Exploding shells! Poisoned cigars! Seductive sex assassins!
The United States’ very own CIA spent years planning and executing over 600 attempts to
take out Cuban leader Fidel Castro, with not a single one being successful, and the insanity
of the attempts themselves blows the number of them out of the water! It was a series of
schemes so harebrained that when the ugly truth eventually came out, then-president Gerald Ford
signed Executive Order 11905 - which read: “No employee of the United States government
shall engage in, or conspire in, political assassination.”
But before we get into the finer points of all of these deranged failed assassinations,
you may find yourself asking why the CIA felt the need to spend so much time and resources
trying to permanently remove the Cuban leader. Well, it was largely thanks to Castro that
Cuba became the first communist state in the Western Hemisphere.
While he was enrolled at the School of Law of the University of Havana, Fidel Castro participated in
resistance movements in the Dominican Republic and Colombia before becoming active in Cuban
politics in the 1950s. But Castro’s political aspirations faced a major hurdle when Fulgencio
Batista seized power over Cuba as a dictator. So, Castro organized a resistance movement against
Batista, using guerilla warfare and propaganda to diminish Batista’s military power and win the
support of the Cuban people, attracting more volunteers to Castro’s revolutionary cause.
Once they had forced Batista to flee the country in 1959, Castro assumed authority over the new
ruling government of Cuba as prime minister and would serve in the role for a tenure of 17 years,
eventually becoming president in 1976, a role he then held until 2008. This all doesn’t seem so
bad - unless you’re working for the CIA that is. Back before Castro was running the show down in
Cuba, the US government had long held suspicions about his political leanings. After all,
he was a fiery, outspoken revolutionary. When he eventually assumed power, Castro’s Cuba aligned
itself with the Soviet Union, which, of course, was a cause for concern for the United States,
especially given how close Cuba is to Florida, and thus the US mainland.
The CIA even proposed a plan to eliminate Castro to President Eisenhower and later to President
John F Kennedy when he was elected in 1960. With that second one, they were really barking up the
right tree - Kennedy couldn’t stand Castro and hoped to make humbling Cuba one of the major
achievements of his presidential administration. The plan began with the United States cutting
diplomatic ties with Cuba and launching an invasion into the Bay of Pigs.
In case that name isn’t ringing any bells, the Bay of Pigs invasion was an attempt by the CIA
to overthrow Castro and prevent the spread of communism into Latin America and the United
States. There had been a mass emigration of Cubans following the Cuban Revolution in 1959,
owing to political repression and disillusionment with life under Castro. These Cuban exile forces
were trained and organized by the CIA. Known as Brigade 2506, this 1400-man
force with the backing of the CIA, attempted to overthrow Castro but was quickly defeated
by the Cuban armed forces. The CIA even tried to use American B-26 bombers disguised as Cuban
Air Force planes to conduct air strikes in Cuba, but ultimately, the Bay of Pigs invasion failed.
So, the United States looked into other ways to take down Castro, and to say that they
got ‘creative’ would be an understatement. The Bay of Pigs invasion was arguably the
first attempt at killing Castro, as the failed US-backed invasion could have easily resulted
in his death. However, when this failed, the Central Intelligence Agency turned to methods
involving a lot more subterfuge. The former head of the Cuban secret service, Fabian Escalante,
who was charged with protecting Fidel Castro from many of these would-be assassins,
claimed that over the course of his life, Castro survived more than 630 assassination
attempts from the CIA, Cuban exiles, and others. One of the most famous ways the CIA tried to
assassinate Castro came close, but no cigar. Well, actually, there was a cigar involved.
Look through some of the photos of Castro in his heyday, and you’ll see that he was never far from
a cigar. The Cuban leader had apparently been smoking them since the tender age of fourteen,
and towards the end of the Eisenhower administration, this penchant for cigars
became a crucial tool in one of the CIA’s plans to make his smoking habit even deadlier.
As revealed by the Church Committee - a congressional oversight committee that hoped
to rein in some of the CIA’s worst behaviors - the CIA attempted to poison a box of Castro’s
favorite cigars in 1960. On August 16th of that year, a member of the CIA’s Office of Medical
Services was handed a box of the Cuban leader’s preferred brand and given instructions to treat
them with a lethal poison: botulinum toxin. This is one of the most poisonous biological
substances in the world, known to cause muscle paralysis, and could have caused Castro to die
when the tainted cigar made contact with his mouth. Fun additional fact for you:
botulinum toxin is also used in Botox injections, in case you ever needed another reason to avoid
those like the plague - because they kind of are a sort of plague, if you think about it.
