Mas: Trump's Venezuela strategy won't work for Cuba's 'failed state'

Cuba is a failed state, incapable of providing citizens with food, electricity, water, or a future.
Mas describes the current condition of the island and the urgency he sees for total transformation.

For more than six decades, the Cuban exile community in Miami has carried the weight of an interrupted homeland — and now Jorge Mas Santos, businessman and heir to a political dynasty, believes the waiting may finally be ending. Armed with constitutional drafts and economic blueprints, Mas is positioning himself not as a politician but as an architect of reconstruction, convinced that a convergence of American pressure, regime exhaustion, and diaspora readiness has brought Cuba to the edge of transformation. History has offered false dawns before, but Mas speaks of weeks, not years — a man of faith who believes the instruments are in place and the moment is at hand.

  • The Cuban regime, cut off from Venezuelan fuel and facing CIA-level diplomatic pressure, is described by Mas as a failed state on the verge of collapse — unable to provide citizens with food, electricity, or a future.
  • Mas has moved beyond hope into preparation, producing a 28-page transitional constitution and a detailed economic roadmap that includes banking reform, tax elimination, and a hybrid healthcare model with universal access.
  • He claims direct alignment with the Trump administration — citing a CIA director's visit to Havana and a personal meeting with Trump in March — framing U.S. strategy as a coordinated push toward total regime change.
  • The exile community, he says, is more unified than at any prior moment, with longtime organizers in constant contact and an estimated $40–80 billion in reconstruction capital ready to flow once legal protections for investors are established.
  • Yet the deepest uncertainty remains: Cuba's institutional void means there is no internal structure to negotiate with, no Machado-equivalent who can speak freely — only a regime that must be replaced entirely before anything new can begin.

Jorge Mas Santos is sixty-three years old, a Miami businessman who owns Inter Miami, runs a thirty-two-billion-dollar infrastructure company, and leads the most powerful Cuban exile organization in the United States. His father helped write the Helms-Burton Act. The son has inherited something harder to quantify: the obligation to imagine what comes after.

In recent months, the landscape has shifted in ways Mas finds significant. The United States captured Venezuela's Nicolás Maduro in January, then began cutting fuel shipments to Cuba — a strategy of economic strangulation. When the CIA director visited Havana last week, Mas read it as the opening move of a coordinated campaign. The day after that meeting, he spoke to a reporter and described two documents he had prepared: a detailed economic roadmap proposing banking modernization, tax elimination, and pharmaceutical development, and a twenty-eight-page transitional constitution drafted with the Cuban-American Bar Association, complete with 115 articles and nine transitional provisions.

Mas has never been to Cuba, though he expects to go soon. He believes change could come in weeks — possibly sooner. The system, he says, is unsustainable. He met with Trump in March and came away convinced that the president and Secretary of State Marco Rubio, a Miami Cuban-American Mas has known for nearly thirty years, share the exile community's vision of total transformation.

The Cuba he envisions is not a restoration of the Batista era — that world is gone. Instead, he imagines one of the world's most open economies, technologically advanced, positioned beside the American market. Reconstruction will require between forty and eighty billion dollars, he estimates, but capital is not the constraint. The diaspora and international investors will provide it, once legal frameworks protecting investment are in place.

What makes Cuba different from Venezuela, in his analysis, is the absence of any functioning institutions. The regime has hollowed out the state so completely that only total leadership change will work. Inside the island, he believes, there are potential leaders — but none who can speak without risking their lives. The exile community, meanwhile, is more unified than ever, all waiting for what they believe is the final stretch.

Mas welcomes an expected indictment of Raúl Castro as justice long overdue. He does not rule out Cuba eventually becoming the fifty-first American state, though he calls it premature. The future, he insists, must be decided by Cubans through elections. He is a man of faith, he said. This path is dictated by God. The only question is whether this time, after decades of false dawns, the corner is truly being turned.

Jorge Mas Santos sits in Miami, sixty-three years old, waiting for a phone call that might change everything. He is not a politician, though he has spent decades orbiting the machinery of power. He owns the Inter Miami soccer club—the team that brought Lionel Messi to Florida in 2023. He runs MasTec, a sprawling infrastructure company worth thirty-two billion dollars on the New York Stock Exchange. He leads the Cuban American National Foundation, the most influential exile organization in the United States. His father, Jorge Mas Canosa, died in 1997 after helping architect the Helms-Burton Act, the law that tightened America's embargo on Cuba. The son has inherited not just wealth and position but a historical mandate: to imagine what comes after.

In January, the United States captured Venezuela's president, Nicolás Maduro, in a military operation that Mas watched closely. What followed was a strategy of petroleum starvation—cutting off fuel shipments to Cuba, squeezing the island toward collapse. Last week, the CIA director, John Ratcliffe, visited Havana in a gesture Mas interprets as the opening move of a coordinated Trump administration campaign. The day after that meeting, Mas spoke to a reporter by phone from Miami. He had prepared two documents. The first, titled "Roadmap for a Prosperous, Democratic, and Free-Market Cuba," proposed modernizing the island's banking system, eliminating income taxes, offering corporate tax breaks for companies with at least ten percent Cuban ownership, and developing pharmaceutical, military, and heavy industrial sectors. The second was a twenty-eight-page "Fundamental Law for Democratic Transition," drafted with the Cuban-American Bar Association, structured like a constitution with a preamble, 115 articles, and nine transitional provisions.

