America’s Shadow War: 10 Shocking Revelations from the JFK Files on CIA Operations Against Cuba

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The recent declassification of approximately 80,000 pages of documents, collectively known as the “JFK Files,” has provided historians and researchers with unprecedented insight into one of the Cold War’s most contentious chapters: America’s covert war against Cuba. While these documents have not yielded the smoking gun many conspiracy theorists hoped for regarding President Kennedy’s assassination, they have exposed in stark detail the extraordinary lengths to which the United States government went in its attempts to destabilize, sabotage, and ultimately overthrow Fidel Castro’s regime in Cuba.

These files, released after decades of secrecy, paint a disturbing picture of a superpower willing to employ methods ranging from economic strangulation to biological warfare in its determination to eliminate what it perceived as a communist threat just 90 miles from American shores. The documents reveal not isolated incidents but a systematic campaign executed over years, involving hundreds of personnel and millions in funding, all directed toward breaking the will of the Cuban people and their revolutionary government.

This article examines ten of the most significant revelations from these declassified documents, providing detailed analysis of operations that were conceived, planned, and executed at the highest levels of the American government.

1. Operation MONGOOSE: The Master Plan for Cuban Destabilization

The newly declassified files provide the most comprehensive view yet of Operation MONGOOSE, the coordinated campaign against Cuba that began in November 1961 following the Bay of Pigs fiasco. Under the direction of Attorney General Robert Kennedy and Brigadier General Edward Lansdale, MONGOOSE became the umbrella program for dozens of covert operations against Cuba.

The documents reveal that MONGOOSE was far more extensive than previously understood, with a dedicated task force of over 400 CIA officers working exclusively on Cuban operations. This represents one of the largest covert operations in CIA history, surpassing even the agency’s efforts in Vietnam during the same period.

A particularly revealing memorandum dated January 18, 1962, outlines the program’s six operational phases:

  1. Intelligence collection and network building
  2. Defection operations targeting key Castro allies
  3. Sabotage and harassment operations
  4. Economic warfare
  5. General uprising preparation
  6. Support for “military intervention”

The document candidly acknowledges that “the ultimate objective is the overthrow of the Target Government,” with Robert Kennedy issuing directives that operations should create “maximum confusion, disorder and instability within Cuba.”

Perhaps most disturbingly, the files contain meeting minutes from a Special Group Augmented session in which Kennedy reportedly demanded “more dramatic results” and questioned why “eliminating Castro” was taking so long — a statement that contextualizes the subsequent acceleration of assassination attempts in late 1962 and 1963.

2. Agricultural Bioterrorism: The War on Cuban Food Security

The files detail extensive plans to target Cuban agriculture through biological means, representing one of the earliest documented cases of state-sponsored agricultural bioterrorism. A February 1961 memorandum, titled “Operation BITTER HARVEST,” outlines plans to introduce plant pathogens targeting key Cuban crops, with rice receiving particular attention due to its importance in the Cuban diet.

The documents reveal that CIA technicians, working with agricultural specialists, developed several crop-destroying agents specifically tailored to Cuba’s agricultural conditions. These included:

A particularly disturbing Technical Services Division report dated May 17, 1962, details successful field tests of these biological agents at a CIA facility in Panama, noting that the rice blast pathogen “demonstrated 97% crop destruction in controlled conditions” and was “suitable for aerial dispersal.”

Operational plans included the contamination of seed supplies being shipped to Cuba, the use of crop-dusting aircraft disguised as pest control operations, and the recruitment of agricultural workers to introduce pathogens directly.

The revelations are significant not only for what they tell us about U.S. operations against Cuba but because they document clear violations of the 1925 Geneva Protocol, which prohibited bacteriological methods of warfare. The timing is particularly notable, as these operations were being developed just as the Kennedy administration was publicly condemning the use of chemical defoliants in Vietnam.

