Cuba's Finished
Trump said it himself. The May 1 sanctions are designed to finish the job
Two presidential signatures, fifteen months apart, tell the story.
In February 2025, Donald Trump signed Executive Order 14203. The order declared that the International Criminal Court’s efforts to investigate American or Israeli personnel posed an “unusual and extraordinary threat” to U.S. national security. By December, eleven ICC prosecutors and judges sat on the same Treasury blacklist normally reserved for drug traffickers and oligarchs. Canadian judge Kimberly Prost was one of them, sanctioned in August in connection with a 2020 ruling on Afghanistan. She told The Irish Times what happened next: credit cards canceled overnight, banks dropping her account, Amazon shutting her out, the Alexa device in her home in The Hague going silent. A colleague’s daughter had her U.S. visa revoked.
On May 1, 2026, Trump signed a second order, declaring open season on a wide circle of Cuban officials, state-linked businesses, and the foreign banks that finance them. Its mechanism mirrors the one used against the ICC: asset freezes, travel bans, secondary sanctions threatening any third-country institution that handles a designated person’s money. A bank in Madrid or Montreal that processes a payment for a sanctioned Cuban port operator now risks losing access to the U.S. dollar system.
Read the two orders side by side, and a working doctrine emerges.
International jurisdiction over American or allied officials, even under a treaty 125 countries have ratified, is denounced as lawfare. American jurisdiction over foreign officials, businesses, and even foreign judges, exercised unilaterally with no treaty basis and no mechanism of consent, is framed as sovereign common sense. Washington’s complaint about the ICC is not really that international law overreaches — it is that someone else has begun reaching.
Criminal law for thee, sanctions for me
Washington dresses its case against the ICC in the familiar grammar of consent. America never joined the Rome Statute that created the court. Successive administrations have insisted that a treaty cannot bind a state which has not signed it, and that ICC jurisdiction over Americans for conduct in Afghanistan, or over Israelis for conduct in Palestine, violates that principle. On paper, sovereignty is the issue.
The argument collapses on contact with U.S. practice. A government that insists The Hague cannot judge its nationals asserts a sweeping right to judge the world through Treasury designations, freezing the assets of foreign officials, blacklisting foreign companies, and threatening foreign banks for conduct that occurs entirely outside U.S. territory, so long as a dollar somewhere in the chain provides a hook. Pressed on the inconsistency, Washington responds that controlling access to American markets and the world’s reserve currency is a domestic matter. Brussels and Brasília call this extraterritorial reach. Washington calls it the right of any sovereign to choose its trading partners.
Two propositions are being asserted at once. A multilateral court built on treaty consent has no business touching American or Israeli officials, even when alleged crimes occur on the territory of states that have accepted the court’s authority. A single state, by contrast, has every right to decide which Cuban general, which Iranian banker, or which Hague-based prosecutor may travel, bank, or do business anywhere on earth that depends on dollars. One proposition rests on a principle. The other rests on market share.
Stripped of its legal vocabulary, the doctrine is a hierarchy. American officials and close allies sit at the top, effectively shielded from international criminal accountability by political and financial muscle. Beneath them, the officials of weaker states find themselves simultaneously subject to ICC jurisdiction and to the U.S. sanctions apparatus.
At the bottom, judges and prosecutors who investigate the wrong suspects find their own names on the list alongside the people they were trying to bring to trial.
How Cuba went dark
“Cuba’s finished. They have a bad regime. They have very bad and corrupt leadership. And whether or not they get a boat of oil, it’s not going to matter.”
—Donald Trump, March 30, 2026
Understanding what the May 1 order expands requires understanding what brought Cuba to the brink in the first place. Washington’s preferred explanation, which blames Cuban mismanagement, will not do the work.
Cuba’s grid was already failing well before 2026. Its thermoelectric plants are Soviet-era infrastructure held together with improvisation, maintenance deferred for decades. Cuba’s 2021 currency unification, pitched as rationalization, landed instead as another shock to an economy already off balance. Major island-wide outages struck repeatedly in late 2024, including a total grid collapse in October that took days to restore. Venezuelan oil shipments, Cuba’s lifeline since the Soviet Union dissolved, had been declining for years as Caracas’s own economy unraveled. Internal corruption is real, state planning a long-running disaster. None of this is in dispute.
