He is the president, but he's not the real power on the island
For the first time in generations, an American administration is moving beyond sanctions and rhetoric to contemplate direct intervention in Cuba, emboldened by the swift removal of Venezuela's Maduro and tightening economic pressure on the island. The Trump administration has begun identifying which figures in Havana hold real power — and which might be workable partners in a transition — yet the architecture of Cuban authority remains deliberately opaque, distributed among aging revolutionaries, loyal functionaries, and family gatekeepers. What the United States seeks is a Venezuela-style outcome; what it lacks, for now, is a Venezuela-style opening — a trusted insider willing to bridge the chasm between sovereignty and change.
- Trump has declared Cuba 'next' after Venezuela, openly musing about military intervention and 'taking Cuba in some form' — language that signals regime change, not mere diplomacy.
- A virtual oil blockade has deepened Cuba's economic crisis since Maduro's fall, creating pressure but also hardening the government's resistance to foreign-dictated political transformation.
- The administration is quietly meeting with Cuban figures, including Raúl Castro's grandson 'Raulito,' who serves as the 94-year-old patriarch's gatekeeper and has become a primary back-channel contact.
- Deputy Prime Minister Oscar Pérez-Oliva Fraga — a Castro great-nephew who recently opened the door to diaspora investment — has emerged as a possible 'Delcy Rodriguez' figure, though analysts say no clear analogue yet exists.
- Cuba has drawn a firm red line: it will discuss economics, but will not allow Washington to dictate its political system or its leaders — a sovereignty claim that may prove the decisive obstacle to any deal.
President Trump has begun speaking openly about a military intervention in Cuba modeled on the operation that removed Nicolás Maduro from Venezuela, declaring that 'Cuba's going to be next' and signaling an appetite for leadership change on the island. With a virtual oil blockade tightening conditions since Maduro's departure, administration officials have been meeting with key Cuban figures to press for reform — though whether a viable path exists, or whether the U.S. has found the kind of internal ally that made Venezuela possible, remains deeply uncertain.
Raúl Castro, 94, formally stepped down from the presidency in 2018 and from the Communist Party in 2021, yet remains widely understood as the island's most influential figure. CBS News has learned the U.S. is preparing to indict him in connection with a 1996 military operation against Cuban exile aircraft. His legacy spans the 1959 revolution, nearly five decades as head of the armed forces, and a brief diplomatic opening with President Obama in 2014 that the first Trump term largely reversed.
Current President Miguel Díaz-Canel, the first non-Castro to hold the office since the revolution, is viewed by the Trump administration as an obstacle rather than a partner. Experts describe him as a loyal functionary — the president in title, but not the real power. His removal, analysts suggest, would pose little difficulty for whoever actually controls authority in Havana.
Oscar Pérez-Oliva Fraga, a 55-year-old electrical engineer and Castro great-nephew, has drawn growing attention as a potential transitional figure. Appointed deputy prime minister last October, he recently announced a policy allowing diaspora Cubans to invest on the island — a striking reversal given that emigrants were once officially derided as traitors. His portfolio also gives him oversight of GAESA, the military-controlled conglomerate the State Department estimates controls 40 percent or more of Cuba's economy and possibly $20 billion in illicit assets, a body now subject to new U.S. sanctions.
Raúl Castro's 41-year-old grandson, known as 'Raulito,' holds no formal title but serves as his grandfather's bodyguard and adviser — and, according to analysts, the essential gatekeeper to the man who still shapes Cuban decisions. He has emerged as the administration's primary back-channel contact, meeting with officials including Secretary of State Marco Rubio.
The Venezuela model is instructive but imperfect. After Maduro's removal, the U.S. recognized Vice President Delcy Rodríguez as interim leader — someone Washington believed it could work with. Analysts have floated Pérez-Oliva Fraga as Cuba's equivalent, but experts caution that no clear analogue has yet been identified. Meanwhile, Cuban officials have drawn a firm line: they will engage on economic questions, but will not permit Washington to dictate their political system or their leadership. That insistence on sovereignty, observers warn, may prove the central and perhaps insurmountable obstacle to any agreement.
