The departure of Jeremy Lewin from the U.S. State Department leaves uncertainty regarding the future of the conversations between Washington and Havana.
The young advisor to Marco Rubio was one of the key figures responsible for the contacts with Raúl Guillermo Rodríguez Castro, known as “El Cangrejo,” the grandson of Raúl Castro and the de facto representative of the family nucleus that maintains a decisive influence in Cuban power.
According to Axios, 29-year-old Lewin is leaving the Trump administration to join the private sector. His departure is reportedly due to personal and professional plans, with no indications of disagreements with Rubio or a direct connection to the stagnation of negotiations.
But his departure comes at a significant moment: after months of talks without substantial agreements and when the United States seems to be combining a willingness to engage in dialogue with an increasingly coercive strategy to extract concessions from the regime.
Two negotiators with access to power
Lewin was not a career diplomat nor a traditional specialist in Cuba. A lawyer trained at Dartmouth and Harvard, he entered the Administration through the DOGE government downsizing program, driven by Elon Musk, and quickly rose to become one of Rubio's trusted collaborators.
In April, he led, alongside the experienced diplomat Michael Kozak, a U.S. delegation that met in Havana with El Cangrejo. His involvement was not incidental: Axios attributes to him the leadership of the bilateral discussions and a prominent role in the implementation of sanctions against the regime, including the military conglomerate GAESA.
The choice of the Cuban interlocutor is even more revealing. Rodríguez Castro is a colonel in the Ministry of Interior, the head of security for his grandfather, and the son of the late General Luis Alberto Rodríguez López-Calleja, who led GAESA. However, he does not hold a governmental position that grants him political representation to negotiate the country's future, nor does he have the democratic legitimacy to do so.
Its authority stems from its membership in the Castro family and from its ties to the military and economic apparatus of the regime. Although leaders of the Communist Party have acknowledged that it acts on the decision of the highest leadership, this appointment highlights the patrimonial nature of a system in which effective power transcends the formal institutions of the State.
Washington seems to have accepted this reality: to negotiate with those who make decisions in Cuba, it has turned to the family core of Castroism, even though its authority does not stem from the people's will.
The contradiction is evident: the United States seeks democratic transformations through discussions with representatives of the same power structure that resists implementing them.
A stalled negotiation and increasing pressure
Contacts, which began in early 2026, came to include proposals for energy cooperation, investments, and possible economic reforms. However, as revealed by The Atlantic in October, the discussions stalled when Washington demanded the departure of Miguel Díaz-Canel and Havana refused to accept that condition.
The regime has reiterated that it will not negotiate its political system, the guiding role of the Communist Party, nor the holding of multiparty elections. It expresses willingness to discuss certain economic reforms, but without relinquishing its monopoly on power.
That limit also conflicts with U.S. legislation. The Helms-Burton Act conditions the lifting of the embargo on the establishment of a transitional government that meets requirements such as the release of political prisoners, the legalization of political activity, and the commitment to hold free elections. Its definitive lifting requires a democratically elected government.
Therefore, an economic agreement that leaves the structure of the regime intact would not be sufficient to eliminate the fundamental restrictions of the embargo, although Washington retains some room to negotiate specific measures.
In response to that blockade, the Trump administration has intensified its pressure signals. Financial sanctions, warnings directed at the military leadership, and the recent calls from Rubio and the CIA to discreetly collaborate with U.S. intelligence services point to a search for cracks within the power structure.
Trump has also repeatedly used the threat of military presence against Cuba, without explicitly ruling out other options. However, there is no public evidence of a decision to intervene militarily or to carry out an operation to capture Cuban leaders.
Rubio himself stated this Monday that Cuba needs a "very drastic change" and that its situation is different from Venezuela's, where Washington reached economic agreements with the government of Delcy Rodríguez after the capture of Nicolás Maduro.
Who will take Lewin's place?
The departure of the advisor does not necessarily signal the end of dialogue. Kozak —a veteran American diplomat who headed the U.S. Interests Section in Havana from 1996 to 1999— played a direct role in the discussions, Rubio still maintains political direction of the strategy, and there are other channels of communication, including those established by intelligence services.
It has not been announced who will take over Lewin's responsibilities or whether Washington will change its negotiating strategy. Last Friday, Trump once again spoke about a possible agreement with Cuba and even mentioned that he would personally send Rubio to finalize it.
The underlying issue, however, goes beyond the replacement of an official. After months of unsuccessful communications, Washington keeps the door to negotiation open while increasing pressure on a leadership that refuses to accept substantial political changes.
The question is whether Rubio will continue to pursue an agreement with Raúl Castro's circle or if the resistance of that elite will eventually shift the focus towards other interlocutors and mechanisms of pressure.
For now, the main obstacle does not seem to be who represents Washington, but rather the refusal of those who control power in Cuba to accept changes that could put an end to their own privileges and their control of the State.
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