Trump admin ratchets up pressure on Communist Cuba to new heights amidst tenuous Iran ceasefire

The Justice Department’s indictment of former Cuban strongman Raúl Modesto Castro Ruz on Wednesday is just the latest example of the Trump Administration’s efforts to launch a maximum pressure campaign against the Communist Cuban regime.  

The DOJ revealed that Raul Castro, the brother of former Cuban dictator Fidel Castro, has been charged in connection with a 1996 attack on two airplanes in which four U.S. nationals, including three U.S. citizens, were killed.

Sanctions targeting the Cuban government’s military and intelligence services

The unsealed indictment against Raul — the second revolutionary leader of Communist Cuba following the stepping down of his brother Fidel — charged him and other co-defendants in connection with conspiracy to kill U.S. nationals, the destruction of aircraft, and four counts of murder for the Cuban MiG fighter jet shoot down of humanitarian supply-and-rescue planes flown by Brothers to the Rescue over international waters near Cuba three decades ago.

These steps by the Justice Department are but the most recent example of the Trump Administration putting pressure on the Cuban regime, including sanctions targeting the Cuban government’s military and intelligence services along with repeated calls by President Donald Trump for the Cuban leadership to end its repression of the Cuban people and to make a deal with the United States.

Cuban leader Miguel Diaz-Canel Bermudez responded to the DOJ charges on Wednesday by tweeting that “the purported accusation against Army General Raul Castro Ruz, just announced by the U.S. government, only reveals the arrogance and frustration that the representatives of the empire feel toward the unyielding resolve of the Cuban Revolution and the unity and moral strength of its leadership.”

“This is a political maneuver, devoid of any legal foundation, aimed solely at padding the fabricated dossier they use to justify the folly of a military aggression against #Cuba,” Diaz-Canel, the First Secretary of the Communist Party of Cuba, added on X.

Trump issued a lengthy Cuban Independence Day statement on Wednesday, arguing that “across generations, the Cuban people have demonstrated an unyielding devotion to the cause of freedom and a resilience of spirit that no regime—past or present—has been able to extinguish.”

“The regime in Havana today is the direct betrayal of the nation their founding patriots bled and died for. For nearly seven decades, the island’s communist government has violently dismantled political freedom, denied its people fair elections, viciously silenced dissent, and strangled the Cuban economy into a state of collapse,” Trump said. 

“While the people suffer, the regime’s kleptocratic elite have hoarded the island’s remaining resources for themselves and their lavish lifestyle. In the way of all radical leftist ideologies, the regime has quashed any hope of prosperity, banished the notion of human dignity, and starved the hopes and dreams of its people. Its military leaders have demonstrated zero care for ensuring the prosperity of the Cuban people, channeling their attention instead only towards maintaining control and the regime’s raison d'être of violently exporting communism and despotism abroad.”

Trump: "Severing the financial lifelines"

The Cuban Constitution touts the centrality of Marxist-Leninist-style communism to the Cuban regime.

“The Communist Party of Cuba, unique, Martiano, Fidelista, and Marxist-Leninist, the organized vanguard of the Cuban nation, sustained in its democratic character as well as its permanent linkage to the people, is the superior driving force of the society and the State,” the Cuban Constitution declares.

Trump said Wednesday that “under my leadership, our Nation is severing the financial lifelines that, for too long, have sustained brutal regimes across Central and South America and funded their transnational criminal and terrorist operations that threaten the United States.”

The president pointed to the U.S. military raid which captured Venezuelan strongman Nicolás Maduro, arguing that “the indictment and removal of Maduro sent a clear message to his socialist allies in Havana: This is our Hemisphere and those that destabilize it and threaten the United States will face consequences.”

America will not tolerate a rogue state

“Following the Maduro raid, I have enacted powerful new sanctions on Cuba’s military and intelligence apparatus, and those who provide it with material and financial support, depriving the regime of resources and its elites from the opportunity to profit from the people’s suffering,” Trump said. “My commitment is ironclad:  harboring hostile foreign military, intelligence and terror operations just ninety miles from the American homeland, and we will not rest until the people of Cuba once again have the freedom their forefathers fought so valiantly to establish over 100 years ago.”

