Politics Oprah for President? Trump's Win Has Winfrey Considering Her Own White House Run Winfrey 2020. By Diana Pearl Published on March 1, 2017 11:41 AM Share Tweet Pin Email When Donald Trump is president, it seems anything is possible — at least, to Oprah Winfrey. The TV mogul sat down for an interview with Bloomberg’s The David Rubenstein Show this week. During the interview, Rubenstein asked her if fellow TV star Donald Trump’s election to the White House had changed her perspective on running for the top job herself one day. Many have asked — including Stephen Colbert in January — but her answer has always remained no. Until now. Winfrey was quick to say that before, she had brushed away any suggestions that she could be president, thinking she didn’t have the requisite political experience. “I never thought about the question,” she said. “I never even considered the possibility. That’s what I thought.” But after Trump, who had no political experience before entering the White House, was elected, she’s seeing things in a different light. “I thought, oh gee, I don’t have the experience, I don’t know enough,” she said. “Now I’m thinking, ‘Oh. Oh.‘” Winfrey 2020?