The Long History Between Donald Trump and Oprah Winfrey

On Feb. 7, 2011, Donald Trump woke up and hopped onto Twitter. “Be sure to watch Oprah today,” he wrote. “I’ll be on with my entire family and it will be an entertaining hour.”

A little over seven years later Trump, now President of the United States, had something different to say about the media mogul’s latest television appearance on 60 Minutes, dubbing her “very insecure” and saying he hoped she would run for president “so she can be exposed and defeated just like all of the others.”

Trump’s opinions about many people to whom he was previously complimentary have changed over the past year as criticisms have mounted about his presidency. But Winfrey is a bigger target—and one he has lavished with praise in years past.

Most famously, of course, was his 1999 comment on Larry King Live that if he were to run for president, he’d want Winfrey as his running mate.

“I love Oprah,” Trump said. “Oprah would always be my first choice. … I’ll tell ya, she’s really a great woman, though. She is a terrific woman. She’s somebody that’s very special.”

(In that same interview, Trump mentions his fondness for Bill Clinton.)

Ironically, it was on Oprah’s show in 1998 that Trump most publicly began teasing a presidential bid.

On Twitter, Trump has publicly endorsed Winfrey on many occasions, on topics ranging from her decision to start a television network to her ability to get people to talk openly during televised interviews.

Trump has quoted some of Winfrey’s inspirational comments.

Trump was also overjoyed when Winfrey’s network cancelled the talk show of his long-time enemy Rosie O’Donnell after five months.

And Trump has maintained his professed love for Winfrey, even as their political views diverged.

Part of the conflict, of course, comes from the roundabout criticisms Winfrey has made about Trump’s presidency. But it’s possible another reason is a NPR/PBS NewsHour/Marist poll taken earlier this year found Oprah could beat Trump in a presidential race—though most Americans don’t want her to run.

Winfrey seems to agree with the public.

“I am actually humbled by the fact that people think that I could be a leader of the free world, but it’s just not in my spirit, it’s not my DNA,” she said just a few days ago.

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