As events unfold in Venezuela, Cuba is keenly observing the developments.
While the specifics of the oil agreement and the policies of the Trump administration aren’t necessary for Havana to draw a strategic conclusion, it’s clear that Washington is open to negotiating with entities linked to the former regime when it believes doing so can stabilize a nation, recover its economy, and advance U.S. interests.
It’s important to note that neither Donald Trump nor Marco Rubio has abandoned the push for a democratic transition. However, this introduces a tactical variable that Havana might exploit: time.
The Venezuelan experience illustrates that an administration might initially need to engage with those holding power, even if they originate from the system Washington aims to change.
Potential Strategies for Cuba
In Cuba, where the Communist Party and state structures have withstood both internal and external pressures for decades, the appeal of adopting a similar strategy is undeniable.
Concessions could be made, negotiations opened, and dialogues maintained—all while playing the waiting game.
Rubio has already adjusted expectations for immediate change. The Secretary of State has also modified his rhetoric regarding Cuba.
Back in July, Rubio emphasized the need for the U.S. to be "realistic" and "patient," reminding everyone that there was never a set timeline for change on the island.
By August, he was more explicit, expressing confidence that before the conclusion of the Trump administration, Cuba would be on an "irreversible path" toward a significantly different future. However, he warned that dismantling a 70-year-old system couldn’t happen overnight, referencing the lengthy political transformations in Eastern Europe.
The Reality of Negotiation
This shift in language doesn’t signal a retreat. In fact, Rubio continues to describe the transformation of Cuba as a U.S. priority, asserting that the goal is for the island to become secure, stable, and aligned with Washington.
Yet, there’s a new reality: the administration is no longer publicly insisting that Cuban political change must occur within months. They’re talking about a trajectory, which can advance or be purposefully slowed.
Havana has long demonstrated a remarkable ability to survive crises, and it doesn’t need to convince Washington that its system is democratic. Instead, it might argue that changes are feasible without a complete overhaul.
Cuba's Potential Moves
The Cuban regime could offer economic reforms, open certain sectors to private enterprise, release prisoners in groups, expand diplomatic contacts, offer migration cooperation, engage in talks, and introduce administrative changes. Then, it could argue that all these steps require time.
Every concession could become a bargaining chip for further negotiations, reducing the U.S. incentive to escalate pressure into a more profound rupture.
This scenario is precisely what the Venezuelan situation brings to mind.
Negotiation vs. Transition
The danger for Rubio is not the act of negotiating. An authoritarian transition doesn’t become democratic simply because Washington refuses to engage with current power holders.
In some cases, talking with those controlling the state is unavoidable. The issue arises when negotiations replace the actual transfer of power.
Washington can engage with figures like Delcy Rodríguez because she holds state control. But what ensures that, once economic relations are normalized, the need for stability doesn’t diminish the incentive for a swift transition?
In Cuba, this problem could be even more significant.
Lessons from Venezuela for Cuba
There isn’t currently a figure like Delcy who could facilitate an organized transition in the Venezuelan style. Cuba’s power structure is more closed, with the Communist Party maintaining institutional control.
Therefore, any negotiated opening might be absorbed by the system itself. Havana has experience in implementing economic reforms without converting them into political reforms.
The Venezuelan precedent can have two opposing effects in Cuba. The first could favor Rubio if Venezuela proves that U.S. pressure, followed by negotiation and economic recovery, leads to free elections, signaling to Cuba that cooperation with Washington opens a transition, not avoids it.
The second is more concerning. If Venezuela manages to restore its economy, integrate with the United States, and stabilize its government without resolving the electoral question convincingly, Havana could conclude that there’s an alternative: making sufficient concessions to normalize relations with Washington without relinquishing political control.
Frequently Asked Questions about U.S.-Cuba Relations and Strategy
How might Cuba leverage time in its negotiations with the U.S.?
Cuba could use time as a strategic tool by making incremental concessions while maintaining dialogue, essentially prolonging negotiations without committing to substantial political changes.
What are the risks of negotiating with an authoritarian regime like Cuba?
The risk lies in negotiations becoming a substitute for actual power transfer, where economic normalization reduces incentives for political change, allowing the regime to maintain control without significant reforms.
What lessons can Cuba learn from Venezuela's experience with the U.S.?
Cuba might learn that it can negotiate economic concessions with the U.S. without necessarily moving toward democratization, as long as it provides stability and some reforms to maintain U.S. interests.