “brutalize” his opponents. Cohn became, in Trump’s words, “like a second father to him.”
So, when the federal government sued Fred Trump and his son Donald in 1972 for racial discrimination in their rental apartments, at Cohn’s urging they countersued for $100 million. The government had found after a careful investigation that black rental applicants were denied, with their cards marked “C” (for colored), whereas a white couple applying immediately afterward would be accepted. The judge threw out the countersuit, identifying the grounds for the countersuit as spurious, and there was an adverse settlement. Trump was to state after this settlement, “I’d rather fight than fold, because as soon as you fold once, you get the reputation,” clearly echoing his new lawyer, Roy Cohn, who was considered one of the most powerful and famous lawyers in America. Although the case was a complete loss for the Trumps, Donald spun it as a terrific win, exemplifying one of Cohn’s lessons, to never admit defeat.
When Trump was applying for a casino operator’s license, he managed to persuade the New Jersey attorney general to limit the scope of the investigation, thus obscuring his mob connections and several major federal investigations. This pattern of limiting investigations of his past, and his awareness of the vulnerability of his less than savory history, continues to the present day.
Roy Cohn, representing Trump interests, played a major role in assisting Abraham Beame in a tight race for mayor of New York in a primary run against Mario Biaggi. Through selective leaks detrimental to Biaggi in the New York Times, Beame fended off a major challenger for the nomination and went on to win the election.
During a time of crisis for Mayor Beame, Trump saw a major opportunity for using the bankrupt Penn Central railroad as a site for the long-promised convention center. Trump’s progress was impeded by Ned Eichler, VP of Palmieri & Co., the firm that was to disburse Penn Central’s real estate holdings. Trump pursued Eichler to his sparse office. Eichler found in Trump “a blond young man fairly bursting with ambition.” When a meeting was arranged, Beame told Eichler, who was representing Palmieri, “Whatever my friends Fred and Donald Trump want in this town, they get.”
Trump had the vision to see the possibilities for refurbishing the Commodore Hotel. He was encouraged by Cohn in pursuing this vision. His father strictly opposed this risky development. By creatively portraying the refurbishing of this hotel next door to Grand Central Station as an act of public service, fighting the deterioration of midtown, Trump managed to persuade the city to aid in financing.
Without detailing all the deals of Trump’s real estate career, as in the “big deal” just reviewed, Trump used charm and creative imagination to portray and get financing for large projects with very little personal money at risk. He describes a very flat organization with no cumbersome bureaucracy, so that if one of his employees had a good idea he could come into Trump’s office, they would review it, and if Trump approved, that was it.
This style is engraved in Trump’s experiential memory, and Trump uncritically seems to assume that the same leadership style he used so effectively as a real estate entrepreneur will work without modification in any way in running the country. One cannot help but be reminded of Robert McNamara, who served as secretary of defense during the Vietnam War under presidents Kennedy and Johnson. All of the brilliant statistics McNamara had used so effectively in his post as president of the Ford Motor Company were of little help in coping with the impact on the American psyche of service personnel returning home in body bags, which were the metric he used for his statistics.
Roy Cohn was a major influence on Trump’s life. And since Cohn’s death in 1989 due to complications from AIDS, Trump has frequently remarked how much he misses him, often asking: “Where is my Roy Cohn?,” a sentiment he has given voice to even as president, following Attorney General Jeff Sessions’s decision to recuse himself.2 The styles of Trump and Cohn were very complementary. And their friendship was equally important to both men, with Cohn serving as emcee for Trump’s birthday party at the nightclub Studio 54, while Trump hosted a birthday party for Cohn in Trump Tower. In fact, it was Cohn who had stressed to Trump the importance of keeping his name in the papers.
The Entertainer
Donald Trump has long sought recognition for his wealth and success by trying to gain celebrity status. As he once stated, “If you don’t tell people about your success, they probably won’t know about it.”3 This need for recognition is an aspect of his narcissism; he has an exaggerated sense of self-importance that is manifested as extreme self-centeredness, egocentricity, and self-absorption, which is compensating for underlying insecurity.
Early Celebrity Status
Since 1981, Donald Trump has appeared in over 130 TV series, fifty TV specials, sixty documentaries, and twenty movies. He has been continuously interviewed on news programs, and in newspapers and magazines. In addition, since 1987 Donald Trump has published fourteen books, as well as a board game and a video game.
During the eighties, Donald Trump first began appearing as himself in TV shows and movies, including two appearances on The Jeffersons. He also began appearing in a number of documentaries, TV miniseries, and such specials as WrestleMania. Throughout the eighties, Trump was often a punchline in popular culture, as a frequent target of the satirical Spy magazine and serving as the inspiration for the villain Biff Tannen in the 1989 movie Back to the Future Part II.
