It's worth considering that Oprah Winfrey could make a strong run for President in 2020. Many feel that a woman president needs to happen for the left as a trophy for equality. Trump has proven that political experience doesn't have to be a prerequisite for being President. Oprah has way less dirt on her than Hillary, and has a very strong grassroots following, name recognition, and money. I think the more relevant question isn't "would she win?", it's "would she run?"
http://money.cnn.com/2018/01/08/media/op...index.html
http://money.cnn.com/2018/01/08/media/op...index.html