Secretary of State Marco Rubio, himself the son of Cuban refugees, also issued a Spanish-language video on Wednesday directed to the people of Cuba.

“The real reason you don’t have electricity, fuel, or food is because those who control your country have plundered billions of dollars, but nothing has been used to help the people,” Rubio said, adding that “in the U.S., we are ready for a new chapter in the relationship between our people and our countries. And currently, the only thing standing in the way of a better future are those who control your country.”

Then-President Joe Biden spent the final days of his presidency weakening the U.S. stance toward the Cuban regime.

Biden rescinded the designation of Cuba as a state sponsor of terrorism in a mid-January 2025 order, claiming that “the Government of Cuba has not provided any support for international terrorism during the preceding 6-month period” and that “the Government of Cuba has provided assurances that it will not support acts of international terrorism in the future.”

Just days before leaving office that month, Biden also rescinded a National Security Presidential Memorandum issued by Trump in June 2017 during his first term which had been focused on “Strengthening the Policy of the United States Toward Cuba.”

Biden insisted in his revocation that “the United States maintains as the core objective of our policy the need for more freedom and democracy, improved respect for human rights, and increased free enterprise in Cuba” but that “achieving these goals will require practical engagement with Cuba and the Cuban people beyond what is outlined in National Security Presidential Memorandum 5, and that takes into account recent developments in Cuba and the changing regional and global context.”

Trump quickly reversed these reversals, including on his second Inauguration Day in January 2025, when he tossed Biden’s rescission of Cuba’s designation as a state sponsor of terrorism.

Cuba has been designated as a state sponsor of terrorism since mid-January 2021, and with Trump’s reversal of Biden’s last-minute rescission, the Cuban regime currently remains so designated.

Rubio, who is of Cuban descent and was born in Miami, Florida, to Cuban parents who immigrated to the United States in 1956, prior to the Cuban Revolution, said in late January 2025 that “within the first two weeks of President Trump’s term, the State Department took decisive action to rescind major last-minute policy changes on Cuba announced by the previous administration.”

“The President acted on his first day in office to keep Cuba on the state sponsor of terrorism list, where it belongs. The Cuban regime has long supported acts of international terrorism. We call for the regime to end its support for terrorism, and to stop providing food, housing, and medical care to foreign murderers, bomb makers, and hijackers, while Cubans go hungry and lack access to basic medicine,” Rubio said.

The Secretary of State said that he had also “approved the re-creation of the Cuba Restricted List, which prohibits certain transactions with companies under the control of, or acting for or on behalf of, the repressive Cuban military, intelligence, or security services or personnel” in an effort to “deny resources to the very branches of the Cuban regime that directly oppress and surveil the Cuban people while controlling large swaths of the country’s economy.”

Trump then said in June 2025 that he was reissuing and beefing up the National Security Presidential Memorandum from his first term, which Biden had thrown out.

“My Administration’s policy will be guided by the national security and foreign policy interests of the United States, as well as solidarity with the Cuban people,” the president said. “I will seek to promote a stable, prosperous, and free country for the Cuban people. To that end, we must channel funds toward the Cuban people and away from a regime that has failed to meet the most basic requirements of a free and just society.”

The Trump White House said that day that the president’s new directive “ends economic practices that disproportionately benefit the Cuban government, military, intelligence, or security agencies at the expense of the Cuban people” and again emphasized that Trump “is committed to fostering a free and democratic Cuba, addressing the Cuban people’s long-standing suffering under a Communist regime.”

The Trump Administration continued to turn the screws on the Communist Cuban regime this year, with the successful U.S. military raid on Maduro seeming to buoy Trump’s confidence that the Cuban regime could be pressured to change course and make a deal with the United States.

“Cuba lived, for many years, on large amounts of OIL and MONEY from Venezuela. In return, Cuba provided ‘Security Services’ for the last two Venezuelan dictators, BUT NOT ANYMORE! Most of those Cubans are DEAD from last week’s U.S.A. attack, and Venezuela doesn’t need protection anymore from the thugs and extortionists who held them hostage for so many years,” Trump posted on Truth Social in mid-January. 

“Venezuela now has the United States of America, the most powerful military in the World (by far!), to protect them, and protect them we will. THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA - ZERO! I strongly suggest they make a deal, BEFORE IT IS TOO LATE” Trump said.

