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 electe
Donald Trump with President Ronald Reagan in 1987, when Trump first considered running for president.
Trump with President Bill Clinton at Trump Tower in 2000
Minnesota Governor Jesse Ventura privately encouraged Trump to run.
Melania Knauss was touted as Trump's potential First Lady.
Melania Trump
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Melania Knauss Trump is a Slovenian and American former model serving as the first lady of the United States since 2025, a role she previously held from 2017 to 2021 as the third wife of Donald Trump,
Donald Trump 2000 presidential campaign
…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…
Trump in 2026
Donald Trump and Melania Knauss in 1999
Melania Knauss (on the right) with then-president Bill Clinton, Donald Trump, and Kylie Bax (listed right to left) in 2000