CIA 638+ Assassination Attempts on Castro

Overview

Fabian Escalante had the strangest job in intelligence. As the head of Cuba’s counterintelligence service, Escalante was personally responsible for keeping Fidel Castro alive — a task that, by his own accounting, required him to foil 638 separate assassination attempts over four decades. The number is almost certainly inflated; Escalante had obvious institutional incentives to exaggerate. But even the conservative count — the eight distinct plots confirmed by the U.S. Senate’s Church Committee in 1975 — reads less like a classified intelligence report and more like the rejected screenplay for a slapstick spy film.

Poison cigars. A wetsuit laced with tuberculosis bacteria. An exploding seashell. Femme fatale operatives. Thallium salt designed to make Castro’s beard fall out (not lethal, but intended to destroy his charisma). And, most improbably, a formal working partnership between the Central Intelligence Agency and the American Mafia.

This is not a conspiracy theory. It is a confirmed historical fact, documented in the Church Committee’s final report, corroborated by declassified CIA documents, and acknowledged by former intelligence officials. The CIA, with the knowledge and at times the explicit authorization of senior government officials, attempted to assassinate the leader of a sovereign nation using methods that ranged from the technically sophisticated to the comically absurd.

The significance of the Castro assassination plots extends far beyond Cuba. They provide documented proof that the United States government engaged in the kind of covert, extralegal operations that conspiracy theorists had long alleged. They raised fundamental questions about executive power, congressional oversight, and the moral limits of Cold War statecraft. And they form an essential piece of context for understanding the JFK assassination conspiracy theories — because if the CIA was willing to assassinate foreign leaders, the question of whether it could have turned that capability inward becomes significantly harder to dismiss.

Origins & History

The Fall of Batista and the Rise of Castro

The CIA’s obsession with assassinating Fidel Castro must be understood in the context of the Cuban Revolution and its place in Cold War geopolitics. Fulgencio Batista, the U.S.-backed dictator of Cuba, was overthrown by Castro’s revolutionary movement on January 1, 1959. The Eisenhower administration initially attempted to work with the new government, but relations deteriorated rapidly as Castro nationalized American-owned businesses, established relations with the Soviet Union, and declared Cuba a socialist state.

By late 1959, the CIA had begun developing plans to overthrow Castro. The initial approach was a Bay-of-Pigs-style invasion by Cuban exiles, which would eventually proceed — disastrously — in April 1961. But alongside the invasion planning, the CIA pursued a parallel track: eliminating Castro personally.

The logic, such as it was, rested on the assumption that the Cuban Revolution was a one-man show. Remove Castro, and the revolution would collapse. This was a fundamental misreading of Cuban politics, but it drove CIA policy for over a decade.

The Mafia Connection (1960-1963)

The most extraordinary chapter in the assassination saga began in August 1960, when CIA officer Richard Bissell authorized the agency’s Office of Security to approach the Mafia about killing Castro. The operational logic was perverse in its elegance: the Mafia had motivation (Castro had shut down their Havana casinos, costing them millions), capability (extensive criminal networks), and deniability (if a Mafia hit was discovered, it would look like a private vendetta rather than a government operation).

The CIA’s point man was Robert Maheu, a former FBI agent turned private investigator who had performed previous sensitive tasks for the agency. Maheu approached Johnny Roselli, a suave Las Vegas figure with connections throughout organized crime. Roselli brought in two of the most powerful Mafia bosses in America: Sam “Momo” Giancana, boss of the Chicago Outfit, and Santos Trafficante Jr., the Florida boss who had operated casinos in Havana before the revolution.

The initial plan was poison. The CIA’s Technical Services Division produced botulinum toxin pills designed to be dissolved in Castro’s food or drink. The pills were passed through the Mafia chain to contacts in Havana. According to multiple accounts, the pills reached Cuba but were never successfully administered. One version of the story has the pills delivered to a restaurant employee who was supposed to slip them into Castro’s milkshake — Castro’s well-known passion for ice cream and milkshakes was a repeated feature of the assassination plots — but the employee lost his nerve, or the opportunity never materialized, or the pills had degraded. The accounts vary.

The CIA-Mafia collaboration continued through multiple iterations. Giancana, in a detail that would be rejected as too absurd for fiction, asked the CIA to wiretap the Las Vegas hotel room of comedian Dan Rowan (of Rowan & Martin’s Laugh-In), whom Giancana suspected of having an affair with his girlfriend, singer Phyllis McGuire. The CIA complied, essentially performing domestic espionage as a favor to a mob boss in exchange for his continued cooperation in the Castro plots. When the wiretap was discovered by the FBI, Attorney General Robert Kennedy was furious — and was informed for the first time about the CIA-Mafia arrangement.

