This past Sunday, Oprah Winfrey set off a storm of speculation regarding her future in politics. With her powerful speech during the Golden Globes, the #Oprah2020 hashtag was trending almost immediately; she'd no doubt be the fire president that many believe she'd be (and that The Boondocks lowkey predicted over a decade ago), and even though Oprah's not outright said she's looking to run for president, it looks like Donald Trump's caught wind of the talk, and made sure he responded during a recent press conference at the White House.
When asked if he'd beat Oprah in a presidential campaign, Trump said, "I'll beat Oprah. Oprah would be a lot of fun." He then made sure he was on one of her last shows, because of course he would. He then ended it by saying, "I don't think she's going to run."
Trump was right, though; he and Oprah used to be cool. The above image is from 1988, during the famed Tyson/Spinks boxing match. This was back when Donald Trump was a rich AF dude trying to rub elbows with anyone popular and Winfrey's hit talk show The Oprah Winfrey Show was roughly two years old. Trump was even on her show that year, talking about what he'd do if he ran for president.
They seemed to maintain some sort of acquaintanceship; fast-forward to 1999, and Trump was practically saying that he'd want Oprah to be his running mate.
When Larry King asked Trump who would be his VP candidate, he told King it would be Oprah, who he called "fantastic. I mean, she’s popular, she’s brilliant, she’s a wonderful woman. I mean, if she would ever do it. I don’t know that she would ever do it. She’s got, you know. She would be sort of like me." And just in 2015, he told ABCthat he'd "easily" win if Oprah ran with him.
The one point that should be made clear is that Oprah hasn't said she'd be running. During CBS This Morning, Oprah's ride-or-die Gayle King had to practically play 20 questions with her coworkers when it came to the possibility of Oprah running for office.