Mas has never set foot in Cuba, though he expects to soon. He believes the change is coming in months—possibly weeks, possibly sooner. The system, he said, is unsustainable. Cuba is a failed state, incapable of providing citizens with food, electricity, water, or a future. When asked how many months, he paused. "It could be from one day to the next," he said. "I calculate before the end of summer. Maybe not even that. In weeks we will see changes." He met with Trump in March, when the president congratulated him on the Inter Miami championship. They discussed Cuba. Mas came away convinced that Trump and Secretary of State Marco Rubio—a Miami Cuban-American whom Mas has known for nearly thirty years—are aligned with the exile community's vision of total political and economic transformation.

The roadmap Mas has drafted is not a return to the pre-Castro era under Fulgencio Batista. That world is dead, he said. Instead, he envisions a technologically advanced nation, one of the world's most open economies, positioned to benefit from proximity to the American market. The healthcare system would be a hybrid: private providers operating within a framework of universal social rights, with the state issuing vouchers to citizens. The legal framework he has drafted is designed to reassure foreign investors that their capital will be protected. Reconstruction will require between forty and eighty billion dollars, he estimates. The exile community alone has the resources to raise that sum. International investment funds will contribute significantly. Capital will not be the constraint.

What distinguishes Cuba from Venezuela, in Mas's analysis, is the absence of functioning institutions. Venezuela had structures—political forces, a military hierarchy—that could be leveraged or replaced. Cuba has nothing. The regime has hollowed out the state so thoroughly that only total leadership change will suffice. Trump's strategy worked in Venezuela, Mas said, but it cannot work in Cuba because Cuba is a failed state. Within the island, he believes, there are many potential leaders—people equivalent to Venezuela's María Corina Machado—but they cannot speak freely without risking their lives. The exile community is more unified than ever, he noted. Rosa María Payá, Orlando Gutiérrez-Boronat, and other longtime organizers are in constant communication. All are waiting for what they believe is the final stretch.

When asked whether he would support trials for the Castro regime, Mas said that decision belongs to a council of Cubans. The best outcome would be for Castroism to be buried like a dinosaur. He expects an indictment of Raúl Castro, now ninety-four, to be announced soon—a move he welcomes as justice for the families of the Brothers to the Rescue pilots shot down in 1996. The question of whether Cuba might become the fifty-first American state he called premature, though he did not rule it out. The future, he said, must be determined by Cubans themselves, through elections. As for the risk of American dominance through commerce, he expressed no concern. The United States is a nation of extraordinary greatness, he said. It opened its arms to his parents' generation when they arrived with nothing. He is a man of faith, he concluded. This path is dictated by God, and they are instruments of it. The only question remaining is whether this time, after decades of false dawns, the corner is finally being turned.

Everything is moving very fast. We're talking about months. It could be from one day to the next.
— Jorge Mas, on the timeline for Cuban transition
What Trump did with Venezuela worked for Venezuela, but it doesn't work in Cuba, because Cuba is a failed state.
— Jorge Mas, distinguishing Cuba's situation from Venezuela's
A Conversa do Hearth Outra perspectiva sobre a história
Inventor

You've drafted a constitution for a country that doesn't yet exist. Isn't that presumptuous?

Model

It's a framework. A legal structure that says to investors: your money is safe here. Right now, there is no law. There is only the will of one man. You cannot rebuild on that.

Inventor

But you're also a businessman worth thirty billion dollars. How much of this is about ideology and how much is about access to markets and property?

Model

They're not separate. A free Cuba benefits me, yes. But it benefits every Cuban. I didn't build MasTec by thinking small. I think the same way about Cuba.

Inventor

You say change could come in weeks. That's a remarkable claim. What if you're wrong?

Model

I've been wrong before. When the Soviet Union fell, I thought that was the end. When Fidel died, I thought that was the end. But we don't surrender. This time feels different because Washington is moving.

Inventor

Different how?

Model

The CIA director doesn't visit Havana for a photo opportunity. Rubio doesn't coordinate with us unless something is happening. Trump doesn't meet with me about Cuba unless he's serious.

Inventor

You mention a failed state repeatedly. What do you mean by that?

Model

A state that cannot feed its people, provide electricity, offer work or hope. Cuba stopped functioning as a government decades ago. It's just a security apparatus now.

Inventor

And you think exile money can fix that?

Model

Not alone. But exile money, foreign investment, a legal system that works—yes, that rebuilds a nation. We have the capital. We have the expertise. We just need the opening.

Inventor

What happens to the people who've been running Cuba all this time?

Model

They go into history. The best thing that could happen to Castroism is to be forgotten.

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