When the Reagan-Bush handover occurred in 1989, Donald J. Trump, forty-three, was already, as a self-publicizing developer of spectacular sites in the throbbing American heart of Manhattan, a man who loved the spotlights, footlights, and limelight, and an accomplished public relations hustler, but also an agile industrialist and financier, and a patriotic military school graduate who already saw the nation’s supreme office as the possible consummation of his accumulation of money and fame. He was now monitoring the currents of public opinion and the political pathways with acute self-interest.
Trump, because of his talents at self-promotion, often of a somewhat grating nature, had been one of the most famous people in the country for some years. His construction of, and name-identification with, radically designed buildings of high quality in choice Manhattan locations, frequent public disputes with local politicians, and general omnipresence in the Manhattan world of celebrity controversy, caused him to be regarded by many with distaste, but also to be regarded by many others—a broad swath of American capitalists, entrepreneurs, and appreciators of showmen—with deep and durable, if vicarious, admiration. Trump had no interest in the usual social and philanthropic eminence of wealthy New Yorkers; he was interested in fame, celebrity, publicity, money, and politics. He began regularly polling American opinion about him, as his name, increasingly prominent and bandied about endlessly in the press, became ever more familiar to the public. He also noted that the political ground and the normal pathways of politics were shifting.
In 1992, after the main party nominations had been locked up by President George Herbert Walker Bush for the Republicans and by five-time Arkansas governor Bill Clinton for the Democrats, billionaire businessman Ross Perot suddenly appeared as a viable, populist third party candidate. Perot’s campaign was launched with a tremendous television blitz as soon as the primaries were over. He tried to win over disaffected voters of both parties with an eclectic platform that promised a balance budget, support for abortion, tightened gun control, a stricter war on drugs, trade protectionism, greater care for the environment, and electronic referenda to promote direct democracy. Perot, unlike Clinton, had been opposed to the First Gulf War, successfully fought by President Bush. Perot played to constituencies of both Right and Left, though his appeal as a Naval Academy graduate and Texas patriot, associated with efforts to recover American soldiers missing in action in Vietnam, appealed largely to blue-collar conservatives unhappy with President Bush’s support for free trade and raising taxes (after saying he would not).
On the Democratic side, Bill Clinton was a very astute politician, one of a new breed who had never really had any career except politics, nor any real ambition except to be president. Such men as Taft, Wilson, Hoover, Eisenhower, and Reagan had been famous from completely separate careers before they sought public office. Truman, Carter, and Bush had had other careers, and Franklin D. Roosevelt had been sidelined for seven years convalescing with and mitigating the effects of polio. Harding, Coolidge, Lyndon Johnson, and Ford went early into politics (after military service in Ford’s case), but none of them were aiming for the White House, and Kennedy and Nixon, who were, at least won some battle stars, got around the world a bit, came from prominent centers (Boston and Los Angeles), and had been a long time in Washington. Bill Clinton ran unsuccessfully for congressman at age twenty-eight, was elected attorney general of Arkansas at thirty, and governor at thirty-two.
Polls had Perot running ahead of both Bush and Clinton prior to the Republican and Democratic conventions, but he abruptly ended his campaign in July, saying he did not want to throw the election to the House of Representatives. However, he burst back into the race two months later, implausibly claiming that he had been forced out by Republicans threatening to disrupt his daughter’s wedding.
Perot could not regain his momentum. He looked increasingly out of his depth, unstable, unable to explain in a convincing way how he would balance the budget, and was seen by most as a political charlatan. President Bush seemed out of touch with the Reagan voters who had put him in office in the first place, ran a half-hearted campaign in which he appeared almost to expect to lose, and focused on issues that most voters at the time thought were irrelevant and unseemly even to talk about—namely, Clinton’s dodging the draft and his scandals involving women. Clinton, cleverly, positioned himself as a centrist Democrat for whom a disaffected Republican could vote in good conscience, and side-swiped Perot with his pitch to the people of modest means and insecure employment; “I feel your pain” came more credibly from him, a former a trailer park resident, than from the billionaire Perot.
Clinton won the election 44.9 million votes to 39.1 million for Bush, and an incredible 19.7 million for Perot (370 electoral votes to 168 to 0). Donald Trump noted how Bush had lost control of his own party; how a political outsider, making an appeal to discontented blue-collar voters, had amassed a sizeable voting bloc; and how a centrist Democrat had managed to overcome personal scandals to win the presidency (and how he later avoided removal from office after being impeached). None of these lessons were lost on him.
