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A renewed push by President Donald Trump toward Cuba has revived hopes among some Cuban exiles that the communist government could fall, while also renewing fears that the restitution or compensation promised for property seized decades ago could be traded away in wider negotiations. Exile attorneys and property owners say the talks between Washington and Havana will confront legal questions shaped not just by politics, but by old statutes and court exposure that remain unresolved.
For Raul Valdes-Fauli’s family, the stakes date to the early days of Castro’s rule. He recalled a November 1960 episode in which an agent of Fidel Castro’s revolution appeared at his family’s Pedroso Bank in Havana with a machine gun and demanded the family leave. Valdes-Fauli said the agent seized the bank and dispossessed a family whose presence in the property stretched to the 16th century, adding that the agent called them “gusanos,” a Spanish-language term Castro used to denigrate people fleeing the island.
Valdes-Fauli, an attorney and former mayor of the Miami suburb of Coral Gables, said the seizure left lasting damage beyond the loss of the bank itself. He said the family could not even take pictures from their office walls. “They told them this was now the people’s bank,” Valdes-Fauli said.
Seven decades later, the exile community’s renewed hopes and fears are tied to Trump’s threats of military intervention and to a naval blockade of fuel shipments that has brought Cuba’s economy under further strain, according to the reporting. Many Cuban Americans, the story said, view 2026 as a possible turning point for “regime change” on the island—though that optimism is tempered by concern that exiles could again be cut out of any deal.
That concern is partly shaped by what Cuban exiles describe as a cautionary precedent from Venezuela. Valdes-Fauli said he fears Trump could follow the same pattern he saw there, including what he described as keeping those he called “thieves” in power even after Maduro’s ouster, a reference that echoes broader worries about whether democratization conditions would survive realpolitik.
A core issue raised by multiple sources is the potential scope of Cuban American property claims. The negotiations, the reporting said, include an emotional and difficult question: how to address “hundreds of thousands” of claims from Cuban Americans whose homes, businesses and land were seized after Castro took power in 1959.
Nick Gutiérrez’s experience reflects the documentation and historical material many exiles say they have been storing for years. As president of the National Association of Cuban Landowners in Exile, he advised exile families on seeking compensation for what the story described as forced collectivism, working with fading land titles, black-and-white photographs, and books such as “The Owners of Cuba, 1958.” Gutiérrez said that for decades the effort often felt like a mission without a real chance of success.
Gutiérrez said the atmosphere has shifted as speculation has grown that the political landscape could change. He said interest in compensation has “exploded” among people who previously viewed litigation as futile, as well as among younger Cuban American entrepreneurs eager to help rebuild a country they know less intimately but whose heritage they carry. “Now we’re talking about the existential issue of whether the Cuban dictatorship will survive until next month,” Gutiérrez said, describing what the heightened political pressure has done to timelines and expectations.
Untangling the property claims, attorneys say, may require dealing with multiple layers of U.S. law and long-standing categories of certified losses. Robert Muse, a Washington attorney who specializes in U.S. laws relating to Cuba, compared the effort to battling a “multiheaded hydra.” Among the strongest U.S.-law bases, Muse said, are the 5,913 claims certified by the Justice Department in 1972 for $1.9 billion—claims that include corporations such as ExxonMobil and Marriott International, whose assets were seized as part of Castro’s nationalization drive.
Muse also described the practical difficulty of resolving disputes in ways that satisfy claimants while keeping negotiations workable for any future administration. Under U.S. law, he said, claims of that type—worth $10 billion today—must be resolved for a full restoration of economic and diplomatic relations. But he said the executive branch is authorized to assume control of private losses for a lump-sum payment, allowing the dispute to be folded into a settlement rather than handled case-by-case for every claimant.
A further point of uncertainty, the reporting said, involves Title III of the 1996 Helms-Burton Act, which allows exiles to sue companies accused of “trafficking” in confiscated property. Muse said earlier U.S. presidents suspended Title III due to concerns from allies, but Trump lifted that suspension in 2019, after which about 50 lawsuits were filed. He said that more litigation could follow depending on two cases before the U.S. Supreme Court argued this year, including one brought by Exxon seeking $1 billion from Cuban state-owned entities and another filed by Havana Docks that names cruise liners that paid Cuba to disembark nearly 1 million tourists at a port Cuba once operated after U.S. diplomatic relations were reestablished under President Barack Obama.
Muse said he likened the legal risk landscape for doing business in Cuba to a stalactite formed over decades, warning that it can deter investment and political compromise. “You can’t have a restitution remedy for hundreds of thousands of claimants,” Muse said. “It’s unworkable.” He described that as a central challenge for any transition: how to align incentives for foreign investment with the expectations of exiled property owners.
Even as the legal obstacles remain, Gutiérrez suggested Havana might have incentives to reach arrangements with Cuban Americans willing to invest if the government genuinely seeks foreign capital. He pointed to compensation models used by former Communist states in Eastern Europe after the Cold War as an example of how property seizures were addressed at the end of that political era.
As negotiations proceed, Muse said Trump may have the “right mix” of political freedom and impatience with conventional legal haggling as a second-term president, citing the president’s past interactions with oil executives after Maduro’s ouster. Muse said Trump told those executives they would have to write off any unpaid claims from asset seizures in Venezuela. Gutiérrez, however, said he worries that the pursuit of a fast political “trophy” could outweigh the longer, harder work of resolving exile concerns, even as he described personal comfort derived from Trump’s longstanding support among Cuban Americans. “Trump doesn’t have moral qualms of doing business with bad guys,” Gutiérrez said. “But he knows how important this is to us, and that gives us some comfort he won’t sell us out.”