President Trump has begun openly discussing a military intervention in Cuba modeled on the swift operation that removed Nicolás Maduro from power in Venezuela months earlier. He has declared that "Cuba's going to be next" and mused about "taking Cuba in some form," signaling an appetite for what he calls "a new dawn for Cuba" — language that suggests he is contemplating a change in the island's leadership structure itself. For decades, American administrations have cycled through sanctions and diplomatic pressure without dislodging Cuba's communist system, watching helplessly as the economy deteriorated. Now, with a virtual oil blockade tightening conditions further since Maduro's departure, Trump administration officials have been meeting with key Cuban figures to press for economic and political reform. What remains unclear is whether the administration has identified a viable path to achieve what it is seeking, or whether it possesses the kind of internal ally that made the Venezuela operation possible.
Raúl Castro, the 94-year-old younger brother of revolutionary leader Fidel Castro, formally stepped down from the presidency in 2018 and relinquished his role as head of the Communist Party in 2021. Yet he remains widely understood as one of the most influential figures in the country. CBS News has learned that the U.S. is preparing to indict him in connection with a 1996 military operation carried out by the Cuban exile group Brothers to the Rescue. Castro served as a guerrilla commander under his brother during the 1959 revolution that toppled Fulgencio Batista, and he later headed Cuba's armed forces while Fidel ruled for nearly five decades. When Fidel stepped aside in 2008, Raúl assumed the presidency and three years later took control of the Communist Party. He is often characterized as more pragmatic than his brother—in 2014, he negotiated an accord with President Barack Obama that opened the most significant diplomatic channels between the countries since the early 1960s, though the Trump administration's first term largely reversed those gains.
Miguel Díaz-Canel has served as president since 2018 and also leads the Communist Party, with his term scheduled to run through 2028. He is the first non-Castro to hold the presidency since the 1959 revolution, hand-selected by Raúl Castro for the role. The Trump administration, according to reports, does not believe the changes it seeks can materialize under his leadership. Díaz-Canel has stated that talks between Cuba and the U.S. should focus on identifying differences and possible resolutions, and he has publicly declared that Cuba would defeat any military takeover attempt. Yet experts view him as fundamentally a functionary—a loyal executor of decisions made elsewhere. Christopher Hernandez-Roy, senior fellow at the Center for Strategic and International Studies, described Díaz-Canel as "not one of the central power brokers in Cuba. He is the president, but he's not the real power on the island." This assessment suggests that removing him would pose little difficulty for whoever actually holds authority in Havana.
Oscar Pérez-Oliva Fraga, a 55-year-old electrical engineer and great-nephew of both Fidel and Raúl Castro, has emerged as a figure of growing significance. Appointed deputy prime minister last October, he also serves as minister of foreign trade and investment and has recently been added to the National Assembly—a legal prerequisite for ascending to the presidency. In March, he announced a policy reversal allowing Cubans in the diaspora and exile to invest in the island, a striking shift given that emigrants were once derided under Fidel Castro as "gusanos," or worms. Hernandez-Roy called this "a fairly significant opening" and evidence of willingness to move the economy in a "slightly different direction." However, the move potentially conflicts with the Helms-Burton Act, which ties the lifting of the U.S. embargo to the establishment of a transition government excluding both Fidels and the introduction of free-market reforms and elections. Pérez-Oliva Fraga's trade portfolio also grants him oversight of GAESA, Cuba's military-controlled conglomerate spanning tourism, finance, and imports. The U.S. State Department, which imposed new sanctions on GAESA in May, estimates the entity controls 40 percent or more of Cuba's economy and may oversee up to $20 billion in illicit assets.