Apparently, this particular poisoned cigar never reached Castro, however,
there have long been some conflicting reports that a CIA agent approached a New York City police
chief inspector with a plan to place an explosive cigar on Castro’s person while
he was in New York visiting the United Nations. There isn’t as much evidence of this exploding
cigar plot, so it’s believed to be more of an urban legend, but the poisoned cigar’s existence
is at least confirmed by the records of the CIA’s Operations Division. Yet another reason to quit
smoking, which Castro actually did in 1985. Some attempts to kill off Castro were a little
less Austin Powers and slightly more of what you’d expect when you picture the CIA assassinating the
United States’ geopolitical rivals. Robert Mahue, an attorney working with the CIA who was also the
former top aide of famous weirdo Howard Hughes, acted as an intermediary and helped to organize
some of the five more conventional assassination squads that were sent to kill Castro after the
Bay of Pigs failed. But just because these attacks were more conventional doesn’t mean they weren’t
the kind of things you’d see in movies. One of the team leaders was a mobbed-up
gambler named John “Handsome Johnny” Roselli. He worked with two other CIA assets, James O’Connell
and William King Harvey, to build an Oceans Eleven-style collection of assassination dream
teams. If this wasn’t weird enough, William King Harvey was also commonly known as “America’s James
Bond.” You really can’t make this stuff up, folks. Of course, despite involving a cast of characters
that George Clooney would probably bust down your door to audition for, all these hit squads
failed to take out Castro. Assassins were stalking Castro around every dark corner,
but they were always thwarted or caught. There was even talk of blowing Castro up
with a grenade during a sports game, which was an audacious plan that - spoilers - never came to be.
Members of the fifth group of assassins were arrested by Cuban authorities in early 1963 as
they were establishing a sniper’s roost in Havana to gun down Castro from a distance. In an example
of eerie irony, Kennedy would be assassinated by a sniper later that very same year,
while Castro continued to live on. Clearly, the CIA needed some more
experienced personnel to give Castro a dirt nap. When encountering trouble getting a certain job
done, sometimes it’s best to call on an expert, someone whose real specialist knowledge of a craft
can help you get the result you’re after. So, with the job in question being the death of another
country's political leader, whose expertise did the CIA decide to call on? Who else but the Mafia!
In an operation codenamed ‘Family Jewels’ - get your laughs out now - the CIA once again
reached out to our good friends Robert Maheu and Johnny Roselli to marshall their Mafia
contacts for the job. The CIA wouldn’t need to get their hands dirty this way,
given that a lot of the Mafia already had their knives out for Castro - his communist regime had
quashed a lot of their financial interests in Havana, and Castro needed to die for the
cash to start flowing back into Mafia pockets. Roseli reached out to two infamous mobsters,
Santos Trafficante and Momo Salvatore Giancana, otherwise known as Sam Gold. These two men were
both among the FBI’s Most Wanted, and here they were about to potentially work hand
in hand with the Central Intelligence Agency. The plan, as recommended by Giancana, was to lace
Castro’s food or drink with a lethal poison, as this would be more reliable than using guns. So,
Giancana recruited a Cuban official named Juan Orta to carry out the hit. Orta had access to
Castro and was even provided with pills containing – you guessed it – more botulinum toxin. However,
after failing several times to poison Castro, Orta got cold feet and backed out.
The CIA wasn’t done trying, though, and dispatched another set of botulism pills
to another candidate, Tony Varona, along with thousands of dollars. This time,
they planned to slip the poison into Castro’s food at a restaurant he frequented in Havana,
which served a chocolate milkshake that the Cuban leader adored. Varona was able to hand the poison
to a worker at the restaurant and instructed them to slip it into Castro’s chocolate milkshake.
Fortunately, he was able to enjoy his chocolatey dairy treat without dying,
as the would-be assassin seemingly botched the attempt out of nervousness. There are conflicting
reports as to exactly how this occurred, with some Cuban intelligence officers saying they found the
poison frozen in the coils of a freezer. Fabian Escalante wrote in his book that the assassin
had accidentally broken the poison capsule in a rush of nervousness, causing it to be
stuck to the freezer shelf, and thus making the poison pill and its contents useless.
