May 19, 2026 — After U.S. forces carried out a bold operation that removed Venezuelan leader Nicolás Maduro, President Trump has signaled he wants to press similar pressure on Cuba, saying “Cuba’s going to be next” and suggesting the U.S. might take action there as well. In the wake of tighter U.S. measures and what U.S. officials describe as an effective oil blockade, living conditions in Cuba have worsened and Washington has held talks with senior Cuban figures to press for political and economic change.
What follows are the key Cuban figures observers say will matter if the United States tries to push for a transition or negotiate reforms.
Raúl Castro
Raúl Castro, the younger brother of Fidel Castro, stopped serving as Cuba’s president in 2018 and left the Communist Party leadership in 2021, but he remains widely seen as one of the country’s most influential people. A veteran of the 1959 revolution and long-time commander of the armed forces, Raúl succeeded Fidel as president in 2008 and later as party leader.
U.S. reporting says steps are underway to indict the 94-year-old Raúl Castro over the 1996 downing of two exile-run planes. Seen as more pragmatic than Fidel, Raúl helped negotiate the brief U.S.-Cuba opening under President Barack Obama in 2014 — a rapprochement largely reversed during the Trump administration. Even out of formal office, analysts say Raúl continues to exert major influence over high-level decisions.
Miguel Díaz-Canel
Miguel Díaz-Canel has been Cuba’s president since 2018 and now leads the Communist Party; his term runs through 2028. He is the first leader who is not a Castro since the revolution and was chosen by Raúl Castro to take the post.
U.S. officials reportedly doubt that Díaz-Canel is the person who can deliver the kind of changes Washington seeks. Experts describe him as a loyal functionary with limited independent authority — the public head of state but not the main power broker. Díaz-Canel has said talks with the U.S. should seek to identify differences and paths forward, and he has vowed Cuba would resist any U.S. military action.
Oscar Pérez-Oliva Fraga
Oscar Pérez-Oliva Fraga, a 55-year-old electrical engineer and great-nephew of Fidel and Raúl Castro, has emerged as a rising figure. Appointed deputy prime minister in late 2025, he also serves as minister of foreign trade and investment and has reportedly been named to the National Assembly — a status that would make a future presidential ascent legally possible.
Pérez-Oliva Fraga led a March policy move to allow Cubans in the diaspora to invest and own businesses on the island, a significant shift from decades of state-dominated enterprise and a notable political and economic opening. He also has some oversight of GAESA, the military-controlled conglomerate that runs major tourism, finance and import businesses.
On May 7, the U.S. State Department announced new sanctions targeting GAESA, saying it controls a large portion of Cuba’s economy (estimates often put it at 40% or more), generates income for the country’s elite, and may hold substantial assets abroad. Analysts warn that moves to liberalize investment could clash with U.S. laws like the Helms-Burton Act, which ties removal of the embargo to a transition that excludes the Castros and moves toward market reforms and free elections.
Raúl Guillermo Rodríguez Castro (“Raulito”)
Raúl Guillermo Rodríguez Castro, nicknamed “Raulito” or “El Cangrejo,” is the 41-year-old grandson of Raúl Castro. Born with a sixth finger, he serves as his grandfather’s bodyguard and adviser and has no formal government post. Still, analysts call him a gatekeeper to Raúl and an important conduit for outside contacts. He reportedly has met with U.S. officials in recent months and has been identified as a potential interlocutor in any negotiations.
Is there a Cuban equivalent to Venezuela’s “Delcy”?
When the U.S. operation in Venezuela removed Maduro, Washington quickly recognized Vice President Delcy Rodríguez as an interim leader it could work with. Observers say Cuba lacks an obvious “Delcy” — a widely recognized, moderate alternative who could be elevated and cooperated with by the United States.
Some analysts suggest Pérez-Oliva Fraga could fill that role, given his trade portfolio and apparent openness to economic change. Others caution it’s not clear there is any reliable Cuban analogue who could serve as an acceptable interim partner. Removing or replacing Cuba’s visible leaders may be easier on paper than in reality, since the real levers of power are dispersed across the party, military and family networks.
U.S. goals and Cuban red lines
U.S. policymakers pushing for a rapid transition say those in power must change. But Cuban officials have drawn firm red lines: they will discuss a range of economic issues but reject U.S. dictation of their political system or who leads it, viewing such demands as violations of national sovereignty. That stance makes any negotiated settlement that includes direct U.S. influence over leadership highly contentious and a likely sticking point in talks.
Outlook
The Castro family — in formal roles and behind the scenes — remains central to Cuba’s politics. Raúl Castro’s continued influence, a president who may be viewed as largely administrative, a rising great-nephew with trade and investment clout, and a grandson who functions as a gatekeeper are the key pieces to watch. Whether Washington can find Cuban partners willing and able to deliver the kind of change it seeks, and whether the Cuban leadership will accept U.S. pressure without surrendering core sovereignty claims, will determine how the next chapter in U.S.-Cuba relations unfolds.