He noted other lessons as well. How Jimmy Carter, and now George H. W. Bush, despite being incumbent presidents, had both been defeated by populist campaigns, and how an independent candidate, even one as successful as Perot, could not win in a two-party system. And he also noted how unpopular an inarticulate, uninspiring, establishment candidate like Bush could be to a discontented electorate. All of these lessons came into play when Trump entered the presidential arena twenty-five years later.
Trump had attended his first national political convention in 1988, when the Republicans chose George H. W. Bush to succeed Ronald Reagan. He told television interviewer Larry King that he came “to see how the system works.” He also told King that if he were ever nominated, he might choose African American daytime television hostess Oprah Winfrey as his vice-presidential candidate.1 (This could be taken as evidence of how much he thought celebrity counted in running for national office.)
His name increasingly popped up in political conversations, and there was serious speculation that he might run as a third-party candidate in 2000, tapping into a conservative electorate unhappy with outgoing President Clinton and unsatisfied with a choice of either Republican George W. Bush (or his primary rival John McCain) or Clinton’s Vice President Al Gore.
But Donald Trump also had other things on his mind. On June 25, 1999, Fred Trump died at ninety-three. He had been fading mentally as Alzheimer’s had taken hold, and it was painful for his family to see his decline. The funeral was at Norman Vincent Peale’s Marble Collegiate Church. Peale was still alive at ninety-five, and still the pastor after sixty-one years, but not well enough to preside. The eulogy was delivered by Mayor Rudolph W. Giuliani, who said that Fred Trump had contributed to making New York “the most important city in the world.” Other family members praised their father, as Donald did, but mainly he stressed some of the ambitious projects he had built with his father’s encouragement.
Donald Trump has said since that this was the saddest and most decisive day in his life, because of the closeness between his father and himself, and that his father’s death may have generated his ambition to be president. Sitting alone near the back of the packed church, and much noticed in the tabloid press the next morning, was the breathtakingly tall and beautiful and magnificently proportioned Melania Knauss, twenty-nine, the Slovenian immigrant and model, who was Donald Trump’s current girlfriend. A couple of weeks later, Trump received a thoughtfully worded letter of condolence from John F. Kennedy Jr., as it turned out, on the day that an airplane he piloted himself crashed into the ocean near Martha’s Vineyard, killing Kennedy and his wife, Carolyn Bessette, and another passenger.2
Donald Trump was now the patriarch of what was a family of varied distinction, including Trump’s elder sister Maryanne Trump Barry, a federal district judge, who had just been nominated by President Clinton to the Third Circuit Court of Appeals. Fred Trump’s widow, Mary MacLeod Trump, eighty-seven, had never entirely recovered from being mugged and beaten up not far from the family home in Queens in 1991. A delivery truck driver had collared the assailant and handed him over to police, and Donald Trump rewarded the driver (with no publicity) with a check large enough to retire the mortgage on his house, which was on the verge of foreclosure. Mrs. Trump died the next year and her obituary was published in her hometown newspaper, the Stornoway Gazette, in Scotland, the land from which she had departed seventy years before to make her way in the new world.
In October 1999, Trump told Larry King on his late-night television program (a favorite place for Trump to air his political bulletins) that, while he was “a pretty conservative guy,” he was leaving the Republican Party and joining the Reform Party and setting up an exploratory committee to see if he might run, as a viable candidate, for president. He went on Meet the Press with Tim Russert and others, and did not have an easy time explaining slightly flippant things he had said about President Clinton’s dalliance with White House intern Monica Lewinsky. He defended his support of a woman’s right to a partial-birth abortion, but acknowledged to his assistant, Roger Stone, afterward, that he didn’t know exactly what a partial-birth abortion was.3
He published a thin volume in 2000 called The America We Deserve, in which he said he was thinking of running for president. (He revisited partial-birth abortion and said that after consultation with doctors, he was opposed to it, that he was “uncomfortable” with abortion but still defended a woman’s right to choose. In February, he and Melania visited Minnesota Governor Jesse Ventura, a former professional wrestler.) In remarks to a local group, Trump dismissed the leading Democratic and Republican presidential candidates (Vice President Al Gore and Senator Bill Bradley for the Democrats; Texas governor George W. Bush, and Senator John McCain for the Republicans), as “stiffs;” not an entirely inaccurate description.
But on February 19, 2000, he wrote an op-ed piece in the New York Times in which he announced that while he had seriously considered running for president, he felt he could not win as a Reform Party candidate because the party was too hopelessly divided. Trump had won two primaries for the Reform Party nomination, in Michigan and California, but then folded the operation. He purported to become a Democrat in 2001, and then supported Fernando Ferrer, borough president of the Bronx, as the Democratic candidate for mayor of New York, saying only a Democrat could now win that office. Ferrer lost the nomination to Mark Green, whom Trump then supported, but billionaire, and nominal Republican, Michael Bloomberg won easily, and remained in office for three terms. This was the beginning of an abrasive political relationship between Trump and Bloomberg. At this point, Trump appeared to be lurching around for a political harbor. His political views, as expressed in The America We Deserve, did not change appreciably—a mostly conservative platform, standing on strong national defense, an America-first trade and foreign policy, education reform (including school choice), regulatory and tax reform, health care and social security reform, and tough anti-crime and anti-terrorism policies—but he did not yet have a firm political home in which to express them as a candidate.
