The First Trump Campaign and What People Thought of Him Then

The show The Simpsons has run since 1989 and many have credited the show for “predicting” certain developments. There are reasons this is not nearly as remarkable as people think it is, and the poster child for this is Donald Trump being president. The reason? They made a joke about it in 2000 in the episode “Bart to the Future”, but Trump was in fact making a run for president then. He had interest in the presidency dating back to 1987 and he had, at the urging of Minnesota Governor Jesse Ventura, announced his candidacy for the Reform Party’s nomination on October 7, 1999.

To promote his campaign, Trump cut a deal with motivational speaker Tony Robbins in which he would pay Trump $1 million to give ten speeches at his seminars, which coincided with his campaign stops (Useem). On these stops and elsewhere he used rhetoric that is pretty familiar to us today, including his statement on his approach to politics, “In business and in life, people want to hear straight talk. We’re tired of being bullshitted by these moron politicians” (Squitieri). Trump hired for this campaign Roger Stone as director of his exploratory committee, who would more famously (or infamously) work for his 2016 campaign. He would say of Trump at the time that “There’s a John F. Kennedy-type charisma that’s very hard to put your finger on. He’s probably the best speaker on the circuit” (Useem). His candidacy was paired with the book The America We Deserve and pushed for “fair trade”, cracking down on illegal immigration, a tax on individuals and trusts worth more than $10 million, wiping out the national debt, and universal healthcare. His primary rival for the nomination was controversial conservative Pat Buchanan, who Trump called a “Hitler-lover” and an “anti-Semite” who “doesn’t like the blacks” and “doesn’t like the gays” (Mark). He would in 2011 apologize to him for those remarks, and Buchanan’s been a fan of Trump ever since. He also had typical rhetoric for his opponents, calling Governor George W. Bush “No Einstein” and Senator Bill Bradley “a total disaster” (Useem). Trump ultimately lost the primary and the Reform Party splintered after a black conservative activist and John Birch Society member Ezola Foster won the VP nomination. Trump also proposed the following cabinet, which is in retrospect, deeply ironic:

Oprah Winfrey – Vice President (She endorsed Clinton in 2016 and said she “couldn’t breathe” after his election.)
Colin Powell – Secretary of State (Endorsed Clinton, and then Biden, instead of Trump)
Jack Welch – Secretary of Treasury
John McCain – Secretary of Defense (Despite still being a Democrat, Trump endorsed him in 2008. He would later call him a “loser” for getting captured in Vietnam in response to McCain’s criticisms of him.)

In 2001, Trump would switch his affiliation to Democrat and be critical of Bush’s presidency, only to switch back to the Republican Party in 2009 and be critical of Obama’s presidency, becoming the best-known promoter of the “birther” conspiracy theory.

What Others Had to Say About Him

Bill O’Reilly (2000) in his book, The O’Reilly Factor:

“Donald Trump is a playboy casino owner and luxury apartment builder who wrote in The Wall Street Journal that America needs him as President. Mr. Trump pointed to his success in building an ice skating rink in New York’s Central Park as an example of his political acumen. The Donald also says he’d like to be “The President” in order to lift “the moral climate” of the country. When asked about his own checkered marital past, Mr. Trump said he never committed “an infidelity,” a statement that sent Ivana Trump and Marla Maples scrambling to find a dictionary” (148).

“Candidate Donald Trump has nominated Oprah Winfrey as Vice President, but the talk show hostess is “not interested at this time.” However, she is “leaving the door open.” This, of course, is terrific news, although I’m not exactly sure why. Word is that Oprah is such a good negotiator that she may be able to continue doing her program and be V.P. at the same time. This would be great for President Trump, who could simultaneously discuss policy and his relationships with many beautiful women “on the next Oprah” (148).

“What’s up with the hair, Donald? Things are bad up there. He tried a scalp reduction operation a few years ago, but that wasn’t a huge success, they say. Maybe that’s why he’s so mean-spirited. Not long ago, he tried to throw some little old lady off her property in Atlantic City. Bad. But she was a tough bird who had run an Italian restaurant for years, and she fought back with lawyers. She won, but it cost her. This is the guy who said he would be good for the country as our next president. How so? Would we all be forced to live in his condos? Trump is rich, which is supposedly good in America, but the man is bad, and he knows it” (196).

