U.S. Secretary of State Marco Rubio is having conversations with Raúl Castro’s grandson in Cuba, an overture amid Trump administration efforts to push for changes on the communist island.

Col. Raúl Guillermo Rodriguez Castro, 41, known as “El Cangrejo,” the Crab, was the head of personal security when his grandfather Raúl Castro was president and is still his bodyguard and right hand, appearing always close to the ailing Cuban ruler in public. Crucially, he is also the Castro family member who oversees the family interests in the Cuban military’s sprawling business empire.

The conversations, first reported by Axios, were confirmed to the Miami Herald by a source with knowledge of the matter who asked for anonymity to discuss the sensitive issue.

“I wouldn’t call these ‘negotiations’ as much as ‘discussions’ about the future,” a senior Trump administration official told Axios.

On Sunday, President Donald Trump again said his administration was in talks with Cuba, led by Rubio on the U.S. side. He has urged Cuban leaders to make a deal after he acted to shut down Cuba’s oil supply from Venezuela and Mexico.

Following the capture of Venezuelan strongman Nicolás Maduro by U.S. forces, administration officials have been asking whether there is a Cuban version of Delcy Rodriguez, the Venezuelan interim president who has appeared to align with Trump on key U.S. demands.

Even without an official title, Raúl Castro continues to be Cuba’s ultimate authority, and his handpicked successor, Miguel Díaz-Canel, has long been perceived by Cuba experts and U.S. officials as a figurehead lacking the power to make the decision to engage in negotiations with the United States. There have been times that decisions made by Díaz-Canel have been overridden by members of the Castro family, a source with knowledge of the matter who asked for anonymity to discuss the matter, told the Herald.

One open question, the person with knowledge of the conversations between Rubio and Rodriguez Castro said, is how much real power Castro’s grandson commands. He has no official government or Communist Party senior position, and he has no seat on the National Assembly.

But he is Raúl Castro’s gatekeeper and oversees the family interests in GAESA, the military conglomerate that controls much of the country’s economy and most of the sources of foreign revenue. Rodriguez Castro is the son of the late Gen. Luis Alberto Rodriguez Lopez-Calleja, who was the head of GAESA until his sudden death in 2022.

Secret accounting statements from GAESA obtained by the Herald revealed the conglomerate reported having about $18 billion in current assets in March 2024 in unknown bank accounts.

A source with knowledge of GAESA’s businesses who asked not be identified out of fear of repercussions told the Herald that Rodriguez Castro has been a frequent presence in GAESA meetings and was personally involved in many of its shadowy business practices, including those with Panamanian businessman Ramon Carretero Napolitano. One of Carretero’s companies, Corporación Logística del Caribe, which obtained millionaire contracts from the Venezuelan government, is also registered in Cuba.

Rodríguez Castro has been identified since at least 2023 as a frequent passenger in private jets heading to Panama, where GAESA’s largest umbrella company, CIMEX, is registered. Records obtained by Panamanian newspaper La Prensa and Venezuelan outlet ArmandoInfo show Rodriguez Castro flew 13 times to Panama in 2024 and at least 10 times the following year, sometimes using the same private jet used by Carretero. At least once, in May 2024, Rodriguez Castro traveled with Brig. Gen. Ania Guillermina Lastres Morera, the current president of GAESA.

Rodríguez Castro “is an octopus. He has tentacles in everything that has to do with money,” the source with knowledge of GAESA’s internal dealings said.

It is unclear if Rodríguez Castro’s unofficial roles would give him enough clout to negotiate changes on behalf of Cuba, or even on behalf of the Castro family. But the administration sees him as a better entry point to the powerful family than his uncle, Col. Alejandro Castro Espín, who negotiated an opening with President Barack Obama’s envoys.

Castro Espín, who authored a book, “Terror Empire,” a reference to the United States, is considered by the current administration as a hardliner. In his memoir, former CIA chief John Brennan described Castro Espín as ideological and too stuck in the past.

One of Axios’ sources described the conversations between Rubio and Rodríguez Castro as “surprisingly” friendly.

“There’s no political diatribes about the past. It’s about the future,” the source told Axios. ”Raulito could be straight out of Hialeah.”

Rodriguez Castro does not hide his love for a luxurious lifestyle. He has made headlines in Miami for appearing in yachts and luxury hotels. He was a regular at Havana’s nightclubs and was a fan of Cuban reggaeton group Gente de Zona.

“It looks like we are in Miami,” he is heard saying in a video recorded on a yacht. Average Cubans are not allowed aboard yachts.

But even Cuba’s elite will have a hard time continuing a posh lifestyle given the country’s dire economic crisis and the lack of prospects of a way out without significant reforms after Cuba lost its Venezuelan patron. On the U.S. side, Rubio has telegraphed that he is pushing for economic changes in Cuba as a first step Cuban authorities need to take to ease Washington’s pressure.

“I think there has to be that opening, and it has to happen, and I think now Cuba is faced with such a dire situation,” he said. “I think certainly their willingness to begin to make openings in this regard is one potential way forward. “

The Herald reached out to both the State Department and Cuba’s foreign ministry. After early denials, Cuban officials have acknowledged “exchanges of messages” with the Trump administration but have denied ongoing talks.

If efforts at talks between the two countries fail, Cuba has few options.

An ongoing humanitarian crisis has worsened after the halt of oil supplies. Cuba ran out of jet fuel, prompting flight cancellations and the evacuation of tourists. GAESA, which is also a major tourism operator, has closed several hotels. Blackouts now last days, public transportation is non-existent, garbage piles rot on the streets and non-emergency surgeries have been suspended. Thousands are soon to become unemployed as the country’s economy paralyses.

In Miami, Cuban American Republicans in Congress and local officials have been advocating for a maximum-pressure approach, urging the administration to cut flights to Cuba and suspend exports licenses authorizing some U.S. companies to do business with the island. They have also called for Raúl Castro’s indictment for the 1996 shoot-down of a Brothers to the Rescue plane that killed four people, including American citizens.

And Cuba’s traditional allies are unlikely to bankroll the country.

News of the talks came when Cuba’s foreign minister, Bruno Rodríguez, arrived in Moscow on Wednesday to meet his counterpart, Sergey Lavrov, after touring the capitals of China, Vietnam and Spain in an effort to secure support.

But for many years, Cuba’s allies have advocated for economic reforms on the island and, while providing symbolic solidarity, they have halted credits to Cuban companies. Russia has promised Havana support but has avoided providing specifics. And even before the meeting of the foreign ministers began, Lavrov nudged his Cuban counterpart towards engaging in negotiations with the United States.

“Together with most members of the international community, we call on the United States to show sound judgment and a responsible approach, and to refrain from plans to impose a naval blockade of the Island of Freedom,” Lavrov said, according to Russian state news agency TASS. “We are well aware that our Cuban friends are always prepared for such sincere negotiations, and we, in turn, will unwaveringly continue to stand by Cuba and the Cuban people in defending their sovereignty and security.”

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