In the early months of 1963, as the Kennedy administration struggled to formulate a coherent post-Missile Crisis policy toward Cuba, a highly unconventional, back-channel proposal emerged to challenge the Central Intelligence Agency’s monopoly on anti-Castro operations. Originally conceived under the name “Operation Leonardo,” this plan was authored by an unusual triumvirate: George Volsky of the United States Information Agency (USIA), the Cuban exile Nestor Moreno, and Tad Szulc, a prominent foreign correspondent for The New York Times who maintained close personal conduits to the Kennedy White House.
Szulc bypassed traditional intelligence channels to present the detailed plan directly to Robert Hurwitch, the State Department’s Coordinator of Cuban Affairs. The core thesis of Operation Leonardo was to eschew another massive, overt military invasion from the outside and instead orchestrate a sophisticated, on-island political operation designed to split the Castro regime by encouraging high-level military defections. Enticed by the prospect of an internal military coup, the State Department and the White House aggressively pressured a highly reluctant CIA to formally adopt the proposal.
The Ideological Rift and Bureaucratic Resistance
Within the CIA, the White House’s insistence on executing Operation Leonardo revived bitter institutional grievances dating back to the disastrous Bay of Pigs invasion of 1961. CIA planners, particularly within the JM/WAVE station in Miami, found the political architecture of the plan highly distasteful. The Kennedy administration’s stated preference was to utilize exiles who had participated in the original 1959 Cuban Revolution but had subsequently grown disillusioned with Castro’s turn toward Soviet communism. These figures, notably the anti-Batista commander Huber Matos and the left-of-center reformer Manolo Ray, championed a political platform of “Fidelismo sin Fidel”—preserving the social and agrarian reforms of the revolution while purging its communist elements.
To the right-wing, conservative Cuban exile factions who had defected earliest and had been long-term clients of the CIA, these “New Left” revolutionaries were considered anathema. By 1963, Ray and Nestor Moreno had organized JURE (Junta Unificadora Revolucionaria Democrática), an independent anti-Castro organization that actively rejected CIA control. CIA counterintelligence deeply mistrusted JURE, suspecting the group of attempting to actively penetrate JM/WAVE’s clandestine operations. The CIA seized upon Volsky’s and Moreno’s close personal ties to JURE as a primary bureaucratic justification to demand the complete termination of the project. Despite a formal recommendation from JM/WAVE chief Theodore Shackley to scrap the operation on the grounds of poor security, the White House overruled the agency, forcing the CIA to officially carry the project forward under the military code name AMTRUNK.
Infiltration and the Recruitment of the Military Dissidents
Despite its internal misgivings, the CIA initiated active AMTRUNK operations in the summer of 1963, focusing its resources on penetrating the domestic networks of the Cuban armed forces. The operational spearhead of this campaign occurred in August 1963, when a clandestine CIA agent successfully infiltrated Cuba and recruited Major Ramon Guin Diaz as a Principal Agent. Guin, a major figure in the Cuban military, was tasked with quietly sounding out high-ranking officers and organizing a domestic nucleus of military conspirators capable of executing a coup d’état.
Simultaneously, the CIA integrated the volatile Cuban army officer Rolando Cubela Secades (code-named AMLASH) into the AMTRUNK planning framework. During a highly sensitive, clandestine meeting in Brazil in September 1963, CIA case officers debriefed Cubela regarding the political loyalties of the Cuban officer corps. Cubela discussed the feasibility of approaching anti-communist officers but warned that most remained paralyzed by fear, terrified that any talk of conspiracy might be a government-orchestrated provocation. Cubela expressed confidence in Major Guin’s ideological alignment but raised serious alarms regarding Guin’s “nervous condition” and severe, chronic alcoholism. The CIA directed Cubela to assist Guin in his intelligence-gathering activities inside the island, while strictly forbidding him from assisting Guin’s attempts to flee Cuba.
The Sabotage Program and Rostow’s “Track Two”
While the political elements of the AMTRUNK coup planning went forward, the operational scope of the project was significantly altered by the introduction of an aggressive program of exile sabotage. Proposed by State Department policy adviser Walt Rostow, this “track two” strategy sought to bypass the direct, CIA-controlled exile forces (such as those led by Manuel Artime) and instead provide direct financial resources to “autonomous” exile groups, including the left-leaning JURE. The strategic objective was to launch sudden, deniable maritime raids against Cuban economic infrastructure to “nourish a spirit of resistance” that would soften up the regime and induce military defections.
These sabotage operations became highly active in late 1963. Operating from the CIA-owned subchaser ship Rex, a newly trained, heavily armed exile group known as the “Comandos Mambises” launched a series of disruptive, high-profile maritime raids against Cuban coastal installations, executing strikes on August 18 and October 21, 1963. While these raids succeeded in damaging the fragile Cuban economy, they also had the counterproductive effect of de-emphasizing and destabilizing the delicate, highly sensitive political negotiations of Plan Leonardo.
The Johnson Era and the Transition to Assassination
The political and strategic coherence of the original AMTRUNK project was permanently shattered by the transition to the Lyndon B. Johnson presidency in late November 1963. Under the new administration’s guidance, the original objective of Plan Leonardo—cultivating a political coalition of moderate, revolutionary military officers to split the government—was completely abandoned. Instead, the AMTRUNK infrastructure was systematically repurposed and subordinated to the CIA’s highly sensitive, unilateral assassination operations.
This transition was marked by the immediate, aggressive purge of the original authors of the plan. In November 1963, the CIA formally terminated Nestor Moreno from any involvement in the sensitive, operational aspects of the project. By early 1964, the AMTRUNK pipeline was entirely hijacked by the Technical Services Division and the AMLASH team. Rather than smuggling political organizers to recruit dissident generals, AMTRUNK teams were utilized to transport high-powered, long-distance scoped Belgian FAL rifles directly into Cuba to facilitate the physical assassination of Fidel Castro. Ultimately, the collapse of Operation Leonardo demonstrated the deep, structural irreconcilability between the Kennedy White House’s desire to foster an internal political revolution and the CIA’s institutional preference for paramilitary sabotage and deniable, executive-action executions.