Better to remain silent and be thought a fool than to speak out and remove all doubt.
—ABRAHAM LINCOLN
THIS BOOK IS NOT A BIOGRAPHY OF DONALD TRUMP before he campaigned for president. Bookshelves of such biographies have been written; four of the best are The Trumps, by Gwenda Blair; Never Enough: Donald Trump and the Pursuit of Success, by Michael D’Antonio; Donald Trump: 45th US President, by Dominick Reston; and Donald J. Trump: A President Like No Other, by Conrad Black.
We will, however, briefly discuss aspects of Trump’s personal and business life that have had a profound impact on his campaign and presidency.
First: Trump has always seen himself as an outsider, and he is very insecure about not being accepted. This came partly from his father Fred Trump’s outsider status in New York business circles, with a real estate enterprise focused in Queens, rather than Manhattan. Fred Trump’s business reputation was not particularly good. (Fred’s father, Friedrich “Fritz” Trump, emigrated from Germany after dodging the draft, and he ran hotels in Washington State and Alaska that were rumored to provide prostitution services on the side.) Fred Trump was skittish around White Anglo-Saxon Protestant (WASP) and Jewish businessmen who ran in Manhattan circles. The Trumps may have been Protestants, but old money WASPs often looked down on them as typical nouveau riches. (Trump’s name has been noted in society pages for its absence in the Social Register.) The Trumps’ German ancestry made them feel so insecure that Fred Trump pretended the family was Swedish in the years after World War II.
As the Trumps acquired more wealth, they were not the type to be invited to join country clubs. Once Donald took over the family real estate business, the Trumps built their own country clubs. They didn’t try to buy an apartment and gain admission to snobbish Upper East Side co-ops, which often discriminated against prospective buyers for a range of reasons. They built their own co-ops and condos.
Those who wanted to get along with the Trumps would join a Trump country club, live in a Trump building, or both—that is how Kellyanne Conway first met Donald Trump.
Social climbing for Donald Trump was not climbing someone else’s ladder but instead perching himself atop a pedestal, lowering a ladder from it, and inviting others to climb up the ladder toward him.
Perhaps there is something admirable in this singular focus on dictating one’s own definition of status and success rather than striving to meet someone else’s definition. But if anyone wonders where Donald Trump’s self-centeredness comes from, this is part of the story. Equally significant was his very deep suspicion of the establishment, whether it be establishment businessmen, social circles, country clubs, parties, or charitable boards of large Manhattan cultural institutions that he almost never joined. If America could ever create a billionaire who even in times of great business success (he had some) was still an anti-establishment outsider, Donald Trump was it.
Second: Trump never had to work for anybody else but himself, and very briefly for his father. He avoided the draft during Vietnam (the unsubstantiated foot maladies). He became a very rich businessman (at times) and worked hard (at times), but he never had to work for an organization or play by someone else’s rules.
He worked for his father at a very young age, but within years of graduating from college, he was given millions in “start-up” capital (apparently about $15 million) and a great deal of autonomy to put together real estate deals in new places where his father had done very little business—at first mostly Manhattan, which his father had always avoided.
Most successful businesspeople have at some point worked in organizations where others make the rules. Law firms and investment banks have partners or managing directors. (Former New York City mayor and billionaire Michael Bloomberg was an employee and then a partner of Salomon Brothers before setting up his own company in midlife.) Corporations have boards of directors that hire and fire top officers. Most organizations—including all public corporations—are bound by disclosure rules requiring that financial books and records be available to investors, and often to the public. Under federal securities laws, executives can be imprisoned for inaccurate records. Accountability and transparency are required.
How well these transparency and accountability rules are enforced for public companies is arguable, but with private family-owned companies such as the Trump Organization, there are no such rules. Business records, including financial statements and the names of foreign and domestic investors and lenders, are kept private. The business owner runs the show.
It is not surprising that a TV reality show such as The Apprentice would have a private company head as its star. Public company CEOs can hire and fire people in their organization but they don’t have absolute power. The public company CEO may very well be told by the board of directors “you’re fired.” By contrast, nobody can fire Donald Trump from a company wholly owned by Donald Trump.
For someone aspiring to be president of a constitutional republic, a résumé showing no experience with transparency and accountability to others is not a good sign. For someone aspiring to head a country such as Russia or Saudi Arabia or North Korea, that résumé might work, but in the United States not so much.
