If Oprah’s Not Running for President, She Has a Funny Way of Showing It

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Oprah. Photo: Paras Griffin/Getty Images

For at least two decades, people have been talking about Oprah Winfrey running for the White House. One of the earliest people to do so was Donald Trump, who was flirting with a run as member of the Reform Party in 1999 when he told Larry King that Winfrey would be his VP pick.

Publicly, Oprah’s largely laughed off the idea of running for president, but in recent months something’s changed. Maybe it was Trump’s election, which proved that political neophytes with gobs of money can win the White House. Or maybe, six years after the end of her show, Stedman is just getting on her nerves.

Whatever the reason, Oprah is no longer shying away from talk about her running for president. She’s leaning right in. The latest example came Thursday night, when Winfrey, or the well-paid social-media maven in her employ, endorsed an article endorsing her for president.

In the piece Oprah tweeted, John Podhoretz writes that she’s uniquely positioned to challenge Trump in 2020, if she so chooses.

If you need to set a thief to catch a thief, you need a star — a grand, outsized, fearless star whom Trump can neither intimidate nor outshine — to catch a star. We’re through the looking glass here. America is discarding old approaches in politics. Democrats will have to do the same to match the mood to the moment.


And that’s where Oprah Winfrey comes in. She is the mirror image of Trump, but more so. Of course, she’s female and he’s male; she’s America’s generous aunt and he’s America’s crazy uncle. And yes, she’s black and he’s white, she’s liberal and he’s whatever he is.

It’s important to note that this piece didn’t just spring from the mind of a political pundit. Oprah courted it with her first segment as a correspondent on 60 Minutes. Titled “Divided,” the piece saw Oprah travel to Michigan to speak to supporters and despisers of President Trump.

We’ve seen plenty of these round tables since the beginning of the Trump presidency, but none that came with Oprah’s thoughtful questions and sympathetic nods. Oprah made billions by being a good listener, a skill that would serve her well as a politician.

If Trump does end up with a challenge from Oprah in 2020, he’ll have no one to blame but himself. In March, she told Bloomberg that Trump’s 2016 win made her realize that she might have been overestimating the qualities and background needed to be president.

“I thought, ‘Oh, gee, I don’t have the experience, I don’t know enough.’ And now I’m thinking, ‘Oh,’” she said.

Oprah Is Inching Ever Closer to Announcing Her Run for 2020