MIAMI—At a sprawling waterfront mansion facing Biscayne Bay, a group of wealthy Cuban-Americans has spent months hatching detailed plans for a country that doesn’t yet exist.
“We have waited for 67 years,” Juan Omar Sixto, 82, a former tobacco farmer who heads the newly formed Cuban-American National Chamber of Commerce, told the group on a balmy evening in June as they met close to a pool ringed by faux-marble statues of seminude Roman nymphs. “We need to start.”
The group has been drawing up blueprints for a Cuban stock exchange and an investment summit in Havana. Elsewhere in Miami, prominent Cuban-Americans are mapping out a provisional government, recruiting engineers to study floating power stations, and strategizing on repairs to the island’s crumbling infrastructure. They have plans to reach out to blue-chip companies, banks and investment funds to invest in a new postcommunist Cuba. As the island sinks deeper into crisis, wealthy and politically connected exiles are racing to plot its future from Miami, where the Trump administration is turning for ideas, political support and private capital to rebuild the country if the regime falls. In living rooms, hotel conference centers, law offices and private clubs across the city, they are gaming out who could lead Cuba’s nine million people. The effort has drawn billionaires and Trump-linked power-brokers, the scions of Cuban-American dynasties built on sugar, and immigrants who amassed fortunes over decades in the U.S. Some of them have a direct line to the Trump administration—most notably to Secretary of State Marco Rubio, the son of Cuban immigrants who built much of his political career on a vow to end communist rule on the island and makes frequent trips to his hometown. The oil blockade has worsened acute fuel shortages and vastly increased the dayslong blackouts , pushing the power grid to collapse and deepening the island’s humanitarian crisis. But Havana has proven to be resilient —and with Trump’s attention consumed by the war in Iran, any plans to focus on Cuba have been put on the back burner. Some senior officials have begun speaking of a campaign that could last the remainder of Trump’s term. “These are complex things that take time. That shift has not gone unnoticed in South Florida. Politically connected Cuban-Americans see an ally in Trump. Many believe the former real-estate tycoon largely sees Cuba as a distressed asset: a sun-soaked island of underdeveloped beaches and decaying properties that could be opened to American investment in a way that leaves it economically dependent on the U.S. They have sought to engage those instincts, pitching Cuba’s future to Trump not only as a political cause and part of his legacy, but also as a vast reconstruction project. Trump Avenue. “People are lining up for a transition that is by no means guaranteed, either gearing up for a friendly takeover or a giant exercise in wheel spinning. A feeling of inevitability was fueled at the beginning of the year by Trump’s avuncular top diplomat in Havana, Mike Hammer, who has shuttled between Miami, Washington and Europe, confidently pushing that communist rule would end this year. “I see it coming. He then danced on stage with salsa star Willy Chirino singing a hit song that calls on Cuba’s rulers to leave. Despite an extraordinary burst of back-channel talks—from a secret meeting between Rubio and Raúl Castro’s grandson at a Caribbean resort to a visit to Havana by CIA Director John Ratcliffe—efforts to pressure officials in Cuba’s entrenched bureaucracy have made little headway. For months, Trump officials have sought to engage figures inside the Cuban system, including Castro’s grandson, known as Raulito. But the efforts stalled when the talks became public and South Florida politicians spoke out against the U.S. working through a member of the Castro family. In June, Cuba approved a wide-ranging package of economic changes, which the U.S. dismissed. The government has refused to discuss political changes. Some Cuban-Americans fear that the White House could try to apply its Venezuela playbook to the island. There, U.S. special forces captured Maduro but left his vice president, Delcy Rodríguez, and the rest of the state apparatus in power in exchange for facilitating oil and other business deals. A democratic transition has been left for an unspecified future date. The same number reject any negotiation with Havana that results in anything less than regime change. The planning in Miami, meanwhile, has extended from financing to the nuts and bolts of a political transition. Mas, the chairman of the Cuban American National Foundation, a powerful lobbying group founded by his father, is working with Miami’s Cuban American Bar Association to develop a transition law that could cover the gap between the present regime and a democratic Cuba. The draft being circulated envisions a transitional government that would spend up to two years preparing for free elections. The American Museum of the Cuban Diaspora, which chronicles the history of how Cubans fled communist oppression on the island and transformed Miami, recently hosted one such discussion. For now, the reality on the ground in Cuba is deteriorating. Lights are off for days at a time. Streets are clotted with uncollected mountains of garbage, which breed clouds of mosquitoes that spread dengue and other diseases. “The country is totally paralyzed. “There’s no electricity for days, you don’t sleep, food spoils. Havana has accused the U.S. of imposing collective punishment by worsening the living conditions of ordinary Cubans.