Third: Trump has never particularly liked playing by the rules. His singular experience with rigid enforcement of rules was apparently not a happy one. When it came time for young Donald to go to prep school, there is no record that he even applied to the prominent day schools and boarding schools favored by New York City’s elite. He did not enter one of New York City’s many good public high schools. He was instead enrolled by his father, seemingly against his will, in New York Military Academy (NYMA), an institution marketing itself to wealthy parents with difficult-to-manage sons. The typical advertisement—in the back pages of the New York Times Sunday magazine section—invariably featured a photo of a boy with short hair wearing a military uniform. It does not appear that young Donald learned much about rules, except that brute force is needed to make and enforce them.
The Washington Post ran an article describing young Trump as a bully who rode through his Queens neighborhood on a bike, shouting and cursing loudly, throwing rocks at others, and beating up smaller kids.
As a seventh grader, he and a friend would sneak out of his Jamaica Estates mansion, take the subway to Manhattan, and walk around. He bought stink bombs, hand buzzers, fake vomit, and switchblades to be like the gang members from West Side Story.
When Fred Trump found the knives and learned of his son’s secret jaunts, he enrolled him at the military academy in Cornwall-on-Hudson, sixty-five miles away. Observers felt this response much too severe for a boy who hadn’t gotten arrested and wasn’t involved in any real mischief. When young Donald suddenly disappeared from the neighborhood, his friends were dumbfounded.
At NYMA, separated from his cook and butler, Trump rebelled, but then fit in very well, getting good grades (presumably—his transcript is a closely guarded secret), and shining on the football and baseball teams. He had a temper, and once after a classmate struck him with a broom, he tried to push his assailant out a second-floor window, only to be stopped by two other students.
During his senior year he was promoted to captain of A Company, but a month into his reign, a platoon sergeant shoved a plebe too hard against a wall, and Trump was accused of not being strict enough with the leaders under him. He was reassigned.
Paul Schwartzman and Michael Miller related this incident in their Washington Post article. After many phone calls, they visited the home of the former NYMA cadet who had replaced Trump as Company A captain. Reluctantly he told them of Trump’s demotion. After the story was published, Trump reacted as all narcissists would to public embarrassment. Three times Trump called the Post to say the writers had done “a lousy interview.”
Trump verbally attacked the interviewee, saying the former cadet’s account was “a fiction” and accusing him of telling the story to get “himself a little bit of publicity.”
Trump insisted he had not been demoted.
“It was a promotion for me,” declared Trump, “and it was a demotion for him.”
Trump called the Post twice more to argue the point.
“I was promoted,” he said. “Promoted. Mark it down.”
Fourth: Trump grew up in the 1960s, and his background and his life experiences could not be more different from the “religious right” he now courts. Trump’s hedonism and materialism gave rise to a lifestyle that was a cross-section perhaps of that described and practiced by famous novelists Kurt Vonnegut and Norman Mailer. Combine that with the free flow of money, and we have a rich-man’s world reminiscent of F. Scott Fitzgerald novels (minus the booze that Donald Trump apparently avoided after his brother tragically suffered from alcoholism).
Trump did not grow up with a Catholic education, and it is not clear that his Protestant family attended church regularly. Fred Trump does not appear to have embraced conspicuous displays of wealth as much as Donald has, but money appears to have been an important part of the family relationship. We learned from a 2018 New York Times story that Fred Trump, with some assistance from Donald and perhaps Donald’s sister Maryanne, spent decades engineering intrafamily wealth transfers to avoid estate taxes.
Trump’s mother was apparently very passive, leaving him with no forceful female role model. He did not experience either the influence of an intellectually engaged professional woman or the domineering societal matriarch that many other wealthy young men had.
Even though his own sister Maryanne later moved beyond this mold to become a federal judge, Donald Trump had very little experience with women being in charge of anything at all, whether a business, a charitable organization board of directors, or even a debutante cotillion. At some early point he formed the opinion that women existed primarily for the pleasure of men, particularly rich men like himself.
Fifth: Donald Trump has always been far more honest than many men about some things, and much more dishonest about others. He is most honest about his own feelings and prejudices.
