The Trump administration is rolling out what experts describe as the most significant expansion of U.S. sanctions on Cuba in decades.

The administration is attempting what supporters say is the first broad application of Cuba-related secondary sanctions against foreign firms, aiming not only at Havana itself but also at foreign companies and banks that continue doing business with the island’s military-linked economic empire. 

The new framework, established under an executive order signed by President Donald Trump May 1, applies pressure beyond U.S. companies for the first time, threatening foreign firms with sanctions exposure if they continue operating in key sectors of the Cuban economy linked to Grupo de Administración Empresarial S.A., or GAESA.

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Supporters say the move closes a loophole that allowed foreign investors to sustain Cuba’s communist regime while the longstanding U.S. embargo largely restricted Americans.

Critics argue the measures risk worsening an already severe humanitarian crisis on the island without meaningfully weakening the government.

"At the top of the month, what the Trump administration did was for the first time extend the application of U.S. sanctions from just prohibiting trade between U.S. firms and U.S. persons and the Cuban island to third-party countries and enablers," Max Meizlish, a former Treasury Department official now serving as a research fellow at the Foundation for Defense of Democracies, told Fox News Digital in an interview.

"For the first time ever in a truly unprecedented fashion, that’s the same logic that the administration is now applying to Cuba," he said.

The sanctions focus heavily on GAESA, a sprawling military-linked conglomerate that analysts estimate controls between 40% and 70% of Cuba’s economy, including tourism, mining, retail, ports and financial services. 

A recent Foundation for Defense of Democracies report authored by Meizlish and Connor Pfeiffer argued that foreign companies doing business in Cuba are effectively helping sustain the regime’s military and political leadership.

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The State Department sanctioned GAESA and several affiliated entities in May under the new authorities, opening the door for potential penalties against foreign companies and financial institutions that continue dealings with them after a June 5 wind-down deadline.

Meizlish argued previous sanctions regimes failed because they isolated American companies while allowing foreign actors to continue financing the Cuban state.

"There’s a lot of Spanish firms, for instance, that have invested millions of dollars in luxury hotel properties, villa properties in Cuba that partner with GAESA, all funding this military enterprise at the expense of the Cuban people," he said.

He also pointed to Canadian involvement in Cuba’s nickel and cobalt sectors, saying foreign investment has generated "huge amounts of money for the regime."

"A lot of people think about the U.S. embargo over the years is actually being responsible for a lot of the problems on the Cuban island, but they don't give consideration to the fact that GAESA, this newly sanctioned entity, has been sitting on an estimated $20 billion in assets and cash over the year while depriving the people of Cuba," Meizlish told Fox News Digital.

But critics of the policy warn the economic fallout could land the hardest on ordinary Cubans.

William LeoGrande, a longtime Cuba expert at American University, said the May 1 measures represent a major escalation because they specifically target foreign businesses rather than just Americans and aim to deter foreign companies from doing business with GAESA by threatening sanctions exposure.

LeoGrande acknowledged the measures could deprive the Cuban government of revenue but argued the broader population is likely to suffer most.

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"This would potentially deprive the Cuban government of funds, but the impact will fall mainly on ordinary citizens because it means the government has fewer resources to import food, medicine and fuel," he said.

The debate comes as Cuba faces its deepest economic and humanitarian crisis in years. 

The World Food Programme says food insecurity is worsening amid fuel shortages, inflation and declining access to imported goods, while U.N. officials have warned that electricity shortages and blackouts are disrupting hospitals, vaccination programs and food distribution networks across the island.

LeoGrande also warned tougher sanctions could contribute to another migration crisis.

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"Another unintended effect is that by making living conditions in Cuba even more desperate, tougher sanctions could trigger a mass migration like we saw in 1980 or 1994," LeoGrande said.

On background, a U.S. official rejected arguments that American sanctions are responsible for Cuba’s humanitarian crisis.

"The suffering of the Cuban people is not caused by the U.S. embargo but by the Cuban dictatorship’s failed Communist policies and human rights violations," the official told Fox News Digital. "The embargo does not prohibit Cuba’s access to world markets or trade with third countries."

The official added that U.S. law explicitly permits exports of food, medicine and medical equipment to Cuba and accused the regime of hiding "billions in overseas bank accounts instead of investing in electricity, infrastructure and the daily needs of its people."

