Rubio's Eight Strategies for Transforming Cuba's Future

The recent revelation by Axios that Marco Rubio is engaged in confidential discussions with Raúl Guillermo Rodríguez Castro, also known as "El Cangrejo" and the grandson and bodyguard of Raúl Castro, signifies a major turning point in the relationship between the United States and the Cuban regime. For the first time in over sixty years, Washington is directly communicating with the inner circle of real power in Cuba, circumventing the official channels of a crumbling regime.

Cuba is currently on the brink of a humanitarian crisis. The island is grappling with severe shortages of fuel and stable electricity, hospitals are struggling to function, and food scarcity has become so dire that Mexico has sent military ships filled with beans and rice as if aiding a disaster zone. With the fall of Maduro, Venezuela can no longer supply oil. Donald Trump bluntly described Cuba as a failed state, unable to even fuel planes for takeoff.

In this scenario, Rubio has a historic opportunity. As a Cuban American who understands the struggles of the Cuban people, he is uniquely positioned to achieve what no Secretary of State has managed: genuine change in Cuba. The Obama administration's engagement in 2014 sparked real hope among Cubans, but the regime hijacked that process to prolong its survival without conceding anything. Rubio can learn from that experience and pursue a different path. Here are the strategies he needs to follow.

Ensure Verified Compromises for Each Concession

The clearest lesson from 2014 is that every concession should be met with a verifiable and irreversible compromise. This means the release of political prisoners with specific names and dates, opening up to independent media with verifiable licenses, and ending the persecution of dissidents and activists. When Obama removed Cuba from the list of state sponsors of terrorism, restored diplomatic relations, and eased travel and remittances, millions of Cubans believed change was imminent. However, the regime seized every concession without making any moves toward openness. As noted by the Council on Foreign Relations, those policies legitimized the regime without benefiting the Cubans striving for freedom. The fault lay not with the one who extended a hand, but with the one who used it to cling to power.

A more effective approach would be a phased and conditional concession mechanism, with independent international verification.

Link Public Gestures to Concrete Results

Public gestures carry significant weight in diplomacy with the Cuban regime. The 2016 experience demonstrated this: while Obama attended a baseball game in Havana as a gesture of rapprochement, the Rapid Response Brigades were assaulting dissidents in the streets. The regime turned that image into a propaganda victory without giving up anything.

The opportunity is to reverse that logic: ensure each public image certifies an achievement, not a premature gift. Let the photos tell the story of progress, not promises.

Judge Interlocutors by Actions, Not Rhetoric

According to Axios sources, Rubio and his team view "El Cangrejo" as part of a "younger, business-minded generation" for whom revolutionary communism has failed. It's worth looking beyond that narrative to the facts.

Raúl Guillermo Rodríguez Castro was the personal bodyguard of the dictator and maintains direct ties with GAESA, the military-business conglomerate controlling about 70% of Cuba's economy. What is presented as a "business mindset" might actually be the military elite's ability to seize business opportunities while most Cubans lack access to similar chances. For decades, the Cuban regime has mastered the art of presenting façade reformers whenever it needs to ease external pressure.

Rubio has a unique advantage: he is familiar with these tactics, allowing him to distinguish between promises and concrete actions.

Economic Opening as a Tool for Liberation

Rubio suggested at the Munich Security Conference that economic freedom could precede political freedom in Cuba. He's right, and therein lies the key to any negotiation.

Despite the obstacles imposed by the regime, Cuban micro, small, and medium enterprises have proven something the regime never wanted to be seen: that Cubans are perfectly capable of creating, innovating, and thriving when given minimal space. These small businesses represent the greatest threat to the totalitarian control because they embody economic independence, which is the first step toward political independence. The regime knows this, which is why it stifles them with regulations, arbitrary taxes, and restrictions on foreign trade.

Expanding the Cuban private sector could be the most transformative condition of any agreement. Allowing Cubans to have their own bank accounts, direct access to international trade without state intermediaries, real private property rights, and the freedom to import and export would be ideal. Every dollar entering Cuba should have a verifiable path to the entrepreneurial citizen, not to GAESA's structures. When remittances and tourism were relaxed during the 2014 rapprochement, the regime captured most of those flows through state-run foreign currency stores and military hotels. Smart negotiation would design mechanisms to prevent a repeat of that.

