Donald Trump and Oprah Winfrey
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Back in 2006, Kelly Ripa admitted that Donald Trump was already discussing a possible political career and run for President. Ripa revealed alongside Seth Meyers, “You know what’s crazy, he was talking about running for president then. Then! And I remember actively having this conversation with him. He said, ‘Everybody wants me to run for president,’ and I said, ‘Who.”


Ripa would go on to reveal that she tried talking Donald Trump out of it – but of course, years later it was clear he did not take that advice.

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His potential political aspirations started even before his convo with Ripa. Given a past interview with Oprah Winfrey during the ’80s, it seems evident Trump had a major interest for politics. We’ll take a look back at his conversation with Oprah, and how the two once had a mutual respect for one another before their relationship soured.


Oprah Winfrey Once Wrote A Letter To Donald Trump Supporting His Political Career In The Early 2000s

Via: Instar

Former President Donald Trump plans to release a book which will also include private letters from higher ups he bonded with along the way. Among those people includes Oprah, who had actually endorsed a possible political run with Donald. She wrote in the note, “Too bad we’re not running for office.”

Oprah did respond to the reveal of the note, downplaying it and claiming that she was just trying to supportive at the time. Writing a note was a norm for Oprah.

“And when I heard that this letter is now going to be a part of a book, I thought, ‘Oh, wasn’t that nice of me to write a note.’ That’s what I thought, because I’m always like, ‘Oh, I should write a note. The person did this, or I should write a note,'” she said. “So I’m really happy that I wrote a note.”

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Oprah would go on to confirm that although she thought it was a good idea back then, she feels differently nowadays.

“I might have thought it back then. I might have thought it 23 years ago. I’m not thinking it today,” she added.

The mutual respect between the two was apparent during Trump’s appearance on Oprah’s show way back in the late-’80s.

Oprah Winfrey Seemed To Be Into Donald Trump’s Takes On Politics During His Appearance On Her Show In 1988

The conversation between the two starts with Donald Trump questioning the US and their foreign policy at the time. Trump didn’t think the country was taking advantage of the situation.

Oprah would then as Donald if he had interest in possibly running for President? Trump said he wasn’t at the time given that he was into what he was doing, but did not like the way the country was being handled. Donald would go on to discuss what he would do differently if he was in charge.

It is obvious that Donald’s opinion seemed to be much more valuable back then with others, and that was especially true during his chat with Oprah, as the host seemed to be very much into what he was saying.

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The moment has over 8 million views, and comments from fans are definitely broad and diverse to say the least.

One fan writes, “You would be a great President.” 30 – 40 years later they’re now insulting eachother.”

“Well, at least now we can definitely say that his political agenda is not just a farce to attract the voters. 28 years had passed, so apparently he actually believes in what he stands for.”

RELATED – Country Star Trace Adkins Told Bill Maher He Still Has No Regrets Over His Relationship With Donald Trump

Despite the moment and relationship between the two, it seems like things soured along the way.

Donald Trump Revealed In A Tweet That His Relationship With Oprah Had Soured

Things seemed to have soured along the way, as Oprah seemed to be backing Hillary Clinton during her political run. Trump would take to Twitter and question some of Oprah’s tactics.

He tweeted out, “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!”

Of course, Oprah did not run for President, and she decided not to comment on Trump’s statement, choosing a positive route instead.

“You don’t win by meeting any kind of negativity head-on”.

“I don’t like giving negativity power, so I just thought, ‘What?'”

Yet another broken relationship former President Donald Trump can add to the list.

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