Oprah and Trump go way, way back together. Here’s proof.

Senior Editor
Yahoo News

Amid frenzied speculation over a potential challenge from Oprah Winfrey in 2020, President Trump told reporters at the White House on Tuesday that running against her “would be a lot of fun,” and he would beat her — but also said he doesn’t think she’s going to run.

If she does, though, expect to see a continuous loop of clips from Trump’s numerous appearances on Winfrey’s daytime talk show — and never-ending analysis of Trump’s long public friendship with his fellow media billionaire, whom he once said would be his ideal running mate.

In 1988, Trump appeared on the “Oprah Winfrey Show” to promote his then just-released business book-cum-memoir, “The Art of the Deal.” And Winfrey asked the real estate mogul how he learned the aforementioned art.

“I really think you have it or you don’t have it,” Trump replied. “And I hate to say that, because it’s something I feel very strongly about. But you either have it or you don’t. And once you have it, if you have it, then you go out and you hone those skills.”

In a 2004 discussion about his hit reality television show “The Apprentice,” an audience member asked Trump and Winfrey for tips on how they approach dealmaking. “There’s an indescribable ‘it’ factor, that, you know, I don’t think you can teach,” Winfrey said. “They don’t teach it in the Wharton School of Business. It’s not something you can even learn — there’s just an ‘it,’ wouldn’t you say, Donald?”

“That’s true,” Trump replied. “And I will tell you, I went to the Wharton School of Finance, and I will say I am sitting next to it.”

The audience erupted in applause.

“There is nobody ever that has had ‘it’ more,” Trump said.

Trump has expressed public admiration for Winfrey on other talk shows. In 1999, when he first explored a run for president, Trump was asked by CNN’s Larry King who he might choose as a running mate.

“Oprah,” Trump replied. “Oprah would always be my first choice.”

Trump said the same thing at a town hall event hosted by MSNBC’s Chris Matthews later that year.

“I think we would be a very formidable team,” he said.

In 2016 — before Trump chose Mike Pence as his running mate — Winfrey, who supported Barack Obama, was asked by ABC’s Jimmy Kimmel what she would say if she got a call from Trump to join his campaign against his Democratic rival, Hillary Clinton.

“I would say, ’Donald, I’m with her,’” Winfrey said to applause.

During the same interview, Winfrey insisted she would never consider a bid for public office.

“It’s the one thing I know for sure, sure, sure is that I will never run for office,” she said. But Winfrey also admitted that Trump’s unlikely candidacy had made her rethink that position.

“Until this election year I thought, ’Wow. Why do people say that? I have no qualifications to run,’” she explained, adding: “I’m feeling pretty qualified.”

In that 1988 interview, Winfrey asked Trump whether he would ever consider running for president.

“Probably not,” Trump said. “I probably wouldn’t do it, Oprah. I probably wouldn’t, but I do get tired of seeing what’s happening with this country. And if it got so bad, I would never want to rule it out totally. Because I am really tired of seeing what’s happening with this country — how we’re really making other people live like kings and we’re not.”

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