A video from November 1999 featuring Donald Trump denouncing Fidel Castro as a "murderer," "criminal," and a "bad person in every way" has recently gained widespread attention on social media. This comes after Fox News and Fox & Friends shared it on Instagram over the past few weeks.
The speech, delivered on November 15, 1999, was made to the Cuban American National Foundation (CANF) in Miami, Florida. At the time, Trump was a businessman contemplating a presidential run with the Reform Party, shortly after establishing his exploratory committee.
During his address, Trump made his position on dealing with the regime unequivocally clear: "I've had numerous offers to go to Cuba for business, real estate, and other ventures. I declined them, stating that I would only go when Cuba is free."
Trump's criticism of the Castro regime was sharp and unambiguous. "Investing money in Cuba doesn't benefit the Cuban people; it lines the pockets of Fidel Castro. He's a killer, a bad guy, and frankly, the embargo on Cuba should remain because it's the only way he'll be overthrown," he asserted.
One of the most striking lines from the speech painted a vivid picture of life under Castro: "Fidel Castro's prisons are full of dissidents, his cemeteries are full of patriots, and his government is full of thugs."
A Staunch Stance Against the Castro Regime
Trump also warned about the dangers of yielding to the regime: "We cannot allow him to get away with this scheme of coming to this country, hiring our best consultants, our best lobbyists, and then, suddenly, senators and other people miraculously siding with Fidel Castro."
The most shared moment from the video is the closing, where Trump merged personal ambition with a direct message to Castro: "I don't know in what capacity I'll be: either the greatest real estate developer in the country or the best president you've had in a long time."
He concluded with the phrase that is now echoing globally: "If I could meet Castro right now, I would have two words for him: goodbye, friend."
This phrase serves as both an ironic farewell and a political prophecy regarding the end of the Castro regime.
The Resurgence of a Historic Speech
The fact that Trump eventually became president years later has turned this clip into viral content nearly three decades on. The video has resurfaced during a period of heightened pressure from Washington on Havana.
After taking office for a second term, Trump re-designated Cuba as a state sponsor of terrorism on January 20, 2025, the same day as his inauguration. In the following months, he tightened the embargo and banned American tourism to Cuba, declaring a national emergency over the island's oil supply in January 2026.
On March 27 in Miami Beach, Trump was more explicit about his intentions, jokingly declaring, "Cuba is next, but pretend I didn't say that."
For the Cuban American community, the 1999 speech holds deep emotional resonance: not only did Trump criticize Castro, but he also acknowledged the suffering of exiles and pledged not to engage in business with the dictatorship while he was still a businessman, 16 years before reaching the White House.
The original video, archived on YouTube by Roll Call Factbase Videos and lasting two minutes and 42 seconds, is still accessible on Facebook.
The closing line of Trump's 1999 speech—"I believe you will have victory. I think you'll have it sooner rather than later. You're going to win"—resonates today with a force few could have predicted back then.
Understanding Trump's Historical Speech on Cuba
What prompted the resurgence of Trump's 1999 speech on Cuba?
The video resurfaced due to Fox News and Fox & Friends sharing it on Instagram, coupled with the current political climate where Washington is exerting significant pressure on Havana.
What was Trump's stance on doing business with Cuba in 1999?
Trump stated that he rejected business offers in Cuba, maintaining he would only consider it when the nation was free, emphasizing that investments in the country benefit only Fidel Castro, not the Cuban people.
How did Trump describe the conditions in Cuba under Fidel Castro?
Trump vividly described Cuba under Castro as a place where prisons are filled with dissidents, cemeteries with patriots, and the government with thugs, highlighting the oppressive nature of the regime.