Oprah in 2020? Allies Send Mixed Messages, Trump Says He'd Win - NBC 5 Dallas-Fort Worth
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Oprah in 2020? Allies Send Mixed Messages, Trump Says He'd Win

"I like Oprah. I don't think she's going to run," Trump told reporters in the White House

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    Trump: I Could Beat Oprah

    President Donald Trump said he is confident he could beat Oprah Winfrey if she chose to run in the 2020 presidential election. (Published Tuesday, Jan. 9, 2018)

    President Donald Trump thinks he would beat Oprah Winfrey in a presidential election, but that she won't run anyway.

    His comments came as Democrats nationwide encourage Oprah Winfrey to seek the presidency in 2020 after she gave an impassioned call for "a brighter morning even in our darkest nights" at the Golden Globes on Sunday night.

    Those closest to the media mogul are sending mixed messages about her political intentions. Her best friend, CBS News host Gayle King, said Tuesday that Winfrey is "intrigued" by the idea of a White House bid.

    "She loves this country and would like to be of service in some way, but I don't think she's actively considering it at this time," King said, noting that she spoke to Winfrey at length the night before. "I also know that after years of watching the Oprah show, you always have the right to change your mind."

    Oprah Winfrey: 'Time's Up' Is for 'Women of the World'

    [NATL] Oprah Winfrey: 'Time's Up' Is for 'Women of the World'

    Oprah Winfrey speaks backstage after receiving the Cecil B. DeMille Award.

    (Published Monday, Jan. 8, 2018)

    On Monday, Winfrey's longtime partner, Stedman Graham, told the Los Angeles Times that "it's up to the people" whether she will be president, adding, "She would absolutely do it."

    But Trump indicated on Tuesday that he'd be up for the challenge, saying a contest between the two former TV stars "would be a lot of fun" but that he'd win. 

    "I like Oprah. I don't think she's going to run," Trump told reporters in the White House, adding that he knows her well and was on her show as it came to a close.

    The presidential buzz follows Winfrey's speech, which left some viewers contemplating the idea of the Democratic Party embracing a celebrity candidate of its own to challenge Trump in 2020. Trump, of course, was little more than a businessman-turned-reality-television-star before his extraordinary political rise.

    House Minority Leader Nancy Pelosi, D-Calif., noted that Winfrey, like Trump, lacks any kind of governing experience.

    "I think one of the arguments for Oprah is 45," Pelosi said, referring to Trump in shorthand for the 45th president. "I think one of the arguments against Oprah is 45."

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    (Published Saturday, June 23, 2018)

    Even so, for Democrats in early voting states, and perhaps for a public that largely disapproves of Trump's job performance, the notion of a popular media figure as a presidential candidate is not as strange as it once seemed.

    "Look, it's ridiculous — and I get that," said Brad Anderson, Barack Obama's 2012 Iowa campaign director, who supports the idea of Winfrey running. "At the same time, politics is ridiculous right now."

    Winfrey's speech as she accepted the Cecil B. DeMille lifetime achievement award touched on her humble upbringing and childhood wonder in civil rights heroes.

    But it was her exhortation of the legions of women who have called out sexual harassers — and her dream of a day "when nobody has to say 'me too' again" — that got some influential political operatives thinking Winfrey might be just what the Democrats need. Her appeal extended well beyond her celebrity, some said, citing her compassion, kindness and devotion to helping others as a badly needed change after Trump.

    "People need to have hope," said Ray Buckley, chairman of the New Hampshire Democratic Party, who encouraged the idea of an Oprah run. "If it means looking at one of these celebrities that have a moral core, that are compassion and intelligent, I think that people should look to where they can during these very, very difficult times."

    Even Trump's daughter Ivanka endorsed Oprah's message, if not a political future, in a tweet Monday. "Just saw @Oprah's empowering and inspiring speech at last night's #GoldenGlobes. Let's all come together, women & men, & say #TIMESUP! #UNITED."

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    (Published Saturday, June 23, 2018)

    Trump's job approval rating sat at just 32 percent in December, according to an Associated Press-NORC poll. And though polls show his approval up slightly since, Trump is the least popular first-year president on record. He has also been accused by multiple women of sexual misconduct, though he has vehemently denied the allegations.

    Winfrey, in September and October, publicly dismissed the notion of seeking the nation's highest office, though she noted that Trump's victory made her rethink the requirements of the office.

    The 64-year-old media mogul has become a cultural phenomenon over the past 30-plus years, born into a poor home in Mississippi but breaking through as a television news and talk show personality in the 1980s. Over 30 years, she became the face of television talk shows, starred and produced feature films, and began her own network.

    Trump himself has lavished praise on Winfrey over the years, including in 2015, when he said that he would consider her as a running mate on his Republican ticket. "I'd love to have Oprah. I think we'd win easily, actually," Trump told ABC News at the time.

    Late-night show host Jimmy Kimmel said Monday that he preferred Winfrey to Trump.

    "Given the choice between Oprah and our current president, I'm on the bus with Oprah traveling the country encouraging people to sign up and vote," he said.

    'Late Night': A Closer Look at Wednesday's Trump Rally

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    (Published Friday, June 22, 2018)

    Some political operatives think she has what it takes to be a viable presidential contender.

    "She would be a serious candidate," said Jennifer Palmieri, former White House communications director under President Barack Obama and the communications director for Hillary Clinton's 2016 campaign.

    Beyond her rise from poverty, Winfrey's success as a multidimensional media figure has come from promoting ways for women to assert themselves, typically outside the political arena. That could soften what Palmieri describes as an enduring resistance among some voters to women with political ambition.

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    Colin Quinn shares his frustration with people critiquing his fashion, as well as what he's gone through in the aftermath of having a heart attack.

    (Published Friday, June 22, 2018)

    "I think lessons we all learned from watching Hillary's run, and how her ambition was unfavorably and unfairly viewed, coupled with Oprah's existing popularity, could give Oprah a strong start," Palmieri said.

    NBC's Asher Klein and Associated Press writers Andrew Taylor and Dave Bauder contributed to this report.