OPRAH DONALD TRUMP

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Donald Trump Teases a President Bid During a 1988 Oprah Show | The Oprah Winfrey Show | OWN

Donald Trump Teases a President Bid During a 1988 Oprah Show | The Oprah Winfrey Show | OWN

Donald Trump is perhaps best known for the money he's made (and lost) in real estate, his less-than-humble demeanor and his hit reality TV show, 'The ...

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Oprah Winfrey on Running for President & Trump

Oprah Winfrey on Running for President & Trump

Oprah talks about her relationship with Donald Trump, her feelings on his insulting tweet about her, and she explains how all of the rumors about her running for ...

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Trump in 1999: Oprah would be my VP choice

Trump in 1999: Oprah would be my VP choice

On October 7, 1999, Donald Trump talk to CNN's Larry King about why he is considering a run for the Reform Party's presidential nomination and that Oprah ...

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Oprah on Donald Trump Calling Her 'Insecure'

Oprah on Donald Trump Calling Her 'Insecure'

Extra's” Tanika Ray sat down with Oprah Winfrey, Reese Witherspoon and Mindy Kaling — stars of the upcoming Disney film “A Wrinkle in Time” — today to talk ...

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Living the Trump Life: "I've Got What I Want, and I Love What I Do" | The Oprah Winfrey Show | OWN

Living the Trump Life: "I've Got What I Want, and I Love What I Do" | The Oprah Winfrey Show | OWN

'Oprah Show' cameras follow entrepreneur Donald Trump through apartment and office to get a glimpse into his daily life. (Original airdate: February 20, 2009).

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If Oprah had 10 minutes with Trump ...

If Oprah had 10 minutes with Trump ...

Oprah Winfrey talks to CNN's Van Jones about what she would say to President Trump if she could talk to him in person for 10 minutes.

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Why Donald Trump Jr. Doesn't Like Using the Trump Name | The Oprah Winfrey Show | OWN

Why Donald Trump Jr. Doesn't Like Using the Trump Name | The Oprah Winfrey Show | OWN

Oprah Winfrey sits down with Donald Trump and his eldest son, Donald Jr., to find out what it was like growing up Trump. (Original airdate: February 20, 2009).

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Trump tells Oprah his political views in 1988

Trump tells Oprah his political views in 1988

Oprah Winfrey interviewed Donald Trump on her show in 1988. He spoke about several issues that he has readdressed recently as a presidential candidate.

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Oprah Winfrey Reacts to President Trump's 'Hate' Tweet

Oprah Winfrey Reacts to President Trump's 'Hate' Tweet

The 64-year-old TV icon opened up on Thursday's 'The Ellen DeGeneres Show' about the President's remarks.

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Donald Trump on Oprah's "It" Factor | The Oprah Winfrey Show | Oprah Winfrey Network

Donald Trump on Oprah's "It" Factor | The Oprah Winfrey Show | Oprah Winfrey Network

Oprah Winfrey and Donald Trump express their thoughts on the 'it' factor, and Donald shares why he believes Oprah is a prime example of someone who has 'it' ...

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Ellen Defends Oprah Against the President

Ellen Defends Oprah Against the President

Ellen noted that the President went too far with his recent tweet about an "insecure" Oprah, but when you mess with Oprah, you mess with Ellen.

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President Donald Trump: Oprah Won't Run In 2020, But I Could Beat Her | The 11th Hour | MSNBC

President Donald Trump: Oprah Won't Run In 2020, But I Could Beat Her | The 11th Hour | MSNBC

Responding with his usual bravado and bluster, Trump brushes off the idea that Oprah Winfrey could challenge him for the White House in 2020. But will she?

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'Extra' with Donald Trump over the Years - Our Rare Interview Moments

'Extra' with Donald Trump over the Years - Our Rare Interview Moments

Just in time for his inauguration on Friday, “Extra” is taking a trip down memory lane with President-elect Donald Trump. “Extra” has been following Trump for ...

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Ivanka on What Growing Up Trump Was Like | The Oprah Winfrey Show | Oprah Winfrey Network

Ivanka on What Growing Up Trump Was Like | The Oprah Winfrey Show | Oprah Winfrey Network

Donald Trump's daughter Ivanka Trump was interviewed about what it was like growing up with a billionaire father. (Original airdate: February 20, 2009).

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Oprah to Marla Maples: Is Donald Trump Controlling? | The Oprah Winfrey Show | Oprah Winfrey Network

Oprah to Marla Maples: Is Donald Trump Controlling? | The Oprah Winfrey Show | Oprah Winfrey Network

Marla Maples opens up to Oprah about her highly publicized affair with Donald Trump during his marriage to Ivana Trump. For more on #oprahwinfreyshow, visit ...

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