3. Operation SWEET TOOTH: The Contamination of Cuban Sugar Exports

Among the most brazenly destructive economic operations revealed in the files is “Operation SWEET TOOTH,” a sustained campaign to contaminate Cuban sugar exports, the island’s primary source of foreign exchange in the early 1960s.

A CIA operational directive from March 1962 details the contamination methodology: “Non-toxic but unpalatable substances will be introduced into sugar shipments via recruited assets at processing facilities, rendering the product unsuitable for human consumption upon arrival at destination.”

The documents confirm that in at least three separate instances between 1962 and 1963, CIA operatives successfully contaminated sugar shipments bound for the Soviet Union, Czechoslovakia, and East Germany. In one particularly successful operation, a CIA agent code-named WIREMAN introduced an unidentified chemical agent into approximately 300 tons of sugar aboard the Soviet freighter Ordzhonikidze in Havana harbor.

A follow-up report gleefully notes that the contaminated sugar caused “significant diplomatic tension” between Cuba and the USSR, with Soviet officials initially suspecting Cuban sabotage. The report estimates the operation cost Cuba approximately $3 million in refused shipments and replacement costs — a substantial sum for Cuba’s struggling economy.

What makes these operations particularly noteworthy is their direct targeting of civilian food supplies. As one internal assessment candidly admits, “The psychological impact of food contamination far exceeds the immediate economic damage, creating distrust in basic commodities and straining Cuban-Soviet relations.”

4. The Castro Assassination Laboratory: Technical Services Division’s Deadly Innovations

While previous releases had confirmed the existence of CIA plots to assassinate Fidel Castro, the newly declassified files provide unprecedented detail about the Technical Services Division’s dedicated program to develop increasingly exotic methods for killing the Cuban leader.

The documents reveal that by late 1962, the CIA had established what amounted to an assassination laboratory focused exclusively on developing methods to kill Castro. This unit, officially designated as “Special Task Force W,” employed chemists, physicians, weapons specialists, and even a magician consultant to develop novel assassination techniques.

The files detail ten specific assassination plots that progressed to operational planning:

The Contaminated Diving Suit: A December 1962 memo confirms the CIA acquired a diving suit, contaminated it with Madura foot, a fungus that causes deep skin lesions, and planned to present it to Castro, an avid diver, through an intermediary. The plan was abandoned when a different diving suit was gifted to Castro by another party.

The Exploding Seashell: Technical Services Division spent over $11,000 developing an explosive device disguised as a conch shell, to be placed in an area where Castro frequently went diving. Documents indicate the device was tested but deployment was canceled due to the difficulty of predicting Castro’s exact diving location.

The Poisoned Pen: Engineers developed a hypodermic needle so fine that the victim would not notice its insertion, to be hidden in a pen and designed to inject blacktail venom, which causes paralysis and death. The device was actually dispatched to Havana but was never successfully deployed.

The Deadly Cigar: Beyond previously known plans to contaminate Castro’s cigars, the files reveal that the CIA developed exploding cigars containing C-4 explosive with enough power to remove “the target’s head.” Testing demonstrated that the device was reliable, but it was never successfully placed in Castro’s cigar supply.

The Poisoned Milkshake: The files confirm that the infamous poisoned milkshake plot progressed further than previously known. A CIA asset working at Castro’s favorite restaurant, the Havana Libre Hotel, was actually provided with botulinum toxin pills designed to dissolve in cold liquid. The operation failed when the pills, stored in a freezer, degraded before use.

The Thallium Salt Shoes: A bizarre plot involved contaminating Castro’s shoes with thallium salts while they were being shined, with the intention of causing the Cuban leader’s iconic beard to fall out, thereby diminishing his charismatic image. The documents indicate this plot was abandoned as “psychological warfare goals shifted.”

The Contaminated Handkerchief: TSD chemists developed a method to treat handkerchiefs with a powerful skin irritant that would cause severe facial inflammation. The files indicate this method was actually deployed but failed to affect Castro.