The Mafia connection was officially terminated around 1963, though the precise timeline is disputed. The collaboration produced no results in terms of actually harming Castro, but it created a web of compromising relationships between the intelligence community and organized crime that would have consequences for decades.

The Technical Services Division’s Greatest Hits

While the Mafia plots relied on brute-force approaches (poison, guns), the CIA’s own Technical Services Division — the Q Branch of the real world — developed a catalog of assassination methods that bordered on the surreal.

The Poison Cigars. In February 1961, the TSD prepared a box of Castro’s favorite cigars treated with botulinum toxin so potent that putting one to his lips would kill him. The cigars were passed to a Cuban contact. They were never used. Whether they reached Castro and were intercepted, or never got close, remains unclear.

The Contaminated Diving Suit. In late 1963, the CIA prepared a diving suit contaminated with a fungal skin disease (Madura foot) and tuberculosis bacteria, to be presented to Castro as a gift during negotiations for the release of Bay of Pigs prisoners. The suit was prepared by CIA officer Desmond FitzGerald’s team. James Donovan, the American lawyer conducting the prisoner negotiations (later portrayed by Tom Hanks in the film Bridge of Spies), was unaware of the plan and, in a coincidence that defies fiction, independently decided to give Castro a different diving suit as a goodwill gesture. The contaminated suit was never delivered.

The Exploding Seashell. FitzGerald proposed placing a spectacularly beautiful seashell, rigged with explosives, in an area where Castro was known to scuba dive. The idea was that Castro would be attracted to the unusual shell, pick it up, and be killed by the detonation. The plan was abandoned when it was determined that no shell could be made both attractive enough to pick up and large enough to contain a lethal charge. It also would have required knowing Castro’s exact diving schedule and location.

The Thallium Beard. Not strictly an assassination attempt, but the CIA explored depositing thallium salt in Castro’s shoes during a trip abroad, which would cause his famous beard to fall out. The rationale was that Castro’s beard was integral to his revolutionary image, and losing it would undermine his authority. The plan was never executed.

The Poison Pen. On November 22, 1963 — the day President Kennedy was assassinated — a CIA officer was meeting with a Cuban agent in Paris to deliver a poison pen designed to inject Castro with a lethal substance. The pen was a ballpoint containing a hypodermic needle so fine that Castro would not feel the injection. The meeting proceeded, but the agent reportedly expressed reservations about the plan, and it was never carried out.

Operation Mongoose (1961-1962)

The assassination plots were part of a larger covert operation known as Operation Mongoose, authorized by President Kennedy after the Bay of Pigs failure. Led by Air Force General Edward Lansdale and overseen by Attorney General Robert Kennedy, Mongoose was a comprehensive campaign to destabilize and overthrow the Castro government. It encompassed economic sabotage, propaganda, support for anti-Castro guerrilla groups, and assassination planning.

At its peak, Operation Mongoose employed approximately 400 CIA officers at its Miami station (JM/WAVE), making it the largest CIA station in the world outside Langley. The operation included plans for biological warfare against Cuban agriculture (introducing swine fever and other crop diseases), industrial sabotage (contaminating sugar exports), and even weather manipulation to damage the Cuban economy.

Robert Kennedy, who served as the de facto manager of Mongoose, pushed the CIA relentlessly for results. His intensity on the subject led some CIA officers to conclude that the Kennedys were explicitly authorizing assassination, though the question of whether the Kennedys specifically ordered Castro’s killing — as opposed to his “removal” — remains one of the most contentious historical debates of the Cold War era.

William Harvey and ZR/RIFLE

CIA officer William Harvey ran ZR/RIFLE, a general capability for assassination that was not limited to Cuba. Harvey, a former FBI agent known for his hard-drinking, gun-toting style (he kept loaded weapons in his desk and was known to brandish them during meetings), was a true believer in the utility of assassination as a foreign policy tool.

Harvey maintained a list of potential assassins — “assets” with the skills and willingness to carry out killings — and developed operational plans for eliminating Castro and other targets. His work overlapped with the Mafia plots, creating a tangled web of operations that the CIA itself had difficulty tracking.

Harvey’s aggressive approach led to his removal from the Cuba portfolio after the Cuban Missile Crisis of October 1962, when his unauthorized dispatch of covert action teams to Cuba nearly undermined the delicate diplomatic negotiations between Kennedy and Khrushchev.