The debate mirrors long-standing arguments surrounding U.S. sanctions on countries like Iran and Venezuela, where supporters view economic pressure as a tool to weaken authoritarian governments while critics argue regimes often survive and civilians absorb the economic damage.

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Meizlish argued sanctions should not be judged simply by whether they immediately topple governments.

"The problem isn’t that the embargo went too far," he said. "It’s that it didn’t go far enough."

Fox News Digital reached out to the Cuban Embassy in Washington for comment but did not receive a response by the time of publication.

Amid President Donald Trump’s Monday announcement that a deal with Iran’s clerical regime is imminent to re-open the Strait of Hormuz and negotiate an end to Tehran’s illicit nuclear weapons program, Iranians who hoped U.S. pressure would force a decisive outcome now fear it may survive while ordinary people absorb the costs.

"Inside Iran, the mood has shifted from early-war optimism to a kind of exhausted resignation, but there is still some hope that this is the moment President Trump will use his leverage to do the right thing. The Iranian people understand this unusually narrow but strategic window," Lisa Daftari, editor-in-chief of The Foreign Desk who keeps in contact with Iranians on the ground, told Fox News Digital.

She continued that ,"The regime is fiscally strained and politically brittle, while the broader population has been disillusioned by years of repression and economic collapse. Iranians do see this as a one‑time opportunity for Washington — and President Trump in particular — to translate military and economic leverage into the potential collapse of an irrefromable regime. If the outcome is a shallow agreement that props up the system without changing its trajectory, that window will likely close for years."

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She continued, "If instead, the U.S. holds firm on sanctions and nuclear red lines, it can weaken the regime’s hand without punishing the Iranian people, who have already paid the highest price."

Daftari, the Iran expert, shared recent correspondence from two Iranians from Tabriz and Tehran.

The resident from Tabriz said, "From my perspective, decades of political tension between Iran and the United States have had their greatest impact on ordinary people rather than those in power. Many families feel their voices are not being heard in international discussions about Iran." Adding, "I respectfully ask whether you might consider sharing or highlighting the human side of this situation, so that the experiences of ordinary Iranian families are not overlooked in political discussions and media coverage."

The Tehran resident said, "Today, the people of Iran believe in the future. On days when economic pressure makes the faces of the Iranian people sad, the word ‘unity’ brings a smile to their lips. Our situation is not good, but we are motivated."

Fox News Digital surveyed a few Iranians and agreed to use only their first names because the clerical regime has declared the use of Starlink to bypass the censor a criminal act. A sophisticated clandestine network has managed to smuggle some satellite internet technology into Iran to allow people to communicate with the world outside the Islamist state.

Hassan, who lives in Tehran, pleaded with President Trump to keep strong in his dealings with the regime, saying that "Things have gotten so bad that even if you wanted to give up and leave Iran and just focus on your own life and work, it feels like there’s nowhere left to turn. Mr. Trump, through these deals and arrangements, has left people feeling trapped, with no road left open."

Mehdi, who resides in Tehran, expressed confusion about the existence of an agreement. He said, "So what exactly are they agreeing on? Are they saying they’re close to a deal or are there other discussions too? Every minute there is a new piece of news, everyone has a new analysis, everything changes every minute. It’s strange. This war achieved nothing. We’re the only ones left paying the price," he complained.

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Hassan from Tehran said that "Mr. Trump, if until yesterday most Iranians thought they were on the same path as America, you caused them all to become disappointed. "Mr. Trump, if you wanted this government to remain in power, why did you blow up factories? Now workers are being laid off, and inflation is out of control. Even with a salary of 18 million tomans, you cannot feed yourself."

Mahsa, from the Caspian Sea city of Rasht, told Fox News Digital that the system [Islamic Republic of Iran] is still fully intact. They don’t care how many people died. If anything, they seem more emboldened now and even take pride in martyrdom. Yesterday I argued with a regime supporter [who] said: "Our leader didn’t give away a single meter of land, didn’t take a step backward, unlike previous kings who gave away Bahrain, Baku, Nakhchivan, and others."

The concerns among many Iranians revolve around the proposed memorandum of understanding between the U.S. and Iran’s regime. The MOU does not address the overthrow of the clerical regime or human rights violations, according to media reports.  Large numbers of Iranians within Iran and among the Iranian diaspora want the Trump administration to topple the Islamist dictatorship in Tehran.

The MOU reportedly involves a 60-day ceasefire extension. Israel and the U.S. launched a joint attack on Iran on February 28. The MOU would also see the reopening the Strait of Hormuz and new talks over Iran's illicit nuclear weapons program.