What changed in the first weeks of 2026 was not Cuban policy. It was American policy.
In December 2025, the U.S. Coast Guard seized the tanker Skipper in the Caribbean as it carried sanctioned Venezuelan crude, an action Cuba’s foreign ministry called an “act of piracy and maritime terrorism.” A week later, Washington formalized a blockade on sanctioned tankers moving in or out of Venezuela. On January 3, 2026, U.S. forces executed Operation Absolute Resolve, capturing Venezuelan president Nicolás Maduro and his wife in a helicopter assault on Caracas. Two days later, the couple were arraigned before U.S. District Judge Alvin Hellerstein in the Southern District of New York on narcoterrorism and drug-trafficking charges. Venezuelan oil shipments to Cuba, already shrinking, ended. Trump’s Executive Order 14380 on January 29 threatened tariffs on any country that picked up the slack. Mexico’s state oil company Pemex, under pressure, halted its shipments. Other suppliers followed.
The New York Times described what resulted as the first effective American blockade of Cuba since the missile crisis. The administration has made no secret of its purpose. Regime change by the end of the year, with Trump musing publicly about having “the honor of taking Cuba” while predicting the government will collapse “within a short period of time.” The blockade is not an unintended consequence of the policy so much as it is the policy.
Run the numbers. Cuban mismanagement was a constant from January 2025 to January 2026. The variable that changed was American policy. Hold one variable steady, change the other, watch the outcome shift, and you can see which input is doing the causal work. Cuban dysfunction is the pre-existing condition.
The U.S. policy put the patient in intensive care.
Independent assessments arrived quickly and bluntly. UN human rights experts in February condemned the January order as “a serious violation of international law” and “an extreme form of unilateral economic coercion with extraterritorial effects” — language UN special rapporteurs have rarely applied to American policy. By March, World Health Organization director-general Tedros Adhanom Ghebreyesus was warning publicly that “thousands of surgeries have been postponed during the last month, and people needing care, from cancer patients to pregnant women preparing for delivery, have been put at risk due to lack of power to operate medical equipment and cold chain storage for vaccines.” UN Secretary-General António Guterres said he was “extremely concerned” the humanitarian situation could “worsen, or even collapse.” Reporting from Havana described medical staff hand-pumping intensive-care equipment during blackouts to keep critical patients alive.
NPR’s coverage of the crisis put the contradiction plainly: the blockade has had “devastating effects on the civilians Trump and Secretary of State Marco Rubio say they want to help.”
Then came the small episode that gave away the rule. In late March, after months of what Cuban officials called a de facto oil blockade, the sanctioned Russian-flagged tanker Anatoly Kolodkin docked at Matanzas carrying 730,000 barrels of crude. Trump waved it through aboard Air Force One: “We have a tanker out there. We don’t mind having somebody get a boatload because they need... they have to survive.” His press secretary, Karoline Leavitt, told reporters the next day this was a humanitarian exception and “not a policy change.”
Five weeks later, Trump signed the May 1 order expanding the very sanctions architecture the tanker had briefly bypassed. The exception confirmed the rule it broke. Washington had reserved itself the prerogative to decide who eats, who has lights, and who treats their patients, on a case-by-case basis, by executive whim.
The architecture of the new order
The May 1 executive order does several things at once. Major sectors of the Cuban economy get designated as high-risk zones: energy, defense, metals and mining, financial services, security. Anyone judged to have operated in those sectors, from cabinet ministers down to mid-level managers, can have property blocked in the United States and entry barred. People deemed responsible for human rights abuses or corruption face the same fate. So do their adult family members, an extension of liability that would not survive a constitutional challenge if applied to American citizens.
Secondary sanctions are the genuinely new feature.
Foreign financial institutions that conduct “significant” transactions for designated Cuban actors face restrictions on their U.S. correspondent and payable-through accounts, the plumbing through which dollar-denominated commerce actually flows. Washington has used the mechanism to police Iran-related transactions for years. Applying it to Cuba treats the entire Cuban economy as a contamination risk to be quarantined.
