The Direct Message
Tension: The U.S. embargo on Cuba is supposed to punish the Cuban government, but after sixty years, it primarily punishes eleven million civilians while reinforcing the state’s narrative of victimhood.
Noise: The debate is framed as hawks vs. doves, embargo vs. engagement, but the real complexity lies in a policy sustained by inherited grief, electoral math, and the sunk cost of six decades of commitment to a strategy that has produced the opposite of its stated goals.
Direct Message: The embargo persists not because anyone can articulate what success looks like, but because admitting failure after sixty years requires a kind of honesty that American foreign policy has never been willing to practice.
Every DMNews article follows The Direct Message methodology.
The common assumption about the U.S. embargo on Cuba is that it punishes the Cuban government. After more than sixty years, the evidence suggests something closer to the opposite: the embargo has become a mechanism that punishes civilians while leaving the state apparatus largely intact, its legitimacy renewed each time Washington tightens the screws.
Power grid failures have led to suspended surgeries, gasoline shortages, and infrastructure collapse across Cuba. Reports describe civilians spending days in fuel lines, hospitals operating without reliable electricity, and a healthcare system under severe strain. This is the predictable human output of a policy that, according to two Democratic lawmakers who visited the island last week, amounts to “cruel collective punishment.”
Representatives Pramila Jayapal and Jonathan Jackson traveled to Cuba and returned with language that was unusually blunt for sitting members of Congress. They described the U.S. energy blockade as “effectively an economic bombing of the infrastructure of the country” that “has produced permanent damage.” The word “bombing” is not accidental. It is designed to reframe what Americans tend to think of as a passive policy, an old embargo that has always just been there, as something active and violent.
And the violence is measurable. Since January, when President Trump issued executive orders threatening tariffs on any nation that supplied fuel to Cuba, the island has experienced national blackouts, gasoline rationing, the suspension of hospital operations, the grounding of flights, and the effective collapse of public transportation. Cuba’s economy, already fragile, buckled under the weight of total energy starvation.
The question sits at the center of a policy contradiction that neither party has been willing to address honestly. The tanker, a sanctioned Russian vessel called the Anatoly Kolodkin, was permitted to dock and unload its cargo. Reports suggest the shipment could produce enough diesel to cover Cuba’s daily demand for nine or ten days. A band-aid on a wound that requires surgery.
The deeper question is about coherence. The United States has spent decades insisting that the embargo exists to promote democratic reform in Cuba. If that is the goal, then the policy has failed by every conceivable metric. Cuba remains a one-party state. The embargo has not toppled the government. What it has done is give the Cuban government an external enemy to point to, a permanent excuse for every domestic failure, a narrative of victimhood that is, unfortunately, largely accurate when it comes to energy.
Jayapal recognized this during her visit. She said that Cuba has taken recent steps that could form the basis for real negotiations, including opening parts of its economy to certain investments and announcing the pardon of over 2,000 prisoners. “We need a longer, permanent solution for the Cuban people and the American people,” she said. Jackson, meanwhile, drew an analogy that landed with particular force. “Our government is fighting to keep the strait of Hormuz open so there is a free flow of oil around the world,” he said. “We want, for humanitarian reasons, a free flow of oil, fuel and energy in our own hemisphere.”
The Hormuz comparison is worth sitting with. The U.S. deploys naval assets to ensure that energy moves freely through a strait thousands of miles away, because any disruption to that flow would destabilize global markets. Ninety miles off the coast of Florida, the same government is actively preventing the flow of energy to an island of eleven million people. The strategic logic of the first action is obvious. The strategic logic of the second is, at this point, mostly inherited. It persists because Florida electoral politics reward it, because the Cuban-American lobby remains organized around it, and because no president wants to spend political capital reversing it.
This generational divide runs through the Cuban-American community like a fault line. Older exiles, shaped by the trauma of dispossession, view the embargo as moral leverage. Their children and grandchildren, many of whom have visited Cuba and seen the consequences firsthand, increasingly view it as moral failure.
The psychology at work here is what behavioral researchers call the sunk cost trap applied to foreign policy. More than sixty years of embargo represents an enormous investment of political will, diplomatic capital, and national identity. Admitting that it has not achieved its stated objectives feels like admitting that six decades of suffering were pointless. So the policy continues, not because anyone can articulate what success would look like, but because abandoning it would require confronting that question.
High-level talks between the U.S. and Cuba are reportedly ongoing, led on the American side by Secretary of State Marco Rubio, himself of Cuban descent and historically a hawk on Cuba policy. The fact that Rubio is at the table at all signals something. Whether it signals a genuine shift or merely the management of an inconvenient Russian oil delivery is another matter entirely. Diplomacy between the U.S. and Cuba has a long history of theatrical openings that lead to quiet closings.
The January executive orders that initiated the current energy blockade came shortly after the U.S. moved against Venezuela, halting oil shipments from Caracas to Havana. Cuba lost its primary energy lifeline almost overnight. The Russian delivery was a stopgap, not a solution, and everyone involved knows it. Nine or ten days of diesel does not rebuild a hospital’s surgical capacity. It does not restart a transit system. It does not turn the lights back on in any permanent sense.
What the Jayapal-Jackson visit reveals is less about Cuba specifically and more about how the U.S. relates to policies that have outlived their original rationale. The embargo was born during the Cold War, when Cuba served as a Soviet foothold ninety miles from Key West. The Soviet Union has been gone for thirty-five years. The strategic rationale evaporated. What remained was a political rationale, and political rationales are harder to kill because they are sustained by emotion rather than analysis.
Observers of U.S. Cuba policy have long noted that the embargo persists not because anyone in government actually defends it on the merits, but because it remains politically untouchable. The policy is sustained by memory, by grief, by a community’s refusal to let go of a wound. Those are real and legitimate feelings. They are not a strategy.
The irony is that the current energy blockade may be accelerating exactly what the embargo was supposed to prevent: deeper Cuban dependence on adversarial powers. When the U.S. blocks Venezuelan oil and the gap is filled by a Russian tanker, the result is not Cuban isolation. It is Cuban alignment with Moscow. The blockade does not cut Cuba off from the world. It cuts Cuba off from the United States, and pushes the island toward the very actors Washington claims to be countering.
The honest answer is that nobody knows what lifting the embargo would produce, because the experiment has never been tried.
What Jayapal and Jackson brought back from Havana was not new information. The humanitarian toll of the embargo has been documented for years by journalists, aid workers, and anyone who has visited the island. What they brought back was the increasingly difficult-to-ignore spectacle of American lawmakers standing in a country where hospitals cannot operate, saying out loud what the policy establishment has known quietly for decades.
The blockade will not end because of one congressional visit. It will not end because of one Russian oil delivery. It will not end because two representatives used the word “bombing” on the record. These are pressure points, not tipping points.
But something is different now. The energy crisis is acute in a way that previous rounds of deprivation were not. Cuba’s grid has essentially failed. The pardoning of prisoners and the opening of certain economic sectors represent the kind of gestures that, in any other diplomatic context, would be met with reciprocal steps. The fact that talks are happening at all, with Rubio of all people at the helm, suggests that the internal calculations in Washington may be shifting, however slowly.
Cubans do not follow American congressional delegations. They follow the schedules posted outside hospitals that tell them whether there will be power tomorrow. Cuban-Americans cannot explain to their parents why the policy they believe in has made things worse for the people they claim to care about. The disconnect between intention and outcome has never been starker.
The embargo persists because admitting its failure requires a kind of honesty that American foreign policy has never been good at: the acknowledgment that a punishment, applied long enough, stops being about the crime and becomes about the punisher’s inability to imagine doing anything else.