The LSD Speech: In one of the stranger plots, the CIA planned to spray Castro’s broadcasting studio with aerosolized LSD before a televised speech, in hopes of causing the Cuban leader to exhibit bizarre behavior that would undermine his credibility. Technical challenges prevented implementation.

The Gamma Ray Brief Case: The files reveal development of a device disguised as a briefcase that would emit focused gamma radiation, designed to be placed near Castro during meetings and potentially cause radiation sickness or cancer over time. Testing showed the device was impractical.

The Depilatory Documentary: In perhaps the most bizarre plot, the CIA considered spraying Castro’s shoes with a strong depilatory chemical while he was being interviewed by an American television crew, causing his beard to fall out on camera. The plot was abandoned when the interview was canceled.

A particularly revealing memo from the Chief of Technical Services Division complains about the resources being devoted to these efforts, noting: “Task Force W activities have consumed approximately 30% of TSD’s operational capacity in fiscal year 1963, at the expense of operations against primary Soviet targets.”

5. Operation ORTSAC: The Shadow Invasion Plan

The newly declassified files provide the first official confirmation of Operation ORTSAC (Castro spelled backward), a comprehensive military contingency plan for a second invasion of Cuba following the Bay of Pigs failure.

Unlike the Bay of Pigs operation, which relied primarily on Cuban exiles, ORTSAC called for direct U.S. military intervention involving up to 90,000 American troops, aerial bombardment, and naval blockade. The operation was designed as a last resort if covert operations failed to destabilize the Castro regime.

The documents reveal that ORTSAC planning accelerated dramatically in the summer of 1962, with a Joint Chiefs of Staff memorandum dated August 15, 1962, calling for “updated targeting packages” and “refined amphibious landing plans.” This timing is significant as it precedes the discovery of Soviet missiles in Cuba by several months, suggesting that military intervention was being actively considered before the missile crisis provided potential justification.

Particularly notable is a declassified Department of Defense estimate predicting that a U.S. invasion would result in “12,000 to 18,000 American casualties” and “potentially 100,000 Cuban military and civilian casualties.” Despite these projections, planning continued, with detailed operational timelines and resource allocations.

The files also reveal that elements of ORTSAC were incorporated into contingency planning during the Cuban Missile Crisis, with some units placed on alert status. A post-crisis assessment dated December 1962 notes that while ORTSAC was “temporarily suspended,” its operational framework remained “viable for future contingencies.”

This revelation is significant because it contradicts decades of official narratives suggesting that direct military intervention in Cuba was considered only in response to the missile crisis. The documents instead show a sustained planning effort for regime change through direct military means, running parallel to the covert operations program.

6. The Economic Strangulation Program

The declassified files provide the clearest evidence yet that U.S. sanctions against Cuba were explicitly designed not merely to isolate the Castro regime politically but to inflict maximum suffering on the Cuban population as a tool for regime change.

A State Department policy directive from September 1961, previously classified as “Top Secret/NOFORN,” contains the remarkably candid statement that economic measures should be calibrated to “decrease monetary and real wages, to bring about hunger, desperation and overthrow of government.”

The documents reveal a multi-faceted economic warfare campaign:

A particularly revealing Treasury Department assessment from 1962 calculates that economic measures had reduced Cuban imports by 75–80% and cut industrial production by approximately 30% within two years, noting with satisfaction that “consumer goods scarcity has reached levels sufficient to generate widespread dissatisfaction.”

The files also detail previously unknown aspects of U.S. economic warfare, including a covert program to introduce counterfeit Cuban currency into circulation, with one memo noting that approximately 30 million counterfeit pesos were produced with “sufficient quality to undermine confidence in the Cuban monetary system.”

Perhaps most disturbing is an April 1963 CIA assessment acknowledging that economic measures were causing “widespread malnutrition, particularly affecting children and the elderly” while admitting this had “thus far failed to generate the popular uprising anticipated.” Despite this acknowledgment, the document recommends “intensifying economic pressure points” rather than reconsidering the strategy’s humanitarian implications or effectiveness.

