The 600 Lives of Fidel Castro

Summary

Conspiracy Theories

Episode: The 600 Lives of Fidel Castro
Date: September 3, 2025
Host: Carter Roy
Production: Spotify Studios

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Main Theme

This episode investigates the infamous and persistent attempts to assassinate Fidel Castro, Cuba’s revolutionary leader—a man reportedly targeted over 600 times by his adversaries, especially the CIA. Blending historical narrative with conspiracy analysis, hosts dissect the intersection of geopolitics, organized crime, and covert operations in one of the world’s longest and most theatrical manhunts.

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Key Discussion Points & Insights

1. The CIA and the Art of Assassination

• Overview: The CIA’s reputation for involvement in assassinations is touched upon, initially referencing high-profile cases such as JFK, MLK, Malcolm X, and Marilyn Monroe ([00:00]–[00:15]).
• JFK Files: Recent declassifications have openly implicated the CIA in plots against leaders like Patrice Lumumba and Rafael Trujillo, but most notably, Fidel Castro ([00:49]).

2. Castro’s Arrival and Symbolism in the U.S.

• Castro in Harlem (September 1960): Amid deteriorated U.S.–Cuba relations, Castro attends the UN and checks into the Hotel Theresa in Harlem, making a symbolic connection with Black American leaders and the Civil Rights Movement ([03:24]–[06:16]).

• Memorable Scene: Castro dines with hotel staff rather than attending a White House luncheon ([05:45]).

  Carter Roy [05:16]: “Each day, hundreds of black Americans gather outside the window of Castro’s corner suite... cheering him on. He… committed his new government to pursue racial equality.”

3. The Seeds of U.S. Hostility

• Nationalizations & Soviet Ties: U.S. animosity intensifies as Castro expels U.S. interests and aligns with the Soviets ([04:24]–[04:37]).

• Public Persona: Castro’s “four and a half hour” UN speech fiercely criticizes U.S. policy and cements him as a public enemy in American eyes ([06:32]–[06:51]).

  Co-host [06:46]: “In the eyes of many, this is the speech that solidifies his position as an outspoken opponent of the U.S. government.”

4. Early Castro, Myth-Making, and Revolution

• Guerrilla Beginnings: Castro survives multiple early death reports during his rise against Batista ([07:16]–[08:54]).

• Havana: A Mob Playground: The city’s pre-revolution glamour was thanks to the Mafia’s U.S.-backed corruption—a symbol Castro would destroy ([10:21]–[12:40]).

  Carter Roy [11:19]: “John F. Kennedy... really let loose and free their inhibitions. This becomes such a distinct period in Cuba’s history, it even makes its way into The Godfather Part 2.”

5. Mobsters, the CIA, and Early Assassination Plots

• "Gangster Type Action": The CIA recruits Sam Giancana and Johnny Roselli, notorious mafiosos, offering them $150,000 to kill Castro ([14:13]–[15:45]).

• Refusal of Payment: The mobsters insist on doing it “for free”—likely for personal and pragmatic reasons ([15:45]).

  Co-host [15:45]: “‘No, no, they’ll do it for free.’ They… claim it has something to do with patriotism.”

• Bizarre Methods: Opting for poison over guns, they attempt to slip a lethal pill into Castro’s food or drink. Their initial plan fails when their woman accomplice is caught and executed, and further missions devolve into disasters ([16:29]–[17:58]).

• Mobster Retribution: Both Giancana and Roselli later die mysteriously, with the implication that their knowledge of CIA operations made them targets ([19:06]–[19:45]).

  Carter Roy [19:06]: “Once he realizes they aren’t planning on helping him out, he threatens to go public with the entire assassination plot… both men turn up dead.”

6. The CIA’s Theatrical Attempts

• Poisoned Cigars and Chocolate Milkshakes: Repeatedly targeting Castro’s personal habits, the CIA concocts elaborate but consistently unsuccessful plans ([20:03]–[20:35]).

• Marita Lorenz Affair: Castro’s former lover is recruited by the CIA to poison him with botulism capsules—she loses her nerve, ruins the capsules, and confesses to Castro, who dares her at gunpoint to kill him ([20:41]–[25:20]).