The “stiff upper lip” of the WASP Society crowd is nowhere to be seen with Donald Trump. If you offend his ego, he lets you know it. Thin-skinned is an understatement. His racial and religious prejudices are laid bare.
The contrast of Trump with other presidents is striking. Everyone knows from the White House tapes that Richard Nixon disliked Jews (except for a few such as Henry Kissinger, his secretary of state). But Nixon did not talk that way publicly. Trump by contrast, forty years later when prejudices are far less socially acceptable, will very publicly say what he thinks of Muslims and Mexicans. His long history of race-baiting African Americans sets him apart from most Americans, including those who harbor similar prejudices but are less open about it.
He even wears his attitude toward women on his sleeve, not only in the infamous interview with Billy Bush (“grab them by the pussy”), but even more notoriously in radio interviews with Howard Stern in which he talked of the sexual attractiveness of his own daughter Ivanka. Shocking people—with brutal honesty about his own prejudices and hedonism—was a part of Donald Trump’s mantra long before he went into politics.
For conventional politics (typified by the genteel mannerisms of the late George H. W. Bush or Barack H. Obama), Trump’s candidacy for any office for this reason alone should have been a nonstarter. For unconventional politics and appealing to a “base” of voters willing to support any candidate bold enough to voice their own disdain for the establishment, minorities, and women, he was the perfect candidate.
In business, by contrast, Trump learned that lying pays off. Because he has never worked for a public company and thus has not been subject to at least some of the legal prohibitions on lying (particularly to investors), business for him is similar to a poker game. Lots of bluff—and also some cheating.
Trump has attracted more lawsuits than just about any other New York businessman, but here also he learned that fighting back with dirt was the way to win. When he and his father needed a lawyer to defend against Nixon Justice Department lawsuits alleging housing discrimination against blacks in the 1970s, Trump retained a notorious lawyer whom he had reportedly met in a nightclub: Senator Joe McCarthy’s former chief counsel Roy Cohn who, entirely apart from his red-baiting at the McCarthy Army hearings, was known as one of the nastiest lawyers in New York. Cover-ups were a Cohn method that Trump admired. (According to the 2019 Mueller Report, Trump criticized his White House lawyers for taking notes that could be used against him, saying that “Roy Cohn never took notes.”)
Lie. If that doesn’t work, lie again and then sue. That became Trump’s way of doing business.
THE UNITED STATES FOOTBALL LEAGUE
If you’re looking for an example of Trump’s business history, look no further than the New Jersey Generals of the United States Football League (USFL).
After the first season of the USFL, thirty-seven-year-old Donald Trump in 1983 bought the Generals from J. Walter Duncan for $10 million, even though Duncan’s asking price was $8.5 million. The USFL played in the spring. The owners felt there would be room for a football league playing when the NFL wasn’t.
Trump’s office was on the twenty-sixth floor of the Trump Tower in Manhattan, and those wishing to meet with him found it curious that before they met, they had to sit through an eight-minute film describing his greatness. The video called him a “visionary builder” and included a sales pitch for Trump Tower.
The video wasn’t optional. If you wanted to see him, you had to sit through the video.
Though Trump had bought a USFL franchise, he had no interest in the success of the USFL. He wanted to get a professional football franchise for himself and take it to the prestigious National Football League (NFL). First he failed to get a number of star NFL players to switch leagues, and then he failed to hire legendary Miami Dolphins coach Don Shula. He publicly announced that Shula was close to signing, angering Shula, who decided to stay in Miami.
Embarrassed, Trump lied to save face, saying he hadn’t signed Shula because the negotiations were too complex and time-consuming.
Despite his public failures, Trump was grabbing headlines. The other owners were furious and felt that he was trying to steamroll them to take over the league. They weren’t wrong.
Not long after he bought the team, Trump angered the other owners when he announced he wanted to move their games from the spring to the fall to compete head-to-head with the NFL. He talked of his Generals playing in the NFL in a new Trump Stadium in Manhattan.
The other owners, who knew it was suicide to switch to the fall, were furious. In a meeting, Trump demanded they schedule the move—now.
“I don’t want to be a loser,” he told them. “I’ve never been a loser before … and I’m not going to be a failure.”