Donald Trump came out with his first book, The Art of the Deal, in 1987. The book, which is coauthored with Tony Schwartz, is part memoir and part business advice. It was number one on the New York Times bestseller list for thirteen weeks, remaining there for a total of forty-eight weeks. In a Washington Post article published in May 2017, Schwartz described his experience working with Trump during the writing of The Art of the Deal. He stated that “early on, I recognized that Trump’s sense of self-worth is forever at risk. When he feels aggrieved, he reacts impulsively and defensively, constructing a self-justifying story that doesn’t depend on facts and always directs the blame to others.”4
Trump has cited this book as being one of his proudest accomplishments, stating that it is his second favorite book after the Bible. During an interview with CNN during the 2016 presidential campaign, Trump said: “I wrote a book called The Art of the Deal, the No. 1 selling business book of all time, at least I think, but I’m pretty sure it is. And certainly, a big monster, the No. 1 bestseller.”5
A component of Trump’s narcissism is that he unrealistically overestimates his abilities and achievements, as seen not only in his great pride for The Art of the Deal, but in his expectations for his board game. In 1989, the Donald Trump board game, Trump: The Game, was released. Following the release of his game, Trump stated, “I didn’t want a game based solely on chance. I wanted a game based on talent. And I wanted to teach people if they have business instincts. It’s great if they can learn that from a game instead of having to go out and lose your shirt.” Although it sold poorly after its initial release, selling only 800,000 copies out of an anticipated two million, the game was released in 2004 following the success of Trump’s show The Apprentice. The board game, which is modeled after Monopoly, is based on Trump’s career and The Art of the Deal. Trump initially assumed he would make millions from his board game, representing the overestimation he had of his abilities and popularity at that time.6
Just as Trump’s narcissism causes an overestimation of success, he views setbacks as conveying a sense of special unworthiness. Trump must control the image that is projected of him to the world, as witnessed during the nineties. By the nineties, Trump, who was gracing the tabloids with his divorces and bankruptcies, focused heavily on his TV persona. He appeared on a number of sitcoms in an attempt to control his own image to the public, including The Fresh Prince of Bel-Air in 1994, The Nanny in 1996, and Sex and the City in 1999. According to Christopher Lasch in his 1979 social commentary The Culture of Narcissism, underneath the surface arrogance and grandiosity of the narcissist is profound self-doubt and inner uncertainty, looking to others for confirmation of his worth: “The other person tends to be used to make the narcissist feel good, and well-being depends upon receiving a continuously adequate quantity of positive regard.”7
In the 1990s, Trump also began associating himself with Playboy, giving interviews there in 1990 and 1997. (In 2000, Trump even had a cameo role in a pornographic Playboy documentary.) In his 1990 Playboy interview, when asked, “With so much poverty on the city streets, isn’t it embarrassing for you to flaunt your wealth?” Trump replied, “There has always been a display of wealth and always will be, until the depression comes, which it always does. And let me tell you, a display is a good thing. It shows people that you can be successful. It can show you a way of life. Dynasty did it on TV. It’s very important that people aspire to be successful. The only way you can do it is if you look at somebody who is.”8 Donald Trump looks not only for a confirmation of his wealth, but admiration. He desires an admiring response from his audience, constantly displaying himself, his wealth, and his success to evoke attention from others.
He cannot be satisfied, craving more attention and recognition from new audiences, as witnessed through his increased TV and movie appearances throughout the 1990s into the early 2000s, as well as his books and his video game. Donald Trump’s video game, Donald Trump’s Real Estate Tycoon, was first released in 2002. In this single-player game the player had to try and defeat Donald Trump by becoming a business magnate.
Miss Universe
This desire for admiration can also be witnessed in Trump’s co-ownership of the Miss Universe Organization, which included the Miss USA and Miss Teen USA pageants from 1996 to 2015. As discussed by former Miss Arizona Tasha Dixon, who had been a contestant in the Miss USA pageant, employees of the pageant encouraged the contestants to lavish Trump with attention when he came into the dressing areas. Trump has come under a great deal of fire over his conduct while co-owner of the Miss Universe Organization. Allegations have been made that Trump would walk into the contestants’ dressing areas while they were partially undressed or completely naked, including during the Miss Teen USA pageant where girls as young as fifteen were undressed. Mariah Billado, who was Miss Teen Vermont in 1997, recalls her experience with Trump during the Miss Teen USA pageant, stating, “I remember putting on my dress really quick because I was like, ‘Oh my God, there’s a man in here.’” Three other teenage contestants from the same year confirmed the story. Similar allegations have been made by former contestants of the Miss USA pageant. Dixon recalled Trump entering the dressing areas during the 2001 pageant, stating:
He just came strolling right in. There was no second to put a robe on or any sort of clothing or anything. Some girls were topless. Other girls were naked. Our first introduction to him was when we were at the dress rehearsal and half-naked changing into our bikinis.
This was coupled with encouragement by the employees to shower him with attention, as Dixon goes on to state:
To have the owner come waltzing in, when we’re naked, or half-naked, in a very physically vulnerable position and then to have the pressure of the people that worked for him telling us to go fawn all over him, go walk up to him, talk to him, get his attention . . .