Demand True Democracy, Not Elite Rearrangements

A source familiar with the discussions told Axios: "They're looking for the next Delcy in Cuba." If this means finding a pragmatic interlocutor within power to facilitate a transition, it can be a valid first step. But only if the ultimate destination is clear: full democracy.

The Venezuelan process is in its early stages, and it's too soon to judge its outcome. Trump captured Maduro and is now negotiating with the remnants of Chavismo. María Corina Machado, the opposition leader who won the elections Maduro stole in 2024, is currently sidelined. If the end goal remains free elections and a complete democratic transition, the journey may justify patience. But if the process stalls in a permanent arrangement where old regime figures recycle themselves without the people reclaiming their voice, it will have been a failure.

Cuba must learn from this experience in real-time. Rubio can talk with "El Cangrejo," seek pragmatic interlocutors within power, but the essential goal must be non-negotiable: a full democracy where Cubans choose their own destiny. Not a change of faces in power, but a change of system.

Leverage the Position of Strength

The current crisis offers the United States its strongest bargaining position over the Cuban regime in decades. The strategic approach would be to use it firmly, easing pressure gradually only as specific conditions are met.

China won't involve itself in a problem 90 miles off the U.S. coast to save an unproductive regime. Russia is entrenched in Ukraine. Venezuela has already fallen. Iran has its own issues. Cuba is more isolated than ever. The regime is the one in a hurry, not Washington.

It's also crucial to clearly communicate to both the Cuban people and the international community that the pressure is a tool to force change, not a punishment against Cubans. For decades, the regime has survived by portraying itself as a victim of the U.S. embargo. Rubio can shatter that narrative by being transparent about what is demanded and why.

Include Cuban Civil Society and Exiles in Discussions

Rubio has a natural advantage here: his direct connection with a diaspora that has been organized, informed, and committed to Cuba's future for decades. Few Secretaries of State in history have had such a bridge.

Incorporating the voices of Cuban opposition, the July 11, 2021 prisoners, independent media, and civil society organizations in the roadmap is not only a moral imperative but also a smart strategy. In 2014, negotiations were conducted exclusively with the regime, excluding dissidents, activists, and the diaspora.

Rubio can do something different. If the transition includes Cubans who have risked their freedom and lives for a different country, it will be legitimate and enduring. And it will also reflect what Rubio has advocated throughout his career.

Set a Concrete Roadmap with Defined Timelines

The Cuban regime has 66 years of experience in stalling, offering crumbs, and buying time while reorganizing its control. The best way to counter that tactic is with clear, measurable objectives and concrete timelines.

Release political prisoners. Open up to independent media. Call for free elections with international oversight. Each of these steps needs a realistic but firm schedule, with clear consequences for non-compliance. Without a concrete roadmap, "future discussions" with "El Cangrejo" risk becoming exactly what the regime needs: time to survive the crisis without yielding anything substantial.

Now is the time. Marco Rubio has a unique combination: cultural closeness to the Cuban people, the power to demand changes, and an unrepeatable historical moment. Cubans have already tasted the bitter disappointment of hope betrayed by the regime. Rubio now bears the responsibility to restore their confidence that this time will be different.

And he has something more: the support of the Cuban people. Cubans inside and outside the island are watching him. They are pleading from endless food lines, from power outages that are now the norm, from exile bleeding from family separations, that he does not disappoint them. That he does not trade their future for crumbs. That he is courageous.

The Cuban people have shown their courage. They took to the streets on July 11, 2021, shouting "Freedom," knowing the price would be prison. They have endured decades of repression without surrendering. They have risked their lives on rafts, in jungles, crossing borders, to seek the dignity the regime denies them. These people deserve that whoever negotiates their future does so with the same courage they showed on July 11.

If Rubio negotiates with the firmness the situation demands and achieves real changes for the Cuban people, he will go down in history as the Cuban American who helped end the longest-lasting dictatorship in the Western Hemisphere.

This time, the power is on the right side.

The Cuban people support him.

He just needs to use it.

Without fear.