After Oprah Winfrey's epic speech at the Golden Globes on Jan. 7, the internet lit up with speculation about a potential 2020 presidential bid being in the cards for the TV legend. But well before "Oprah 2020" began trending on social media, there was one other person who kept throwing her name into the ring as a potential running mate on more than one occasion — and that man happens to be our current president, Donald Trump.
The first mention came in 1999, when Trump appeared on CNN's Larry King Live. "I love Oprah," he told King, adding that when it came to his vice president, "Oprah would always be my first choice." But it didn't stop there. The second time Trump floated Winfrey as a potential VP was a mere two years ago, when he told ABC's George Stephanopoulos that she was his dream second-in-command. "I'd love to have Oprah," he said. "I think we'd win easily, actually."
Obviously, the pairing did not work out — and as we all know, despite Trump's lavish praise of Winfrey in a variety of settings, she did not endorse him in the 2016 election. But the long history here does provide a bit of a reality check to all those hyping a 2020 bid — one that becomes even more stark when considering that in 1988, Trump confessed to Winfrey on her national television show that he might have presidential aspirations in mind for the future.
"I think I'd win," Trump says in the decades-old clip, which you can watch in full below. But it's the second part of what he says that will stick with you and haunt you in all sorts of ways. "I tell you what," he says, "I wouldn't go in to lose. I've never gone in to lose in my life. And if I did decide to do it — I would be inclined to think I'd have a hell of a chance of winning."