Had you ever heard of the campaign that the eventual 45th and 47th president ran years before his 2016 campaign?

Even a few years before the hit show The Apprentice aired, the businessman was already laying the groundwork and exploring the possibility of a future presidential run.

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Photo by Jed Jacobsohn/Allsport/Getty Images
Photo by Jed Jacobsohn/Allsport/Getty Images
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In 1999, speculation about a presidential run by Donald Trump began to grow, with reports that Jesse Ventura encouraged him to consider running.

While Trump and his advisors explored the idea through polling and even a political book project, he publicly downplayed the possibility. However, polls showed some early support against figures like George W. Bush and Al Gore, signaling that the idea of a campaign was gaining attention.

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Two months later, as Pat Buchanan prepared to seek the Reform Party nomination, Donald Trump said he would consider running against him.

Trump considered a run while sharply criticizing Buchanan’s views and preparing for what he expected would be a ‘nasty’ primary battle. As media attention grew, Trump fueled speculation through a planned book, public statements, and interviews, ultimately saying he would only run if he believed he could win and confirming he was ‘very serious’ about a campaign.

On October 7th, 1999, during an appearance on Larry King Live, Trump announced the formation of an exploratory committee for a Reform Party presidential run.

Doing so, Trump floated Oprah Winfrey as a possible running mate. He outlined a mix of conservative and liberal positions—supporting universal healthcare while opposing NAFTA and gun control—but faced skepticism from critics who believed the effort was more about publicity than a genuine campaign.

Trump withdrew from the 2000 presidential race on February 14th, 2000, citing infighting within the Reform Party and saying it was no longer a viable path to victory.

He criticized the party’s direction and leadership, said he didn’t believe he could win the general election, and later explained that factors such as debate rules, John McCain’s rising campaign, and Ventura’s political departure also influenced his decision, while still leaving the door open for a future run.

Photo by Diane Freed
Photo by Diane Freed
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And there you have it! Before he ran and eventually won campaigns in 2016 and 2024, Trump had vied for the office in 2000.

What are your thoughts on this? We’d love to hear from you! Feel free to join the conversation by messaging us on the app.

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