New York real estate magnate Donald Trump announced the creation of a presidential exploratory committee on the October 7, 1999, edition of Larry King Live on CNN. Although Trump had never held elected office, he was well known for his frequent comments on public affairs and business exploits as head of The Trump Organization. He had previously considered a presidential run in 1988 as a Republican, but chose not to run. For 2000, Minnesota Governor Jesse Ventura persuaded Trump to seek the presidential nomination of the Reform Party, which was fracturing despite achieving ballot access and qualifying for matching funds as a result of businessman Ross Perot's 1996 presidential campaign on the party's ticket.
Trump focused his campaign on the issues of international trade, eliminating the national debt, and achieving universal healthcare as outlined in the campaign companion piece The America We Deserve, released in January 2000. He named media proprietor Oprah Winfrey as his ideal running mate and said he would instantly marry his then-girlfriend, Melania Knauss (Melania Trump), to make her First Lady. Critics questioned the seriousness of Trump's campaign and speculated that it was a tactic to strengthen his brand and sell books. Trump defended his candidacy as a serious endeavor and proclaimed that he had a chance to win the election. Although he never expanded the campaign beyond the exploratory phase, Trump made numerous media appearances as a candidate, travelled to campaign events in Florida, California, and Minnesota, and qualified for two presidential primaries. Veteran campaign strategist and later longtime Trump aide Roger Stone was hired as director of the exploratory committee.
Internal conflict caused Ventura to exit the Reform Party in February 2000, removing Trump's most vocal proponent. Trump officially ended his campaign on the February 14, 2000 airing of The Today Show on NBC. Although he believed he could still win the Reform Party presidential nomination, he felt the party was too dysfunctional to support his campaign and enable a win in the general election. A poll matching Trump against likely Republican nominee George W. Bush and likely Democratic nominee Al Gore showed Trump with 7% support. Despite his withdrawal, Trump won both primaries for which he qualified. Paleoconservative commentator Pat Buchanan would go on to win the nomination of the Reform Party, receiving 0.4% of the vote.
After the election, Trump gained greater fame as the host of The Apprentice on NBC. He also notably considered running as a Republican in the 2012 presidential election against incumbent Barack Obama, but instead endorsed and supported eventual nominee Mitt Romney. Four years later, he initiated a full-scale presidential campaign, became the Republican Party's 2016 presidential nominee and was elected as the 45th president of the United States. Following his loss to Joe Biden in the 2020 presidential election, Trump initiated another full-scale presidential campaign, became the Republican Party's 2024 presidential nominee and was elected as the 47th president of the United States.
Background
Trump, head of The Trump Organization since 1971, first dabbled in presidential politics in the early summer of 1987. Republican political organizer Mike Dunbar, unimpressed with the candidates for the 1988 Republican presidential nomination, founded the "Draft Trump for President" organization. Believing Trump had the makings of a president, Dunbar pitched Trump the idea of speaking at an event for Republican candidates in the first-in-the-nation primary state of New Hampshire. According to Dunbar in a later interview, Trump was receptive to this idea. Then a registered Democrat, Trump officially changed his registration to Republican in July 1987. Speculation that he would actually run for president intensified when he purchased $94,801 (~$ in ) worth of full-page advertisements in The New York Times, The Boston Globe, and The Washington Post with the heading "There's nothing wrong with America's Foreign Defense Policy that a little backbone can't cure." The advertisements reflected Trump's concerns that Japan, Saudi Arabia, and Kuwait were taking advantage of American money and protection without providing any benefit to the United States. The next month, as Dunbar had proposed, Trump appeared at a Rotary Club luncheon in New Hampshire. There, he delivered what The New York Times described as an "impassioned speech," in which he expressed concern about the U.S. being "pushed around" by its allies and proposed that "these countries that are ripping us off pay off the $200 billion deficit." In the audience, college students held placards reading "Trump for President." Nevertheless, Trump proclaimed, "I'm not here because I'm running for President. I'm here because I'm tired of our country being kicked around and I want to get my ideas across." Later, Trump appeared on The Phil Donahue Show on WNBC. After the appearance, he received a letter from former President Richard Nixon in which Nixon explained that his wife Pat, "an expert on politics," had seen Trump on the show and "predicts that whenever you decide to run for office you will be a winner!" In November 1987, Trump released The Art of the Deal, which became a New York Times bestseller.
