Sources: Oprah Winfrey 'actively thinking' about running for president - Oprah Winfrey in 96 seconds - Oprah Winfrey is "actively thinking" about running for president, two of her close friends told CNN Monday. - The two friends, who requested anonymity in order to speak freely The Case Against President Oprah - Nope-rah? - BuzzFeed Editor-in-Chief - When Donald Trump was elected in the fall of 2016, some analysts saw the end of normal politics and the rise of a new wave of celebrity candidates.