7. Operation NORTHWOODS: The False Flag Proposal

While some aspects of Operation NORTHWOODS have been previously disclosed, the newly released files provide the most comprehensive documentation yet of this disturbing chapter in American military planning — a series of proposed false flag operations designed to create a pretext for military intervention in Cuba.

The complete NORTHWOODS documents, bearing the signature of Joint Chiefs Chairman Lyman Lemnitzer, outline an astonishing array of proposed false flag operations, including:

What makes the newly released documents particularly significant is the inclusion of interdepartmental communications showing that while Kennedy rejected the NORTHWOODS proposals, modified versions continued to be developed throughout 1962 and early 1963.

A previously undisclosed CIA memorandum dated November 1962 outlines a scaled-back version called “TRINIDAD ALTERNATIVES,” which maintained the false flag concept but with “plausibly deniable operations of limited visibility.” These included manufactured evidence of Cuban attacks on neighboring Caribbean nations and fabricated evidence of Cuban-sponsored terrorism against U.S. citizens abroad.

Even more disturbing is a February 1963 document revealing that elements of the NORTHWOODS proposal were incorporated into contingency planning despite Kennedy’s formal rejection, with one national security planning memo noting that “while direct false flag operations have been removed from active consideration, engineered provocations remain a viable path to necessary intervention.”

8. Project AMLASH: The Castro Assassination Plot That Wouldn’t Die

The files provide unprecedented detail on Project AMLASH, one of the CIA’s longest-running and most controversial assassination operations, targeting Castro through high-level recruitment within his inner circle.

AMLASH centered on Rolando Cubela, a Cuban military official with access to Castro who was recruited by the CIA in 1961. The newly declassified files reveal that the operation was far more extensive than previously understood, continuing well after Kennedy’s assassination and the Church Committee investigations that supposedly ended CIA assassination programs.

The documents show that on November 22, 1963 — the very day Kennedy was assassinated — CIA case officer Desmond FitzGerald provided Cubela with a poison pen device for assassinating Castro. This meeting, occurring just hours before Kennedy was shot in Dallas, has fueled decades of speculation about potential connections between the Castro assassination plots and Kennedy’s murder.

What’s new in these files is the revelation that AMLASH continued well beyond this point. Documents show that in February 1964, under the Johnson administration, the CIA provided Cubela with high-powered rifles, explosives, and additional poisoning devices. A operational directive from September 1964 authorized “expanded operational parameters” for AMLASH, including the recruitment of additional assassination teams.

Perhaps most shocking is a previously undisclosed 1965 memo indicating that elements of AMLASH continued even after the operation was supposedly terminated, with assets maintained in “inactive but available status” as late as 1966.

The AMLASH revelations are significant because they contradict the official narrative that assassination operations were largely a product of the Kennedy administration and were discontinued after his death. Instead, they show a continuing commitment to assassination as policy across administrations.

9. Operation BOUNTY: The Cuban Head-Hunting Program

Among the most disturbing revelations in the declassified files is “Operation BOUNTY,” a CIA program that established what amounted to a price list for the assassination or capture of Cuban government officials.

The documents include a CIA field order, dated November 1961, establishing a schedule of payments for the death or capture of various Cuban officials, ranging from $100,000 for government ministers and $57,000 for “department heads” to $5,000 for “officials in public office.” Castro himself carried a $150,000 reward.

What makes BOUNTY particularly notable is that it was not designed as a targeted assassination program but rather as a system to incentivize widespread violence against the Cuban government. The operational directive explicitly states that BOUNTY’s purpose was to “create an atmosphere of mistrust, suspicion, and fear among Cuban officials through the knowledge that substantial rewards were being offered for their death or capture.”

The documents reveal that leaflets detailing the reward structure were airdropped over Cuba in at least six separate operations between 1961 and 1963. These drops focused on areas with military installations, with the apparent intent of encouraging defections or violence from within Cuba’s armed forces.

