"I Wouldn’t Go In It To Lose": Oprah's 1988 Interview With Donald Trump Reveals His Early Aspirations To Win The Presidency

Date July 20, 2018 14:51

Say what you will about Donald Trump, but this man knows how to get what he wants. And if he’s in it, he is in it to win. Trump made a spectacular career in business and entertainment industry, but eventually set sights on something more: becoming President.


READ ALSO: Did Donald Trump Just Admit He Regrets Running For Presidency?

Trump finally decided to run for the highest office in 2015, but he entertained this idea decades before, as we now know. One old interview reveals his views (some of which are surprisingly consistent) and his tentative intentions.


Back in 1988, long before his feud with Oprah, Trump made an appearance at The Oprah Winfrey Show. When asked by Oprah what he would do differently regarding his country’s foreign policy, Trump told her he would “make our allies pay their fair share.” Sounds familiar, right? Trump went on to criticize Japan and Kuwait and complain about unfair trade deals.

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Oprah responded with this:

This sounds like political presidential talk to me. I know people have talked to you whether or not you want to run. Would you ever..?

Trump answered:

Probably not, but I do get tired of seeing out country ripped off…

Oprah interrupted:

Why would you not?

Trump said:

I just really don’t think I have the inclination to do it. I love what I’m doing, I really like it.

OWN / YouTube

READ ALSO: 2018 Presidential Greatness Ranking: Donald Trump Came In Dead Last

The discussion briefly turned to the 1988 Presidential race, and Trump predicted George H.W. Bush would win. Then, Oprah continued to press Trump on his own presidential ambitions:

You’ve said, though, if you did run for President, you believe you’d win.

Trump responded with:

Well, I don’t know. I think I’d win, and I’ll tell you what: I wouldn’t go in it to lose. I’ve never gone in to lose in my life. And if I did decide to do it, I think I’d be inclined… I would say I would have a hell of a chance of winning.


It took him almost three decades to finally dare to run. And, as Donald Trump predicted, he did win. During his campaign, very few political commentators believed he had a realistic chance of becoming President, but Trump came out on top in the end.

READ ALSO: Presidency Of Donald Trump: Did He Make America Great Again?

Donald Trump