By Maverick
For today’s blog, we dive into Operation 40, a secretive anti-Castro group reportedly formed under the Eisenhower administration and allegedly connected to the CIA. Get yourself something to eat and or drink, then pull up a comfortable chair because you’re not going to want to miss out on this story.
While much of Operation 40’s documented mission focused on undermining Fidel Castro’s communist government, the mysterious nature of the unit, the high-profile figures rumored to be involved, and the political climate of the early 1960s have led many to connect Operation 40 to one of the most controversial events in American history, the assassination of President John F. Kennedy. Let’s explore the origins of Operation 40, what potentially ties it to the JFK assassination, the Bay of Pigs Invasion, and how it continues to fuel conspiracy theories today.
Operation 40 was reportedly established in 1959–1960, during the last year of President Dwight D. Eisenhower’s administration, as part of a larger U.S. effort to counter the growing influence of communism in Cuba following Fidel Castro’s successful revolution in 1959. That’s evidently why Operation Northwoods was proposed in 1962.
The unit was allegedly approved by then Vice President Richard Nixon and overseen by Allen Dulles, then Director of the Central Intelligence Agency (CIA). Its name, Operation 40, referred to the original number of members involved, though over time, the group is believed to have expanded. Its official purpose, according to limited declassified materials and historical accounts, was to conduct covert operations, including:
• Intelligence gathering on Cuba and communist sympathizers
• Sabotage missions and infiltration plans
• Psychological warfare
• Coordination with anti-Castro Cuban exiles
However, numerous journalists, whistleblowers, and researchers claim that Operation 40’s mission was far darker, functioning as a “shadow assassination unit”, a CIA hit squad, capable of carrying out political killings, black operations, and other deniable acts in places like Latin America. These are some of the known members of Operation 40:
• Frank Sturgis – later arrested in the 1972 Watergate burglary and reportedly part of anti-Castro efforts.
• E. Howard Hunt – another key Watergate conspirator and veteran of CIA black operations. Also admitted to his son on his deathbed in 2007 that the CIA killed JFK. This supposed confession was recorded and is publicly available online.
• David Morales – a senior CIA operative involved in the Bay of Pigs invasion and later associated with the JFK assassination in several conspiracy theories.
• Porter Goss – alleged by some sources to have been connected to early anti-Castro operations despite Goss denying it.
• Barry Seal – a pilot later tied to CIA drug-running allegations in the 1980s.
The supposed link between Operation 40 and the assassination of President John F. Kennedy on November 22nd, 1963, stems from both motive and overlap. After taking office in 1961, President Kennedy inherited ongoing plans for a CIA-backed invasion of Cuba, the Bay of Pigs invasion. It was a failed U.S.-backed military operation aimed at overthrowing Fidel Castro’s communist government in Cuba that took place from April 17th to 20th, 1961, on the southern coast of Cuba in a remote area called the Bahía de Cochinos (Bay of Pigs). The invasion was planned and financed by the CIA, authorized originally under President Dwight D. Eisenhower, and later executed under President John F. Kennedy, despite his reluctance to conduct the operation.
Not to go off on a tangent here, but let me break it all down in simple terms as to why this all happened. Before 1959, Cuba was ruled by Fulgencio Batista, a U.S.-backed dictator who allowed American corporations to dominate Cuba’s economy and hot commodities like sugar and tobacco. In 1959, Fidel Castro led a successful revolution that overthrew Batista. Castro claimed his revolution was nationalist, not communist. So much for that because after taking power, he nationalized industries, seized American-owned businesses, and aligned politically and economically with the Soviet Union. By 1960, Cuba had become the first communist country in the Western Hemisphere. Both Batista and Castro were horrible for Cuba and its interests.
The U.S. lost its shit and saw this as a severe threat during the Cold War, fearing Soviet influence so close to U.S. shores. As a response to this, the U.S. cut diplomatic ties with Cuba in January 1961. Eisenhower and the CIA began planning to remove Castro through covert means. The CIA proposed recruiting Cuban exiles (anti-Castro refugees) to form a paramilitary force that would invade Cuba and overthrow Castro without direct U.S. involvement.
There was a problem for JFK. As mentioned earlier, when he assumed office in January 1961, the operation was already in motion. JFK was wary of a visible U.S. military intervention and approved the plan but insisted it appear to be a Cuban exile operation, not an American invasion.
About 1,400 Cuban exiles known as Brigade 2506 were trained by the CIA in Guatemala and Nicaragua and sent to the Bay of Pigs. The government really messed up immensely here since the plan wasn’t top secret, as Cuban intelligence and even The New York Times had reported it before it happened. JFK refused to authorize full U.S. air support to maintain plausible deniability. This severely weakened the invasion. The Bay of Pigs was swampy, isolated, and hard to reinforce, with no local uprising. Castro’s forces quickly mobilized 20,000 troops and surrounded the invaders. Within 72 hours, most of the invasion force was killed or captured.
The world saw the U.S. attempt to overthrow a sovereign government and failed miserably. It damaged America’s credibility, reputation, and JFK’s image. The Soviet Union or USSR promised to defend Cuba from future invasions, paving the way for the Cuban Missile Crisis in 1962, which was a 13-day political and military standoff between the United States and the Soviet Union over the placement of nuclear missiles in Cuba. It is widely regarded as the closest the world ever came to full-scale nuclear war.