Key Claims

• The CIA attempted to assassinate Fidel Castro using a variety of methods over more than a decade. Status: Confirmed. The Church Committee documented at least eight distinct plots between 1960 and 1965.

• The CIA collaborated with the American Mafia to carry out assassination attempts. Status: Confirmed. The Giancana-Roselli-Trafficante connection is documented in Church Committee records and has been acknowledged by former intelligence officials.

• 638 assassination attempts were made on Castro’s life. Status: Unverified. This figure comes from Cuban intelligence and is almost certainly exaggerated. The confirmed CIA plots number eight; additional attempts by exile groups and other parties may have occurred but are not independently documented.

• Presidents Eisenhower and Kennedy authorized the assassination attempts. Status: Mixed. The Church Committee found that senior officials, including the presidents, knew about and encouraged anti-Castro operations, but the question of whether explicit “kill orders” were given remains unresolved. The CIA’s culture of “plausible deniability” was specifically designed to insulate presidents from direct knowledge of assassination operations.

• The Castro assassination plots are connected to the JFK assassination. Status: Unresolved. Some theories hold that Castro, aware of the plots against him, ordered Kennedy’s assassination in retaliation. Others argue that the Mafia figures involved in the Castro plots used the same networks to kill Kennedy. The JFK assassination files remain partly classified, and these connections have not been definitively established or ruled out.

Evidence

The Church Committee Record

The primary source for the Castro assassination plots is the Church Committee’s 1975 report, Alleged Assassination Plots Involving Foreign Leaders. The report, based on testimony from CIA officials, review of classified documents, and investigation by committee staff, documented the following plots:

1. The Mafia poison pill plots (1960-1963)
2. The botulinum toxin cigar plot (1961)
3. The contaminated diving suit plot (1963)
4. The exploding seashell plot (1963)
5. The poison pen plot (November 22, 1963)
6. Multiple attempts to use Cuban agents with CIA-supplied weapons and poisons (1961-1965)

The Church Committee also documented assassination plots against Patrice Lumumba of the Congo, Rafael Trujillo of the Dominican Republic, and Ngo Dinh Diem of South Vietnam, establishing a pattern of U.S. government-sponsored political assassination during the Cold War.

Declassified Documents

Since the Church Committee investigation, additional details have emerged through declassified CIA documents, including:

• The CIA Inspector General’s 1967 “Report on Plots to Assassinate Fidel Castro” (declassified in 1993), which provided internal documentation of the plots
• Documents released under the JFK Records Act showing connections between assassination planning and other anti-Castro operations
• Oral histories and memoirs from former CIA officers, including those of E. Howard Hunt, who participated in anti-Castro operations and later became infamous for his role in the Watergate scandal

Castro’s Own Account

Castro himself discussed the assassination attempts publicly, including in a lengthy 2006 documentary by British filmmaker Dollan Cannell, 638 Ways to Kill Castro. While Castro had obvious motivations to exaggerate the threat for domestic political purposes, his accounts of specific plots generally aligned with what the Church Committee had confirmed.

Debunking / Verification

The Castro assassination plots are classified as confirmed. The core facts are not in dispute:

• The CIA planned and attempted multiple assassinations of Fidel Castro
• These plans were developed and executed with the knowledge of senior U.S. government officials
• The CIA collaborated with the American Mafia
• The methods employed ranged from conventional (poison, firearms) to bizarre (exploding seashells, contaminated diving suits)
• None of the plots succeeded; Castro died of natural causes in 2016 at age 90

The primary area of ongoing dispute concerns the scope of the plots (8 confirmed vs. 638 claimed) and the degree to which U.S. presidents personally authorized assassinations as opposed to merely encouraging anti-Castro operations in general terms.

Cultural Impact

The Castro assassination plots have had an outsized impact on American political culture, intelligence community reform, and the public understanding of covert operations.

Intelligence reform. The Church Committee’s revelations led directly to President Gerald Ford’s Executive Order 11905 (1976), which banned political assassination by the U.S. government. This prohibition was strengthened by President Reagan’s Executive Order 12333 (1981), which remains in effect. The creation of permanent congressional intelligence oversight committees — the Senate Select Committee on Intelligence and the House Permanent Select Committee on Intelligence — was a direct response to the abuses documented by the Church Committee.

Public trust. The Castro plots were one of several Cold War-era revelations (alongside MKUltra, COINTELPRO, and domestic surveillance programs) that fundamentally damaged public trust in the U.S. government and intelligence community. They established that the government had engaged in activities that were not only illegal but, in many cases, incompetent and absurd.