Tucker Carlson (1999) in Slate:

“I’d love to add something even meaner to your description of Donald Trump–he’s the sort of person I want to keep kicking once he’s down–but I don’t think I can. You’ve said it all: He is the single most repulsive person on the planet. What a wonderfully pithy, accurate sentence. Congratulations.
That said, I still plan to write about him some time. I don’t think I’ll be able to help it. Horrible as he is (or perhaps because he is so horrible), Trump is interesting, or at least more so than most candidates.”

William F. Buckley Jr. (2000) in Cigar Aficionado:

“What about the aspirant who has a private vision to offer to the public and has the means, personal or contrived, to finance a campaign? In some cases, the vision isn’t merely a program to be adopted. It is a program that includes the visionary’s serving as President. Look for the narcissist. The most obvious target in today’s lineup is, of course, Donald Trump. When he looks at a glass, he is mesmerized by its reflection. If Donald Trump were shaped a little differently, he would compete for Miss America. But whatever the depths of self-enchantment, the demagogue has to say something. So what does Trump say? That he is a successful businessman and that that is what America needs in the Oval Office. There is some plausibility in this, though not much. The greatest deeds of American Presidents — midwifing the new republic; freeing the slaves; harnessing the energies and vision needed to win the Cold War — had little to do with a bottom line.”

Jerry Useem (2000) in Fortune:

“For Donald Trump is to business what professional wrestling is to sports: part of it, certainly, but also a cartoonish parody of it.”

“The most impressive aspect of Trump’s celebrity, to begin with, is not its grandeur but its durability. Not only has he far outlasted the decade that produced him, but – unlike other products of the 1980s who’ve managed to stay in the limelight through self-reinvention a la Michael Milken – Trump has done it without any discernable personal growth. Like a cryogenically frozen Austin Powers, he stands as an almost perfectly preserved specimen of the era, an unreconstructed hedonist who persists in calling plantings on his new golf course the “Rolls-Royce of oak trees”.”

“Trump is, in short, a workingman’s plutocrat: a nonbusinessman’s idea of what a businessman should be.”

“No one’s saying Trump ought to be held to the same standards of truthfulness as everyone else; he is, after all, Donald Trump. But when Trump says he owns 10% of the Plaza hotel, understand that what he actually means is that he has the right to 10% of the profit if it’s ever sold. When he says he’s building a “90-story building” next to the U.N., he means a 72-story building that has extra-high ceilings. And when he says his casino company is the “largest employer in the state of New Jersey,” he actually means to say it is the eighth-largest.”

“And while Trump can spend workaholically long hours at the office, sleeping only four hours a night and consuming as many as eight newspapers a day, one wonders how much of that time is spent calling celebrities like Leonardo DiCaprio or simply turning the media wheels.”

“While at first blush Trump can come off as a thick-skinned believer in the adage that there’s no such thing as bad publicity, that doesn’t quite hit the mark: Like a true publicity-holic, Trump repeatedly indulges in publicity and then rails against the consequences.”

“A foreign-sounding woman on the street recognized him. “Are you going to be a President?” she asked. “Absolutely,” said Trump. “No doubt about it”.”


Buckley, W.F. (2000, March/April). On Donald Trump and Demagoguery. Cigar Aficionado.

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Carlson, T. (1999, November 29). Reckless Gossip Merchants vs. Media Hand-Wringers. Slate.

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Mark, D. (2019, July 21). Trump apologized to Pat Buchanan for calling him an anti-Semite who ‘doesn’t like the blacks’. Washington Examiner.

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O’Reilly, B. (2000). The O’Reilly factor: the good, the bad, and the completely ridiculous in American life. New York, NY: Broadway Books.

Squitieri, T. (2015, October 7). A look back at Trump’s first run. The Hill.

Retrieved from

Useem, J. (2000, April 3). What Does Donald Trump Really Want? Fortune.

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