Of course, all the world knows how Donald Trump made the great leap from Real Estate Tycoon and reality show star to the President of the United States. Recently, because of a speech she made at the Golden Globes, and because she is universally beloved, Oprah Winfrey is being touted as the next celebrity to become president, supplanting the one who is already in the Oval Office.
The prospect of a Trump vs. Oprah 2020 presidential death match causes us to go back 30 years ago when a young Donald Trump sat with Oprah and talked about the idea of his running for president.
Trump and Oprah in 1988
Donald Trump 30 years ago was a well-known New York wheeler and dealer whose lifestyle was the subject of endless tabloid stories. He had just published “The Art of the Deal” which was a runaway best-seller. He used his newfound media visibility to ruminate about his opinions concerning the issues of the day, which made him a favorite on the television talk show circuit and hence his appearance on Oprah’s show.
“The Apprentice” and a variety of business ventures, solid and shady, were still in his future.
Oprah Winfrey’s talk show, which started locally in Chicago, had gone national a couple of years later. “The Oprah Winfrey Show” had started to become dominant, overtaking “The Phil Donahue Show” which had ruled the 1980s. Oprah’s show was still in a tabloid format, her decision to go to more positive guests and subjects still in the future. Oprah was also famous for having appeared in Steven Spielberg’s “The Color Purple” three years earlier for which she was nominated for an Academy Award. Her media empire that includes a movie production company and a cable network was still in the future.
The interview between the two future potential rivals
In many ways, the 1988 interview was just another celebrity gabfest. However, Trump, according to the Washington Post, had put out a full-page newspaper ad criticizing American foreign policy and was articulating the same kind of protectionist views that helped to propel him into the Oval Office 28 years later. Ronald Reagan was still president, the fall of the Berlin Wall was a year in the future, and then-Vice President George H. W. Bush and then-Governor Michael Dukakis were engaged in a political knife fight for the right to follow him.
As for whether Trump would ever run for president, Oprah went there, and Trump demurred answering directly.
He stated that he loved doing what he was doing then, which was making real estate deals. However, he did not entirely rule the idea out. Much later, when he ran for president for real, Trump speculated that Oprah would make a great vice president. The rest, as they say, is history.