Raúl Guillermo Rodríguez Castro, known as "Raulito" and nicknamed "El Cangrejo" (The Crab) for a sixth finger he was born with, is Raúl Castro's 41-year-old grandson. He holds no formal government position but serves as his grandfather's bodyguard and adviser. Despite his lack of official title, Hernandez-Roy identifies him as crucial—"the gatekeeper to his grandfather, who even though he's 94, remains absolutely central to decisionmaking in Cuba." Raulito has been identified as the primary point of contact with the Trump administration, meeting with officials over recent months, including Secretary of State Marco Rubio. He could potentially play a role in any negotiated settlement.
The Venezuela template offers a suggestive model. After Maduro was removed by U.S. military forces within hours, the Trump administration recognized his vice president, Delcy Rodríguez, as interim president—someone the administration believed it could work with. Hernandez-Roy has suggested that Oscar Pérez-Oliva Fraga might serve as Cuba's equivalent "Delcy." However, Ryan Berg, former director of CSIS's Americas Program, noted a critical obstacle: "for now, it doesn't seem as if there is an analogue to the Venezuela situation—meaning there is a kind of Delcy Rodriguez that we can identify in Cuba to work with as a kind of interim leader." The U.S. may be exploring options, with Castro family members emerging as the most plausible candidates, though their exact role in any future arrangement remains undefined.
William LeoGrande, a Latin American politics specialist at American University, offered a sobering assessment of the diplomatic landscape. While he acknowledged that Secretary of State Rubio insists "the people in charge have to change," he expected significant resistance. "The Cubans are willing to discuss a wide range of economic issues," LeoGrande told CBS News, "but they've already drawn a red line on letting the United States dictate either the shape of their political system or who their political leaders are. To them, that's a matter of their national sovereignty." That fundamental disagreement, he suggested, is likely to become the central obstacle to any agreement.
Notable Quotes
He is the president, but he's not the real power on the island. If he were to step down or if he would be removed, that's a fairly easy concession for the true power brokers in Cuba to make.— Christopher Hernandez-Roy, Center for Strategic and International Studies
The Cubans are willing to discuss a wide range of economic issues, but they've already drawn a red line on letting the United States dictate either the shape of their political system or who their political leaders are. To them, that's a matter of their national sovereignty.— William LeoGrande, American University
The Hearth Conversation Another angle on the story
Why does Trump think he can replicate what happened in Venezuela? What made that operation work?
Speed and internal collapse. Maduro's military fractured, his economy was in freefall, and there was a figure—Delcy Rodríguez—already positioned to step in. The U.S. recognized her as interim president and moved fast. Cuba's different. The military is still cohesive, and there's no obvious "Delcy" waiting in the wings.
So who is the "Delcy" of Cuba, if anyone?
That's the question nobody can answer yet. Oscar Pérez-Oliva Fraga looks like the best candidate—he's got the trade portfolio, he's a Castro relative, he's been positioned in the National Assembly. But he's not a household name, and it's not clear the real power brokers would accept him.
You said "real power brokers." Who actually runs Cuba?
That's the puzzle. Raúl Castro is 94 and officially retired, but everyone says he's still central to decisions. His grandson Raulito is the gatekeeper. Díaz-Canel is president on paper, but experts describe him as a functionary—someone executing orders, not making them. The actual power is diffuse and opaque.
What does Cuba want from these negotiations?
Economic relief, mainly. They're willing to talk about investment, trade, opening up some sectors. But they've drawn a hard line: the U.S. cannot dictate their political system or their leaders. That's sovereignty to them. It's non-negotiable.
And the U.S. position?
Rubio keeps saying the people in charge have to change. Trump wants something big—a "new dawn." But without a clear internal ally and with Cuba refusing to let Washington pick its leaders, there's a fundamental mismatch. One side wants regime change; the other wants economic negotiation.
What happens if neither side budges?
Then you're back where you've always been—sanctions, isolation, and a stalemate that lasts another decade. The Venezuela playbook only works if there's someone inside willing to flip. Right now, that person doesn't exist.