The Havana Handshake
After Sixty Years of Embargo, Exile, and Failed Revolutions, America and Cuba Are Finally Making a Deal — Just Not the One Anyone Fought For
The priest rides his bicycle nine miles to say Mass. The cranes at Mariel port sit idle for lack of fuel to run them. Drivers memorize each other's license plates in hundred-car gasoline queues that stretch into the next day. In the eastern provinces, people cook on charcoal. Hospitals postpone everything but the most urgent surgeries. Three times in five months, the national electrical grid has gone dark from one end of the island to the other.
This is Cuba in the spring of 2026. And into this freefall, the Trump administration has inserted the oldest instrument in its foreign policy toolkit: the deal.
Since January, when the United States effectively cut off Cuba's oil supply by seizing Venezuela's Nicolás Maduro and threatening tariffs on any country that stepped in to replace the lost crude, the pressure campaign has been relentless and specific. An oil blockade. Diplomatic isolation. The quiet threat of indictments against Cuba's military and political leadership on drug trafficking and espionage charges — the same legal architecture that preceded Maduro's capture. And a recurring message from President Donald Trump, delivered with his characteristic mix of menace and invitation: “Cuba's next."
But next for what, exactly? That question (the one that neither Trump nor Secretary of State Marco Rubio has answered clearly) is the central uncertainty shaping Cuba's future. The answer will determine whether 11 million people get electricity and investment, a military intervention and chaos, a slow-motion humanitarian catastrophe, or something the Western Hemisphere has not seen in sixty years: a genuine, if imperfect, opening.
“There’s billions of dollars to be made there. He’s interested in Cuba as a market for him, and completely agnostic about the politics.”
Step off the plane in Caracas today and the strangeness hits you immediately. Wanted posters for the opposition’s presidential candidate still line the arrivals hall. Arabic, Chinese, and Russian signs appear alongside Spanish and English at immigration booths. Three months ago, Americans were the arch-imperial enemy. Then U.S. special forces seized Nicolás Maduro in a pre-dawn raid. Now the same regime, minus its old head, greets Americans with handshakes.
This is the model. This is what the Trump administration is offering Havana.
The Venezuela operation — swift, surgical, and strategically imprecise enough to leave the underlying power structure largely intact — produced an outcome that satisfied Trump’s primary requirements: a visible rupture, a capturable villain, and a compliant successor willing to reopen the country to American economic interest. Delcy Rodríguez, Maduro’s former vice president, now leads a government that is meeting with U.S. officials from the 17th floor of the Caracas Marriott. Republican-aligned businessmen in pricey suits stride the hotel lobby, enthusing about being “super-bullish” on Venezuelan commodities.
“The goal would resemble what happened in Venezuela, where rather than installing an opposition government, the U.S. cooperated with Maduro’s former vice president.”
Cuba’s back-channel has the same architecture. The United States is not, primarily, negotiating with Miguel Díaz-Canel — the man who technically holds the presidency and party leadership. It is negotiating with Raúl Guillermo Rodríguez Castro, known inside Havana’s power circles as “El Cangrejo,” or The Crab. He is 41 years old, a lieutenant colonel, the personal bodyguard and closest confidant of his grandfather Raúl Castro, and reportedly a central figure in GAESA, the military conglomerate that controls 40 to 70 percent of the Cuban economy. He has never given a public interview. He is, in the language of the intelligence world, the principal who operates without a title.
The outlines of a deal that reflects this architecture have emerged from multiple reporting streams. Diáz-Canel, who has two years left as president and five as party leader, steps aside, providing the visible rupture Trump needs for a political announcement. The Castro family and the GAESA generals they command retain their economic empire. Cuba opens to American investment, particularly in energy, hospitality, and infrastructure. Political prisoners are released in staged batches. Cuban-Americans are permitted to return as business owners, fulfilling a promise that resonates in South Florida’s politically crucial exile community.
Trump, in this scenario, gets his Cuba announcement. Rubio gets a deal he can frame to Miami’s Cuban-American voters as the culmination of their six-decade struggle, even as the Castros retain power behind a new face. And Cuba’s generals get to keep the cut they’ve been taking for thirty years, now legitimized by American investment dollars flowing through GAESA’s unaudited accounts.
THE VENEZUELA PARALLEL
In Venezuela, the U.S. seized Maduro but left the governing apparatus intact under Delcy Rodríguez. Political prisoners have been released selectively. American investors are active in Caracas. Elections have been promised but not scheduled. The country’s deep state — military, intelligence, party — remains in place. This is not democracy promotion. It is transactional regime modification. The Cuba deal, if it closes, will look identical.
WHAT COMES AFTER THE HANDSHAKE
The Havana Handshake, in its most likely form, delivers several things quickly and several things never. In the short term: the oil blockade eases, electricity returns to most of the island on a reliable schedule, and American investment begins flowing into the energy and hospitality sectors. Diáz-Canel leaves the presidency. Trump gets his announcement. Rubio gets his South Florida moment. Cuban-Americans with capital get the right to return and own businesses for the first time in sixty years.
What the deal does not deliver, at least not initially: democratic elections, independent courts, freedom of the press, or accountability for the political prisoners who will not be included in the staged prisoner release batches. The Castro family’s wealth, GAESA’s $18 billion in assets, the generals’ cut of every economic transaction on the island, remains intact. The monitoring architecture needed to ensure that private-sector investment doesn’t flow through GAESA’s unaudited accounts is a work in progress.
“A deal focused on economic opening alone would crush the aspirations of Cubans both on the island and in exile who have fought to establish democratic rights in their homeland.”
The political scientist’s objection is right: a deal focused on economic opening alone will crush the democratic aspirations of Cubans who have fought for them. But after 67 years of tyranny and a blockade that has taken the island to the edge of humanitarian collapse, the question of what is achievable in the next 18 months matters more than the question of what should, in a more just world, have been achievable decades ago.
The Havana Handshake, if it comes, will not be the deal Cuba deserved. It will be the deal Cuba got. Whether it is better than the alternatives — continued blockade, humanitarian catastrophe, Chinese strategic entrenchment, or a military operation that produces chaos — is the only comparison that matters now. And on that comparison, imperfect as the handshake is, the answer is probably yes.