Three days before Trump signed the order, the Senate had a chance to weigh in. Tim Kaine of Virginia introduced a war powers resolution that would have barred the president from launching military action against Cuba without congressional approval. Kaine argued the United States was already engaged in hostilities, and pointed to the oil blockade as evidence: “The U.S. is using force to block energy from going to Cuba.” If another country did this to America, he added, Washington would consider it an act of war. Senate Republicans blocked the procedural vote 51-47. Florida senator Rick Scott called the issue “moot” because Trump had not yet deployed troops. The blockade itself, in this telling, was not hostilities. The boats turning back, the hospitals running on fumes, the surgeries postponed: none of it counted.
Cuba’s role in this story is functional, not symbolic. The island has served sixty years as a laboratory for aggressive sanctions design, and tools developed against Havana have routinely migrated to other targets. The blueprint Trump signed on May 1, with its declared national emergency, broad sectoral designations, and secondary reach into third-country banks, is now portable. It is also self-renewing, requiring no congressional buy-in beyond the president’s annual notice that the emergency continues.
Set the Cuba policy beside the Russia policy, and the doctrine becomes difficult to defend with a straight face. Sanctions on Moscow are sold as essential to containing the war on Ukraine and deterring further aggression in Eastern Europe. Treasury, meanwhile, has repeatedly issued general licenses allowing certain Russian oil shipments to clear, ostensibly to avoid shocks to global energy markets. Russian crude finds its way to market when American consumers might otherwise feel the price. Cuban hospitals, which exert no comparable pressure on the price of gasoline in Ohio, receive no such accommodation.
What comes after the lights go out
“Cuba is going to be next,” Trump told the Associated Press. “It’s going to fail. And we will be there to help it out.” Pressed on the Russian tanker, he laughed off its significance: “He loses one boatload of oil. That’s all it is... It’s not going to have an impact. Cuba’s finished.”
Look closely at the framing.
Trump describes a country whose collapse he is engineering as a country collapsing on its own. The “help” he offers is reserved for Cuban-Americans in Florida, the political constituency that votes in U.S. elections, not for the ten million Cubans currently on the island whose hospitals are running out of fuel. The Castro brothers are both dead; the man Trump is starving out of power is Miguel Díaz-Canel. None of this slows him down. Cuba is finished, and the United States will be there.
Cuba is one stop on a route. Replay the past sixteen months, and the rhythm is the same each time. Pick a target. Manufacture the crisis. Take out the leadership. Move on before anyone has to govern what’s left. Venezuela was the precedent. Greenland was the trial balloon. Cuba is the test of whether financial weapons alone can do what helicopters did in Caracas.
Maduro had been in U.S. custody for less than 48 hours when Trump told reporters that the United States would “run” Venezuela “until such time as we can do a safe, proper and judicious transition.” Asked about elections, Trump said: “Well, I think we’re looking more at getting it fixed, getting it ready first, because it’s a mess.” Almost in the same breath, he announced that U.S. oil companies would enter Venezuela to “fix” its energy infrastructure and would be “reimbursed for their efforts.” Maduro’s vice president, Delcy Rodríguez, was sworn in as acting president. The Trump administration signaled it was willing to work with her, the same Rodríguez who had been deeply implicated in Maduro’s repression and corruption.
Elliott Abrams, who served as Trump’s first-term Venezuela envoy, called the arrangement “a recipe for an Iraq-style disaster.” Ten weeks after the capture, Abrams wrote in The Washington Post that “almost invisible so far is any progress toward a democratic transition.”
RAND researchers analyzing the aftermath put it more bluntly: “regime decapitation does not equal regime change.” Most of the ruling structure remained: the colectivos, the secret police, the corrupt military leadership, the Cuban intelligence officers embedded throughout. What had changed was that an American president had captured a sitting head of state on foreign soil, declared an interest in the country’s oil, and offered no plan for governance beyond “fixing” things on his own timeline.
Trump cited the Venezuelan template approvingly when asked about Cuba.
In a phone interview with CNN’s Dana Bash on March 6, he said Cuba was “going to fall pretty soon” and announced he was sending Rubio to handle the negotiations: “I’m going to put Marco over there and we’ll see how that works out.” In the same call, asked about the broader playbook, Trump pointed to Venezuela as the model. “It’s gonna work very easily,” he said. “It’s going to work like did in Venezuela. We have a wonderful leader there. She’s doing a fantastic job.” His “wonderful leader” was Delcy Rodríguez. Trump also took personal credit for the Cuban collapse: “I’ve been watching it for 50 years, and it’s fallen right into my lap because of me.”
