Fox News airs Trump's 1999 speech about Cuba as US holds talks with country: 'Adios amigo' Castro

WASHINGTON,DC: A decades-old speech by President Donald Trump criticizing Cuba’s communist leadership resurfaced on 'Fox & Friends' on Sunday, March 15. 

During the broadcast, the morning show aired a clip from a 1999 address in which Trump spoke to Cuban-American activists and delivered a blunt message directed at then-longtime Cuban leader Fidel Castro.

Revisiting Trump's pointed jab at Fidel Castro

In the brief segment played on air, Trump predicted political change in Cuba while addressing the crowd.

“You are going to win,” he said, referring to Cuban activists. “And I'm going to be down here and I'm going to watch you win.”

Trump then joked about what role he might play in the future, drawing applause from the crowd.

“I don't know what capacity I'll be,” he said. “I'll either be the greatest developer in the country or the greatest president that you've had in a long time. I'm not sure.” He ended the clip with a pointed message directed at Castro.

“If I could meet Castro right now, something I'd prefer not have to do, but if I could meet Castro right now, I'd have personally two words for him - adios, amigo.”

Trump rejected business deals in Cuba

The clip comes from a longer speech Trump delivered on November 15, 1999 at an event attended by Cuban-American activists and political organizers. 

In the full address, Trump told the audience he had declined several business opportunities involving Cuba because he did not want to financially benefit the Castro government.

“I've had a lot of offers, to go into Cuba on deals, business deals, real estate and other deals,” Trump said during the speech.

“And I've rejected them on the basis that I will go when Cuba’s free.” Trump argued that investment in the country at the time would primarily benefit Castro’s regime rather than ordinary citizens.

“Putting money and investing money in Cuba right now doesn't go to the people of Cuba,” he said. “It goes into the pockets of Fidel Castro.”

During the speech, Trump also spoke at length about economic revival and political change, using New York City as an example of how fortunes can shift over time.

He described the city’s struggles in the early 1990s when crime and economic decline dominated headlines and contrasted it with its later resurgence.

“The city was a disaster,” Trump said of that period. “And now, just a few years later we have the greatest and the hottest city in the world.”

“The point is that things can turn around, and they can turn around very rapidly,” he told the audience.

Trump's harsh criticism of Fidel Castro

Trump repeatedly criticized Castro’s rule during the speech, describing the Cuban government as oppressive and accusing it of jailing critics and silencing dissent.

“Castro’s jails are full of dissidents,” he said. “His graveyards are full of patriots.”

Despite noting that Castro had remained in power longer than many Cuban exiles had expected, Trump predicted the regime would eventually fall.

“I saw Castro the other night on television and he’s not looking good,” Trump said at the time. “He’s lasted a lot longer than a lot of you hoped, but it’s not looking good right now.”

The speech concluded with the remark that would later become the most widely remembered moment.

Revisiting the line that Fox & Friends replayed, Trump told the crowd he had a simple message for Castro if they ever met face-to-face.

“If I could meet Castro right now, I'd have personally two words for him, adios, amigo.”

The remark drew loud applause from the audience as Trump wrapped up his remarks and thanked attendees, many of whom were Cuban Americans who had long opposed the Castro government.

Ongoing US-Cuba talks after Trump's 'takeover' threat

President Trump had threatened a "friendly takeover" of Cuba amid its economic collapse from US oil sanctions.

This rhetoric escalated after Venezuela's Maduro was ousted in January 2026, cutting Cuba's key fuel lifeline, and led directly to secret talks confirmed publicly on March 13.

Trump declared a national emergency in late January 2026, imposing tariffs on oil shipments to Cuba and citing national security threats like Russian espionage and ties to Iran and extremist groups it backs. 

By February, he suggested informal discussions were underway, noting Cuba's desperation without Venezuelan support. On March 9-10, in Florida, Trump warned of a humanitarian crisis with "no energy, no money," tasking Secretary of State Marco Rubio to handle it, possibly via "friendly takeover."

Talks, led by Rubio on the US side, focus on easing Cuba's humanitarian plight in exchange for political concessions like prisoner releases (51 via Vatican mediation) and potential democratic reforms.