Cuba is closely watching what is happening in Venezuela.
No need to know all the details of the oil agreement or share the Trump administration's policy on extraction to reach a strategic conclusion: Washington is willing to negotiate with structures linked to the former regime when it believes that doing so helps stabilize a country, recover its economy, and advance its national interests.
That does not mean that Donald Trump or Marco Rubio have abandoned the idea of a democratic transition. However, it does introduce a variable that Havana may be able to exploit: time.
The Venezuelan experience shows that an administration may first need to work with those who control the institutions, even if those same actors come from the system that Washington intended to overcome.
For Cuba, where the Communist Party and state structures have survived for decades under both internal and external pressures, the temptation to apply a similar strategy is evident.
Grant something. Negotiate. Keep the dialogue open. And wait.
Rubio has already lowered expectations for an immediate change
The Secretary of State himself has altered the language used regarding Cuba.
In July, Rubio stated that the United States should be "realistic" and "patient" and reminded that he had never set a timeline for change on the island.
In August, he was even more explicit: he stated that he was convinced that, before the end of the Trump administration, Cuba would be on an "irreversible path" toward a very different future, but he warned that it was not possible to uproot a system that has been established for 70 years overnight. As a reference, he cited the duration of political transformations in Eastern Europe.
Changing the language does not equate to a renunciation. In fact, Rubio continues to describe the Cuban transformation as a priority for the United States and asserts that the goal is for the island to finally be safe, stable, and aligned with Washington.
But there is a new reality: the administration is no longer publicly suggesting that political change in Cuba must happen within a matter of months.
It is speaking about a path. And a path can move forward. But it can also be deliberately slowed down.
That difference can be leveraged by Havana
The Cuban regime has spent decades demonstrating a remarkable ability to survive periods of crisis.
No need to convince Washington that the system is democratic. You can try to convince it of something simpler: that it is still possible to modify it without replacing it.
The regime can offer economic reforms. It can create certain opportunities for the private sector. It can release prisoners in groups. It can expand specific diplomatic contacts. It can provide cooperation on migration. It can agree to discussions. It can implement administrative changes.
And then he can argue that all of this needs time.
Each concession can serve as a basis for a new round of negotiations. And each new round may diminish the U.S. incentive to shift from pressure to a deeper breakdown.
This is the scenario that Venezuela allows us to imagine.
The danger for Rubio is not the negotiation
An authoritarian transition does not become democratic simply because Washington refuses to engage with the existing power.
In some cases, negotiating with those who control the State is inevitable. The problem arises when negotiation becomes a substitute for the transfer of power.
The Venezuelan experience raises exactly that question. Washington can work with Delcy Rodríguez because she controls the state. But what guarantees that, once the economic relationship normalizes, the need for stability won't end up reducing the incentive to accelerate the transition?
In Cuba, the problem would be even greater.
There is currently no equivalent figure to Delcy who can present an orderly transition in the Venezuelan style. The power structure is more closed off and the Communist Party maintains institutional control.
For this reason, any negotiated opening can be absorbed by the system itself. Havana has experience implementing economic reforms without turning them into political reforms.
The Venezuelan precedent can produce two opposing effects in Cuba
The first would be favorable to Rubio.
If Venezuela demonstrates that U.S. pressure, followed by negotiation and economic recovery, ultimately leads to free elections, Cuba will receive a very clear signal: cooperation with Washington serves to initiate a transition, not to prevent it.
The second would be much more concerning.
If Venezuela manages to recover its economy, integrate with the United States, and stabilize its government without convincingly resolving the electoral issue, Havana may conclude that there is an alternative: make sufficient concessions to normalize relations with Washington without relinquishing political control.
That would be a much more dangerous lesson.
For a regime, time can be a tool
This is the point that should probably concern Rubio the most.
The Cuban regime does not need to win an ideological debate with Washington. It only needs to survive the window of American pressure.
The United States midterm elections will take place in November 2026, and Donald Trump's presidential term will end on January 20, 2029.
This does not mean that U.S. foreign policy will disappear after those dates, nor that Rubio's strategy automatically depends on them.
But it does mean that the current Administration has a limited political window to demonstrate that its strategy is working.
La Habana has another advantage: it does not need to demonstrate results before an election date. It can wait.
The regime may consider it sufficient for Trump to reach 2028 without causing an irreversible political break. For Washington, on the other hand, the question will be what structural changes have been consolidated by January 2029.
Rubio has chosen an important word: "irreversible."
Precisely for that reason, the expression used by Rubio in August deserves more attention than any date.
