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When Trump ran for president in 2000 as a Reform Party candidate, Winfrey was, ironically, his choice for a running mate. But 18 years later, his views on his former almost running mate have drastically changed. Here is the transcript of a 1999 interview with CNN's Larry King in which Trump describes his plans.
"Just watched a very insecure Oprah Winfrey, who at one point I knew very well, interview a panel of people on 60 Minutes. The questions were biased and slanted, the facts incorrect. Hope Oprah runs so she can be exposed and defeated just like all of the others!" Trump tweeted Sunday evening.
But with Trump, there's always a tweet demonstrating either his complete hypocrisy or willful ignorance of his own Twitter history.
In 2012, Trump praised Oprah about her ability to win. "Oprah will end up doing just fine with her network--she knows how to win." Trump tweeted as Winfrey was launching her own TV network.
Trump may love having Winfrey as a presidential challenger in 2020, but she has denied any interest in seeking the nation's highest office.
In January, Winfrey told 60 Minutes she had no interest in running for president.
"I've always felt very secure and confident with myself in knowing what I could do and what I could not," she said. "And so it's not something that interests me. I don't have the DNA for it. ... That's not for me."
This point was reiterated on Sunday night. Winfrey said that while she appreciates the public's enthusiasm about her, "it has never felt to me that that was supposed to be political — and it still does not feel that to me. So I am actually humbled by the fact that people think that I could be a leader of the free world, but it's just not in my spirit, it's not my DNA."