The USFL could have succeeded if Trump had allowed their original plan to play in the spring. But Trump was insistent, even though his desire to play in the fall wasn’t based on anything but his gut and his ambition, as he ran roughshod over the other owners.
“He understood nothing about football,” said TV producer Mike Tollin. “He knows less than the average fan.”
“He was great entertainment,” said Charley Steiner, the announcer for the Generals, “but he was also poisonous. He didn’t care about the league, about his players. He cared about one person, and one person only. He cared only about Donald J. Trump.”
Trump bullied the owners to move to the fall. He told them that he was the richest owner, that this was his intention whether they liked it or not. He disparaged USFL commissioner Chet Simmons, who saw Trump clearly for what he was: a huckster. Trump became known as a “charlatan, dead set on getting his way.”
Independently, Trump asked the top executives at CBS and NBC if the networks would carry the USFL if they played in the fall. They said yes.
Trump then lied to the owners, saying that the network execs told him they preferred that the USFL played in the fall.
“He held sway, even when his sway made no sense,” said author Jeff Pearlman.
Trump billed himself as the savior of the USFL when the USFL might well have succeeded if he hadn’t steered them toward oblivion.
When the New York Times quoted Trump saying that the USFL was going to play in the fall because it was “the only logical way for the league to continue,” Tampa Bay Bandits owner John Bassett said, “[The story] is absolute nonsense. I hate to see [the Times] used by a con man. At this point there is absolutely no basis to [the story] whatsoever.”
Trump arranged a secret meeting with NFL commissioner Pete Rozelle but didn’t let Rozelle get a word in. At the end of the meeting, Rozelle told him, “Mr. Trump, as long as I or my heirs are involved in the NFL, you will never be a franchise owner in the league.”
The USFL paid $600,000 for a report that said its best chance for its survival was to play in the spring. Trump immediately called the report “bullshit.” He threatened to quit if the league played in the spring. He and Eddie Einhorn, owner of the Chicago team, bullied the others into agreeing they would play the next season in the fall.
Trump had overwhelmed his peers to do his bidding. Sharon Patrick, who conducted the study, told the owners that playing in the fall meant sure death to the league. The owners voted with Trump anyway.
In the end the league folded. Ticket sales across the league plummeted. Owners closed up shop. Trump insisted he would find new owners.
The league was down to eight teams for the 1986 fall season. More than seventy-five USFL players switched to the NFL.
Meanwhile, Trump asked the other USFL owners to trust him. He insisted the USFL sue the NFL for being a monopoly and hired Roy Cohn to represent them. Trump promised that the suit would bring down the NFL. (Trump’s use of antitrust laws to attack his enemies has been a reoccurring theme in his presidency, including an antitrust suit brought in 2017 against Time Warner, the corporate owner of CNN.)
When Cohn became ill with AIDS (he died in 1986), Trump hired a new lawyer, Harvey Myerson. Said Jeff Pearlman, “He was the personification of slime.” Attorney Myerson was unduly beholden to Trump, and he was a disaster.
The trial took eleven weeks. The USFL sued for $1.69 billion, plus punitive damages. Myerson didn’t call a single USFL owner except Trump. The litigation was essentially between Trump and the NFL.
“Donald wanted to be the star of the trial,” said Pearlman.
The NFL’s lawyers made it clear that the USFL had failed because Trump insisted on a fall schedule. Trump said NFL Commissioner Pete Rozelle had asked him to own an NFL franchise. Rozelle did no such thing.
Wrote Richard Hoffer in the Los Angeles Times, “[NFL lead attorney Frank] Rothman characterized Trump as the worst kind of snake who was selling his colleagues down the river so he could effect a merger of a few rich teams.”
Said one of the jurors about Trump, “He was not believable in anything he said. He came off as arrogant and unlikeable.”
On July 29, 1986, the jury ruled that the NFL was guilty of being a monopoly. The USFL had won.
The jury then awarded damages. The USFL was to get exactly one dollar.
Which was tripled, because it was an antitrust violation.
When the verdict was announced, New York Giants owner Wellington Mara handed a one-dollar bill to Donald Trump.
Thanks to Donald Trump, the USFL was officially dead.
