In the wake of a bold but brief military intervention that led to the ousting of Nicolás Maduro from his position as Venezuela’s leader, President Trump has hinted that a similar operation could be on the horizon for Cuba. He has remarked, “Cuba’s going to be next,” and contemplated potential actions to “take Cuba in some form.”
For many years, various U.S. administrations have attempted to instigate significant change within Cuba’s communist regime through sanctions, yet these efforts have yielded minimal results as the nation’s economy continues to deteriorate.
As conditions in Cuba decline further due to an effective oil blockade enacted by the Trump administration following Maduro’s removal, U.S. officials have been engaging with influential Cuban figures to advocate for economic and political reforms.
President Trump has indicated a desire for substantial change in Cuba, possibly mirroring the operation that led to Maduro’s exit. He expressed his intention to “bring about a day 70 years in waiting — it’s called a new dawn for Cuba.”
The implications of this for Cuba’s current leadership remain uncertain, but several key individuals are crucial to observe.
Raúl Castro, the younger sibling of the iconic revolutionary Fidel Castro, relinquished the presidency in Cuba in 2018 and stepped down as the head of the Communist Party in 2021. Despite this, he continues to be perceived as one of the most influential figures in the nation.
Reports from CBS News suggest that the U.S. is considering indicting the 94-year-old Raúl Castro for his involvement in the 1996 downing of two planes operated by the Cuban exile organization, Brothers to the Rescue.
Raúl Castro was a commander during the guerrilla conflict that led to the downfall of U.S.-backed dictator Fulgencio Batista in 1959. Following his brother Fidel’s nearly five-decade leadership, Raúl took over the presidency in 2008 and later succeeded him as the leader of the Communist Party in 2011. Fidel Castro passed away in 2016.
Unlike Fidel, Raúl is viewed as a more pragmatic leader and was instrumental in reaching an agreement with then-President Barack Obama in 2014, which marked the most significant thaw in U.S.-Cuban relations since the early 1960s. However, many of these advancements were largely undone during Trump’s first term.
Since 2018, Miguel Díaz-Canel has held the presidency in Cuba and also leads the Communist Party, with his term set to last until 2028. He is the first leader outside the Castro family to govern Cuba since the 1959 revolution and was chosen for the role by Raúl Castro himself.
It has been reported that the Trump administration doubts the feasibility of the desired changes under Díaz-Canel’s leadership.
Díaz-Canel has stated that the discussions between Cuba and the U.S. aim to pinpoint differences and explore potential resolutions for future collaboration. In response to Trump’s military takeover threats, he asserted that Cuba would prevail against such actions.
However, many experts regard Díaz-Canel as more of a figurehead, lacking significant power. Christopher Hernandez-Roy, a senior fellow at the Center for Strategic and International Studies, noted, “He’s not one of the central power brokers in Cuba. If he were to step down or be removed, that would be an easy concession for the actual power holders in Cuba.”
Deputy Prime Minister Oscar Pérez-Oliva Fraga, who does not carry the Castro name but is a great-nephew of both Fidel and Raúl, is already a member of the government. At 55, he has a background as an electrical engineer and was appointed to his deputy prime minister role last October while also serving as Cuba’s minister of foreign trade and investment.
Recent reports suggest he has been elected to the National Assembly, which positions him legally to potentially ascend to the presidency. His responsibilities in trade and investment include facilitating a March announcement that allows Cubans in the diaspora to invest and own businesses in Cuba, a significant shift from the past when those who emigrated were disparaged as “gusanos” or “worms.” This development indicates a willingness to steer the economy in a new direction, according to Hernandez-Roy.
Nonetheless, this approach might conflict with the Helms-Burton Act, which stipulates that the U.S. embargo on Cuba can only be lifted once a transitional government is established that excludes Fidel and Raúl Castro, and that proceeds toward a free-market economy and democratic elections.
Pérez-Oliva Fraga’s role as trade minister also gives him some authority over GAESA, the military-controlled conglomerate that dominates Cuba’s tourism, finance, and import sectors. The U.S. State Department, which imposed new sanctions on GAESA on May 7, estimates that this entity controls over 40% of Cuba’s economy and generates revenue primarily benefiting corrupt elites. It is believed that GAESA’s income is significantly greater than the national budget and may hold up to $20 billion in illicit assets.
Raúl Guillermo Rodríguez Castro, affectionately known as “Raulito,” is the 41-year-old grandson of Raúl Castro and serves as his bodyguard and adviser. Although he does not hold an official government position, Hernandez-Roy describes him as a pivotal figure, acting as a “gatekeeper” to his grandfather, who, despite his advanced age, remains vital in Cuba’s decision-making processes.
Rodríguez Castro has been recognized as the primary contact for discussions with the U.S., meeting with officials from the Trump administration in recent months, including discussions in mid-April.