Having failed in their collusion with the Mafia to poison Castro, the CIA began really thinking
outside of the box when it came to their plans for putting the Cuban leader inside one. They were
aware that Castro had a particular fondness for scuba diving, and so tried to orchestrate multiple
other attempts on his life around that fact. This included trying to poison him with a wetsuit and
building an explosive sea shell – how artistic! As also revealed by the Church Committee, in 1963,
the head of the CIA’s anti-Castro Task Force, Desmond Fitzgerald, contemplated whether or not
an exotic seashell could be rigged to explode and deposited in an area in the Caribbean Sea
where Castro frequently went diving. The idea was that this spectacular shell would attract
Castro’s attention while underwater, but would, in actuality, be booby-trapped with explosives. So,
when Castro would pick it up, it would detonate and take him with it.
Unsurprisingly, this plan was highly impractical, not just because it relied
on the pure happenstance of Castro spotting this spectacular shell and picking it up,
but also because the CIA couldn’t find a shell large enough to fit the amount of
explosives required to successfully kill him. Another scheme that was discussed by the CIA
but never put into action involved James Donovan, the man responsible for negotiating a deal with
Castro regarding the release of prisoners taken during the Bay of Pigs invasion. While Donovan was
successful in securing the release of thousands of imprisoned Cuban exiles, spoiler alert:
he didn’t actually end up killing Castro. But the CIA had, at one point, considered
giving Donovan a scuba diving suit that Donovan would then pass on to Castro. This suit would’ve
contained a fungus that passes on an infection known as Madura's foot, which causes damage to
the skin tissue and bones of the hands, feet, and other parts of the body. The CIA’s Technical
Services Division actually did purchase a diving wetsuit, coated its insides with the fungus,
and even infected the breathing apparatus with tuberculosis bacilli. However, the suit never left
the CIA laboratory, and an uncontaminated suit was given to Castro by Donovan.
The CIA was back to the drawing board again and considering using pills again since their
more outlandish ideas didn’t exactly… hold any water. Of course, in order to administer
poison to Castro, they would need someone to get close to the communist leader. And,
well, it’s often been said that the ones we love end up being the ones who hurt us
the most – and that almost ended up being the case! Fidel Castro wasn’t just a revolutionary,
lover of chocolate milkshakes and keen scuba diver; he was a notorious ladies' man, too.
Some reports even suggest that he was ‘close’ with around thirty-five thousand women, with
rumors that his guards would recruit women from the beaches around Havana. Castro was a pretty big
flirt, littering his speech with innuendos, and even once joked about having multiple children,
but no fewer than a dozen. Needless to say, the man got around, and the CIA saw
an opening to use Castro’s ‘fraternizing’ as their way in. Enter one Marita Lorenz.
Marita was a German-American woman whose mother had worked for the OSS – the precursor
to the CIA – along with the US Army and the Pentagon following the Second World War. As
for Marita’s father, he operated a line of cruise ships, and it was by being aboard one
of these that Marita first met Fidel Castro. In February of 1959, when the Cuban Revolution
had just taken control of the county, Martia was working aboard a ship called the MS Berlin
with her father. They had pulled into the Havana harbor, when Castro and his men appeared and asked
to board the vessel. Marita had no idea Fidel was the man who had just seized control of Cuba, but
he certainly made an impression on her, and the two began a long, tumultuous affair from then on.
Castro would fly her to Havana aboard a private jet, and it’s believed that Marita
fell pregnant during their affair. There are a lot of contradictory accounts about the exact
details of this; while Lorenz claims that Casto is the father of her son, she also claimed to have
been seven months pregnant in 1959, meaning there was likely more than one pregnancy.
When she revealed this to Castro, he apparently wanted nothing to do with
the child, and Marita was drugged by one of his aides, and woke up in hospital,
with the pregnancy having been terminated. Naturally, this caused the Cuban leader’s
now-former lover to turn on him. Returning to the United States,
thanks to her mother’s spy connections, Marita was put in touch with anti-communist groups in
Miami that were backed by the CIA, where she was ultimately recruited and convinced to carry out
an assassination attempt on the Agency’s behalf. She received several weeks' worth of training in
order to get close to Castro and dose him with more of the CIA’s favorite snack for foreign
political leaders: botulism toxin pills. So, in the winter of 1960, likely fuelled by her scorn
for her former lover, Marita boarded a plane and flew back to Cuba under the guise of taking care
of her personal matters with Castro. Her mission was, as it had been with the failed mob hit,
to meet with the Cuban leader for long enough to sneak the pills into his drink,
and if successful, he would be dead in under a minute, and she’d have her revenge.
However, as soon as Marita made her way back to the city of Havana, she realized that she felt
conflicted about the mission and couldn’t follow through with it. Some reports indicate that she
had stored the pills in a face cream jar, and this had caused them to melt, meaning she’d have little
chance of forcing them into Castro’s mouth while he slept. Others, including Marita Lorenz herself,
claim that she had been having doubts about the whole thing from the moment she boarded the plane.
