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The Trump Administration Must Be Wary of the Castro Family’s Traps

March 20, 2026

U.S. Secretary of State Marco Rubio issued a sharp rebuke to The New York Times on Tuesday. “The reason so many in the American media continue to spread fake stories like this is that they keep turning to charlatans and liars — who claim to be privy to the facts — as their sources,” he wrote.

What story could so thoroughly exasperate the head of U.S. diplomacy? At the center of his reaction was a report claiming that Washington would be willing to accept a transition in Cuba that left the Castro family’s power intact.

Given his deep knowledge of the region and the Cuban situation — stemming from his public service in Florida and his upbringing within a family and a large community of exiles from the island — it is understandable that The New York Times headline would border on the offensive.

Only one thing is certain: the administration is indeed in contact with Havana. After weeks of Trump mentioning these contacts — and the regime denying them — dictator Miguel Díaz-Canel finally confirmed them during a televised appearance on Friday, March 13.

Among those present were generals, ministers, and other high-ranking officials of the tyranny. However, the most significant figure in the room was a young man holding no formal office whatsoever. With a penetrating gaze, he listened intently to the speech being read by Díaz-Canel. It was Raúl Castro’s grandson, Raúl Guillermo Rodríguez Castro — known as El Cangrejo (The Crab) — who is charged with the security of his nonagenarian grandfather, the true source of power on the island to this day.

According to Axios, Rubio is reportedly negotiating with Raúl Guillermo.

Everything seems to indicate that this is true, though one important detail must be added to the story: Rubio himself reportedly did not speak directly with the youngest of the Castros, but rather his team did.

The aging dictator has once again placed his trust in members of his own family — rather than in the professional cadres of the Communist Party — to conduct negotiations with the United States. As early as 2014, he tasked his son, Alejandro Castro Espín, with leading the secret negotiating team for the “thaw” in diplomatic relations between Cuba and the Barack Obama administration.

Now, Castro Espín reportedly has a distinct role within these negotiating duties — as I reported in an article two months ago. In this instance, he has reportedly been entrusted with negotiations involving a team from the Central Intelligence Agency, which are said to be taking place in Mexico.

Since the Castros have ruled Cuba like a private estate for nearly 70 years, state affairs are handled by the family, much like the Mafia. Now, it is the turn of Raúl Guillermo, 41, who serves as his grandfather’s primary caregiver.

Although the deal initially proposed by Trump to the regime’s leadership included an exit into exile, Raúl Castro reportedly requested to be allowed to die at Cayo Saetía — his mansion and private hunting reserve with exotic animals — located in the eastern part of the island.

Although he has no choice but to negotiate — with Venezuela and Mexico having ceased oil shipments under pressure from the White House — the aging leftist revolutionary has decided to proceed, but only through someone in whom he places his absolute trust.

Raúl Guillermo is the son of Débora Castro Espín — Raúl Castro’s eldest daughter — and the late Luis Alberto Rodríguez López-Callejas. The latter was one of the most powerful figures in the Castro regime, heading the military conglomerate Grupo de Administración Empresarial S.A. (GAESA), which controls a significant portion of the Cuban economy: hotels, hard-currency retail stores, imports, ports, and more.

While Fidel and Raúl Castro spent decades in their speeches calling upon ordinary citizens to endure ever-greater privations and sacrifices, their descendants flaunted lives of luxury. Raúl Guillermo was one of them.

He is “a man who lives in a world of luxuries inaccessible to the vast majority of Cubans — people mired in blackouts, endless queues, and chronic shortages,” the Spanish press has reported. He is credited with an insatiable appetite for expensive pleasures and a penchant for ostentation — discreet, yet constant. He takes frequent trips on luxury yachts throughout the Caribbean, where he shares fresh lobster, gourmet seafood, imported spirits, and loud music with friends and business associates.

According to Axios, Rubio’s team reportedly views Raúl Guillermo and his inner circle as part of a younger generation — one with an “entrepreneurial” mindset — that regards revolutionary communism as a historical failure and recognizes the economic potential of a rapprochement with Washington.

However, that perception regarding the Castro family elite’s supposed yearning for a free market may well be a poisoned chalice. I believe it could prove to be a trap for the Trump administration.

This week, Oscar Pérez-Oliva — Cuba’s Deputy Prime Minister and Minister of Foreign Trade and Foreign Investment — announced that Cuba will open its doors to allow Cubans residing abroad to invest in the private sector. He made this announcement during an interview with the U.S. network NBC.

The announcement, echoed by the Castro regime’s Ministry of Foreign Affairs, explained that the measure aims to expand economic opportunities on the island. It will also allow Cubans residing in other countries to participate in investment projects within the national territory, amidst a reform process driven by the government.

Pérez-Oliva indicated that the initiative will not be limited to trade. According to the minister, the opening encompasses larger-scale investments. These will include infrastructure projects in sectors considered priorities for the Cuban economy. Among the strategic areas, he cited tourism, mining, and energy.

The message itself should be newsworthy, but so should who is delivering it — because, once again, the Castro bloodline is directly connected to it. Pérez-Oliva is, as I stated in a previous article, part of the Castro generational shift. Not only ideologically, but above all, familially.

Although the surname doesn’t appear in his name, this electronics engineer is the grandson of Ángela Castro, the older sister of Fidel and Raúl Castro.

In just 22 months, he rose from technical positions to the highest echelons of the executive branch on the island and was recently appointed a deputy to the unicameral National Assembly of People’s Power. This last detail is significant: it formally qualifies him for possible access to the presidency of the Republic.

His career included management positions in state-owned import companies and in the Mariel Special Development Zone, where foreign companies are located. He then rose to Deputy Minister and Minister of Foreign Trade and Foreign Investment, and in October 2025, to Deputy Prime Minister and member of the Council of Ministers.

“His profile combines technical training with party discipline, presenting himself as a generational replacement who guarantees the continuity of the current system,” emphasized Diario Las Américas. “Without prior experience in the Communist Party apparatus, his political capital resides in his family background and his management of state finances under the supervision of the old guard.”

A gesture of relief was woven among many Cubans and Cuban-Americans, after Secretary Rubio’s response to Pérez-Oliva’s announcement. He stated that the measures “are not enough” to resolve the deep crisis the island is experiencing.

Although it remains unclear where the negotiations are headed, what concessions are being made, and what progress is being achieved or is expected to be achieved on the ground, one thing that gives many of us hope is that Rubio is the architect of a possible way out of the Cuban disaster. A way out toward a transition that, clearly, he is trying to make bloodless and without bloodshed, but which must be expedited. That much is certain. Because the tyranny hopes that in November, during the midterm elections, the Trump administration will be weakened, and a Democratic wave will give it a reprieve.

Yoe Suárez is a writer, producer, and journalist, exiled from Cuba due to his investigative reporting about themes like torture, political prisoners, government black lists, cybersurveillance, and freedom of expression and conscience. He is the author of the books "Leviathan: Political Police and Socialist Terror" and "El Soplo del Demonio: Violence and Gangsterism in Havana."



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