Miami's wealthy Cuban exiles plan post-Castro future amid island's deepening crisis

On a evening in Miami, the kind where the air off Biscayne Bay carries the weight of money and expectation, a plastic surgeon's home filled with some of Florida's oldest Cuban-American fortunes. The fourth gathering of the Cuban-American National Chamber of Commerce was underway—rum in hand, Rolexes visible, surnames like Bacardi and Babun threading through conversations about the island's collapse and the political tremors that might finally topple it.

Juan Omar Sixto, the organization's president and a real estate developer in his early eighties who fled Cuba as a teenager, had assembled these entrepreneurs with a specific purpose: to be ready for what he calls "the day after." The CANCC has already begun drafting blueprints for that moment—a Cuban Stock Exchange, committees on energy infrastructure and food security, detailed plans for reconstruction. Sixto and his peers are convinced the moment is close. They have waited since 1959, when Fidel Castro seized their lands and nationalized their family companies, and they believe the Trump administration's pressure campaign on the island, coupled with connections to Secretary of State Marco Rubio, means change is finally within reach.

But the island itself tells a different story. While Sixto's group meets poolside, Cuba announced 176 economic liberalization measures—moves that look to outsiders like capitalism creeping in, allowing private businesses to hire and fire freely, permitting ownership of multiple enterprises. Yet the CANCC attendees dismissed these reforms as window dressing, refusing to invest a single dollar while the current regime holds power. Miguel Díaz-Canel, Cuba's president, framed the measures as advancing socialism and social justice. His critics saw something else entirely. The gap between what Miami imagines and what Havana is actually doing remains vast.

Mike Bustamante, a historian at the University of Miami, offers a sobering counterpoint. The high expectations created by Washington that regime change was imminent have been "kicked down the road," he argues. The Trump administration is entangled in the Iran conflict, mid-term elections loom in November, and there is little appetite for another foreign intervention. What remains is what Bustamante calls a "drip-drip-drip" of sanctions—but even that has teeth. Since January, Cuba's oil supply has been effectively cut off, creating what amounts to a significant escalation. Yet even this has not produced what analysts call a "political inflection point." The suffering is real and widespread; the catalyst for collapse has not materialized.

The question of land ownership sits at the center of Miami's reconstruction vision. Sixto's father lost five properties and a farm in Pinar del Rio province to the revolution. Sixto says he does not intend to displace anyone currently living on those lands, but he wants compensation or restitution—"even if they give me just a penny on the dollar, I'll take it." He frames it as moral justice. The Cuban government counters that such claims come from a corrupt landed gentry who built fortunes on the backs of indentured workers and enslaved people. The government also points out that Castro's land reforms distributed fields to workers and the state—a transfer the exiles could never accept.

Nicolás Gutiérrez, president of the National Association of Sugar Mill Owners of Cuba, an exile organization, speaks of recovering dismantled sugar mills and converting them to ethanol production, solar panels, water purification. He promises real wages for Cuban workers and a multiplier effect across the economy. The vision sounds coherent on a manicured lawn with ice clinking in glasses and palm trees rustling in the breeze. Within hours of the CANCC gathering, Cuba experienced its sixth nationwide blackout of the year.

The disconnection is stark. Most Cubans face acute shortages in food, water, fuel, and medicines. The island's electrical grid alone would cost between eight and ten billion dollars to repair. Before any industry—agriculture, tourism, manufacturing—can be revitalized by diaspora capital and connections, the basic infrastructure of survival must be addressed. Miami's ambitious plans, however well-intentioned or self-interested, sit in a different universe from the daily reality of an island in crisis. The exiles believe transformation is imminent. The people living through the blackouts and shortages are simply hoping their circumstances improve, sometime soon.