Trump's Oil Blockade Triggers Cuba's Worst Crisis in Decades as Administration Pushes for Regime Change

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The Trump administration has imposed what The New York Times described as the United States' first effective blockade of Cuba since the Cuban Missile Crisis, cutting off virtually all oil shipments to the island through a combination of military action, executive orders, and diplomatic pressure. The campaign has triggered what experts and UN officials call an existential humanitarian crisis on the island of nearly 10 million people. On February 27, Trump told reporters he envisioned a "friendly takeover" of Cuba and claimed Cuba's government was in negotiations with the United States, while on February 25, the administration began allowing limited private oil sales to the island in what analysts described as a first step toward easing civilian suffering without strengthening the regime.

How the Blockade Developed

Cuba's energy crisis escalated through a series of actions beginning with the January 3 U.S. military capture of Venezuelan President Nicolás Maduro, which removed Cuba's primary oil supplier. Venezuela had been providing roughly 50% of Cuba's imported oil—approximately 35,000 barrels per day—under a barter arrangement in place since 2000 in which Cuba provided education, healthcare, and security services in return for discounted fuel. On January 11, the administration announced that no more Venezuelan oil or money would flow to Cuba.

Trump then signed Executive Order 14380 on January 29, 2026, declaring a national emergency with respect to Cuba and establishing a framework to impose tariffs on goods from any country that directly or indirectly provides oil to Cuba. The order described Cuba as an "unusual and extraordinary threat" to U.S. national security. Mexico, which had become Cuba's last major oil supplier, suspended its shipments after the executive order. According to Cuban President Miguel Díaz-Canel, Cuba has not received an oil shipment since December.

On February 20, the U.S. Supreme Court struck down the administration's IEEPA tariff authority in a 6-3 ruling (Learning Resources, Inc. v. Trump), holding that the International Emergency Economic Powers Act does not authorize the president to impose tariffs. Trump subsequently signed an executive order ending all IEEPA-based tariffs, including those threatened against Cuba's oil suppliers, though the underlying national emergency declaration remains in effect and the practical blockade has continued through other means, including U.S. Coast Guard interception of tankers and the ongoing seizure of Venezuelan oil infrastructure.

Humanitarian Impact

The blockade's effects have been severe. A Bloomberg News analysis of satellite imagery found nighttime light levels across Cuba dropped as much as 50% compared to the historical average, with eastern cities like Santiago de Cuba and Holguín particularly affected. Cuba relies on oil for roughly 80% of its electricity generation.

According to Francisco Pichón, the UN resident coordinator in Cuba, 5 million people on the island live with chronic illnesses whose treatments are at risk, including thousands of cancer patients. There are more than 32,000 pregnant women requiring services. Food security is deteriorating without fuel for delivery trucks, and 1 million people face water shortages without electricity to pump wells.

The crisis has disrupted nearly every aspect of daily life. On February 9, Cuba announced it could no longer refuel aircraft at its airports, leading Air Canada and Russian airlines to suspend service—a devastating blow during peak tourist season. The government imposed limited operating hours on government buildings, banks, trains, and ferries. Schools have suspended classes and workers have been furloughed. Private businesses importing food from the U.S. suspended operations because they could no longer refrigerate products during daily blackouts. A fire at the Nico López refinery in Havana on February 13 further worsened the energy situation.

Jorge Piñon, director of the Latin America and Caribbean Energy Program at the University of Texas at Austin, told The Hill that Cuba faces a "zero hour" if no oil tanker arrives by mid-March. He estimated Cuba's remaining reserves could be completely depleted by then.

Private Oil Sales Policy Shift

On February 25, the U.S. Department of Commerce made two key changes allowing limited oil to reach Cuba's private sector. The first allows petroleum products to be sent to Cuba without a special license, provided shipments are not destined for any entities tied to the Cuban government, military, or labor unions. The second permits Venezuelan fuel to be sold to private businesses in Cuba.

Experts characterized the move as largely symbolic given the scale of Cuba's needs. Piñon estimated the deliveries amount to roughly 150 barrels per day, compared to the country's needs of 22,000 barrels per day. Ricardo Herrero, executive director of the Cuba Study Group, told The New York Times the strategy is to demonstrate that "the only lifeline that Cuba has left is the United States" and to use oil as "leverage to extract concessions from the Cuban regime."