While Trump’s political campaign failed to respond to these allegations in 2016, Trump himself admitted to and even bragged about this conduct on the Howard Stern show in 2005.
Trump: Well, I’ll tell you the funniest is that I’ll go backstage before a show.
Stern: Yes.
Trump: And everyone is getting dressed and ready, and everything else and then there are no men anywhere, and I’m allowed to go in because I’m the owner of the pageant and therefore I’m inspecting it. You know, I’m inspecting it.
Robin Quivers [female co-host]: Right.
Trump: You know I’m inspecting it, I wanna make sure that everything is . . .
Stern: You’re like a doctor, you need to be there.
Trump: Yeah, the dress . . . “Is everyone okay? Is everybody okay?” And you see these incredible looking women. And so I sort of get away with things like that, but . . .
Trump viewed his co-ownership of the Miss Universe Organization as reinforcing his business and his brand, often having the Miss Universe pageant hosted in cities where he had business interests. Finalists normally came from countries where the competition had strong television ratings. One former Miss Universe contestant from 2012, Adwoa Yamoah, who competed as Miss Canada, stated that after contestants first met Trump:
He made comments about every girl: “I’ve been to that country.” “We’re building a Trump Tower there.” It was clear the countries that he liked did well. He’d whisper to Paula [Shugart, president of the Miss Universe Organization] about the girls, and she’d write it down. He basically told us he picked nine of the top fifteen.
Similar sentiments have been made by other former contestants, including two contestants from 2013, Kerrie Baylis and Shi Lim. Baylis, who was Miss Jamaica, stated that when the finalists were announced, “the list looked like the countries that Donald Trump did business with, or wanted to do business with.” Lim, who was Miss Singapore, also stated that “the finalists were picked by Trump. He was really in charge. We called it the Trump card.”
The Apprentice
Donald Trump has often sought to control his image in the media, and following business downturns he has always attempted to use his celebrity status to alter his image to the world. Donald Trump rather successfully did this through his TV show The Apprentice. His reality TV game show first aired in January 2004, with Trump starring until 2015. On The Apprentice, contestants compete for a one-year $250,000 contract to run one of Donald Trump’s companies. It was on The Apprentice that Donald Trump coined one of his signature phrases, “You’re fired!” As was discussed in “The TV That Created Donald Trump” by Emily Nussbaum in the New Yorker:
It’s become a wearying, ugly observation, a media truism at once superficial and deep: if The Apprentice didn’t get Trump elected, it is surely what made him electable. Over fourteen seasons, the television producer Mark Burnett helped turn the Donald Trump of the late nineties—the disgraced huckster who had trashed Atlantic City; a tabloid pariah to whom no bank would lend—into a titan of industry, nationally admired for being, in his own words, “the highest-quality brand.”9
Trump himself recognized how popular The Apprentice made him, stating in an interview for Playboy in 2004:
Certainly a businessperson on television has never had anything close to this success. It’s like being a rock star. Six people do nothing but sort my mail. People come in and want my secretary Robin’s autograph. If a limo pulls up in front of Trump Tower, hundreds of people gather around, even if it’s not mine. I ask, “Can this be a normal life?” Maybe it’s the power that comes from having the hottest show on television, but people like me much better than they did before The Apprentice. And if you think about it, all I did on the show was fire people, which proves how bad my reputation must have been before this.10
And in fact, one of the main purposes of the show was to help rebrand Donald Trump’s image. In an interview for the New Yorker, author Patrick Radden Keefe discusses how The Apprentice’s producer Mark Burnett “resurrected Trump as an icon of American success”:
The Apprentice portrayed Trump not as a skeezy hustler who huddles with local mobsters but as a plutocrat with impeccable business instincts and unparalleled wealth—a titan who always seemed to be climbing out of helicopters or into limousines. “Most of us knew he was a fake,” [video editor Jonathon] Braun told me. “He had just gone through I don’t know how many bankruptcies. But we made him out to be the most important person in the world. It was like making the court jester the king.” Bill Pruitt, another producer, recalled, “We walked through the offices and saw chipped furniture. We saw a crumbling empire at every turn. Our job was to make it seem otherwise.”11
While the show provided viewers with a false image of Trump’s business success, it did more than just that: it provided an almost mythical figure to the audience. A successful and immensely wealthy businessman who could make others successful and rich like him. And the shows were debuted at times when Americans needed a success story, they needed to believe in something. The Apprentice itself debuted in 2004, nearly a year after the invasion of Iraq and at the same time it had been announced to Congress that no evidence was found of Saddam Hussein harboring weapons of mass destruction. Then the show’s spin-off, The Celebrity Apprentice, debuted in 2008 following the United States entering one of the worst economic downturns that had been seen since the Great Depression. The show didn’t just provide the American people with the amusement of a reality TV series, it gave them someone to admire, an admiration Trump had always wanted from the American public. An admiration he would seek once again from the American public by running for president of the United States.