Thirty years ago, Wayne Smith, the former chief of the U.S. Interests Section in Havana, argued in a 1996 essay that Cuba might follow something resembling Spain’s path under Francisco Franco. Economic liberalization would create new interests, those interests would demand political representation, and the system would evolve into something else. It was a plausible argument. It was also wrong.
Cuba did change, but the political opening never followed. The regime permitted enough economic freedom to relieve pressure and restricted it whenever that freedom threatened political control. This week, Washington made clear it will not wait another 30 years.
Secretary of State Marco Rubio told Fox News host Sean Hannity on Sept. 28 that “you cannot have economic freedom in Cuba if you don’t have political freedom first,” calling the island “a failed state in every sense of the word.” That sentence is the whole negotiation in miniature.
Havana is offering markets. Washington is demanding power.
That creates an awkward contrast with the administration’s policy next door. In Venezuela, Washington has put economic stabilization before democratic transition, arguing that recovery is necessary to create conditions in which elections can succeed. In Cuba, the sequence is reversed. There may be good reasons for the distinction, but Washington has not clearly explained them.
In June, Cuba approved 176 reforms that would have been unimaginable under President Fidel Castro, from private banking and real estate development to direct hiring and diaspora investment. They represent perhaps the largest economic concessions the Communist Party has ever made. They are aimed at a buyer who has already said the price is something else.
The rhetoric suggests a showdown. At the U.N. General Assembly on Sept. 22, President Donald Trump called Cuba “an absolutely failed state … failing like never before, and it will fall,” and said Rubio was “deep into negotiations with Cuba.” Foreign Minister Bruno Rodriguez led his delegation out. Fifteen days earlier, Rodriguez said there were no negotiations and no agenda for any.
The military signals are just as mixed. On Sept. 25, CBS News reported that Army Reserve headquarters had asked whether medical, engineer, sustainment, and military police formations could be available to the U.S. Southern Command within 90 to 120 days. The message never named Cuba, and no deployment order was issued. The next day, Trump said, “Cuba and us will make a deal. I don’t think we’ll need the military.”
Anyone who has planned stability operations recognizes that unit list. These are not primarily formations that seize terrain. They sustain forces, restore infrastructure, provide medical support, and impose order after something breaks.
So this is not yet a showdown. It is a slowdown, and each capital believes the clock is working in its favor.
Washington’s clock
The administration’s clock is a siege. A Jan. 29 executive order cut off Cuba’s oil by threatening tariffs on suppliers, while subsequent sanctions drove away foreign banks, shippers, and investors. Rubio described the method in August: “Every time they create a new mechanism in which they try to get out of the noose, we just close it off.”
Joy Gordon, writing in Lawfare on Sept. 23, calls this “siege warfare by other means.” She cites an estimated 3 million Cubans without running water and a 60% drop in food production since January, reported by the U.N. human rights office. Gordon overreaches when she argues that nothing Havana did could have softened the blow, since Cuba’s economy had already shrunk sharply since 2020.
The better answer is that both forces are working at once. The Cuban model spent decades hollowing out the state; Washington’s pressure has compressed what remained into months. Sieges end when the garrison surrenders, the attacker storms the walls, or relief arrives. Relief is scarce: Venezuelan oil stopped after former dictator Nicolas Maduro’s capture on Jan. 3, and a Russian tanker in March provided only temporary respite.
Havana’s clock
Havana’s public posture is endurance. At the July 26 Moncada anniversary in Pinar del Rio, the Guardian reported about 5,000 faithful gathered before dawn. Raul Castro, indicted by the United States on murder charges in May, missed the ceremony for the first time in 30 years. The government even handed the 79-year-old singer Silvio Rodriguez an AK-47 on television.
Hal Klepak of the Royal Military College of Canada described Cuba’s “war of all the people” as resting on a reserve that has atrophied since 1990. Nobody in Havana seriously expects to defeat the United States militarily. That leaves endurance.
Waiting has an obvious attraction. Every week survived is another week closer to the American midterm elections, another U.N. vote condemning the embargo, and another opportunity for international pressure on Washington to grow. The General Assembly takes up its annual embargo resolution Oct. 27 and 28, just before Americans vote.
Recent contacts have run through Raul Guillermo Rodriguez Castro, Raul’s grandson, known as El Cangrejo, a businessman with no government post. In March, Diaz-Canel said Raul himself was involved in talks with Washington, and the channel may simply have narrowed since.
Either way, the family is visible, and the party’s institutions are not.
What waiting costs
One European diplomat called today’s Cuba “authoritarian anarchy.” The government can still arrest opponents, but increasingly cannot deliver electricity, water, healthcare, or public order. An authoritarian state can become weaker without becoming more democratic, and the slowdown makes that danger worse every month it lasts.
Since 2020, Cuba’s population is estimated to have fallen between 13% and 25%, overwhelmingly through emigration. Much of who has left is precisely what a transition would need: young workers, professionals, and people with the means and ambition to start businesses. The siege accelerates that drain and burns through the water pumps, grid technicians, and food logistics that any successor government will need on its first morning.
There is a second cost. In May, Canadian miner Sherritt entered a preliminary agreement that could give Gillon Capital a 55% stake in the company at a discount as Sherritt struggled with sanctions affecting its Cuban operations. Gillon is the family office of Ray Washburne, who served as vice chairman of the Trump Victory Committee in 2016.
I watched in Afghanistan how quickly reconstruction money finds the well-connected, and how thoroughly that can poison the population you claim to be liberating. Every such transaction hands Diaz-Canel the story he most wants to tell.
Meanwhile, Havana argues that Washington is preventing the very economic reforms it says Cuba needs. Cuba’s top trade official said this week that U.S. pressure is obstructing implementation of the 176 measures approved in June. That brings the argument back to where it began.
In Venezuela, Washington’s theory is that economic recovery can create the conditions for political transition. In Cuba, Washington insists that a political transition must create the conditions for economic recovery. The difference may be defensible. What remains unclear is why one clock should run forward while the other runs backward.
CHINA AND CUBA DON’T NEED AN INVASION, JUST A BROKEN DOMINICAN BORDER
Rubio calls Cuba “a failed state in every sense of the word,” and Trump says it “will fall.” Smith spent his career waiting for a Cuba that would reform its way toward freedom, and it never came. The administration has decided to force the question instead.
But the slowdown is not dead time. Whoever inherits Cuba will inherit whatever the waiting leaves behind.