The foreign policy establishment is currently obsessed with a single, tired question: Will Donald Trump dismantle the "thaw" with Cuba? They treat the island like a fragile chess piece in a Cold War revival, hyper-ventilating over sanctions, travel bans, and the "hitlist" rhetoric.
They are asking the wrong question. In other developments, we also covered: The Sabotage of the Sultans.
The obsession with whether Trump will "attack" Cuba ignores the reality that the Cuban government has already been defeated—not by American missiles or Treasury Department memos, but by its own catastrophic economic obsolescence. Focusing on Trump’s potential aggression is a lazy distraction from the real story: the total structural collapse of the Caribbean’s last command economy and the vacuum it leaves behind for adversaries far more competent than the aging leadership in Havana.
The Sanctions Myth and the Scapegoat Strategy
The "lazy consensus" argues that U.S. sanctions are the primary driver of Cuban misery and that a Trump-led escalation will be the final blow. Al Jazeera has also covered this fascinating subject in great detail.
This is a fundamental misunderstanding of economic gravity.
Sanctions are a mosquito bite on a patient with stage-four organ failure. Cuba’s economic collapse is a result of a centralized planning model that has remained static since 1959. When the Soviet Union collapsed, Cuba entered the "Special Period." When Venezuela’s oil subsidies evaporated, Cuba entered a second, even more dire, era of scarcity.
The U.S. embargo is the ultimate political gift to the Cuban Communist Party. It provides an external villain for every blackout, every bread line, and every failed harvest. If Trump "hits" Cuba harder, he isn’t destroying the regime; he is providing them with a more convincing script for their own failure.
The nuanced truth: The Cuban regime needs a hostile Trump. They thrive on the "hitlist" narrative because it justifies the suppression of internal dissent as "national security." Without the specter of a belligerent Yankee neighbor, the leadership has to explain why they can’t provide basic electricity or clean water in a country that hasn't seen a kinetic conflict in sixty years.
The China and Russia Vacuum
While the D.C. punditry debates whether Trump will ban American cruise ships from docking in Havana, they are missing the strategic shift that actually matters.
Cuba is no longer just a socialist outpost. It is becoming a high-value real estate play for China and Russia.
Imagine a scenario where the U.S. continues to obsess over travel restrictions while China quietly builds out the Port of Mariel and establishes signals intelligence facilities at Lourdes. Trump’s "hitlist" approach—if it relies solely on isolation—is a strategic gift to Beijing.
Isolation creates a power vacuum. And power vacuums in the Caribbean are always filled by someone.
I have seen policy analysts blow millions of dollars in research time debating "democratic transitions" while ignoring the fact that the Cuban military (GAESA) already owns the economy. They aren't going to "transition" into a democracy because a U.S. president tweets about them. They are going to transition into a Caribbean version of the Egyptian model: a military-industrial complex that sells hotels to tourists while maintaining an iron grip on the citizenry.
The "counter-intuitive" move isn't more sanctions. It is aggressive, predatory engagement.
If you want to dismantle the Cuban regime, you don't ban tourists. You flood the island with iPhones, Starlink terminals, and capital that isn't filtered through the central bank. The regime survives on control. You kill control with chaos—the beautiful, messy chaos of a functioning market.
The Myth of the Cuban "Hitlist"
Is Cuba on a hitlist? No. Cuba is a footnote in the Trumpian "America First" doctrine.
The media loves the hitlist narrative because it’s dramatic. It suggests a focused, ideological campaign. The reality is far more transactional.
Trump views foreign policy through the lens of leverage. If Cuba doesn't offer a deal that benefits his domestic base—specifically the South Florida electorate—it’s not a "hitlist" item; it’s an annoyance. The danger isn't that Trump will invade; the danger is that he will ignore the island while its infrastructure rots, creating a migration crisis that dwarfs the 1980 Mariel boatlift.
People often ask: "Will Trump’s policies lead to a regime change in Cuba?"
