The 42-year-old grandson of Cuba's former president sat in his grandfather's old office atop Havana's Convention Center and told American journalists what no member of the Castro family has ever said on the record: he wants to cut a deal with Donald Trump.
Raúl Guillermo Rodríguez Castro, a colonel in Cuba's interior ministry, a de facto power broker with no formal government title, and the eldest grandson of 95-year-old Raúl Castro, gave his first-ever interview to a U.S. media outlet over two days in June. USA TODAY reported that Rodríguez Castro declared himself ready to negotiate with anyone the United States designates, and, given the chance, directly with the president himself.
"If given the opportunity, claro que con Trump," he said. "Of course, with Trump."
The interview lands at a moment when the Trump administration has imposed an oil blockade, leveled sanctions, and raised a military threat against Cuba unseen since the 1962 missile crisis. Thirty-two Cuban soldiers working security for Venezuelan President Nicolás Maduro were killed in a U.S. military raid in Caracas that also captured Maduro and his wife, Cilia Flores. Cuba's economy has cratered. Its people face a humanitarian crisis. And the man offering to broker a way out wears Hermès sneakers, carries a Salvatore Ferragamo briefcase, and claims his luxury lifestyle is funded by "wealthy friends and admirers."
That is the contradiction at the heart of this story, and it is one American policymakers should examine with clear eyes.
Rodríguez Castro is not merely floating a wish. He has already been in direct contact with the Trump administration's most senior diplomat on the Cuba file. He spoke with Secretary of State Marco Rubio for the first time in January, shortly after the Caracas raid. A month later, the two met in person in St. Kitts.
In April, Jeremy Lewin, described as the State Department official who until recently oversaw all U.S. foreign assistance and who serves as Rubio's de facto Cuba envoy, met Rodríguez Castro at Havana's Convention Center. AP News confirmed that a senior State Department official met with Rodríguez Castro during a recent trip to Havana, and that the visit marked the first U.S. government flight to land in Cuba outside Guantanamo Bay since 2016. The discussions reportedly covered economic reforms, political prisoner releases, and even a proposed Starlink internet connection for the island.
President Trump himself has described Cuba as a "failing nation" that "has been a terribly run country for a long time," adding, "We may stop by Cuba after we finish with this." The administration has signaled that Havana "wants to talk very badly", and the White House has made clear the communist regime must make "dramatic changes very soon."
Fox News reported that a senior U.S. official characterized the contacts carefully: "I wouldn't call these negotiations as much as discussions about the future." Another senior official stated bluntly: "Our position, the U.S. government's position, is the regime has to go. But what exactly that looks like is up to [President Trump] and he has yet to decide. Rubio is still in talks with the grandson."
Those talks are bypassing Cuba's official government channels entirely. Cuban President Miguel Díaz-Canel has warned his country is "close to failing" as the U.S. cuts off fuel and food supplies. Yet the man the Trump administration is engaging is not Díaz-Canel. It is the grandson, a figure with no elected office and no formal diplomatic standing.
Rodríguez Castro is tall and thickset, with piercing light-green eyes and a buzz cut. USA TODAY journalists described him wearing light-blue skinny jeans, a black Hugo Boss T-shirt, and Hermès sneakers, with a stainless-steel Rolex on his left wrist. Around his neck hung a gold medallion bearing the faces of Fidel and Raúl Castro.
"If there's anything I believe in, it is these two men."
He told reporters he wakes around 5 a.m. and reads classified briefings from Cuba's interior, foreign, and military ministries. He trains at the gym at least six times a week. An unnamed person familiar with his fitness routine called him "The Hegseth of Cuba", a reference to Defense Secretary Pete Hegseth.
His biography reads like a product of Cuba's revolutionary aristocracy. His grandmother, Vilma Espín, was a socialite whose father was a Bacardi Rum executive; she fought alongside the Castros in the mountains and became an influential member of Cuba's Communist Party. His father, Gen. Luis Alberto Rodríguez López-Calleja, ran GAESA, the opaque military conglomerate that underpins large swaths of Cuba's economy, until his death in 2022.
Rodríguez Castro grew up in the same building as his grandparents, moved in with them at 18, and sat in on every important meeting on Cuban state affairs from his teenage years. He attended military school "Los Camilitos," named after revolutionary hero Camilo Cienfuegos, and graduated from the University of Havana with a degree in accounting and finance.
Frank Mora, a professor of politics and international relations at Florida International University, offered a direct assessment:
"He's el nieto preferido. He is the favorite grandson. Raúl Castro trusted his father, and he's the grandson he most liked."
Understanding Rodríguez Castro requires understanding GAESA, the Grupo de Administración Empresarial S.A. The military-run conglomerate has tentacles across Cuba's economy: hotels, real estate investments, construction companies, ports, currency exchanges, customs services, and more.