Trump since then has done all he can to get back at the NFL. When Colin Kaepernick in 2015 knelt to protest the number of African Americans shot and killed by white policemen, Trump declared that Kaepernick was dishonoring America by kneeling during the national anthem. This was Trump’s revenge for the NFL refusing to allow him to become a team owner as much as it was yet another opportunity for him to engage in race-baiting the African American community.
More importantly, Trump’s disastrous leadership showed how his lust for power, insistence on making decisions by the seat of his pants, and inability to be swayed by logic and research could lead to total disaster.
OTHER TRUMP VENTURES
Separating investors from their money has made Trump rich. One of many disastrous ventures was Trump University, in which students put up as much as $35,000 to learn how to become rich selling real estate. The come-on was that these students would learn from “Trump’s hand-picked instructors,” when in fact Trump had little to do with the instructors.
Trump University shut its doors after five years in 2010, leaving thousands of tuition-paying students in the lurch. Students sued, and in one case Trump countersued, a favorite strong-arm tactic of his, demanding $1 million from the student. (The countersuit was thrown out.) Trump was accused of using Trump University to cheat thousands of people out of millions of dollars.
Before the lawsuits were settled, Trump in 2016 launched an attack on the federal judge, Gonzalo Curiel, saying that because the judge was “Mexican,” he couldn’t be impartial. He said Curiel made “bad rulings” and said he had been “treated very unfairly.” Curiel was born in Indiana.
In November 2016 Trump agreed to settle all the lawsuits for $25 million.
It could have ended far worse for Trump if law enforcement had stepped in, but the Florida attorney general saved the day. A raft of Floridians who were scammed by Trump University contacted Florida attorney general Pam Bondi. Bondi said she was considering whether to join the lawsuit filed by New York State attorney general Eric Schneiderman, when Bondi called Trump and asked him for a $25,000 donation to her campaign. He complied. Bondi’s office dropped the inquiry.
Before becoming president, Trump was accused of violating antitrust laws, entering into deals with known mobsters and other criminals, refusing to pay workers and contractors, hiring undocumented workers at all three casinos, and operating a phony charitable foundation. He was also accused and fined for housing discrimination and paid a settlement to tenants who accused him of intimidation when he tried to evict them and charge higher rents.
One of his biggest moneymaking schemes was hatched in 2006. In the 1990s he had paid $2 million for 436 acres north of New York City with the idea of building a golf course. When he couldn’t get past the environmental restrictions, he sought to sell it. Four years later he donated the land to New York State for a park named after him.
During the dedication of the Donald J. Trump State Park, a reporter asked him the value of the land.
“People have told me about $100 million,” he said.
A town official said it was worth closer to $15 million.
The question arose whether Trump claimed a $100 million charitable deduction in his income tax return of 2006. Did he lie about the $100 million valuation? Did he cheat the government with a $100 million valuation?
Only his tax returns can tell us.
THE APPRENTICE
The Apprentice, the reality show that made Donald Trump nationally famous, was the brainchild of Mark Burnett, who made his reputation with the Survivor franchise.
Burnett needed to find a host—someone “bigger than life and very colorful, someone who would be likeable, tough, and fascinating enough to interest an audience for a full season.”
In 2002 Burnett found what he was looking for when he rented the Wollman Rink in Central Park for a live broadcast of the Season 4 finale of Survivor: Marquesas. Donald Trump, who had leased the rink in 1986, was in attendance with girlfriend Melania Knauss.
Burnett noticed that TRUMP was plastered all over the ice-making machine and the walls of the rink. By 2002 The Donald was a local celebrity, a real estate mogul, and the author of The Art of the Deal, a book written largely by Tony Schwartz that stayed at the top of the New York Times bestseller list for thirteen weeks.
Burnett immediately saw in Trump the host for his new show. To get him to sign on, Burnett told Trump the premise—teams of job seekers would vie for his approval—and he told Trump that the show would showcase his helicopter, jet, Mar-a-Lago, his casinos, fancy apartment, and all that splendor. Trump would be The Boss. He would be judge, jury, and executioner in a weekly contest to see which desperate go-getter would work in one of Trump’s businesses for $250,000 a year.
Trump worried the show would take up too much of his time. Burnett promised him it would only take three hours a week and would be filmed in Trump Tower.
On impulse, without doing any research or talking to consultants, Trump shook hands with Burnett to become equal partners. The show was ingenious. It was about “what makes America great”—contestants fighting to become rich. Trump, the quintessential New York tycoon, would pick the winner after each session.