Trump continued to believe that in both business and politics, celebrity and fame was more important than money and when British expatriate reality television producer Mark Burnett pitched an idea of a show to him, Trump was interested, though he had reservations. Trump worried about how time-consuming it would be, and he did not like reality television, which he considered to be for “the bottom-feeders of society” (an amusing lapse for Trump into almost dowagerish snobbery). But once satisfied that his part in the show could be shot entirely in the Trump Tower, and that he could work in a great deal of free publicity for his casinos and other properties, he was persuaded. The show would be called The Apprentice, and on a handshake with Burnett, they were equal co-owners. Trump’s executives, still battle-scarred and shell-shocked from the near death financial crisis they had all just gone through, thought it a waste of time. Trump liked it intuitively and proceeded without consulting anyone; and Burnett and Trump eventually negotiated a deal with NBC, after Burnett failed to agree to a deal with ABC. (Trump refused to work with CBS because it had had declined to televise his Miss USA and Miss Universe pageants.)
The show debuted in 2004, and Trump, hard-working as always, prepared assiduously for his role. NBC had originally thought it might rotate executives in Trump’s part; but the network executives were so pleased with his performance that they made Trump the show’s star, and his tagline—“You’re fired!”—often employed humorously, became part of his national branding. The program was aggressively promoted, and when NBC asked for candidates to be the apprentice seeking to work for the star (Trump), in the first sixteen episodes of the program, two hundred fifteen thousand candidates came forward. The Apprentice’s audience rose from an impressive twenty million viewers in its early episodes to a formidable twenty-seven million. The programs were almost continuous advertisements for Trump and his assets, with the rather threadbare theme of Trump trying to help the various contestants learn about his businesses and get on in the world. Trump showed considerable talent as a performer, and he came across as a generous man who regretted having to fire people, though that was an important part of the show.
Trump has always been a highly amusing raconteur, with a gift for tossing off one-liners, and this television experience only added panache to his already greatly accomplished skills as a storyteller, schmoozer, and public speaker. The television experience also softened the public impression of him as a ruthless businessman and narcissistic megalomaniac. He appeared a more human and entertaining man, as well as a capable executive. Trump was proud of the show’s high ratings, and was briefly crestfallen when the Fox show American Idol did better.4 Trump explained at this time to one of the contestants that “All publicity is good publicity….When people get tired of you is when you do more publicity, because that’s when you become an icon.”5
NBC’s public relations director, James Dowd, was close to Trump at this time, and he observed the metamorphosis of Trump from a well-known but not necessarily likeable businessman to an immensely popular public idol of executive success and performance. Trump implied to Dowd that through The Apprentice, he had “won the love and respect of Middle America.”6 Trump also came across in The Apprentice as a reasonable person who could say harsh truths with becoming honesty. The political class still regarded Trump as a rich blowhard, useful for donations but little else. Trump, however, saw himself building a persona and popular support that went behind celebrity and business; he was building trust and a political base among middle Americans.
While The Apprentice improved and vastly expanded Trump’s public image and created new ways for Trump to capitalize on his brand in both business and politics, he assessed his political prospects. After dalliances with the Reform Party and the Democrats, any presidential run he made would be as a Republican. It was by far the best fit for him as a candidate whose major appeal was to blue-collar conservatives; and if his protectionist and anti-illegal immigration positions put him at odds with much of the Republican establishment, which was wedded to free-trade orthodoxy and, in practice, loose immigration policies, his nationalist positions were even more at odds with most Democrats, who saw illegal immigration as a boon to their voter base and free trade as part and parcel of a liberal globalist agenda. Trump was no fan of President George W. Bush, but he couldn’t run against a Republican incumbent in 2004, and he knew couldn’t defeat either Hillary Clinton or Barack Obama in 2008, as the Republicans had to carry the can for the endless imbroglio in Iraq and the housing bubble and the Great Recession. If he was ever going to have a shot at running for president, and winning, it would have to be the end of the Obama era, when there would be plenty of populist discontent, and Trump’s signature issues on trade, immigration, the economy, foreign policy, and the courts, would be to the fore. He was content, then, in the interim to raise his profile and build his bank account.