A video from November 1999 in which Donald Trump calls Fidel Castro a "murderer," "criminal," and "a bad person in every way" has been widely circulating on social media after being reposted by Fox News and the Fox & Friends program on Instagram in recent weeks.
The speech was delivered on November 15, 1999, before the Cuban American National Foundation (CANF) in Miami, Florida, when Trump was a businessman exploring a presidential candidacy for the Reform Party, just weeks after announcing his exploratory committee.
Approximately 1,000 supporters of the CANF gave him a standing ovation multiple times.
In his remarks, Trump was direct about his stance on business with the dictatorship: “I have received many offers to go to Cuba for business, real estate, and other ventures. And I declined them on the grounds that I will only go when Cuba is free.”
His criticism of the Castro regime was unequivocal.
“Investing money in Cuba does not go to the people of Cuba; it goes to Fidel Castro's pockets. He is a murderer, a bad person, and frankly, the embargo against Cuba must be maintained because it is the only way he will be overthrown,” he stated.
One of the most powerful statements in the speech described the reality of the island under Castro: "Fidel Castro's prisons are filled with dissenters, his cemeteries are filled with patriots, and his government is filled with thugs."
Trump also warned about the consequences of yielding to the regime:
"We cannot allow him to get his way with this program of coming to this country, hiring our best consultants, our best lobbyists, and suddenly senators and other people miraculously side with Fidel Castro."
The most shared moment of the video is the closing, where Trump combined personal ambition with a direct message to Castro: "I don't know in what capacity I will be: either I will be the biggest real estate developer in the country or the best president they have had in a long time."
And he concluded with the phrase that is now making headlines worldwide: “If I could meet Castro right now, I would personally have two words for him: goodbye, friend.”
The phrase operates on two levels: as an ironic farewell and as a political prophecy regarding the end of Castroism.
That Trump actually became president years later is what has turned this fragment into viral material nearly three decades later.
The video resurfaces at a time of intense pressure from Washington towards Havana.
Since assuming his second term, Trump reincorporated Cuba to the list of state sponsors of terrorism on the very day of his inauguration, January 20, 2025.
Months later, Trump strengthened the embargo and prohibited U.S. tourism to Cuba, and in January 2026 declared a national emergency regarding the oil supply to the island.
On March 27th, in Miami Beach, Trump was even more explicit about his intentions when he stated with laughter: “Cuba is next, but pretend I didn't say that”.
For the Cuban-American community, the speech from 1999 carries a particular emotional weight: Trump not only criticized Castro but also validated the suffering of exile and committed to not doing business with the dictatorship when he was still just a businessman, 16 years before reaching the White House.
The phrase with which Trump closed that speech in 1999: "I believe you will have victory. I believe you will have it sooner rather than later. You are going to win," resonates today with a force that few would have anticipated back then.
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