The Cuban side of the equation comes with its own freight. Thirty-two Cuban military and intelligence officers were killed in Caracas during Operation Absolute Resolve, where they had been embedded with Maduro’s security detail. Their bodies returned to Havana in mid-January. Cuban president Miguel Díaz-Canel addressed crowds at the U.S. Embassy and vowed no concessions. Rubio is now preparing to negotiate with a government still mourning thirty-two of its own people, killed by the same United States now demanding they accept “new people in charge.”
Greenland came and went on a parallel track. Through January 2026, Trump refused to rule out military force to acquire the territory, slapped a 10% tariff on Denmark and seven other European countries with a threat to escalate to 25%, and demanded “Complete and Total Control of Greenland.” His own press secretary said “utilizing the U.S. military is always an option.” Trump backed down at Davos only after sustained European pushback and counsel from his own aides, settling for a vague “framework of a future deal.” Greenland remained nominally Danish. Trump kept the option open.
The throughline across all three campaigns is the absence of a plan for what comes after. Each operation begins with a national-security framing, narcotics in Venezuela, communism and migration from Cuba, Russian and Chinese ships near Greenland. Each one ends with an executive order or a special-forces operation. None of them comes with a coherent answer to the question that always follows: then what? In Venezuela, the answer was Delcy Rodríguez and a foreign-investor-friendly oil law. In Cuba, the answer is a country with a collapsing healthcare system and a million-dollar question about who runs the place once the lights stay off. In Greenland, the answer was a Truth Social post and a tariff threat aimed at Denmark.
The premise driving all three campaigns: destruction is the same as design. Break the existing order, the thinking goes, and something better will fill the vacuum, possibly run by the United States, possibly run by people Washington approves of, possibly run by no one in particular while American oil companies move in.
Trump articulated the post-war theory of governance recently while discussing Iran. The Iranian military, he explained, had been disabled in days. The Navy first, the Air Force after that, the anti-aircraft soon after. American jets were flying over Iran unopposed. The electricity grid could be eliminated “in a matter of minutes.” The oil infrastructure had been deliberately spared, not out of restraint, but because rebuilding it would “take them forever.”
Then came the governance plan, in his own words: “whoever it is that’s going to be running that, and we’re going to try to get people that are going to run it well.” That sentence, casually delivered, is the entire public framework. Disable the country. Then try to find acceptable replacements.
The same logic governs their Cuba campaign.
Trump turned to Rubio in the same interview and asked him to explain. “Cuba has an economy that doesn’t work and a political and governmental system they can’t fix,” Rubio said. “It’s not dramatic enough. It’s not going to fix it. So they’ve got some big decisions to make over there.” Pressed by a reporter on whether the embargo could be eased in exchange for cooperation, Rubio went further. The embargo, he confirmed, “is tied to political change on the island.” Cuba had survived “for 40 [years] on subsidies from the Soviet Union and now from Venezuela. They don’t get subsidies anymore. So they’re in a lot of trouble. And the people in charge are — they don’t know how to fix it. So they have to get new people in charge.”
Rubio cited the loss of Venezuelan subsidies as proof Cuba’s economy cannot survive. He neglected to mention that the United States itself eliminated those subsidies in January by capturing the Venezuelan president and seizing the tankers carrying oil to Havana. Trump’s framing of the same situation has been less guarded:
Trump: I think Cuba — I don’t know, is, in its own way, if you know tourism and everything else, it’s a beautiful island, great weather, they’re not in a hurricane zone, which is nice for a change, you know, they won’t be asking us for money for hurricanes every week.
But uh, but I think Cubans see the end. You know, all my life, I’ve been hearing about the United States and Cuba — when will the United States do it. I do believe I’ll be the honor of — having the honor of — taking Cuba. That’d be, that’s a big honor.
Reporter: Taking Cuba?
Trump: Taking Cuba in some form. Yeah. Taking Cuba. I mean, whether I free it, take it. I think I could do anything I want with it, you wanna know the truth. A very weakened nation right now.
Six weeks later, with hospitals scaling back surgeries and the Cuban peso in freefall, neither man has named the “new people.”
The May 1 order locks the architecture in place. There is no stabilization plan, no transition framework, no offer to rebuild what the blockade has broken. The order extends the architecture of pressure indefinitely while the consequences play out somewhere else, on a timeline determined by how long ten million Cubans can be kept in the dark before something breaks. The Senate, given the opportunity to ask whether any of this counted as hostilities, voted not to ask.