The president then issued an executive order in late January where he declared that “the policies, practices, and actions of the Government of Cuba constitute an unusual and extraordinary threat […] to the national security and foreign policy of the United States.”

Trump noted that the Cuban regime “aligns itself with — and provides support for — numerous hostile countries, transnational terrorist groups, and malign actors adverse to the United States” including Russia, China, Iran, Hamas, and Hezbollah.

The Trump White House quickly put out a fact sheet which noted that Trump “signed an Executive Order declaring a national emergency and establishing a process to impose tariffs on goods from countries that sell or otherwise provide oil to Cuba, protecting U.S. national security and foreign policy from the Cuban regime’s malign actions and policies.”

The fact sheet noted that Trump “may modify the Order if Cuba or affected countries take significant steps to address the threat or align with U.S. national security and foreign policy objectives.”

“All my life I’ve been hearing about the United States and Cuba. You know, ‘When will the United States do it?’ I do believe I’ll be having the honor of taking Cuba. That’d be good. That’s a big honor,” Trump said. The president added, “Whether I [freely] take it — think I could do anything I want with it, you want to know the truth.”

Rubio also weighed in in March. “Cuba has an economy that doesn’t work and a political and governmental system that can’t fix it,” Rubio said. “So they have to change dramatically […] They’re in a lot of trouble. And the people in charge don’t know how to fix it. So they have to get new people in charge.”

The so-called “humanitarian” trips to Cuba in March were in large part organized by groups within the activist network tied to and funded by wealthy Marxist and China-based businessman Neville Roy Singham, as well as by the far-left Progressive International (which counts the leftist anti-war group Code Pink, which is personally and financially tied to Singham, as one of its member organizations).

The State Department soon increased the pressure on Cuba. Rubio announced in early May that “the Trump Administration is taking decisive action to protect U.S. national security and deprive Cuba’s communist regime and military of access to illicit assets” as he laid out the sanctioning of a number of Cuban government-linked actors.

“GAESA, a Cuban military-controlled umbrella enterprise, is the heart of Cuba’s kleptocratic communist system,” the Secretary of State said of the designation of one of the Cuban groups. “Controlling an estimated 40 percent or more of the island’s economy, GAESA is involved in various sectors of the Cuban economy and is designed to generate income not for the Cuban people, but only for the benefit of its corrupt elites. While the Cuban people suffer from hunger, disease and chronic under-investment in critical infrastructure such as its power grid, much of the proceeds of GAESA’s activities are funneled away to hidden overseas bank accounts.”

Rubio: "National security threats posed by Cuba" only 90 miles away

Rubio added: “These sanctions are part of the Trump Administration’s comprehensive campaign to address the pressing [of the] communist regime and hold accountable the regime and those who provide it material or financial support. Just 90 miles from the American homeland, the Cuban regime has brought the island to ruin and auctioned off the island as a platform for foreign intelligence, military and terror operations.”

The Trump White House put out a Cuba sanctions fact sheet which said the president had “signed an Executive Order imposing new sanctions on the Cuban regime, protecting U.S. national security.”

The fact sheet also hinted at possible military action aimed at the Cuban regime.

“President Trump continues to demonstrate his commitment to directly addressing national security threats from abroad. Operation Absolute Resolve captured Venezuelan dictator and indicted narcoterrorist Nicolás Maduro and his wife to face American justice,” the White House said. “Operation Southern Spear eliminated 186 narcoterrorists in strikes against fentanyl-trafficking vessels, stemming the deadly flow of drugs into America.”

The Cuba-related fact sheet continued: “In Operation Midnight Hammer, President Trump decisively eliminated Iran’s nuclear weapons capability via targeted military strikes, escalated sanctions, and intelligence operations. Operation Epic Fury successfully completed all of its military objectives in less than six weeks. Iran no longer poses the nuclear and terror threat it did, and no longer has the nuclear ambitions it held before.”

Granma — the house organ of the Communist Party of Cuba — relayed remarks by Political Bureau member and Foreign Minister Bruno Rodriguez Parrilla earlier in May: “The current exclusionary international order has been practically destroyed by the US attempt to make it unipolar again, through an imperialist agenda based on military force, supremacism, and fascist neoconservatism,” the Communist Cuban official raged.