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Washington / Havana / Tehran, May 21, 2026 — Three months ago, the plan was elegant in its ambition and catastrophic in its execution. US and Israel strikes would kill Supreme Leader Khamenei, free Mahmoud Ahmadinejad from house arrest, and install a post-Islamist government amenable to Western engagement. The Strait of Hormuz would reopen. Oil
Washington / Havana / Tehran, May 21, 2026 — Three months ago, the plan was elegant in its ambition and catastrophic in its execution. US and Israel strikes would kill Supreme Leader Khamenei, free Mahmoud Ahmadinejad from house arrest, and install a post-Islamist government amenable to Western engagement. The Strait of Hormuz would reopen. Oil prices would fall. Trump would claim one of the most consequential foreign policy victories in modern American history.
Ahmadinejad survived injured, disillusioned, and missing. The IRGC consolidated power. The Strait of Hormuz remains closed for the 82nd consecutive day. Brent crude sits above $110. And the US-Iran agreement that was supposed to follow a swift regime transition is mired in its fifth round of collapsed talks, most recently in Rome.
So Trump has found a new theatre. As CNN’s political analysis confirmed, the president is now “chasing the kind of regime-altering triumph in Cuba that has eluded him in Iran” a pivot toward the Caribbean that combines the familiar toolkit of maximum pressure, legal warfare, and the implicit threat of military force, applied to a target far smaller and far more isolated than the Islamic Republic.
The architecture of Trump’s Cuba campaign has been assembled methodically. Executive Order 14380, entered into force on January 30, 2026, declared a national emergency authorising tariffs on imports from countries supplying oil to Cuba effectively a secondary sanctions regime targeting every nation willing to keep Havana’s lights on. By February, the US was actively blocking oil tankers heading to Cuba, including vessels from Mexican state-owned Pemex.
The results have been total. On May 14, Cuban Minister of Energy and Mines Vincent De La O’levy announced the unthinkable: “The sum of the different types of fuel: crude oil, fuel oil, of which we have absolutely none; diesel, of which we have absolutely none.” Cubans are enduring 20–22 hour daily blackouts. Grocery shelves are empty. Hospitals are suspending surgeries. One million Cubans have fled since 2021. Protests residents banging pots and pans, setting fire to trash cans have broken out across Havana and the eastern provinces, as Al Jazeera reported.
On May 20, the US Justice Department indicted 94-year-old Raúl Castro over the 1996 shootdown of civilian planes operated by humanitarian group Brothers to the Rescue. The indictment is legally theatrical Castro has not left Cuba in years but its strategic purpose is pointed. It mirrors the legal pretext used before the January 3, 2026 raid in Venezuela that captured and extracted President Nicolás Maduro, a precedent Trump has not been shy about invoking. On April 13, Trump told reporters: “We may stop by Cuba after we’re finished with Iran.” Two weeks later: “Cuba is going to be next.”
Secretary of State Marco Rubio followed on May 20 with a Spanish-language video offering Cubans a “new path” businesses, voting rights, $100 million in aid distributed through the Catholic Church, free Starlink internet. The offer was addressed to the Cuban people, not their government. As Euronews confirmed, the framing was a regime-change pitch dressed as humanitarian diplomacy the same approach applied to Iran, recalibrated for an island 90 miles from Florida.
The parallel to Iran is impossible to ignore and analysts are drawing it explicitly. The Council on Foreign Relations notes that Trump’s “maximum pressure” playbook worked in Venezuela where the capture of Maduro delivered the kind of dramatic visual that Trump’s foreign policy narrative craves but has demonstrably failed in Iran, where control of the Strait of Hormuz gives Tehran a leverage instrument that no oil sanction, naval blockade, or targeted strike has dislodged in 82 days of the US-Iran War.
Cuba has no Strait of Hormuz. It has no nuclear programme. It has no proxy network stretching from Yemen to Lebanon. It has no oil quite literally, as of this week. What it has is a collapsing economy, a population already in revolt over blackouts, and a government that the Quincy Institute’s Lee Schlenker told Al Jazeera will likely experience a “rally-around-the-flag effect” from the Raúl Castro indictment but that may ultimately lack the institutional resilience to resist the combined weight of an oil embargo, domestic collapse, and the Venezuelan precedent.
Foreign Policy’s assessment of the Iran war as Trump’s potential “greatest foreign policy failure” captures the stakes precisely: the regime change in Tehran that was supposed to be the capstone of Trump’s second-term foreign policy legacy has instead produced a closed strait, a $110 oil price, a Senate war powers revolt, and an IRGC military council that has hardened rather than fractured under pressure.
Cuba is not a substitute for that failure. But it is, for a president whose foreign policy identity is inseparable from the performance of dominance, the nearest available stage.
Cuban President Miguel Díaz-Canel’s response to Trump’s January ultimatum was four words: “No one dictates what we do.” Cuba’s UN ambassador has stated that the island’s independence “is not up for negotiation.” High-level US-Cuba negotiations following the April 10 Havana delegation visit the first US government flight to Cuba since Obama have produced, by Cuba’s own account, “no progress.”
The Iran strikes failed to produce regime change in a country of 90 million with the world’s most important oil chokepoint. Cuba has 11 million people, no oil, and no Hormuz. The arithmetic of coercion is different. Whether it produces a different outcome depends on whether Cuba’s government breaks before its population does and on whether Trump’s foreign policy machinery, which the Carnegie Endowment has described as suffering from “broken national security decision-making,” can execute a sustained pressure campaign without the contradictory signals that have defined every phase of the US-Iran agreement process.
History offers a cautionary note. Sixty-five years after the Bay of Pigs, Cuba is still there.
How control of the strait became the defining leverage point in the Iran negotiations.
Inside the back-channel diplomacy pushing toward a signed agreement.
The fragile ceasefire is holding even as broader negotiations hit roadblocks.
