How Venezuela's Oil Deal Poses a Challenge for Rubio on Cuba's Future

The recent oil agreement between the United States and Venezuela's interim government not only marks a new chapter for Venezuela's energy sector but also raises crucial questions for Washington's policy towards Cuba:

Can a strategy that focuses on stabilizing and boosting the economy inadvertently provide authoritarian regimes with the time and resources they need to stay in power?

This question doesn’t suggest that the Trump administration has abandoned its goal of fostering democratic change in either country. Nor is there any evidence indicating that Washington is deliberately negotiating a plan to preserve the regimes in Venezuela or Cuba.

However, the Venezuela deal necessitates a closer look at the gap between the pressure exerted to initiate political change and the economic arrangements that may arise during this process.

Rubio's Perspective on Political Transition

Secretary of State Marco Rubio has emphasized the importance of political transition from the outset of his strategy for Venezuela, which included a third phase aimed at establishing a democratically legitimate government.

In Cuba, although the rhetoric has shifted to a focus on a long-term process, Rubio maintains that the administration aims to guide the island towards an irreversible transformation.

For Washington, the challenge lies in the fact that regimes have the luxury of time, whereas a presidential administration does not.

Changing Rhetoric on Cuba

On July 22, when asked if the U.S. intended to force regime change in Cuba through economic collapse or military intervention, Rubio avoided setting a timeline. He stated that Washington was willing to be "very realistic" and "patient" regarding a process that would allow Cubans to achieve prosperity, security, and a better life. He also noted that he never set a timetable for when change would occur, acknowledging the regime's long-standing existence since 1959.

By August 11, Rubio expressed confidence that before the end of Trump's administration, Cuba would be on an "irreversible path towards a very different future." However, he cautioned against expecting a system entrenched for 70 years to be dismantled overnight. Citing Eastern Europe, he noted countries like Poland needed three to five years for their transformations.

This shift does not mean abandoning the goal of transition but does lower expectations for immediate political change, focusing instead on a trajectory that should be established by January 2029.

Venezuela's Complex Path to Change

Rubio's strategy for Venezuela followed a logical sequence: stabilization, recovery, and transition. The initial phase aimed to prevent chaos, the second to rebuild the economy and normalize, and the third to lead the country towards democratic legitimacy.

However, the unfolding situation has exposed a structural challenge: economic recovery can progress faster than institutional transformation. The oil deal exemplifies this issue.

Washington reached an agreement with Delcy Rodríguez's government to develop 17 oil fields, boosting Venezuelan production to over 1.5 million barrels daily. Rodríguez claims the agreement will last 25 years, potentially yielding Venezuela $209.335 billion, assuming oil prices at $65 per barrel.

While the deal might economically benefit Venezuela, politically, it raises a separate question: the operation progresses while the democratization process remains incomplete, lacking a clear timeline for competitive presidential elections.

The Economic Dynamics at Play

If the economy improves before irreversible institutional change is achieved, recovery ceases to be solely a tool for transition and may become an incentive to maintain the status quo. This is not necessarily Washington's intent, but any investment generates interests, which in turn create incentives for stability.

The caution of major American oil companies adds another dimension to this debate. In early January, when Trump urged industry leaders to make massive investments to rebuild Venezuela's oil sector, Darren Woods, ExxonMobil's CEO, called the country "unviable for investment" without significant changes in legal and commercial structures, lasting investment protection, and alterations to oil laws. Other companies expressed similar reservations amidst political and legal uncertainties.

For businesses, the logic is straightforward: a company investing billions with returns measured over decades needs to know which government will be in power, what laws will apply, and whether contracts will be honored by future administrations. This is an economic consideration but also an institutional one.

Significantly, the finalized agreement relies on an extraordinary structure and controversial actors while major oil companies proceed cautiously. The Financial Times highlighted Alejandro Betancourt's role and the uncertainties surrounding the deal's structure, while the Associated Press noted lingering doubts about the private operator, financing, and the duration of certain rights.

While this doesn't prove the agreement is a mechanism to preserve the regime, it underscores something Washington should heed: institutional uncertainty has a cost, and private capital recognizes it before committing.

Cuba's Lessons and Strategic Timing

It's crucial to avoid drawing overly mechanical parallels. Cuba and Venezuela present different challenges, with distinct economic structures, and Washington wields different levers in each case. The useful parallel is this: both countries have political structures that have shown remarkable resilience against external pressure and have adapted economically without relinquishing fundamental political control.

The question for Cuba is broader: Can the regime offer enough economic, social, or diplomatic ground to convince Washington of progress while retaining the institutions that ensure its survival? The risk is recognizable: partial prisoner releases can be framed as progress, economic openings as reforms, dialogue with select political actors as reconciliation, and new private sector licenses as openness.