Months later, during an April 1988 appearance on The Oprah Winfrey Show on ABC, Trump discussed his displeasure with the U.S.'s status as a "debtor nation" and its seeming inability to compete with Japan. Winfrey asked Trump if he would ever run for president. He replied, "Probably not, but I do get tired of seeing the country get ripped off ... I just don't think I have the inclination to do it." Furthermore, he asserted that if he ever did run, he would win the election. He later appeared at the 1988 Republican National Convention. In an interview on the floor, NBC News reporter Chris Wallace asked whether Trump's visit to his first national convention would induce him to "take the plunge" into a presidential campaign. In response, Trump downplayed his prior exploration into presidential politics, though repeated that he would win if he ever ran, and praised then-presumptive Republican presidential nominee George H. W. Bush. During another convention interview on Larry King Live, Trump said, "I doubt I'll ever be involved in politics beyond what I do right now." Talk of a potential Trump candidacy grew silent for much of the next decade.
In 1995, industrialist Ross Perot, who had received 18.9 percent of the vote during his independent 1992 run for president, formed the Reform Party of the United States of America. Although Perot won the party's 1996 nomination and garnered 8.4 percent of the popular vote, rifts had begun forming within the party. Former Colorado Governor Richard Lamm, who unsuccessfully challenged Perot for the 1996 presidential nomination, accused Perot of using the party as a personal vehicle, and broke off with his supporters to form a new party. In 1998, former professional wrestler Jesse Ventura was elected Governor of Minnesota as a member of the Reform Party—the party's most significant victory—but Perot and his followers were not receptive to Ventura and his political allies. The Perot faction adamantly, though unsuccessfully, attempted to prevent the election of Ventura supporter Jack Gargan as party chairman in 1999 when Perot backer Russ Verney chose not to stand for re-election for his term ending January 1, 2000. Opting not to run for president himself in 2000, Ventura searched for candidates. Initially, he courted WWF Board Member and former Connecticut governor Lowell P. Weicker Jr. He then turned to Donald Trump.
Early stages In 1999, The New York Times reported that Jesse Ventura first approached Trump about a possible 2000 presidential run while both were in attendance at a wrestling event in Atlantic City. But Trump's ambitions may have formed earlier. The America We Deserve co-writer Dave Shiflett said Trump first thought about running in late 1998, when he looked at his political advantages in money and name recognition, and concluded that he was "at least as competent" as then President Bill Clinton. According to Shiflett, this prompted Trump to ask top aide Roger Stone to find the "most eminent hack writer in America" to put Trump's political ideas into a book. Stone reached out to Shiflett, a contributor to The American Spectator. In spring 1999, Shiflett met with Trump about the project that would later become The America We Deserve. During the initial meeting, Shiflett claims Trump raised concerns about a suitcase bomb destroying Manhattan.
In July 1999, the Democratic polling firm Schroth and Associates conducted a poll of 400 Reform Party leaders and found Trump tied for third place for the Reform Party presidential nomination. Both the Reform Party and Trump denied having commissioned the poll. Days later, Newsweek raised speculation when it cited an unnamed "close friend" of Trump who said Trump was "toying" with the idea of a presidential campaign, allegedly in response to rumors of Ventura's courting of Weicker for a run. Trump purportedly held a grudge against Weicker for blocking his plans to build a casino in Bridgeport in 1994. The two had an exchange of insults in which Weicker labeled Trump a "dirt bag" and Trump referred to Weicker as "a fat slob who couldn't get elected dog catcher." In response to the Newsweek report, Trump sent out a press release in which he criticized the two party system, praised the Reform Party, and stated "If the Reform Party nominated me, I would probably run and probably win." However, he added that if the party nominated him, he would ask for "an immediate recount." In an interview, he told The New York Times, "I'm honored and I'm flattered [by the speculation], but the fact is I've never had more fun than I'm having right now, building the most spectacular buildings in New York." Chairman Verney denied that the Reform Party had any interest in Trump, explaining that party members had "never spent one second thinking about him." A CNN-Time poll conducted later in July showed Trump with seven percent support nationally in a match up against Republican candidate George W. Bush and Vice President Al Gore.
Two months later, amid reports that paleoconservative political commentator and adviser Pat Buchanan was about to join the Reform Party to seek the nomination, Trump announced that he would consider running as a sign of respect for Ventura. He labeled the views of Buchanan as "prehistoric", and commented that even though he liked Pat, "I'm on the conservative side, but Buchanan is Attila the Hun." He expected that a primary battle between the two would be "nasty." According to columnist Robert Novak, Bush operatives concerned about a third party run by Buchanan contacted Ventura indirectly about preventing Buchanan's nomination. Novak argued that Trump "seems a bad match with Perot's party, but he may be the GOP's last hope to stop Buchanan." When Weicker decided not to seek the party's nomination due to internal bickering, Ventura reportedly went all in for Trump. The media capitalized on a potential Trump versus Buchanan challenge, and Saturday Night Live satirized it with a skit in which Darrell Hammond portraying Trump and Chris Parnell as Buchanan pitched their candidacies to Ross Perot, played by Cheri Oteri. The segment also featured an appearance by Will Ferrell as Ventura.