He said that Cuba must find itself on an "irreversible path" towards a different future before the end of the administration.
The essential word is not "future." It is "irreversible." Because a reversible change does not alter the fundamental incentives of the regime.
A more open economy can close again. A business permit can be rescinded. A freed prisoner can be detained again. A negotiation can be interrupted. An administrative reform can be repealed.
The question that Washington should be asking itself, therefore, is not how many concessions it can obtain from Havana. It is: What reforms can survive a change of government and make it impossible to return to the previous system?
In politics, irreversibility often begins with institutions.
The Venezuelan agreement may help answer that question
The Trump administration will have the opportunity to demonstrate in Venezuela what it understands by a transition that truly changes the rules of the game.
If the new investments and oil agreements are accompanied by: independent electoral institutions; freedom for political parties; guarantees for the opposition; release of political prisoners; safe return of exiled leaders; and a binding electoral timetable, then the economic recovery can be seen as a tool for transition.
If the economic agreements progress while those elements remain in the background, the interpretation will be much more problematic.
And the Cuban regime will be taking note.
The private sector is also part of this equation
The administration has indicated that it wants to support an independent private sector in Cuba and prevent economic benefits from strengthening the state apparatus.
The idea can make sense as an instrument of transformation. But there is also a condition here: creating private activity is not the same as producing politically free citizens.
A small business owner can have more economic autonomy without the ability to create a political party. A private enterprise can operate without judicial independence. Trade can grow without press freedom. Economic openness can even enhance the administrative capacity of the state without diminishing its political monopoly.
Therefore, U.S. policy needs to distinguish between economic liberalization and democratic transition. One can assist the other. But they are not equivalent.
Havana could try to prove that they are
That would be a smart move by the regime.
Cuba could offer Washington a package of economic and administrative reforms, presenting these measures as a historic change and requesting time, investment, and a reduction of pressure in return.
If the United States accepts that logic without establishing verifiable political objectives, the regime will have achieved something very valuable: transforming the discussion from «when will they stop ruling?» to «how much more can they reform without ceasing to rule?».
That would represent a complete change in the nature of the negotiation. And the Venezuelan precedent could be crucial in determining what response is obtained.
The difference between Delcy and Havana may be significant
It should not be assumed that Cuba will adopt the Venezuelan model.
Venezuela has a gigantic oil resource that makes its relationship with the United States particularly attractive and alters the structure of incentives. Cuba does not offer the same economic advantage.
Therefore, Havana will need to identify other areas where it can become an essential interlocutor: migration, security, intelligence, strategic location, telecommunications, regional cooperation, or specific economic opportunities.
This, in fact, can reinforce the dilemma.
The more beneficial the regime is for U.S. interests, the harder it may become for Washington to determine when the benefits no longer justify the continuation of the current interlocutor.
Rubio's personal challenge
Rubio has taken a particularly tough stance against the Cuban regime.
He insisted that this must entail real changes and that the United States will continue to use the available tools to pressure him. In July, he urged Cuban leaders to commit to genuine reforms “before it is too late.”
But in August, he also acknowledged that the transformation will necessarily be gradual.
There is no contradiction between the two statements. The difficulty lies in making them compatible.
Patience cannot mean permissiveness. Process cannot mean indefinite postponement. Economic reform cannot mean a substitute for political reform. And, above all, stability cannot become the ultimate criterion of success.
Because an authoritarian regime can provide stability for decades. The challenge is to build institutions that make such a regime unnecessary.
The lesson Rubio must take away from Venezuela
The Venezuelan experience could ultimately become the strongest argument in favor of the Cuban strategy under the Trump administration or its biggest warning.
If Washington demonstrates that it is possible to negotiate with the structures of the old regime, rebuild a devastated economy, and subsequently transfer power through free elections, it will have created an innovative model of pressure and transition.
But if economic recovery indefinitely precedes democratization, Havana will have received another message: the United States can be persuaded to wait.
And waiting is precisely what an authoritarian regime knows how to do best.
The policy towards Cuba should therefore avoid an apparently minor but strategically crucial trap: confusing the evidence that the regime is shifting with the evidence that the regime is willing to stop governing in the same manner.
Rubio does not need to prove that he can change Cuba in a year. He needs to show that each year of negotiation leaves the system with less ability to revert.
That should be the true meaning of their promise of an “irreversible path.”
And Venezuela has just given a test of enormous importance.
Because the question is no longer just what Washington gets from Caracas.
The question is what Havana learns from what Washington is willing to accept in Caracas.
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