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.

[2] Speculation that he would actually run for president intensified when he purchased $94,801 (~$218,169 in 2023) 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.

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."

[6] Months later, during an April 1988 appearance on The Oprah Winfrey Show on ABC,[7] Trump discussed his displeasure with the U.S.'s status as a "debtor nation" and its seeming inability to compete with Japan.

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.

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.

"[19] 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.

[21][22] 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 identified France, Japan, Germany, and Saudi Arabia as nations taking advantage of badly negotiated trade deals with the U.S.[54] In an effort speculated to implore the media to view the campaign more seriously,[55] Trump rolled out a tax proposal that became the subject of attention.

In a series of telephone interviews in early November,[55] Trump proposed a one-time 14.25 percent "net worth tax" that would apply to individuals and trusts with assets greater than $10 million.

He projected a 35 to 40 percent increase in economic activity as a result and eliminate $200 billion in federal interest payments, half of which would be used to fund middle class tax cuts and the rest to allocate for Social Security.

Ed Koch elevated his criticisms of the campaign, calling it "fraudulent" and arguing that Trump is the "greatest con artist in the world when it comes to trumpeting his own name ... [M]y gut tells me that he knows nothing [about policy].

[64] On November 17, 1999, as a further step in organization, Trump set up a campaign website at the domain www.donaldjtrump2000.com and used Ventura's webmaster, Phil Madsen, to create an online community of supporters.

[67] The foundation invited Trump after he wrote a Miami Herald article denouncing Cuban President Fidel Castro and favoring the U.S. embargo against Cuba several months earlier.

Covering the event, columnist Maureen Dowd wrote that the fascination with Trump was the "apotheosis of our Gilded Age," where "money, celebrity, polling, and crass behavior" warp politics and the television show Who Wants to Be a Millionaire dominates the culture.

[61] Following this theme, Saturday Night Live performed a sketch in which Darrell Hammond reprised his role as Trump, holding a press conference announcing Millionaire winner John Carpenter as his running mate.

[71] As the World Trade Organization (WTO) negotiations collapsed amid protests at a summit in Seattle, Trump appeared on the December 5 airing of ABC's This Week.

During the stop, Trump held a press conference, appearing with his campaign entourage that included Melania Knauss, Roger Stone, and bodyguard Matt Calamari.

"[73] In Burbank, Trump appeared on The Tonight Show with Jay Leno where he attacked Buchanan as "having a love affair with Adolf Hitler" and discussed his own upcoming book, The America We Deserve.

[71] After the Tonight Show appearance, Trump attended a meeting of one hundred Southern California Reform Party members, to whom he delivered a speech and answered questions.

Crowds cheered Trump when he discussed his opposition to NAFTA, but some were offended[73] when he questioned the existence of a Reform Party platform and, after receiving a copy, left it on the podium when he exited.

Responding to a poll of probable Reform Party voters that showed him with only 14% support, fourth place behind Ventura (20%), Perot (25%), and Buchanan (30%), Trump pointed to the spike in ratings each television network received whenever he appeared on air.

"[88] Dave Saltonstall of the New York Daily News, labeled it as autobiographical and reported that it contains "enough details to paint a fairly comprehensive picture of what a Trump presidency might look like.

"[84] On January 7, Trump appeared in Brooklyn Park, Minnesota, where he spoke before the Chamber of Commerce, attended a Reform Party fundraiser, and held a joint press conference with Ventura.

[90] Describing himself and Ventura as self-made and not part of the "lucky sperm club," Trump made an indirect jab at both the Republican front-runner George W. Bush, the son of former President Bush, and Democratic front-runner Al Gore, son of the late Senator Albert Gore, Sr.[91] Trump and Ventura released a written statement opposing the Commission on Presidential Debates' decision to limit debate participation to candidates polling above 15 percent in the general election and urging the Federal Election Commission to take action.

This marked a victory for Buchanan's supporters, including leftist activist Lenora Fulani, who had hoped to prevent Trump from appearing on the ballot in his home state.

He voiced dissatisfaction with the presidential contest, explaining that Pat Buchanan was running "virtually unopposed" and receiving support from former Ku Klux Klan leader David Duke; something with which Ventura could not associate.

[104] Ventura's move came just ahead of the Nashville meeting where, with the rationale of failing to "faithfully perform and execute the duties of his office," Gargan was removed by a 109 to 31 committee vote.

[107] The chaotic meeting, dominated by Perot-faction members, featured shoving matches and physical squabbles as the Metropolitan Nashville Police Department intervened to restore order.