Flirts with a 2000 presidential run
Donald Trump briefly tested the waters for a presidential run in 1988, but it wasn't until 1999 when the Trump self-promotion machine went into full force.
Fresh off his divorce from Marla Maples, flaunting his new girlfriend (and now-wife) Melania Knauss, and promoting a new book that laid out his political views, Trump sensed a possible political opening. The Reform Party, the party created by Ross Perot after his 1992 presidential run and the vehicle for his 1996 run, was set to receive federal funding in 2000 after Perot received eight percent of the vote in 1996. Trump started talking up a possible Reform Party bid, pitting him against famous conservative Pat Buchanan.
In his book, "The America We Deserve", he proposed a one-time 14.25 percent tax on those worth more than $10 million (he was on that list) and suggested the country could use a wily businessman like him as president.
"The dealmaker is cunning, secretive, focused and never settles for less than he wants," Trump wrote. "It's been a long time since America had a president like that."
And, perhaps leaving some wiggle room in case he didn't follow through with his presidential flirtation, Trump added, "Do I need to be president to feel good about myself? I feel pretty good right now."