She did meet with Castro in a hotel room before he was scheduled to give a speech and had every
opportunity to kill him. Instead, she confessed that she had been sent there with the intention
of assassinating him. He asked if she was meeting with counterrevolutionaries in Miami,
to which she said yes. When he asked if she was working with the CIA, Martia denied that
she was – perhaps to avoid angering him, or possibly unaware of their involvement in the
anti-Castro group that had recruited her. According to Lorenz’s own account of the
encounter, Castro then produced his pistol, but not to shoot his lover-turned-assassin. Instead,
Castro reportedly handed the gun to Marita and offered her the chance to shoot him. Faced with
someone sent to end his life, Castro was not only unsurprised but was almost chivalrous
in his actions, allowing Marita to finish the job. But instead, unable to kill him,
she unloaded the pistol, which equally didn’t seem to surprise Castro, who apparently replied with:
“You can’t kill me. Nobody can kill me.” Immediately, Marita fell into his arms and… well,
how can we put this in a way that’s safe for YouTube? It might have been her job to go kill
the Cuban leader, but as it turned out, Marita got to fiddle Castro one more time. They do
say you should try to love your work; maybe it’s possible to love it a little too much.
Some of the saddest CIA attempts to take out Castro gave up the ghost of killing him
entirely - Instead choosing to assassinate his reputation, with equally embarrassing results.
In 1960, Castro was planning to give an important radio address to the people of Cuba. Immediately,
the CIA sprung into action with the diabolical plan of spraying an aerosolized LSD compound
into the radio station - Hoping that Castro would start tripping and sound
like a maniac during his speech, reducing his credibility in the eyes of the Cuban people.
An effect that, even if it had worked, would only have been effective for as long
as it took for the Cubans to realize that Castro was not, in fact, insane - But had
just been drugged with psychedelics by the CIA. However, their plot involving thallium salts was
truly a new low - Where the objective was not to assassinate Castro but to assassinate his iconic
beard. Yes, we’re being serious. The plan was to dust the chemical onto Castro’s shoes, which
would cause him to lose his beard, eyebrows, and pubic hair - Though like many other wild murder
moon shots, this one never came to fruition. Given that the CIA was now officially resorting
to the classic college party prank of squirting Nair into someone’s pants while they’re black-out
drunk, it’s clear that the well was running dry. The craziest thing is that the scope of these
assassinations went way beyond Eisenhower and Kennedy. Lyndon B. Johnson hosted his fair
share of Castro assassination attempts, and Richard Nixon’s tenure saw the largest number
of botched attempts to kill Castro of all US Presidents - Coming in at a whopping 184 attempts.
As the CIA and the Cuban exiles who were eager to see the country return to its prior non-communist
ways became more desperate, their ideas for murdering El Commandante became a lot less
subtle - Well, if you can call literally any of this subtle. Despite Gerald Ford’s
executive order to put a stop to all the wacky assassination attempts, in the year 2000, when
Castro was due to give a speech in Panama, the idea was floated to put 200 pounds of explosives
under his podium and blow him to kingdom come. Once again, this would never come to fruition.
The four-man explosives team, composed of angry Cuban exiles, were intercepted by Castro’s
security team and arrested. Their ringleader was Luis Posada, who, you may have guessed,
was a CIA operative. They would later be pardoned and go to live in Florida, with many
other Cuban exiles, because it seems that Castro was strangely forgiving of attempts on his life.
Until his death in 2016, Castro developed a reputation for being seemingly immortal after
surviving all these attempts. The truth is, while Castro was no doubt a very lucky man,
he likely owes his longevity to a mix of his extremely competent security team and
the extreme incompetence of many of the CIA assets sent to take his life. Castro
was always on the move, with a huge cadre of body doubles to ensure that if ever the CIA
did get a windfall, it wouldn’t be on him. But strangely, while modern dictators like
Vladimir Putin and Kim Jong Un are practically paranoid wrecks about the prospect of being
assassinated by one of their many enemies, Castro didn’t let the knowledge that people
were almost constantly trying to kill him put a damper on his daily activities. When once
asked about whether he wears a bullet-proof vest, he responded: “I have a moral vest.”
And if his track record is anything to go by, maybe more world leaders should look into wearing
moral vests. It certainly worked for Fidel Castro. For more on the US’ Communist thorn in their side
check out “How a Nuclear World War 3 Almost Happened” Or watch this video instead!