Oprah Winfrey And Donald Trump: Inside Their 30-Year History Together

John SalangsangAP Images

Oprah Winfrey has never claimed to best friends with Donald Trump, but for decades she had a warm and friendly relationship with the future president. Now it seems to be game on for Oprah and Donald after the President called out the media mogul for a discussion with voters she moderated for 60 Minutes. Oprah and the panel talked about Trump’s stability and sexual harassment claims against him, and they questioned if he is fit for office. The President promptly issued an angry retort after Winfrey’s 60 Minutes segment aired, taking to Twitter to write the following.

“Just watched a very insecure Oprah Winfrey, who at one point I knew very well, interview a panel of people on 60 Minutes. The questions were biased and slanted, the facts incorrect. Hope Oprah runs so she can be exposed and defeated just like all of the others!”

Donald Trump’s angry words about Oprah are in stark contrast to his past comments about her. Donald and Oprah have engaged in friendly banter for at least 30 years. According to IMDB, Trump made at least eight appearances on Winfrey’s talk show between 1988 and 2011. One of the appearances included a rare sit down with all five of Donald’s kids.

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In one of his earliest appearances on The Oprah Winfrey Show, Donald Trump teased a future presidential run. At the time, Donald said he didn’t think he would ever run for office, but he added that he would never rule anything out. Trump and Winfrey even joked that the presidency doesn’t pay as well as his job as a businessman.

Oprah has long been a big fan of Donald Trump’s Mar-a-Lago resort. In happier times, Oprah even convinced Donald to shut down his popular club for a long weekend so she could host pal Maya Angelou’s 80th birthday party there in 2008. According to the Daily Meal, Oprah also featured some of the recipes from Mar-a-Lago on The Oprah Winfrey Show. Winfrey once said of Mar-a-Lago’s turkey burger: “I believe [it] may be the best turkey burger in the entire world.” Winfrey even posted the recipe for the burger, which is topped with a pear chutney, on her website. Mar-a-Lago’s key lime pie also made it on to Oprah’s website.

In 1999, Trump spoke glowingly of Oprah Winfrey, telling talk show host Larry King she would be his top pick for a vice presidential running mate should he ever decide to run.

“I love Oprah,” Trump said at the time. “Oprah would always be my first choice. She’s a terrific woman, she’s somebody that’s very special. If she’d do it, she’d be fantastic. She’s popular, she’s brilliant, she’s a wonderful woman.”

Trump even referred to Oprah as his “friend” in an interview with Hardball‘s Chris Matthews that same year.

“I threw out the name of a friend of mine, who I think the world of,” Trump told Matthews of his idea for a potential running mate. “She’s great. And some people thought it was an incredible idea, some people didn’t, but Oprah. I said, ‘Oprah Winfrey,’ who’s really great. And I think we would be a very formidable team.”

As a further show of support for Oprah, in 2005, Donald and Melania Trump went to the opening night of Winfrey’s Broadway play The Color Purple. Trump has also publicly praised Oprah on Twitter, tweeting in 2012 that he “adore[s]” her. Donald called Oprah “terrific” in a 2013 tweet.

As recently as 2015, Donald Trump touted his love for Oprah, telling ABC News that he would love to have Winfrey as his running mate.

“I like Oprah, what can I tell you?” Trump told ABC’s George Stephanopoulos in 2015. “She’s great, she’s talented, she’s a friend of mine, she’s a good person…I’d love to have Oprah, I think we’d win easily, actually.”

More recently, Trump’s tune has changed. While Oprah maintains she has no interest in running for office, rumors recently surfaced that she’s considering a political run. Last month, the president told reporters in the Cabinet Room that he had no fear of Oprah, but he still said he liked her as a person.

“Yeah, I’ll beat Oprah,” Trump said. “Oprah would be a lot of fun. I know her very well… I like Oprah. I don’t think she’s going to run.”

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While she made it clear she was Team Hillary during the 2016 Presidential election, Oprah told Entertainment Tonight she felt reassured after seeing then-president-elect Trump at the White House with President Obama, saying it gave her “hope.” Shortly after the election results were announced, Winfrey even told the Associated Press that she noticed a change in Donald Trump’s demeanor after he won the election.

“I could sense, maybe I’m wrong, but I could sense from Donald Trump’s body language even when he came out for the acceptance speech, that brotha has been humbled by this world thing,” Oprah told the AP. “I think it’s a humbling process that now you literally have the weight of the world on your shoulders.”

But in an interview with the Los Angeles Times, Oprah said she didn’t really know the man who would ultimately become the 45th President of the United States.

“Both Gayle and I know Donald and we have seen him around and have had conversations with him,” Oprah said. “Every time we see him, and we say, ‘What is going on?’ and he’s like, ‘Well, you know me,’ and I’m like, ‘I thought I did’… I don’t know this person that he is presenting to the world. That’s all I’ll say.”