Why Does Donald Trump Hate Oprah?

Donald Trump has had his fair share of feuds since he became president, but his shots at Oprah Winfrey seem a bit strange considering the two used to be friends. She was targeted after many thought she was going to run against him in 2020, even though she has since tried to dispel those rumors.

So why is he still going after her now and how has she responded to all this? Here’s a little more about their past relationship and their current feud.

Trump once said he wanted Winfrey to be his running mate

A composite image of Donald Trump and Oprah

Left: Donald Trump | Chip Somodevilla/Getty Images, Right: Oprah Winfrey | Jemal Countess/Getty Images

In 1998, Trump appeared on Winfrey’s talk show and spoke then about a possible presidential bid someday. Then, in 1999 while on Larry King Live, Trump revealed that he would want Winfrey to be his running mate.

“I love Oprah,” he 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. I think if she’d do it, she’d be fantastic. I mean she’s popular, she’s brilliant, she’s a wonderful woman.”

Next: Nothing but love over the years

Trump praised Lady O many times over the years

President Donald Trump

Trump has supported Winfrey in the past. | Pool/Getty Images

Not only did Trump speak so highly of Winfrey on King’s show, he also continued to sing her praises for years and endorsed her on many occasions via social media.

In regards to her OWN network, he tweeted that “she knows how to win” in 2012. And in 2013, he applauded her interviewing skills and ability to get Lance Armstrong to open up about doping. Trump has even tweeted inspirational quotes from Lady O.

Next: A very presidential speech

2020 talks heat up after Winfrey’s Golden Globes speech

Actress and TV talk show host Oprah Winfrey poses with the Cecil B. DeMille Award during the 75th Golden Globe Awards

Winfrey gave a rousing Golden Globes speech. | Frederic J. Brown/AFP/Getty Images

Talks of Winfrey running for president one day is nothing new, but those talks really heated up after she gave a powerful and uplifting speech when she accepted the Cecil B. de Mille Award at the 75th Golden Globes.

Winfrey brought the crowd to their feet, and almost immediately, reports surfaced that she was going to run for office in 2020.

Next: Was this the turning point?

Poll shows Winfrey could unseat Trump

Oprah Winfrey smiling

Winfrey has an edge. | Mike Windle/Getty Images

Winfrey and Trump have very different political views, and a poll that showed Winfrey could win in a presidential race is the point that likely tipped the scales and ticked off Trump.

The NPR/PBS NewsHour/Marist poll had Winfrey with 50% of the votes compared to Trump’s 39%.

Next: Guess who feels differently?

Trump says he would defeat Winfrey if she ran

Us President Donald Trump walks from Marine One on the South Lawn of the White House as he returns from his weekend trip to Mar-a-Lago, on February 12, 2017, in Washington, DC.

Trump is sure he could take her. | Molly Riley/AFP/Getty Images

Despite what the results of any hypothetical poll showed, the president said he is confident that if Winfrey went up against him, he would defeat her.

“Yeah, I’ll beat Oprah,” he told reporters in the Cabinet Room during a meeting on immigration with members of Congress. He then added that he didn’t think she would actually run though.

Next: And the name calling begins

Trump calls Winfrey ‘very insecure’

Donald Trump at World Economic Forum

Trump has resorted to name calling. | Fabrice Coffrini/AFP/Getty Images

Whether or not Trump still feels Winfrey will run for office, he decided to call her out and dare her to do so following a piece she did for CBS’s 60 Minutes, which addressed his presidency.

“Just watched a very insecure Oprah Winfrey, who at one point I knew very well, interview a panel of people on 60 Minutes,” he tweeted. “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!”

Next: What Lady O had to say to that

Winfrey responds to Trump’s tweets about her

Oprah Winfrey in 2016

Winfrey let Trump’s comments slide off her back. | Paras Griffin/Getty Images

Winfrey did not respond to Trump on Twitter, but she did talk about what she thought of his tweet when she appeared on The Ellen DeGeneres Show the next day.

“I woke up and I just thought …” Winfrey said, raising her hands and shrugging. “I don’t like giving negativity power, so I just thought, ‘What?’ …  I was working very hard to do the opposite of what I was hate-tweeted about, [but] it’s OK.”

In that same show, DeGeneres defended Winfrey and had this warning for the president, “Oprah is my friend and when you mess with Oprah, you mess with me.”

Follow Michelle Kapusta on Twitter @philamichelle.

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