U.S. extends timeline as Havana rebuffs demands for political change
At a June gathering at a waterfront mansion facing Biscayne Bay, Juan Omar Sixto, 82, a former tobacco farmer who heads the newly formed Cuban-American National Chamber of Commerce, told a group of fellow Cuban-Americans: “We have waited for 67 years. We need to start.”
Sixto’s audience is part of a broader effort in Miami to draft detailed economic and political blueprints for a Cuba the exiles believe will emerge once the current government falls. The Wall Street Journal reported that 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.
The exiles are 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 post-communist Cuba.
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. According to people familiar with the discussions, 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. A State Department official described the steady drumbeat as a pressure tactic intended to create the impression that further U.S. action could be imminent.
The preparations have been fueled by three words President Trump has repeated since the U.S. capture of Venezuelan strongman Nicolás Maduro in January: “Cuba is next.” His administration has imposed an oil blockade on the island and floated the idea of a “friendly takeover.” Earlier this year, senior officials told Florida politicians and wealthy Cuban-Americans that the Cuban government could fall by this summer, and certainly by the end of the year.
But Havana has proven resilient, and with Trump’s attention consumed by the war in Iran, 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. 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.
Pressed about earlier expectations that Cuba’s government could fall this year, Rubio bristled at the idea of a fixed timetable during a July trip to Manila. “We’re not a miniseries, like you get in three episodes and it’s over,” he told reporters. “These are complex things that take time.”
That shift has not gone unnoticed in South Florida. “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 government.
At a June lunch, 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,” said Ric Herrero, director of the Cuba Study Group, a Washington-based think tank that advocates for civil society development. “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.”
Politically connected Cuban-Americans see an ally in Trump. Many believe the former real-estate tycoon largely views Cuba as a distressed asset — a perspective they have sought to engage by pitching Cuba’s future to Trump not only as a political cause and part of his legacy, but also as a vast reconstruction project.
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 Trump, 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.
Mas, the chairman of the Cuban American National Foundation, a 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 current government and a democratic Cuba. The draft being circulated envisions a transitional government that would spend up to two years preparing for free elections.
Architect Willy Bermello, 75, who designed the proposed Trump library in Miami, has convened airline, airport management and investment fund executives every two weeks over video calls to firm up $8 billion plans to overhaul eight of the island’s airports once its government changes. The remaking of Cuba’s airports will pay for itself, Bermello said. “We have our people on speed dial,” he added.
Other debates have focused on whether a free Cuba should temporarily revive its 1940 constitution while a new one is drafted. 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. “This is our Berlin Wall moment,” said Marcell Felipe, the museum’s chairman.
The Miami planning extends to recruiting. Sixto told the Wall Street Journal he plans to begin recruiting legions of volunteer Cuban-Americans next week to teach islanders the ways of modern capitalism when the government falls. “Cuba can’t advance with the people who are on the island,” Sixto said. “It’s not their fault, but they are not modern. They are backwards.”
In Hialeah, the most Cuban-American city in the country, Mayor Bryan Calvo expressed a sense of urgency. “I don’t think we’ve ever been as close,” the 28-year-old said of the end of communist rule. “But at the same point, if it doesn’t happen now, it’s never gonna happen.” Hialeah, a deep-red stronghold, has renamed its main thoroughfare Donald J. Trump Avenue.
Some Cuban-Americans fear the White House could try to apply its Venezuela playbook to the island. 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.
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. They see him as someone whose connections and ambition could be used to shake up the government from within, according to people familiar with the discussions. 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 their meetings with Cuban counterparts, 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 oil blockade and other sanctions. In June, Cuba approved a wide-ranging package of economic changes, which the U.S. dismissed. The Cuban government has refused to discuss political changes.
A sense of momentum at the beginning of the year was fueled by Trump’s senior diplomat in Havana, Mike Hammer, who has shuttled between Miami, Washington and Europe, pushing confidently that communist rule would end this year. “There has to be change,” Hammer told a ballroom of Cuban-American lawyers at a February bar association gala in Miami. “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. But Hammer has quietly stopped pushing a 2026 timetable, according to people in contact with him.
On the ground in Cuba, the oil blockade has worsened acute fuel shortages and vastly increased the dayslong blackouts, pushing the power grid to collapse and deepening the humanitarian crisis. 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. People walk around like zombies,” said Omar Everleny Perez Villanueva, a Havana-based economist working on plans to restructure the island’s economy. “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. President Díaz-Canel told an international audience recently that the island’s infant mortality rate had doubled and that Cuba had a waiting list of nearly 100,000 patients — 12,000 of them children — for surgery. An attack by the United States would provoke a “bloodbath of incalculable consequences,” Díaz-Canel wrote on X in May.
A Miami Herald poll of some 800 Cuban-Americans published in April found that four out of five South Florida respondents favor U.S. military intervention, whether to topple the government or to address the humanitarian needs of the population. The same number reject any negotiation with Havana that results in anything less than regime change.
Longtime Cuba observers quoted by the Journal said there is little chance that increased deprivation will spark a popular rebellion. They noted that for almost seven decades, Cuba has not tolerated any organized political opposition, and that significant protests have only erupted twice — once in Havana in 1994 and again five years ago in towns and cities throughout the island. Both were quickly put down.
More than a million Cubans, a majority of them young, have left the island since 2021, sharply reducing the number of potential demonstrators. Today’s Cuba is poorer, older and more racially mixed after years of mass migration. The voice of the Cuban people is largely absent in debates of the country’s future.
“We are the children of abuse,” said Luis Fonseca, a Havana day laborer. “You try to survive and subsist.”