The CIA's Infiltration of Maduro's Inner Circle: Is a Similar Strategy Possible in Cuba?

The capture of Nicolás Maduro on January 3rd wasn't simply a matter of U.S. special forces entering Caracas. The groundwork had been laid months earlier when the CIA successfully infiltrated Maduro's inner circle, meticulously mapping his routines and gathering detailed intel on his movements and security systems.

This operation underscored the power of human intelligence, combined with technological surveillance and military might, to overcome security measures surrounding an authoritarian leader. It also highlighted the shortcomings of the Cuban apparatus that had long provided protection to Maduro.

As Washington now calls for collaborators in Cuba and strengthens its intelligence presence around the island, a pressing question arises: Can the United States replicate a similar strategy against the Havana regime?

The answer hinges on factors far beyond American military capability. Considerations include the depth of Cuban intelligence penetration, the prospect of securing insiders within the ruling circle, and the presence of interlocutors capable of navigating a post-regime political landscape.

The Crafting of the Maduro Operation

According to a Reuters investigation, the CIA had deployed a covert team in Venezuela since August 2025, tasked with collecting data on Maduro's daily life. The agency had a close contact who tracked the leader's movements, ready to relay his exact location at the operation's onset.

The New York Times reported that the CIA had an informant within the Venezuelan government and used stealth drones for near-constant surveillance of the leader. General Dan Caine of the U.S. Joint Chiefs of Staff later explained that intelligence services had scrutinized Maduro's residence, travel habits, frequent haunts, diet, and even minor personal routines.

This meticulous surveillance enabled the creation of a "pattern of life," a detailed reconstruction of a target's routines to predict movements and expose vulnerabilities. The precise knowledge of Maduro's location was crucial for his capture.

The CIA's intelligence allowed U.S. special forces to locate and extract the leader, but intelligence alone was insufficient. The Delta Force rehearsed the raid multiple times using a replica of Maduro's fortified residence, while the Pentagon amassed over 15,000 troops, an aircraft carrier, numerous warships, and fighter jets in the Caribbean.

The Cuban Security Failure

For Havana, a major takeaway was the failure of the security apparatus that Cuba had helped build around Maduro. For years, Cuban services played a key role in intelligence, counterintelligence, and the security of the Venezuelan leadership, including agents sent by the Cuban regime to go beyond merely guarding the leader.

However, on January 3rd, this apparatus failed to prevent the U.S. from pinpointing Maduro's location, infiltrating the military complex where he was, and capturing him and his wife, Cilia Flores. Havana later acknowledged the deaths of 32 military and security personnel during the operation.

A Center for Strategic and International Studies (CSIS) analysis, based on satellite imagery, indicated that U.S. strikes focused on specific facilities linked to air defense and target protection. The operation aimed not to dismantle the entire Venezuelan military but to temporarily neutralize capabilities that could thwart the capture.

Maduro's vulnerability wasn't just due to leaked information but also the inability of his security forces to effectively respond when that information was put to use.

Rewards, Charges, and Pressure: A Multi-Front Strategy

The covert operation unfolded while Washington ramped up other pressures against Maduro. Since March 2020, the Venezuelan leader faced U.S. federal charges for narco-terrorism, cocaine trafficking conspiracy, and related weapon offenses.

In August 2025, with Marco Rubio as Secretary of State, the reward for information leading to Maduro's arrest or conviction rose to $50 million. This initiative broadened incentives for providing information, though there's no public confirmation that the CIA's source received the reward. The program's conditions also excluded government officials and employees from claiming rewards.

Washington also sought a negotiated exit. As per Reuters, Trump offered Maduro an opportunity to leave Venezuela on November 21, 2025. Maduro demanded amnesty guarantees and other conditions, which were rejected. The deal didn't materialize, and weeks later, the U.S. executed the military operation.

The judicial process continued post-capture. On October 8th, the Department of Justice filed new charges against Maduro and Flores for conspiracy to commit torture, adding to previous accusations. Both maintain the presumption of innocence.

The Venezuelan experience illustrates how Washington combined legal proceedings, financial incentives, negotiations, covert information gathering, and military pressure—a strategy increasingly familiar to Havana.

Cuba: A Different Adversary

The U.S. success against Maduro doesn't imply that a similar operation in Cuba is feasible. The primary difference lies in the security structure. While Venezuela partially relied on Cuban intelligence cooperation, Cuba directly controls its counterintelligence, military security, and leader protection agencies, developed over decades under the supervision of the Armed Forces and the Ministry of the Interior.