The administration also sent $6 million in humanitarian aid to Cuba earlier in February, distributed through the Catholic Church and Caritas rather than the Cuban government.

Secret Talks and "Friendly Takeover"

Axios reported on February 18 that Secretary of State Marco Rubio has been holding secret talks with Raúl Guillermo Rodriguez Castro, the 41-year-old grandson of former Cuban leader Raúl Castro. The talks have bypassed official Cuban government channels, with a senior administration official telling Axios: "I wouldn't call these 'negotiations' as much as 'discussions' about the future." The administration views the elder Castro, now 94, as Cuba's true decision-maker, and sees his grandson's circle as representing younger, business-minded Cubans open to rapprochement with the U.S.

Rodriguez Castro holds no official government or Communist Party position but serves as his grandfather's closest aide and bodyguard. He is also believed to oversee GAESA, the Cuban armed forces' economic conglomerate that controls much of the island's economy. The Miami Herald reported in 2024 that GAESA had approximately $18 billion in assets.

On February 25, Rubio's advisers met again with Rodriguez Castro on the sidelines of the CARICOM conference in Saint Kitts and Nevis. Rubio did not deny the reports, and told reporters that Cuba "needs to change" but "doesn't have to change all at once."

Cuba's government has denied the existence of high-level talks, issuing a statement saying: "There is no high-level dialogue between the government of the United States and Cuba. There is not even dialogue at an intermediate level."

On February 27, Trump raised the stakes further, telling reporters as he left for Texas: "Maybe we'll have a friendly takeover of Cuba," adding that Cuba is "a nation in deep trouble, and they want our help." He described Rubio as dealing with the issue "at a very high level."

Speedboat Incident

A deadly confrontation on February 25 complicated the diplomatic picture when Cuban coast guard forces killed four people and wounded six others aboard a stolen Florida-registered speedboat that entered Cuban territorial waters near Villa Clara province. Cuban authorities said the men opened fire first, wounding the patrol commander, and that the group was attempting an "infiltration for terrorist purposes." Weapons, Molotov cocktails, ballistic vests, and camouflage gear were reportedly found aboard.

The group was affiliated with Autodefensa del Pueblo (ADP), a small militant Cuban exile organization based in Florida. At least one of the dead, Michel Ortega Casanova, was confirmed to be a U.S. citizen. Secretary of State Rubio called the incident "highly unusual" and confirmed it was not a U.S. government operation.

The incident drew parallels to the 1996 Brothers to the Rescue shoot-down, which occurred during back-channel U.S.-Cuba talks and led the Clinton administration to strengthen the embargo rather than improve relations. The speedboat incident occurred one day after the 30th anniversary of that event. Analysts expressed concern it could be used to derail the current diplomatic efforts, though both sides have so far sought to de-escalate.

International and Legal Response

UN Secretary-General António Guterres stated he was "extremely concerned" about the humanitarian situation in Cuba, warning it could "worsen, or even collapse" without restored oil supplies.

A panel of UN human rights experts condemned the executive order as "a serious violation of international law and a grave threat to a democratic and equitable international order," describing it as "an extreme form of unilateral economic coercion with extraterritorial effects." They challenged the characterization of Cuba as a national security threat to the United States as lacking credibility.

Cuban Foreign Minister Bruno Rodríguez Parrilla denounced the blockade before the UN Human Rights Council, and Mexican President Claudia Sheinbaum warned that Trump's actions would unleash a "humanitarian crisis of great scope."

Expert Analysis

Experts are divided on whether the pressure campaign will achieve its aims. Sebastián Arcos, interim director of the Cuban Research Institute at Florida International University, told The Hill: "These people are really, really bad guys, and they have shown this capacity to survive difficult crises. I don't think they can survive this one." However, he cautioned that Cuba's tightly controlled Communist system makes its trajectory far harder to predict than Venezuela's.

Daniel Batlle of the Hudson Institute suggested the Cuban regime may prove flexible to ensure its survival, describing it as "less of an ideological regime than a mafia state that lives off controlling the tourism industry and the other profitable parts of the economy."