The 28-year-old mayor of Hialeah leads the most Cuban-American city in the country and a deep-red stronghold that renamed its main thoroughfare Donald J. The gatherings of planners tend to be dominated by the gray-haired patriarchs of the older exile community—men who left Cuba as children or young adults soon after the 1959 revolution, along with the children they raised on the expectation that they would one day reclaim the properties and businesses seized by Fidel Castro . But Hammer has quietly stopped pushing a 2026 timetable, say people who are in contact with him. In their meetings with the Cubans, U.S. officials have demanded an overhaul of the country’s economy and political system and freedom for more than 1,000 political prisoners in exchange for lifting the U.S.’s oil blockade and other sanctions imposed on Havana. Four out of five Cuban-Americans living in South Florida favor a U.S. military intervention in Cuba, be it to topple the government or to address the humanitarian needs of the population, according to a Miami Herald poll of some 800 Cuban-Americans published in April. Other debates have focused on whether a free Cuba should temporarily revive its 1940 constitution while a new one is drafted. Willy Bermello, 75, the architect who designed the proposed Trump library in Miami, has his eye on remaking Cuba’s airports. Every two weeks, he convenes a small group of airline, airport management and investment fund executives over video calls to firm up $8 billion plans to overhaul eight of the island’s airports once its government changes—a development he expects to happen soon. Cuba had a waiting list of nearly 100,000 patients, 12,000 of them children, for surgery, he said.
Trump has repeatedly told aides he needs to wrap up the conflict in the Middle East before devoting resources to Cuba or other foreign-policy priorities, according to people familiar with the discussions. “We’re not a miniseries, like you get in three episodes and it’s over,” he told reporters during a trip to Manila in July. Rubio has instructed his staff to keep up weekly Cuba-related announcements—news about indictments, sanctions, reports—even as administration officials have quietly begun to stretch the timeline, according to people familiar with the discussions. The steady drumbeat is itself a pressure tactic, a State Department official said, intended to create the impression that further U.S. action could be imminent. “They have not changed the goal, but they have moved the goal post,” said Tony Costa, 86, a former owner of one of the world’s largest growers of ornamental plants, who retired years ago to devote all of his time to ousting the Communist regime. Jorge Mas, the billionaire co-owner of the Inter Miami soccer club and a close friend of Rubio, says Trump once asked him what it would cost to rebuild the island. “We could invest multibillions of dollars in Cuba,” Mas says he told him, adding that it would be child’s play for wealthy Cuban-American friends and associates to come up with the $90 billion he estimates fixing the country will take during its first three years of transition. “I don’t think we’ve ever been as close,” says Bryan Calvo about the end of communist rule in Cuba. “But at the same point, if it doesn’t happen now, it’s never gonna happen,” he says. At a lunch in June, Pedro Freyre, chair of the international practice at the Akerman law firm, told a visiting U.S. policy group that his phone was ringing off the hook with queries from Cuban-Americans seeking compensation for properties confiscated decades ago. “Anybody who is hoping for a swing at the Cuban piñata is retaining lawyers and lobbyists, particularly in the Trump inner circle,” says Ric Herrero, the director of the Cuba Study Group, a Washington-based think tank that advocates for civil society development. “There has to be change,” Hammer told a ballroom of Cuban-American lawyers at a February bar association gala in Miami. They see him as someone whose connections and ambition could be used to shake up the regime from within, according to people familiar with the discussions. An attack by the U.S. would provoke a “bloodbath of incalculable consequences,” said President Miguel Diaz-Canel on X in May. “This is our Berlin Wall moment,” said Marcell Felipe, the museum’s chairman. The remaking of Cuba’s airports will pay for itself, he said. “We have our people on speed dial,” he says. People walk around like zombies,” says Omar Everleny Perez Villanueva, a Havana-based economist working on plans to restructure the island’s economy. Díaz-Canel told an international audience of sympathizers recently that the island’s infant mortality rate had doubled.
Pressed about earlier expectations that Cuba’s regime could fall this year, Rubio bristled at the idea of a fixed timetable.
Longtime Cuba observers say that there is little chance that increased deprivation will spark a popular rebellion. They note that for almost seven decades, Cuba hasn’t tolerated any organized political opposition. On both occasions, the protests were quickly put down. The voice of the Cuban people is largely absent in debates of the country’s future.
Significant protests have only erupted twice —once in Havana in 1994 and the other five years ago in towns and cities throughout the island. In addition, Cuba observers say, more than a million Cubans, a majority of them young, have left the island since 2021, sharply reducing the number of potential demonstrators.
“We are the children of abuse,” said Luis Fonseca, a Havana day laborer. “You try to survive and subsist.” Today’s Cuba is poorer, older and more racially mixed after years of having its population depleted by mass migration.
The feverish preparations have been fueled by three words President Trump has repeated since the capture of Venezuelan strongman Nicolás Maduro in January: “Cuba is next. He has slapped an oil blockade on the island and floated a “friendly takeover. Back in Miami, Sixto, of the Cuban-American National Chamber of Commerce, plans to begin recruiting legions of volunteer Cuban-Americans next week to teach islanders the ways of modern capitalism when the regime finally falls. “It’s not their fault, but they are not modern. They are backwards. Write to José de Córdoba at [email protected] and Vera Bergengruen at [email protected]
Earlier this year, senior officials told Florida politicians and wealthy Cuban-Americans that regime change could happen by this summer, and certainly by the end of the year. “Cuba can’t advance with the people who are on the island,” he said.
