Here's What Trump Has Said About Oprah In The White House

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Back in March 2017, Oprah Winfrey's best friend Gayle King said the following about the media mogul's potential of running for president in 2020: "I would bet my first, second-born, and any unborn children to come, that ain't never happening. Never. I'll say never on this one. Nevah, N-E-V-A-H. Nevah."
In a brief interview she gave as she was getting into her car right after the Golden Globes last night, King was singing a different tune. "President Winfrey, doesn't that have a nice sound? It could be Madame President. But you know, the people have to decide. She's always said no, but I did think the speech took things to a different level tonight," King told X17 Online's videographer.
Oprah does like to say that everyone deserves the right to change their mind.
Long before her soul-stirring Golden Globes speech, speculation had swirled about Oprah running for president, a testament to our national fascination with celebrity politicians that goes back at least as far back as Ronald Reagan's presidency.
Although Oprah denied that she was going to run in a backstage interview after the awards show, earlier today CNN reported that two of her close friends anonymously said she is "actively thinking" about it, although she hasn't made up her mind. (Gayle? Is that you again?) And her longtime partner, Stedman Graham, told The L.A. Times that if the people wanted it, "She would absolutely do it." Judging by the popularity of #Oprah2020, many people do want it, but throughout the years she has both hinted at running and said she would never run.
"We welcome the challenge, whether it be Oprah Winfrey or anybody else," White House deputy press secretary Hogan Gidley told reporters today, adding that Donald Trump is "absolutely…going to run for president again" (provided he finishes his first term).
Before the turmoil of 2016, Oprah apparently also had the chance to participate in national politics in a different way — as the vice president. Discussing his rising star and the formation of a committee to explore a presidential run, Trump said in 2000's The America We Deserve (co-written with Dave Shiflett):
"At that time I announced that my first choice for vice president would be Oprah Winfrey. Again the political elites chortled — Oprah Winfrey! They just don't understand how many Americans respect and admire Oprah for her intelligence and caring. She has provided inspiration for millions of women to improve their lives, go back to school, learn to read, and take responsibility for themselves. If I can't get Oprah, I'd like someone like her."

Again the political elites chortled — Oprah Winfrey! They just don't understand how many Americans respect and admire Oprah for her intelligence and caring.

Donald Trump
Shiflett tells Refinery29 that he interviewed Trump for the book back in 1999. "At the time, I didn't think he was truly serious about running for president. In fact, he stopped 'considering' the possibility of pursuing the office not too long after the book came out. Oprah, of course, was very well-known — she had name recognition any politician would die for, including Trump."
In 1999, Trump again said he'd like Oprah to be his running mate during a town hall with MSNBC's Chris Matthews. "Would you consider a woman for your running mate, and if so, who?" Matthews asked. "Oprah Winfrey, who's really great," Trump said. "And I think we would be a very formidable team." That same year, he also told CNN's Larry King, "Oprah would always be my first choice."
And as recently as 2015, he told ABC that "I'd love to have Oprah" as a VP and "I think we'd win easily, actually." Over the years, he's also tweeted inspirational quotes by Oprah, and compliments to her.
It's easy to see why Trump would want another name-brand celebrity on his ticket. But it's difficult to imagine how a Trump/Oprah ticket would ever actually have happened, given his history of lashing out at prominent women with sexist comments. Also, if she were to run against him in 2020, would he dare defy...Oprah?
While Oprah has always been diplomatic about Trump — even getting into hot water when she tweeted, "Everybody take a deep breath! #HopeLives," after the 2016 presidential election — if she did run, she would still be squaring against a man who has been accused of sexual harassment by at least a dozen women.
Here's what Oprah had to say about powerful men like him abusing their power at the Golden Globes, as she accepted her Cecil B. DeMille lifetime achievement award: "For too long, women have not been heard or believed if they dared to speak their truth to the power of those men."
She added: "But their time is up. Their time is up!"

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