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Raul Valdes-Fauli, a Miami attorney, recalled a November 1960 day when an agent of Fidel Castro’s revolution arrived at his family’s Pedroso Bank in Havana with a machine gun, demanded the family leave, and seized the bank. Valdes-Fauli said the agent then referred to those fleeing the island with a term “gusanos,” and he said the family lost not only the property but even access to personal belongings after the takeover. For him, the resurfacing of those memories comes as U.S.-Cuba talks take on new urgency amid Trump’s threats of military intervention and a naval blockade aimed at fuel shipments.
Valdes-Fauli and other Cuban Americans described a mix of hope and fear: hope that 2026 could bring major political change on the communist-run island, and fear that exiles could be left out of any deal. They point to what they call a cautionary precedent from Venezuela, where Trump ousted President Nicolás Maduro and then moved toward an arrangement that, exiles worry, deprioritized demands for democracy as business deals advanced.
In interviews, Valdes-Fauli said he hopes the approach taken in Venezuela does not repeat in Cuba. He cited his own worry that any settlement could effectively preserve the power of those he described as “thieves,” leaving dispossessed families to wait again for remedies that have long appeared remote. “I hope that he doesn’t do what he did in Venezuela, which is keep the thieves in power,” Valdes-Fauli said.
A central concern for Cuban Americans is how a potential transition would handle property claims arising from confiscations after Castro took power in 1959. The AP reported that negotiations include an emotional element tied to possible legal claims by Cuban Americans whose homes, businesses and land were seized in the decades following the revolution. Nick Gutiérrez, president of the National Association of Cuban Landowners in Exile, said interest in the issue has surged as regime-change speculation has spread.
Gutiérrez described advising families on pursuing compensation for forced collectivism, a task that he said for decades had been largely ignored because there was little expectation that Cuba would pay. He said “A lot of it just fell on deaf ears,” and he described a shift among exile families and younger entrepreneurs who now see the subject as “the existential issue” of whether the dictatorship will last into next month. He said the talks are now framed around the possibility of whether “the Cuban dictatorship will survive until next month,” adding that the question has driven more people to consider legal options.
The legal landscape, however, remains complex. Robert Muse, a Washington attorney who specializes in U.S. laws relating to Cuba, compared the process of sorting property claims to a “multiheaded hydra,” and he outlined how U.S. law already certified a set of claims in 1972. Muse said those include 5,913 claims certified by the Justice Department for $1.9 billion, including assets seized during Castro’s nationalization drive that involved companies such as ExxonMobil and Marriott International.
Under U.S. law, Muse said the certified claims—he described their modern value as $10 billion—must be addressed for full restoration of economic and diplomatic relations. He also said the executive branch can assume control of private losses for a lump-sum payment and fold the disputes into any settlement. The AP reported that, in a break from the past, Cuba signaled it could discuss the claims as part of broader negotiations over compensation for damages the island says it suffered from the U.S. trade embargo enacted in 1962.
Muse said additional legal hurdles stem from Title III of the 1996 Helms-Burton Act, which lets exiles sue companies it deems to be “trafficking” in confiscated property. He said past U.S. presidents suspended Title III due to objections from allies, and he noted that he and many exiles previously viewed it as a threat unlikely to produce results while Cuba’s government remained bankrupt. The AP reported that Trump lifted the suspension in 2019 and that about 50 lawsuits were filed since then, with possible expansion linked to two cases argued before the U.S. Supreme Court this year.
Muse said one case brought by Exxon seeks $1 billion from Cuban state-owned entities, while another filed by the Delaware-based company Havana Docks involves four cruise liners that paid Cuba to disembark nearly 1 million tourists at a port it once operated after President Barack Obama reestablished diplomatic relations. He said the legal risks of doing business in Cuba, which he likened to a “stalactite,” can deter investment and compromise even over time, and he said “You can’t have a restitution remedy for hundreds of thousands of claimants. It’s unworkable.”
Even with those limits, Muse argued that if Cuba wants foreign capital, it could negotiate mechanisms with Cuban Americans willing to invest, drawing a comparison to former Communist states in Eastern Europe that compensated for property seizures at the end of the Cold War. Valdes-Fauli and Gutiérrez both expressed that their concerns hinge on whether Trump—who they described as impatient with legal haggling—will push a settlement quickly and with business realities in mind rather than insisting on restitution that would fully satisfy the largest number of claimants. Gutiérrez said he is reassured by Trump’s long-standing ties to Cuban Americans, but he also warned that exiles want assurances that a political transition will not leave them stranded again.