Leaked financial records published by the Miami Herald showed GAESA's 2023 revenue reportedly exceeded Cuba's entire state budget by more than three times. Rodríguez Castro claims the company represents about 15% of Cuba's overall economy and that its revenue goes toward purchasing food, medicine, and fuel. USA TODAY stated it could not independently verify that claim.
After his father's death, Brigadier General Ania Guillermina Lastres Morera inherited the GAESA empire. She has been sanctioned by the United States for her GAESA involvement. Rodríguez Castro describes his own role as apoyar, "to support." But experts paint a different picture.
Pablo Uchoa, an expert on Latin American security at University College of London, told USA TODAY:
"Raulito offers them more flexibility because he is a quasi-official. He is a military officer. But his role is much larger than it is on paper."
Leaders in official roles, including Díaz-Canel himself, reportedly deem it necessary for Rodríguez Castro to advise on investment opportunities, negotiations, and policy decisions. That makes him far more than a bodyguard, the career he claims he always wanted.
Rodríguez Castro says he has no wealth of his own. He claims his designer wardrobe, luxury foreign vehicles, and expensive overseas travel are all paid for by wealthy friends and admirers. That assertion sits uneasily alongside the documented record.
A joint investigation by Panamanian newspaper La Prensa, Venezuelan outlet Armando.Info, corruption watchdog Transparencia Venezuela en el Exilio, and Costa Rica-based Centro Latinoamericano de Investigación Periodística documented at least 23 private jet trips by Rodríguez Castro to Panama between 2024 and late 2025. The trips were described as involving luxury shopping.
In his twenties and thirties, he earned a reputation as a party boy while traveling the world as an attaché to his grandfather. A 2017 video caught him dancing onstage with popular reggaeton group Gente de Zona in Varadero, a resort town known for powder-white beaches and largely inaccessible to ordinary Cubans, wearing a New York Yankees shirt with "El Cangrejo" embroidered on the back. He told reporters his favorite player is Derek Jeter and that he attended Yankee games in premium seats in New York City.
He admires New York for its "round-the-clock vibrancy and bustle," Paris for its "romantic flair and cuisine," and Moscow for "its opulence." Meanwhile, the Cuban regime buckles under sanctions pressure, and ordinary Cubans struggle to find fuel and food.
Rodríguez Castro acknowledged the gap:
"It pains me that many people can't live the way I do. It weighs on me how people struggle. And I'm working every day to change that situation."
The back channel has attracted more than credentialed diplomats. Victor Mellor, a Republican congressional candidate in Rhode Island, traveled to Havana twice in June to meet Rodríguez Castro. The State Department said it did not authorize Mellor's trips. The nature of his discussions with the Castro grandson remains unclear.
An unnamed source who dined with Rodríguez Castro in Havana several times in recent months said the grandson "doesn't appear to covet political power" but "feels he might be the only one who can appease the Americans' demands for change without giving up the ideals of the revolution."
Rodríguez Castro himself framed his potential role with characteristic ambiguity:
"I've never been interested in politics. It's never been a calling of mine. But if at some point the revolution needs me to step up, I will do it."
That formulation, reluctant duty in the name of the revolution, is one of the oldest scripts in the Castro family playbook. Fidel Castro himself built free universal health care and education systems while imprisoning entire generations of Cubans, overseeing summary trials, denying fundamental human rights, nationalizing the economy, and sending hundreds of thousands into exile. Forbes estimated Fidel's personal wealth at roughly $900 million before his death at 90, an estimate he vehemently denied. He famously wore two Rolexes at the same time and gifted them to valued military commanders.
Now a grandson who wears one Rolex and insists he owns nothing asks the United States to trust him as the face of change. The Senate debate over Cuba war powers and the broader legal reckoning over seized Cuban property both underscore how high the stakes run for any deal with Havana.
The Trump administration is right to keep every channel open. Pressure works, and Cuba is feeling it. The oil blockade, the sanctions, the military posture, all of it has brought the regime closer to the table than at any point in decades.
But talking to a Castro grandson who lives in Hermès while his countrymen go hungry, who oversees a military conglomerate whose revenue dwarfs the national budget, and who claims to hold no power while advising the president of Cuba on policy, that is not the same as talking to someone who represents the Cuban people.
Rodríguez Castro told reporters he believes in the two faces on his gold medallion. He said the men who made the revolution "were just, but they weren't stupid." American negotiators would do well to remember the second half of that sentence.
The Cuban people have spent sixty-seven years waiting for the revolution's promises to arrive. A grandson in designer sneakers is not the delivery they had in mind.