The leaked elements of the MOU have not been confirmed by the Trump administration.

When asked about the concern among Iranians about a deal with the Islamic Republic, Anna Kelly, a spokeswoman for the White House, told Fox News Digital that "For 47 years, American Presidents and countless other world leaders talked about the threat posed by Iran, but no one had the courage to address it. President Trump took decisive action to ensure that Iran could never harm our homeland, our troops, or our allies again. Once Iran’s nuclear threat is removed for good, the entire region and its people will be safer and more stable."

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However, Trump said last week during his cabinet meeting, "We didn’t set out for regime change," adding, "But by the fact that we’re dealing with a totally different group of people than we were at the beginning … This is regime change."

Reza Farnood, an Iranian American who supports the Trump administration and is a researcher, writer and activist, urged that President Trump continue with his maximum pressure campaign against Tehran.

Farnood told Fox News Digital, "We welcome the bombing and attacking the regime because we are aiming to overthrow the regime." He urged that Trump continue the blockade of Iran’s vessels and deny money to the regime. He said sanctions relief will be used by Iran "against the U.S. and Israel and their allies and innocent Iranians."

Farnood stressed that the clerical regime is holding the Iranian people "hostage."

Kianoosh, who lives in the northern city of Karaj, the capital of  Alborz province, said about Trump’s proposed deal: "You threw six months of our lives into hell. What answer are "you going to give to the mothers of all those children who were killed? Why did you give people false hope? Why did you hand down a death sentence to everything so many people believed in?"

Leading U.S. Senators well-versed in foreign policy have praised Trump’s approach to the Islamic Republic. Sen. Lindsey Graham, R-SC., recently told Fox News’ Sean Hannity "On Trump’s watch, they’re [Iran’s regime] becoming poorer and weaker. That’s the difference."

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Graham juxtaposed Trump’s Iran policy with his predecessors. "Obama and Biden screwed Iran up, and Donald Trump is fixing it. On Obama and Biden’s watch, Iran became rich and lethal," he said. "On Trump’s watch, they’re becoming poorer and weaker. That’s the difference."

Iran is running dangerously low on oil storage capacity and could face a severe economic breaking point if forced to halt production, former U.S. Energy Secretary Dan Brouillette recently told Fox News.

Trump has said that Iran’s regime murdered as many as 45,000 Iranian demonstrators in January 2026. He urged just days after the mass murder that protesters keep going and promised them that "help is on its way."

Lawdan Bazargan, a prominent Iranian-American activist who the regime imprisoned in its infamous Evin Prison in Tehran in the 1980s for political dissent, told Fox News Digital that the Iranians she’s spoken with are discouraged by Trump’s dealings. "He was one of the few world leaders who repeatedly spoke about the thousands of Iranians killed in January 2026 and expressed disgust at the sheer brutality of the Islamic Republic. He had promised support for the Iranian people and raised expectations that meaningful change might finally come."

She continued: "Now, 88 days later, many people feel they are left facing the same regime, one that appears more emboldened, more ideological, and still willing to repress, execute, and arrest people. The economy has been devastated, and many feel trapped between a government with no mercy and a future with no clear path forward.

For years, 90 million Iranians have lived as hostages of the Islamic Republic. Now, many fear that the consequences no longer stop at Iran’s borders, through threats to global energy routes, regional stability, and even digital infrastructure."

According to Bazargan, "The question many ordinary Iranians are asking is simple: How are people expected to fight a system that feels victorious, controls the weapons, controls the narrative through a massive propaganda machine, and possesses countless tools of repression?"

Ali, who is also from the sprawling capital city of Tehran, complained about the spiraling prices and inflation and disappointment that the regime is still in place.

"For a government with state-provided housing and billions in patronage and privileges, what difference did any of this make for its supporters?"

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Ali added: "We’re the ones who are paying the price and getting crushed. How are our children ever supposed to afford these housing and car prices, and how are they supposed to get married?"

The U.S. State Department referred Fox News Digital to the White House for a comment.

New sanctions were imposed on Cuba’s President Miguel Díaz-Canel, along with four other individuals, according to a filing Thursday on the U.S. Treasury Department website.

New sanctions were imposed on Cuba’s President Miguel Díaz-Canel, along with four other individuals, according to a filing Thursday on the U.S. Treasury Department website.

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