The Time When Donald Trump Took a Dig at Oprah Winfrey, Daring Her to Run for President
In early 2018, a war of words erupted between former President Donald Trump and media mogul Oprah Winfrey. It all started after Winfrey hosted a segment on CBS's 60 Minutes. There she interviewed a panel of Michigan voters - half who had voted for Trump and half who had not.
The segment looked at whether Trump's pro-voter panelists still backed him after his first year in office. It delved into topics like his alleged "shithole countries" comments, America's reputation abroad under his leadership, questions about his stability and fitness for office, and accusations of inappropriate sexual behavior against him.
Trump was not pleased with how Winfrey moderated the discussion. On February 19th, 2018, he fired off an angry tweet calling Winfrey "very insecure" and accusing her of posing "biased and slanted" questions with "incorrect" facts.
He defiantly added, "Hope Oprah runs so she can be exposed and defeated just like all of the others!" The tweet referenced rising calls for Winfrey to run for president in 2020 after her inspiring speech at the Golden Globes that praised the #MeToo movement. Speculation reached a fever pitch, with one poll even showing her leading Trump by 11 percentage points in a hypothetical match-up, as per CNN.
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 J. Trump (@realDonaldTrump) February 19, 2018
Winfrey repeatedly dismissed the notion, telling 60 Minutes, "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 in my DNA."
She said she never felt a calling from God to run. The media titan stood by her 60 Minutes reporting as fair and balanced. "I was working hard to do the opposite of what I was hate-tweeted about," she told Ellen DeGeneres, revealing she re-watched the tapes and had the team add a pro-Trump voice to make it more impartial, as per ABC News.
When Jimmy Kimmel asked if she ever felt insecure in light of Trump's insult, Winfrey paused, struggling to think of a time she had insecurity issues in the past 35 years. She made it clear she never considered tweeting Trump back.
While Trump hoped Winfrey would run so he could "expose and defeat" her, their relationship wasn't always so adversarial. In 1999, he told Larry King that Winfrey would be his first pick for vice president if he ever ran, calling her "brilliant," "a wonderful woman," and saying they'd make a "pretty good ticket" together.
The boldness of Trump attacking such a beloved media figure sparked outrage. Many felt it was racist and misogynistic of the former president to go after Winfrey, a self-made African American woman who had achieved enormous success through hard work and inspirational leadership. In the end, Winfrey opted not to run in 2020, leaving Trump to seek re-election against a different opponent.
