“I wasn’t even aware that Trump had run before in 1999.”
Probably because he didn’t LOL!
(Though he did ‘consider’ it).
"The Donald Trump presidential campaign of 2000 for the nomination of the Reform Party began when real estate magnate Donald Trump of New York announced the creation of a presidential exploratory committee on the October 7, 1999 edition of Larry King Live. Though 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 convinced 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 the presidential campaign of industrialist Ross Perot, the party's 1996 presidential nominee. Trump's entrance into the Reform Party race coincided with that of paleoconservative commentator Pat Buchanan, whom Trump attacked throughout the campaign as a "Hitler-lover."
"Trump focused his campaign on the issues of fair 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 girlfriend Melania Knauss 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. Though he never expanded the campaign beyond the exploratory phase, Trump made numerous media appearances as a candidate, traveled to campaign events in Florida, California, and Minnesota, and qualified for two presidential primaries. Veteran campaign strategist and 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. Though 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 seven percent support. Despite his withdrawal, Trump won both primaries for which he qualified."