An internal assessment dated March 1963 claims that BOUNTY had “measurable psychological impact,” noting that several Cuban officials had increased their security measures in response to the program. The document also records two “unconfirmed attempts” on lower-level officials allegedly motivated by the rewards.

Particularly chilling is a planning document discussing the “psychological leverage” of paying rewards even for failed assassination attempts, noting that “confirmation of payment will encourage additional operations, potentially generating a self-sustaining cycle of violence within the target government.”

The BOUNTY revelations are significant because they move beyond targeted assassination attempts against Castro himself to show a program designed to foment widespread political violence throughout the Cuban government — essentially, state-sponsored terrorism directed at an entire governmental structure.

10. The Cuban Project: Infiltration of American Media and Politics

Perhaps one of the most consequential revelations in the files concerns “The Cuban Project,” a sophisticated CIA operation to influence American public opinion and policy regarding Cuba through the systematic infiltration of media organizations, academic institutions, and political circles.

The documents reveal a comprehensive domestic influence operation that would have been illegal under the CIA’s charter prohibiting domestic operations. To circumvent these restrictions, the program operated through cutouts, front organizations, and “unofficial cover” operatives.

The files identify three main components of this influence campaign:

A particularly revealing memo from 1963 boasts that approximately 67% of American news coverage of Cuba contained “elements provided by or influenced by Agency operations,” claiming that this had “successfully shaped public and political opinion toward supporting maximum pressure policies.”

The Cuban Project’s domestic focus represents a clear violation of the CIA’s charter, which prohibited the agency from operations within the United States. The documents suggest awareness of this problem, with operational security protocols requiring “maximum deniability” and special handling procedures for any documentation related to domestic activities.

Conclusion: The Legacy of America’s Cuban Obsession

The newly declassified JFK Files provide the most comprehensive picture yet of America’s covert war against Cuba — a campaign of extraordinary breadth, dubious legality, and questionable effectiveness. From agricultural sabotage to assassination plots, from economic warfare to domestic propaganda, these operations represent one of the most sustained covert action programs in CIA history.

Perhaps the most significant aspect of these revelations is what they tell us about the disconnect between America’s stated values and its operational practices during the Cold War. While publicly championing democracy and human rights, the United States simultaneously engaged in activities — targeting food supplies, contaminating exports, incentivizing political violence — that violated international norms and, in some cases, international law.

The documents also force a reevaluation of the effectiveness of these policies. Despite decades of economic sanctions, scores of sabotage operations, and numerous assassination attempts, the Castro regime endured. Fidel Castro outlived most of his American adversaries, dying peacefully in 2016 at the age of 90, having survived over 600 documented assassination attempts according to Cuban security sources.

Moreover, the campaign against Cuba absorbed enormous resources that might otherwise have been directed against more significant adversaries. As one frustrated CIA assessment from 1964 notes, “The disproportionate allocation of assets to Cuban operations has measurably reduced our operational capability against primary Soviet Bloc targets.”

For historians and policymakers, these documents provide a sobering case study in the potential blowback of covert operations. Far from achieving their objectives, these operations may have strengthened Castro’s position by providing evidence for his central claim — that Cuba faced an existential threat from an imperialist neighbor determined to destroy its revolution. Every failed assassination attempt, every act of economic sabotage, validated this narrative and helped cement Castro’s grip on power.

As we continue to sift through these thousands of pages of newly declassified material, one thing becomes clear: America’s obsession with Cuba represented not just a moral failure but a strategic one — a case study in how a superpower’s overwhelming resources, when deployed without strategic clarity or moral constraints, can not only fail to achieve their objectives but actively undermine them.

The JFK Files thus offer not merely historical curiosity but a powerful cautionary tale about the limits of covert action, the unpredictable consequences of foreign intervention, and the dangers of allowing means to corrupt ends in the pursuit of national security objectives.

Note: This article is based on recently declassified documents and represents current historical understanding. As scholars continue to analyze the extensive JFK Files, interpretations may evolve with new information.