So following the Bay of Pigs debacle, Fidel Castro feared another U.S. attack. To deter it, he secretly allowed Soviet Premier Nikita Khrushchev to deploy nuclear missiles in Cuba. For the Soviets, the move balanced U.S. nuclear missiles already stationed in Turkey and Italy, aimed at the USSR. On October 14th, 1962, an American U-2 spy plane photographed Soviet missile sites under construction in Cuba. JFK was informed and rejected immediate airstrikes or invasion.
Instead, on October 22nd, he announced a naval “quarantine” (blockade) of Cuba to prevent further Soviet shipments of missiles. He demanded that existing missiles be removed and warned of retaliation if Cuba launched an attack. Several tense incidents occurred, including the shooting down of a U-2 plane over Cuba. On October 28th, 1962, Khrushchev agreed to remove the missiles from Cuba in exchange for the U.S. pledging not to invade Cuba and for the U.S. to agree to remove American missiles from Turkey. The crisis ended peacefully, leading to the signing of the Nuclear Test Ban Treaty, but left a lasting scar on U.S.–Soviet relations.
The Bay of Pigs debacle didn’t end U.S. efforts; it made them more covert and aggressive, leading directly to Operation Mongoose and other proposals. Operation Mongoose was a top-secret CIA program initiated in November 1961 under the direction of Attorney General Robert F. Kennedy, JFK’s brother. JFK approved the plan, and U.S. Air Force intelligence officer Edward Lansdale ran the op. The goal was to help Cuba overthrow Castro and his communist regime. It was Bay of Pigs 2.0, but this time, nobody knew about it. Mongoose included hundreds of bizarre and aggressive schemes to undermine Castro, such as assassination attempts, sabotaging the economy by destroying their crops and sugar mills, and poisoning the agriculture. Mongoose called for psychological warfare tactics such as fake stories and disinformation, as well as staging false-flag operations just as Operation Northwoods stipulated. They also continued to arm and fund Cuban exiles.
Mongoose was effectively shut down after the Cuban Missile Crisis when JFK realized further aggression against Cuba could trigger World War 3 and nuclear war with the Soviet Union. The Bay of Pigs and Operation Mongoose solidified hostile U.S.–Cuba relations for decades. The U.S. imposed a trade embargo or a ban against Cuba, which is still largely in effect today.
After the Bay of Pigs and Operation Mongoose, JFK became deeply distrustful of the CIA, famously saying, “I want to splinter the CIA into a thousand pieces and scatter it to the winds.” Then he was assassinated by a supposed communist named Lee Harvey Oswald in 1963, who had ties to the CIA. That’s a whole other topic for another day. As I always say, what a coinkydink.
When Kennedy refused to provide full-scale U.S. military support, many within the CIA and anti-Castro exile community blamed him for the failure. Researchers argue that it was from that point on that JFK would be taken out at some point because he actually held the government accountable and didn’t falter to them every time they wanted him to do something dangerous and unethical. Operation 40 members, many of whom were Cuban exiles and CIA operatives involved in the invasion, felt deeply betrayed. According to conspiracy theorists, a rogue network of intelligence and military operatives plotted revenge against Kennedy for his perceived softness on communism and his moves to limit CIA power after the Bay of Pigs. The CIA wanted an invasion and an all-out war with Cuba, and Kennedy wanted peace and resolution.
E. Howard Hunt and Frank Sturgis, two men I mentioned earlier, became central figures in the JFK assassination conspiracy discussions. Both men were rumored to have been in Dallas on the day of the JFK assassination, despite denying it. Again, both were later implicated in the Watergate scandal, further reinforcing the image of a shadowy intelligence underworld capable of domestic operations. Skeptics also assert that Operation 40 evolved into or overlapped with a covert team that executed the assassination, allegedly framing Lee Harvey Oswald as the lone gunman to mask a broader plot. Of course, there is no tangible proof of this, but it does make a ton of sense. E. Howard Hunt confessed to this plot and said it was originally supposed to take place in Miami, FL, but was later moved to Dallas, TX.
The Warren Commission in 1964 and later the House Select Committee on Assassinations (HSCA) in 1979, found no credible evidence linking CIA operations to the assassination, though the HSCA did conclude that Kennedy’s murder was “probably the result of a conspiracy” without identifying who was involved. That’s helpful. However, supporting evidence for the Operation 40 connection remains circumstantial, based largely on overlapping personnel between CIA anti-Castro operations and figures linked to Dallas, statements from former operatives, journalists, or whistleblowers, often decades later.
Declassified CIA documents showing extensive secret operations in Cuba and Latin America, proving the existence of such covert groups (though not directly tying them to JFK). Skeptics argue that the Operation 40/JFK theory stretches the available evidence, blending historical fact with unverified allegations. The CIA’s own records acknowledge the group’s existence but maintain it was an intelligence coordination cell and not an assassination squad. Should we choose to believe them?
Operation 40 stands as one of the most enigmatic covert groups of the Cold War, a secretive task force born from the fear of communism and the ambition of American intelligence. While its exact mission and scope remain uncertain, its existence is undisputed, and its legacy continues to echo through modern conspiracy culture. The alleged link to the JFK assassination, though lacking direct evidence, persists because it embodies a larger distrust of power, secrecy, and the unseen machinery of government. Ultimately, Operation 40 reminds us how the blurred lines between truth, secrecy, and speculation can shape our understanding of history and how even a single classified operation can fuel decades of debate and unanswered questions. Please share your thoughts in the comment section. Be well.