Critics warn the strategy risks uncontrolled escalation. As Newsweek noted, if protests spread or security forces lose control, Cuba could experience mass migration toward Florida—a politically damaging outcome for an administration that has made immigration enforcement a central priority. Cuba has seen multiple waves of migration to the U.S., the most recent during the COVID-19 pandemic, when nearly 2 million people fled due to economic instability.

Fulton Armstrong, a former CIA officer, told The Hill that the best path forward might resemble the Obama-era normalization, allowing the Cuban regime to open up to U.S. trade and implement liberal economic reforms gradually.

March 4 Blackout: Grid Collapse

On March 4, Cuba's largest power plant — the Antonio Guiteras thermoelectric plant in Matanzas — suffered a boiler pipe burst that collapsed the national electrical grid from Pinar del Río to Camagüey, blacking out roughly two-thirds of the country including Havana. The U.S. Embassy in Havana issued a security alert confirming the outage.

The plant failure was a trigger rather than the underlying cause. Before the Guiteras plant went offline, the grid was already generating only 1,180 megawatts against a national demand of 2,250 megawatts — a deficit of more than 1,000 megawatts. Cuban state media reported that two additional power plants were offline because of a lack of petroleum. Officials warned that full restoration could take three to four days.

Cuba's Ministry of Energy and Mines said on X that the electrical system was operating "in a limited capacity, prioritizing basic services, primarily health and water supply." This was the second major blackout to hit western Cuba in three months, following one in early December that lasted nearly 12 hours.

Public Opinion and the "Special Period" Comparison

A Food Monitor Program survey released in early March found that 80% of Cubans perceive the current crisis as worse than the Special Period of the 1990s — the economic collapse that followed the fall of the Soviet Union and is widely considered the most difficult era in modern Cuban history. The report linked this perception to sustained price increases, partial dollarization of the economy, and the decline in agricultural production, noting that Cuba imports 70–80% of the food it consumes.

Average state salaries are around 6,500 Cuban pesos per month — less than $13 at informal exchange rates. A carton of 30 eggs costs over 3,000 pesos. Cuba's GDP fell 4% in the first nine months of 2025 alone.

Iran War and Regional Escalation

The outbreak of the U.S.-Israel war against Iran on February 28 has complicated Cuba's crisis in several ways. The war immediately spiked global oil prices, with Brent crude surging above $80/barrel, making any oil Cuba might acquire more expensive. Iran's closure of the Strait of Hormuz — through which 20% of global oil passes — has added further price pressure.

More ominously, the war raised the volume of regime-change rhetoric directed at Havana. Senator Lindsey Graham, a close Trump ally, said after the Iran strikes began: "Cuba's next." Par Kumaraswami, a professor of Latin American Studies at the University of Nottingham, told CNBC that U.S. strikes on Iran had "increased the mood of uncertainty and anxiety in Havana" and that "Cubans are increasingly concerned about how they will survive in the midst of such global chaos."

However, analysts noted that no military buildup comparable to the Venezuela operation has been observed near Cuba, suggesting the U.S. may take a different approach. Meanwhile, Ecuador expelled Cuba's ambassador and diplomatic staff on March 4, declaring them persona non grata without providing a public reason — a move that came as the U.S. announced it had deployed Special Forces to Ecuador for joint military operations.

Trump's "Pro-Peace" Campaign

The Cuba blockade, combined with the January military operation in Venezuela, represents a sharp departure from Trump's central 2024 campaign messaging. Trump and his allies ran explicitly on an anti-war platform:

The official GOP account posted on November 4, 2024: "Vote the pro-peace ticket. Vote Trump-Vance." Trump's now-Director of National Intelligence, Tulsi Gabbard, posted on October 28, 2024: "A vote for Kamala Harris is a vote for Dick Cheney and a vote for war, war and more war. A vote for Donald Trump is a vote to end wars, not start them." Senior advisor Stephen Miller posted on November 1, 2024: "Trump = Peace."

On election night in November 2024, Trump told supporters he was "not going to start a war, I'm going to stop wars." In his 2021 farewell address, he called himself "especially proud to be the first president in decades who has started no new wars." At a National Guard conference in Detroit in August 2024, he promised to "end the endless foreign wars" and to "expel the warmongers from our government."