US President Donald Trump has once again turned his focus towards Cuba, suggesting the island should strike a deal with Washington or face severe economic consequences. Speaking on Sunday, Trump warned that Cuba would no longer receive oil or money from Venezuela.
He wrote on his Truth Social platform, "THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA - ZERO! I strongly suggest they make a deal, BEFORE IT IS TOO LATE."
Trump argued that without Venezuelan support, Cuba's government was on the verge of collapse. "I don't think we need [to take] any action," he said earlier, adding that without Nicolas Maduro and Venezuela's oil supplies, "Cuba looks like it's ready to fall."
Secretary of State Marco Rubio went a step further and suggested that Washington may not simply sit back.
"I'm not going to talk to you about what our future steps are going to be," Rubio told NBC's Meet the Press. But he added, "If I lived in Havana and I was in the government, I'd be concerned."
Trump later reposted a post suggesting Rubio could one day become Cuba's leader, writing, "Sounds good to me!"
Why Venezuela Operation Changed The Equation
The renewed focus on Cuba follows the US military operation that led to the capture of Venezuelan President Nicolas Maduro. This time, Washington hit Havana where it hits the most.
For years, Cuba has depended on Venezuelan oil to keep its economy running, exchanging security and medical personnel in return. With Maduro removed and Trump pressuring interim Venezuelan President Delcy Rodriguez to redirect oil supplies to the United States, Cuba now faces a serious energy crisis.
"Cuba lived, for many years, on large amounts of OIL and MONEY from Venezuela," Trump said.
Both Trump and Rubio have made clear that they see the weakening of Cuba's government not just as a side effect of Maduro's fall, but as a potential outcome they would welcome.
Why Rubio Sees This As Personal
For Marco Rubio, the idea of Cuba's government collapsing carries deep emotional weight. His parents left Cuba three years before Fidel Castro's 1959 revolution. During his early days in Florida politics, Rubio built his identity as an opponent of Castro, whom he once described as "an evil, murderous dictator." Seeing the Cuban government fall would represent the fulfilment of a lifelong political mission.
This is not the first time Washington has tried to weaken Cuba by targeting its allies. In 2019, Trump and Rubio backed a push to remove Maduro from power in Venezuela. That effort collapsed in April of that year.
According to a memoir by former national security adviser John R Bolton, Cuban intelligence warned Maduro of the plot. Cuban operatives inside Venezuela helped him crush the attempt, and a plane was reportedly ready to fly Maduro to Havana if needed.
Since the collapse of the Soviet Union, Cuba has endured decades of isolation. It continues to draw support from Russia and China and is now less dependent on Venezuela than it was a decade ago.
A Long History Of Failed Regime Change
US efforts to remove Cuba's leadership did not begin with Trump. According to Cuban intelligence and declassified US documents, there were hundreds of attempts to unseat former President of Cuba Fidel Castro, ranging from full-scale invasions to covert assassination plots.
The Bay of Pigs Invasion (1961)
The CIA trained and funded a force of Cuban exiles to invade the island and lead an uprising. The operation collapsed within three days.
Operation Mongoose (1961-62)
After the Bay of Pigs, President John F Kennedy authorised a secret campaign of economic sabotage, psychological warfare and covert action designed to destabilise the regime.
Declassified records show that some CIA plans bordered on bizarre:
The Exploding Cigar: A booby-trapped cigar meant to detonate.
Poisoned Milkshake: A poison pill was to be slipped into Castro's drink at the Havana Libre hotel.
Poisoned Diving Suit: A wetsuit lined with tuberculosis bacteria and a contaminated breathing device.
Explosive Seashell: A brightly coloured shell rigged to explode where Castro liked to dive.
The Ex-Lover Plot: A former lover was asked to poison him. Castro reportedly handed her a gun and told her to shoot him. She refused.
Character Assassination: Attempts to humiliate him, including plans to make his beard fall out.
Many of these schemes never went beyond planning, dismissed as impractical or too risky.
Since 1962, the US has imposed a trade embargo on Cuba to create economic pressure.
How Many Times Was Castro Targeted?
Official US Count
The 1975 Church Committee confirmed eight CIA plots to assassinate Castro between 1960 and 1965.
Cuban Intelligence Claim
Fabian Escalante, former head of Cuban counter-intelligence, claimed 638 attempts, arguing that the Nixon era alone accounted for 184.
Despite decades of pressure, embargoes, covert action and diplomatic isolation, Cuba's government has endured. Today, even as Washington sees an opportunity following Maduro's fall, there is an underlying realisation that real change would require sustained political, economic and possibly military involvement.
As Rubio put it, "These things take time."