Yet none of these measures alone equate to competitive elections, political pluralism, institutional independence, or the rule of law. The Cuban regime doesn't need to reject all U.S. demands outright. It can manage concessions to reduce pressure faster than the political power of the system.

For an administration with a limited timeframe, this presents a serious problem. Washington's political clock favors those who can afford to wait.

Washington's Political Timing and Strategic Implications

The U.S. mid-term elections are scheduled for November 3, 2026, and Trump's presidential term ends on January 20, 2029. While U.S. policy toward Cuba or Venezuela won't be dictated solely by the electoral calendar, these dates are significant political milestones for any long-term strategy.

An authoritarian regime can contemplate timelines spanning years. A U.S. administration must demonstrate results sooner. This asymmetry creates a potential incentive for a strategy of partial concessions and waiting.

Havana might wonder how long it must endure before political conditions in Washington change. Caracas might ask how much time it needs to cement an economic relationship that makes future ruptures costly. Both governments could have an interest in keeping political issues within a negotiation process without a definitive end date.

The challenge for Washington is to prevent "process" from becoming synonymous with "postponement."

Potential Risks for Rubio's Strategy

Rubio's strategy for Venezuela holds political logic if economic recovery leads to transition. The problem arises if the sequence reverses: stabilization → recovery → economic normalization → institutionalization of the status quo → indefinite transition. This would be the most dangerous scenario for Rubio.

Not because seeking investments or rebuilding the oil industry would be a mistake. Venezuelan economic development can be a legitimate and desirable goal. The issue would emerge if economic results are verifiable and rapid, while democratic outcomes remain promises.

In this scenario, critics might pose a politically challenging accusation: that the U.S. changed Venezuela's economic relationship with Washington without sufficiently altering the relationship between Venezuelan power and its citizens.

For a Secretary of State who presented a democratic phase as part of his strategy's outcome, this would be a significant reputational cost.

Cuba's Observations on Venezuela

Havana has reasons to scrutinize developments in Venezuela. The Cuban regime has received a clear geopolitical signal: Venezuela, one of its historical allies, has shifted from an energy provider to a space where the U.S. seeks to exert profound economic influence.

But Cuba might also observe another factor: Washington is willing to negotiate with existing power if it believes doing so advances its strategic objectives.

This realization could have two opposing effects. It might convince the Cuban regime that absolute resistance is unsustainable and that deep changes are necessary. Alternatively, it might lead to a different strategy: granting enough to show progress to Washington without surrendering what allows the system to retain power.

This second approach would be harder to detect than open confrontation.

Rubio's New Metric: "Irreversible"

In August, Rubio introduced a new metric: "irreversible." He didn't promise Cuba would become a democracy before the term's end. He said it would be on an irreversible path towards a different future. This allows for gradual transformation but raises a question Washington should answer precisely:

What does "irreversible" mean? A more open economy? Less state dependency? Greater freedom for the private sector? Release of political prisoners? Return of exiles? Freedom of association? Electoral system reform? Party pluralism? Judicial independence? Or a combination of these elements?

Without specific indicators, "irreversible" risks becoming an overly broad political category. Almost any concession can be presented as progress in the right direction. And a regime that seeks time can comfortably exist within this ambiguity.

A Public Policy Warning for Rubio

If the U.S. goal is for economic pressure to produce political transition, Washington should ensure that economic agreements don’t become independent of the institutional process.

In Venezuela, this means that oil recovery should not be measured solely by barrels produced, investment mobilized, or fiscal revenue. It should also consider the conditions Rubio identified as necessary for free elections: credible electoral institutions, political freedom, party organization capacity, and opposition guarantees.

In Cuba, the same logic requires something even more fundamental: that economic and diplomatic concessions can be linked to verifiable political changes, not just promises of future transformation.

The principle should be straightforward: relief can accompany change, but not replace it. Likewise, greater economic openness should not be automatically confused with democratic transition.

Rubio's political capital depends on more than the number of sanctions imposed or the economic damage inflicted on regimes. It hinges on something more challenging: if, by the end of the administration, there is a political process that regimes cannot easily reverse.

This is a much higher standard. It's also why Venezuela is so important for Cuba. If the administration shows that economic recovery can coincide with effective political transition, it sets a powerful precedent for its Cuban strategy.

If the opposite occurs—if recovery solidifies a new economic relationship with existing power while democratization is postponed—Havana may learn a different lesson: that survival against U.S. pressure is possible by offering enough concessions to keep negotiations open and gain time.