Burnett knew how to treat his new partner. Burnett flattered Trump as often as he could, knowing how much he liked flattery. Trump often told people that the two had invented the show together, and Burnett never corrected him. Burnett saw the importance of never upstaging him. Trump used the show to advertise his properties. The contestants stayed at Trump Tower, did events at his Trump National Golf Club, and sold various Trump products.
Trump saw how the show would promote his brand and how it would allow him to rebrand his image.
Twenty million viewers tuned into the first episode of The Apprentice.
When the show began, Trump was deeply in debt, but it didn’t take long for Trump to be seen as someone who had fought his way back to respectability.
At the start of the first show, Trump’s voice-over intoned, “I own buildings all over the place. Model agencies, the Miss Universe pageant, jetliners, golf courses, casinos, and private resorts like Mar-a-Lago … I’ve mastered the art of the deal and have turned the name Trump into the highest-quality brand. And as the master, I want to pass along some of my knowledge to somebody else.”
Trump never read a script. He wasn’t always coherent, but editors removed the worst of his garbled syntax and malapropisms. On air he was bombastic, overbearing, and clearly in charge. The final lines of each show, “You’re fired,” weren’t in the script. He just blurted it out. The line became a symbol of Trump’s toughness.
“The Apprentice offered a promise not only of enrichment,” wrote David Frum, “but of justice, at a time when Americans craved that fantasy even more than usual.”
By the end of the first season The Apprentice was the highest-rated show of the week. It had twenty-seven million viewers. Trump would be liked for his honesty, the way he told bad contestants to take a hike. He was blunt. Sometimes he’d humiliate a contestant. Viewers ate it up.
“Above all,” wrote Michael Kranish and Marc Fisher in Fortune magazine, “Apprentice sold an image of the host-boss as supremely competent and confident, dispensing his authority and getting immediate results. The analogy to politics was palpable.”
The Apprentice ran for fourteen seasons. With his newfound fame, Trump began to talk politics. He appeared on the Imus in the Morning show every week, and he talked with Don Imus about the possibility of running for president one day.
When Trump made his grand entrance down the gold-colored escalator to the atrium of the Trump Tower to announce his candidacy in 2015, it was choreography that Burnett had used often for The Apprentice. Those who cheered his speech that day were extras paid fifty dollars for the event.
Burnett also tried to market a reality show starring Vladimir Putin. The show was to be called Destination: Mir, and the idea was that the winner each week would be launched into space. When Russia shut down the Mir space station, Burnett scuttled the idea. In 2015 Burnett again brought up the idea of a reality show starring Putin. It would be a hymn to the glory of Russia, he said.
On August 12, 2015, NBC announced that Donald Trump, then a Republican candidate for president, had been fired from The Apprentice. After Trump made negative comments about Mexican immigrants, NBC cut their ties. It also cancelled its airing of the Miss USA pageant, which Trump owned.
“Due to the recent derogatory statements by Donald Trump regarding immigrants, NBC Universal is ending its business relationship with Mr. Trump,” NBC said in a statement, adding, “At NBC, respect and dignity for all people are cornerstones of our values.”
In response, Trump blasted NBC, saying it was “so weak and so foolish to not understand the serious illegal immigration problem.” He has never let go of his anger at NBC.
In sum, there is one aspect of business that Trump is extraordinarily good at: sales. Trump is the consummate salesman. He can usually sell just about anything to anybody. He can close the deal. Some observers have argued that without help from his father, Trump never would have been successful in business, but that is probably not true—even starting at the lowest levels selling any product, he most likely would have been a successful salesman.
At a certain point a sales pitch becomes so “convincing” and “compelling” that it becomes a fraud. Most salespeople who become con artists get sued or perhaps go to jail. Once again Trump, because of family circumstances, was protected from this aspect of the real world. He had the political connections—and tough lawyers including Roy Cohn and Michael Cohen—to fight allegations, plaster over lies with more lies, and get away with it.
The salesperson unchecked by the long arm of the law at some point becomes a con artist. Many businesspeople (in addition to the holders of some $900 million in Trump casino bonds in the mid-1990s) believe that is exactly what happened with Donald Trump.