Will Raúl Castro be the next Maduro?

At 95, Raúl Castro has outlived most of his enemies and allies. Arguably, he has also outlived much of the world's patience with the Cuban revolution.

He survived the Cold War, the Special Period, Barack Obama's diplomatic opening and Donald Trump's first term. Whether he can withstand the second is now an open question.

On 20 May, the US Department of Justice indicted the former Cuban president on charges of conspiracy to kill US nationals, destruction of an aircraft and murder. The charges stem from the 1996 shootdown of two civilian aircraft belonging to the Cuban-American humanitarian group Brothers to the Rescue.

The announcement came on the same day the Cuban diaspora commemorated independence from Spain. In Havana, many residents viewed the timing as political provocation.

What makes this moment different from previous episodes in the long US-Cuba confrontation is what happened in Caracas four and a half months earlier, when Venezuelan leader Nicolás Maduro was captured by US forces.

Trump has repeatedly said Cuba is "next" after Venezuela. He has warned that Maduro's capture changed the calculus for authoritarian leaders across the Western Hemisphere.

Acting Attorney General Todd Blanche was even more direct. He said the Justice Department expects Castro to "show up here, by his own will or another way".

Decades-long confrontation

The feud stretches back over six decades — through the Bay of Pigs, the Missile Crisis, assassination attempts too numerous to fully catalogue, and the long, grinding misery of the US embargo. 

The Brothers to the Rescue incident, which forms the legal basis of the indictment, was itself a product of that unresolved hostility. The four men killed on 24 February 1996 were searching for Cuban rafters in the Florida Straits. Cuba shot down their planes, claiming they had violated Cuban airspace. Washington called it murder. The case was never prosecuted until now.

What the Trump administration has done is revive a 30-year-old grievance and place it within a broader strategic framework — the so-called "Donroe Doctrine", a modernised version of the Monroe Doctrine that reasserts US influence over the hemisphere in unusually direct terms.

The Maduro operation gave that doctrine its first proof of concept. The Castro indictment may be preparing its second.

Will the pressure work? 

For months, the Trump administration has been laying economic siege to the island with the systematic thoroughness of a long-planned campaign. 

When US forces ousted Maduro, the resulting blockade of Venezuelan oil destined for Cuba left the island without adequate supply. The United States then began blocking oil tankers heading to Cuba from February 2026, threatening countries that resisted with tariffs. 

A complete regime collapse in Havana risks triggering a migration crisis on a scale that would immediately consume Trump's domestic political agenda. While Trump claims the Cuban government is "desperate" to make a deal, he said the same about Venezuela and Iran, where negotiations abruptly ended with US military strikes. 

The effects have been profound. A March 2026 survey found that 80% of Cubans believe the current crisis is worse than the Special Period of the 1990s. Blackouts last up to 22 hours a day. 

The tourism sector, which sustained much of the remaining economy, is also deteriorating. US sanctions, worsening fuel shortages and direct pressure on the Cuban military conglomerate GAESA are accelerating the sector's decline.

The tourist sector, which sustained what remained of the economy, is imploding: the convergence of US sanctions, a worsening fuel shortage, and direct targeting of GAESA is hastening the collapse of Cuba's air connectivity, with Iberia, Air Transat, and Sunwing all suspending or curtailing services to the island. 

But Cuba is not Venezuela

The most obvious is geography. Cuba is 90 miles from Florida. Venezuela is 1,400 miles away. A complete regime collapse in Havana risks triggering a migration crisis on a scale that would immediately consume Trump's domestic political agenda. 

While Trump claims the Cuban government is "desperate" to make a deal, he said the same about Venezuela and Iran, where negotiations abruptly ended with US military strikes. 

But the refugee dynamics are different. Since 2021, more than one million Cubans — mostly productive young people — have already fled the island. A sudden power vacuum could accelerate that exodus into a flood, arriving on the shores of a president who has staked his entire second term on stopping illegal immigration. 

There is also the question of what, precisely, the US would be capturing. Castro is 95, reportedly using a wheelchair, and though he remains the revolution's most powerful symbolic figure, he is viewed by some analysts as the "living embodiment of the revolution" rather than its operational engine. The US may end up making him the symbol of Cuban resistance, like Khameini in Iran. 

The "Crab" and the off-ramp

The emergence of a diplomatic back-channel suggests Washington may be pursuing leverage rather than a literal raid.

Cuba's Colonel Raúl Guillermo Rodríguez Castro — grandson of the former president and known as "El Cangrejo", or "the Crab" — has appeared alongside President Miguel Díaz-Canel at several public events.

His growing visibility has raised questions among analysts about his role in Cuba's leadership as the island faces increasing calls for regime change from the United States.

Raul's emergence is widely interpreted as a signal that the Castro family is exploring the existence of a personal off-ramp through a deal that preserves family interests and avoids the fate of watching the patriarch wheeled into a Miami courtroom. 

The indictment, in this reading, is not a prelude to a raid but a bargaining chip. 

This could include forcing Cuba to remove Russian and Chinese intelligence assets from the island. It could also involve settling billions of dollars in unresolved property claims or dismantling key structures within the regime before any military option is considered. 

However, a lot may unfold in the coming days. 

Raúl Castro is not Nicolás Maduro. He is older, frailer, but more symbolic and more strategically difficult to remove.

But he is now indicted, blockaded and living just 90 miles from a country that recently demonstrated its willingness to extract a sitting head of state from a fortified compound.

For a 95-year-old revolutionary who spent decades warning that imperialism was always at the door, the threat may now feel more immediate.