Prediction: Oprah Winfrey is not going to run for President.
Winfrey has spent decades making herself a beloved figure in the media, and even many on the Right express a lot of admiration for her even as her partisan affiliation has been more direct. But the reality is that the minute you run for President you automatically become a polarizing figure, and Winfrey will be no exception to this rule. Her Leftist views and kooky conspiracy theories (especially playing to anti-vaxxers) will bring attacks hard and fast. In fact, that has already happened across conservative media.
I do not believe Winfrey has any appetite for becoming a polarizing figure, despised by half of the country. That will happen if she runs, and for the last several decades she has been comfortable with being generally loved or at least admired. The inevitability of being hated by half the country is not a slam on Winfrey: That happens to every major party candidate for President, win or lose. I cannot imagine her wanting that.
The scorn heaped on her over the last week since the “Oprah 2020” speculation started is a tiny taste of what she will get if she actually runs for President. The prospect of being a historic President (second black and first woman) would fade in comparison to the partisan rancor that will come. Winfrey is not Hillary Clinton, who has endured brutal political attacks for decades. She will quickly determine that this is not for her and drop out well before the 2020 primary season starts in the summer of 2019.