The CIA understands the challenges of operating against these structures. A New York Times investigation revealed in August that the agency formed a task force specifically for Cuba, with officers specializing in source recruitment, intelligence analysis, cyber operations, and covert influence.

Their mission is to identify divisions within the ruling elite and encourage the emergence of more pragmatic leaders willing to negotiate the changes demanded by Trump. Washington has also elevated Cuba to “Priority 1” in its national intelligence priorities, alongside countries like China, Russia, and Iran.

Other U.S. agencies have started dedicating more satellite and surveillance resources to Cuban territory. Politico reported that U.S. reconnaissance aircraft had logged over 150 hours of missions around the island since February.

This activity increase suggests Washington seeks a clearer picture of Cuba's defenses, military capabilities, communications, and regime operations. However, it also indicates a limitation: the New York Times reported concerns among U.S. military and intelligence officials about outdated information on Cuba.

While the CIA demonstrated its ability to infiltrate Maduro's circle, there is no public evidence of similar access to Cuba's leadership. The campaign launched on October 23-24 by Marco Rubio and the CIA, inviting Cubans to discreetly collaborate with the agency, may be seen as an effort to expand available sources while also sending a pressure message to the governing apparatus.

Publicizing the invitation introduces uncertainty within Cuban institutions: the regime must consider that individuals with access to sensitive information might decide to engage with Washington. However, this potential effect doesn't prove the existence of high-level collaborators or successful recruitment by the campaign.

The Challenge of Post-Change Governance

The second major difference between Venezuela and Cuba is political rather than military. Maduro's capture ended his rule, but didn't dismantle the Chavista state apparatus. Delcy Rodríguez assumed interim presidency, allowing Washington to engage with a figure from within the system.

This outcome became a reference for U.S. strategy towards Cuba. According to New York Times investigations, the Trump administration has instructed its intelligence agencies to identify current or former officials who could play a similar role to Rodríguez.

However, evaluations raise significant challenges. U.S. services believe that Cuban succession presents greater obstacles than the Venezuelan one, given the scarcity of figures clearly identified who combine influence within the regime, control over its institutions, and willingness to negotiate substantial changes.

The Cuban political apparatus, organized around the Communist Party, the FAR, the MININT, and economic networks linked to the ruling elite, doesn't offer an easy separation between political power, military control, and economic administration.

This concentration of functions serves as a regime survival mechanism but also complicates any attempt to promote a transition from within. Even if Washington managed to neutralize or displace certain leaders, the question of who would control the armed forces, security services, and the state's main economic resources remains unresolved.

Available information indicates that the CIA continues to seek answers to this question.

The Military Threat and Its Limits

The Venezuelan precedent has also influenced the Cuban regime's defensive decisions. The New York Times revealed in August that Havana had bolstered the security of Raúl Castro and Miguel Díaz-Canel against potential U.S. operations aimed at capturing or eliminating them.

The paper didn't detail the measures taken or suggest that Trump had ordered such an action. Meanwhile, CBS News reported in September that the U.S. Army Reserve was evaluating its capacity to provide logistical, medical, and military police units to the Southern Command, in planning related to Cuba.

The network clarified that the examined document contained no deployment orders. The CIA task force dedicated to Cuba also had no authorization for lethal operations, though its mandates could change by presidential decision.

Intelligence gathering can serve to negotiate from a position of greater knowledge, identify regime vulnerabilities, exert political pressure, or update military plans. It doesn't necessarily imply Washington has decided to use all these capabilities in an intervention.

Lessons from Venezuela and the Cuban Enigma

Maduro's capture left three lessons for intelligence services and governments studying that precedent. First, a leader's protection can be compromised when an adversary obtains precise information from within their circle.

Second, a military operation with limited objectives requires exceptional conditions of intelligence, preparation, surprise, and operational superiority. And third, possibly the hardest to replicate, is that removing a leader doesn't guarantee control over what happens next.

In Venezuela, the U.S. combined these capabilities and found an interlocutor within Chavismo to manage the aftermath. In Cuba, Washington is trying to improve its understanding of the ruling apparatus and locate potential interlocutors, but comparable results are yet to be seen.

The critical question isn't just whether the CIA can infiltrate the security circles of Raúl Castro and Díaz-Canel, but whether the U.S. has a viable political strategy for the day after a potential power shift. So far, information on the CIA task force, the search for a "Cuban Delcy," and U.S. military planning indicate that both issues remain under study and evaluation by Washington.