I wonder how many people will remember this one…
A 1988 video featuring Donald Trump and Oprah Winfrey has taken the internet by storm.
When Donald Trump appeared on Oprah Winfrey’s popular talk show in 1988, the two had been longtime friends.
It’s a reminder of the close friendship they once shared, which was sadly short-lived due to their political differences.
Years later, a video clip from that episode went viral, leaving Americans astonished as it contained prophetic words from the future president.
While their political differences have caused their relationship to sour, this article looks back at what happened during the fateful meeting between these two celebrities.
In 1988, Donald Trump appeared on Oprah Winfrey’s popular talk show to promote his best-selling book “The Art of the Deal” and discuss his business life.
However, the conversation soon shifted to international policy and how he would take a stronger position with America’s allies if given the chance.
When asked what he would do differently, Trump said he’d make sure our allies paid their fair share for being part of America saying, “We let Japan come in and dump everything right into our markets… They come over here, they sell their cars, their VCRs. They knock the hell out of our companies.”
This is something that many people agreed with at the time—but no one could have predicted what happened next.
Oprah asked him if he ever considered running for president, to which he replied that while it was unlikely, he wouldn’t rule it out completely due to his frustrations with how other countries were taking advantage of America financially.
He even went so far as to say that if he did run, he would win, adding “I wouldn’t go into it to lose.”
Since its release, this video has gone viral with viewers expressing shock at its contents both former friends seeing very different sides of each other now when it comes to politics.
One fan expressed admiration for Donald Trump stating “I respect this man for living up to his very own words 20+ years after saying them.”
Another user alleged Winfrey was showing support for a possible presidential bid claiming “Basically, Oprah gives Trump a huge platform to talk about becoming president. 30-40 years later they’re insulting each other!”
This prophetic moment has become known as one of the most memorable in American television history—and something “the Queen of all Media” can never live down.
For many years after this interview aired, Donald Trump and Oprah Winfrey enjoyed a close friendship—with him famously declaring in 1999 that she would be his running mate if ever ran for president.
However, when their respective political views became clear over time (Trump becoming an avid Republican while she declared herself Democrat), things between them slowly began deteriorating until they were no longer on speaking terms.
In 2019, Trump told CNN’s Larry King that “Oprah loved me until I decided to run for office.”
And there hasn’t been much contact between them since then…
What started as admiration quickly turned into resentment over time —making the resurfaced video from 1988 seem like such an ironic reminder of where it all began and where it ended up going wrong.