The premise is flawed. No U.S. policy since the Bay of Pigs has "led" to regime change in Cuba. The only thing that will change the Cuban regime is the internal realization that they can no longer feed their people.
The Hard Truth About Migration
The establishment worries about "instability." They should be worried about the math.
Cuba is currently experiencing the largest exodus in its history. Not because of a hitlist, but because of a total lack of hope. Between 2022 and 2024, hundreds of thousands of Cubans entered the U.S. through the southern border. This is the real "hit" to the U.S.—the strain on domestic resources caused by a neighboring state in terminal decline.
If Trump wants to "hit" Cuba, he doesn't need to sign an executive order. He just needs to wait.
The regime is currently cannibalizing itself. They have legalized small businesses (SMEs) out of desperation, not out of a sudden love for Milton Friedman. These SMEs are the Trojan Horse. They are creating a class of Cubans who don't rely on the state for their paycheck.
The "hit" is already happening from within.
Why the "Thaw" Was a Failure
The Obama-era "thaw" was criticized for "giving too much for too little." But its real failure was its politeness.
It was a top-down diplomatic maneuver that allowed the Cuban elite to pick and choose which parts of the modern world they wanted. They wanted the tourist dollars, but not the free internet. They wanted the trade, but not the labor rights.
A "hitlist" approach that reverts to 1960s-style isolation is just as stupid. It’s a retreat.
The superior strategy—the one the "status quo" refuses to acknowledge—is to weaponize the very things the Cuban government fears most: transparency and competition.
Don't ban the travel of American citizens. Make it a requirement that every American dollar spent in Cuba goes directly to private bed-and-breakfasts (casas particulares) and private restaurants (paladares), bypassing the state-owned GAESA hotels entirely.
Force the regime to choose: Do they shut down the private sector and face a total popular uprising, or do they let the private sector grow and lose their monopoly on power?
The Geopolitical Reality Check
Let’s be brutally honest: Cuba has zero strategic value to the U.S. in 2026, other than as a potential base for adversaries.
The old arguments about the "threat" of Cuban socialism are over. Socialism failed. It’s dead. The only thing left is a mafia-state trying to keep the lights on.
If you think Trump’s next move is a focused, ideological crusade against communism in Havana, you haven't been paying attention. The "hitlist" is a media creation designed to sell clicks to people who still think it’s 1962.
The actual policy will be a series of transactional demands: stop the migration flow, stop hosting Chinese spy stations, or face even tighter financial screws. It’s not a hitlist. It’s a shakedown. And in the world of high-stakes geopolitics, a shakedown is often more effective than a crusade.
Stop Asking if Cuba is Next
The question isn't whether Cuba is on a hitlist. The question is whether the Cuban leadership can survive the next five years of their own mismanagement.
They are out of oil. They are out of credit. They are out of food.
The U.S. president—whoever they are—is just a spectator to a slow-motion wreck. If Trump decides to kick the wreckage, it might make for a good headline, but it won't change the physics of the crash.
The Cuban people are already voting with their feet. The regime has already lost the mandate of heaven. The "hitlist" narrative is a distraction from the reality that the Cold War in the Caribbean didn't end with a bang or a treaty—it’s ending with a blackout and an empty grocery store shelf.
Stop looking at the White House for the answer to Cuba’s future. The answer is in the streets of Havana, where the people have realized that the revolution promised them a paradise and delivered a prison.
The hitlist is a myth. The collapse is the reality.
If you want to actually "hit" the Cuban regime, stop talking about sanctions and start talking about the $50 billion in remittances that keep the lights on. That is the only lever that matters. Everything else is just theater for the cable news cycle.
The regime isn't afraid of Trump’s hitlist. They are afraid of their own people finally realizing that the world has moved on without them.
Kill the distractions. Watch the data. The island is drifting away, and no executive order can tether it back to a failed ideology.
Stop worrying about the hitlist. Start preparing for the aftermath of the inevitable.
