"Yeah, I'll beat Oprah", Trump said when asked about Winfrey's potential candidacy by a White House pool reporter on Tuesday, as seen in the video below. He then shared his opinion that he didn't think Winfrey would run but that she "would be a lot of fun".
"I think Oprah's an icon in this country and frankly throughout the world, and she's got a huge following that's really not political and she clearly speaks very powerfully to women at this point in our political discourse and our society".
Donald Trump's former Press Secretary said Oprah doesn't have the "political infrastructure" to win a presidential campaign. It was very nice...
"I do think she's intrigued by the idea, I do think that", King said on the CBS This Morning program.
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 odd as it once seemed.
The presidential buzz follows Winfrey's impassioned call for "a brighter morning even in our darkest nights" at the Golden Globes on Sunday night in a speech that left some viewers contemplating the idea of the Democratic Party embracing a celebrity candidate of its own to challenge Trump in 2020.
Two of Winfrey's friends, who were not identified, told CNN on Monday that she was "actively thinking" about running for president.
Oprah confidante Gayle King said earlier there was no change in Oprah's past position, that she was not interested in running for president.
This isn't the first time Winfrey's name has been tossed into the political ring.
Reagan does not believe Winfrey purposely tried to stoke talk of a presidential 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 hard times".
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.
Ahead of taking the Golden Globes stage, Winfrey read her speech to King, who knew that it was "going to be killer". I want all the girls watching here and now to know that a new day is on the horizon.
Oprah has always been associated with Democratic politics and fundraising and was a vocal early supporter of former president Barack Obama. "I will do whatever it takes because I am so concerned about what's happening, '" she discloses.
"She really wanted to give a message of hope, which she did", King says of Winfrey's intention behind the message.
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