Conspiracy theory culture. The confirmed reality of the Castro assassination plots has been cited by conspiracy theorists as evidence that “if they did this, what else are they doing?” The plots provide a documented precedent for government-sponsored political assassination that makes other conspiracy theories — particularly those involving the JFK assassination — seem more plausible.

The JFK connection. The temporal overlap between the Castro assassination plots and Kennedy’s assassination has generated one of the most enduring conspiracy theories in American history. The fact that the CIA was working with the Mafia to kill Castro at the same time that Kennedy was killed — and that some of the same figures appear in both narratives — has fueled decades of speculation about whether the two events are connected.

Cuban-American relations. The assassination plots have been a persistent irritant in U.S.-Cuba relations, cited by the Cuban government as evidence of American hostility and used domestically to justify the continuation of the revolutionary government’s security apparatus.

In Popular Culture

The Castro assassination plots have been depicted and referenced across media:

• Documentary: 638 Ways to Kill Castro (2006), directed by Dollan Cannell, features interviews with former CIA operatives and Cuban intelligence officials
• Film: The plots feature in Oliver Stone’s JFK (1991) and serve as background for The Good Shepherd (2006)
• Television: Referenced in The Americans, Homeland, and various historical documentaries
• Literature: Extensively documented in books including Thomas Powers’s The Man Who Kept the Secrets and Evan Thomas’s Robert Kennedy: His Life
• Comedy: The absurdity of the plots has made them a staple of political comedy, including references in The Simpsons, Saturday Night Live, and stand-up comedy

Timeline

• January 1959 — Castro’s revolution overthrows Batista; U.S. relations deteriorate
• March 1960 — Eisenhower approves CIA plan to overthrow Castro
• August 1960 — CIA approaches Mafia through Robert Maheu; Roselli, Giancana, and Trafficante recruited
• 1960-1961 — Multiple Mafia-assisted poison pill attempts fail
• February 1961 — Poison cigars prepared and passed to Cuban contact
• April 1961 — Bay of Pigs invasion fails disastrously
• November 1961 — Operation Mongoose launched under Kennedy administration
• 1962 — William Harvey oversees ZR/RIFLE and multiple assassination plans
• October 1962 — Cuban Missile Crisis; Harvey’s unauthorized operations nearly disrupt negotiations
• 1963 — Contaminated diving suit and exploding seashell plots developed and abandoned
• November 22, 1963 — Poison pen meeting in Paris occurs on the day of JFK’s assassination
• 1963-1965 — Additional CIA-supported plots against Castro; all fail
• 1967 — CIA Inspector General compiles internal report on Castro assassination plots
• 1975 — Church Committee investigates and publicly reveals the assassination plots
• 1976 — Executive Order 11905 bans political assassination
• 1993 — CIA Inspector General’s 1967 report declassified
• 2006 — 638 Ways to Kill Castro documentary released
• November 25, 2016 — Fidel Castro dies of natural causes at age 90

Sources & Further Reading

• U.S. Senate Select Committee to Study Governmental Operations with Respect to Intelligence Activities (Church Committee). Alleged Assassination Plots Involving Foreign Leaders. U.S. Government Printing Office, 1975.
• CIA Inspector General. “Report on Plots to Assassinate Fidel Castro.” 1967 (declassified 1993).
• Escalante, Fabian. CIA Targets Fidel: The Secret Assassination Report. Ocean Press, 1996.
• Thomas, Evan. Robert Kennedy: His Life. Simon & Schuster, 2000.
• Powers, Thomas. The Man Who Kept the Secrets: Richard Helms and the CIA. Knopf, 1979.
• Weiner, Tim. Legacy of Ashes: The History of the CIA. Doubleday, 2007.
• Kornbluh, Peter, ed. Bay of Pigs Declassified: The Secret CIA Report on the Invasion of Cuba. The New Press, 1998.
• Hersh, Seymour. The Dark Side of Camelot. Little, Brown, 1997.

Related Theories

• JFK Assassination — Theories about President Kennedy’s assassination, with possible connections to the Castro plots
• CIA JFK Files — The still-classified documents about the Kennedy assassination and CIA operations
• MKUltra — Another confirmed CIA program revealed by the Church Committee
• CIA Drug Trafficking — Allegations of CIA involvement in drug trafficking, connected to the same Cold War covert operations culture
• Bay of Pigs — The failed 1961 invasion of Cuba that preceded and paralleled the assassination plots