Judges as fair game
Sanctioning ICC judges and prosecutors marked a major break with prior U.S. practice. The Bush administration refused to join the court and pursued bilateral immunity agreements aggressively, but had not attacked the judiciary nor designated a sitting judge by name. Trump has crossed that line and kept walking. Eleven ICC officials are now on the SDN List alongside Hezbollah financiers and North Korean front companies for the offense of doing their jobs.
Prost’s account, given to The Irish Times in December, captures the practical effect. Banks immediately closed her credit cards. Online retailers cut her off. Currency transfers to family members became unworkable, because SWIFT routes through American infrastructure. Her sanctioning, as Prost noted, was punishment for a 2020 ruling on a now-dormant Afghanistan investigation.
Sanctions cannot deter what has already happened. They can only punish.
NGOs and academics who interact with sanctioned ICC officials face their own exposure under the order’s “material support” provisions. A law professor advising a designated judge on a procedural question could, in principle, find herself on the same list. The order has been challenged in federal court on First Amendment grounds, with injunctions issued for some plaintiffs, though the underlying authority remains intact.
Layer the May 1 Cuba order atop E.O. 14203, and the architecture clarifies. A foreign bank that processes a payment for a sanctioned ICC official’s legal team could, in theory, trip the same secondary sanctions rules now threatening institutions that handle Cuban state business. A judge in The Hague and a port operator in Havana are not equivalent actors in any moral sense, but they face the same instruments now: asset freezes, travel bans, financial isolation. All ordered from Washington, none subject to any meaningful external review.
To governments outside the United States, the picture resembles a loyalty test more than a rules-based order. Investigate Russian war crimes in Ukraine and Washington applauds. Apply the same legal framework to Israeli or American conduct and your name may appear on an OFAC list.
The court has not changed, nor have the standards. Only the identities of the suspects have, which is precisely the point.
The quiet part, said aloud
The strongest argument for U.S. policy is the one defenders are usually too embarrassed to make in public. It runs roughly as follows: international criminal law is selectively enforced anyway, sanctions are a normal tool of statecraft, and the United States is entitled to use the leverage its financial centrality provides. If the world wanted a different system, the world should not have made the dollar its reserve currency.
There is something honest in this. The ICC has had an uneven record. Sanctions are not prison sentences. A sovereign state controlling access to its own markets is not the same as a treaty-based court asserting jurisdiction over non-members. American courts can review some sanctions designations. Congress, in theory, can rein in an overreaching president.
The argument cannot, however, rescue the principle of consent that the United States invokes against the ICC. If consent is the operative legal value, it is operative everywhere. American officials cannot be subject to a tribunal whose jurisdiction the United States has not accepted, fine; then Cuban officials, foreign bankers, and ICC judges should not be subject to American jurisdiction they have not accepted either. The position only coheres if you assume what it is supposed to prove: that some sovereigns are more sovereign than others, and that the United States stands at the top of the list because it has the power to put itself there.
The May 1 order quietly ratifies that position.
A government comfortable asserting near-universal authority where it holds structural power, in finance and trade, while denying that any other actor, court or treaty or multilateral body, may exercise comparable authority over Americans. Foreign ministries in U.S.-allied and non-aligned capitals alike have been saying so with growing volume: the rules-based order is, in practice, a power-based order with rules-based marketing.
A different approach would require concessions Washington has never been willing to make. It would mean accepting, in principle, that American and allied officials are not beyond the reach of international courts when alleged crimes occur on consenting territory. It would mean narrowing the emergency economic powers under which sanctions designations are made, with clearer standards and meaningful judicial review. It would mean acknowledging that secondary sanctions on third-country banks raise legal questions, not merely diplomatic ones.
None of that is on offer. Trump’s May 1 decree reinforces the working doctrine: jurisdiction that touches Americans or close allies is overreach, jurisdiction that ensnares foreigners is prerogative.
No one is fooled. The contradiction is visible to anyone outside Washington who cares to look — to allies, to adversaries, and increasingly to the central banks building payment systems that route around the dollar. American power as currently configured depends on the rest of the world choosing not to notice. The two signatures Trump put on EO 14203 and the May 1 order assume that choice will hold.
They are a poor wager on how long it will last.