  Carter Roy [25:20]: “Instead, he laughs and says, ‘You can’t kill me. Nobody can kill me.’ He just smiles and chomps on his cigar, knowing he has her all figured out.”

7. The Bay of Pigs and Operation Mongoose

• Bay of Pigs Fiasco (April 1961): The CIA-backed invasion by Cuban exiles quickly unravels, with major missteps and no U.S. reinforcements leading to a humiliating defeat ([26:17]–[28:05]).
• Operation Mongoose: Approved post-invasion, it was Robert Kennedy’s charge to “stir things up on the island with espionage, sabotage, general disorder, run and operated by Cubans themselves” ([28:38]–[29:45]).

8. The Most Eccentric Plots

• Deadly and Ridiculous: Proposals included explosive seashells, fungus-laden diving suits, poison pens, LSD-like aerosols to embarrass Castro live on-air, and salt to make his beard fall out ([29:45]–[31:17]).

  Co-host [30:54]: “One plot involved an aerosol of a chemical similar to LSD… in the hopes he would hallucinate on air and humiliate himself.”

9. Conspiracy Reversal: Who Killed JFK?

• Castro’s Ominous Warning: Shortly before JFK’s assassination, Castro hints that U.S. leaders involved in assassination plots “will not be safe” ([32:10]–[32:27]).
• Oswald’s Cuban Connections: Lee Harvey Oswald’s pro-Castro sympathies, his ties to Cuba, and a failed attempt at entry into Cuba in 1963 fuel theories of Cuban involvement in JFK’s murder ([33:14]–[33:53]).

10. Castro’s Legacy of Survival

• Outliving Assassins & Journalists: Castro evades over 600 known attempts and outlives 11 U.S. presidents as well as some journalists who had pre-written his obituary ([35:12]–[36:02]).

• Final Word: Castro finally passes away in 2016 at age 90, not by assassination but “peacefully in his sleep” ([36:07]).

  Carter Roy [34:15]: “‘It’s not my fault the CIA has failed to kill me even after five decades in power.’”

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Notable Quotes & Memorable Moments

• On the Mob’s Motivation:

  Carter Roy [16:04]: “Plus, they figure working with the feds would guarantee them a much needed get out of jail free card at some point down the line.”

• On Surviving Repeated Plots:

  Carter Roy [34:15]: “It’s not my fault the CIA has failed to kill me even after five decades in power.”

• On Symbolism and Public Relations:

  Co-host [06:11]: “At the peak of the civil rights movement in the U.S., Cuba sympathizes with the black American struggle.”

• On the Absurdity of CIA Schemes:

  Co-host [30:54]: “One plot involved an aerosol of a chemical similar to LSD… in the hopes he would hallucinate on air and humiliate himself.” Carter Roy [31:17]: “But the attempts to destroy his pride, much like the attempts on his life, were unsuccessful.”

• On Irony and Obituaries:

  Carter Roy [36:02]: “Occasionally the original writer would have their own obituary published in the paper before Castro’s.”

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Timestamps for Important Segments

• Intro & CIA’s Track Record: [00:00]–[01:34]
• Castro in Harlem & Civil Rights: [03:24]–[06:16]
• Mobster Collaboration: [14:13]–[19:45]
• Creative Assassination Attempts: [20:07]–[21:14]; [29:45]–[31:17]
• Marita Lorenz Story: [20:41]–[25:20]
• Bay of Pigs & Mongoose: [26:17]–[29:45]
• Reverse JFK Theories: [31:41]–[34:17]
• Castro’s Legacy & Survival: [35:12]–[36:02]

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Conclusion

The episode delivers a riveting, sometimes darkly comedic tour through the near-mythical saga of Castro’s survival, exploring the murky relationship between covert U.S. actions and retaliatory conspiracy, the blurred lines between fact and legend, and Castro’s ability to outlast not just deadly plots but the very narrative of his own death.

Carter Roy [36:07]: “The truth isn’t always the best story, and the official story isn’t always the truth.”

Transcript

[Carter Roy]

In the court of public opinion, the CIA is thought to have been responsible for countless assassinations of iconic figures. Malcolm X, John F. Kennedy, Martin Luther King Jr.

[Co-host or Narrator]

Some even think the agency had a.

[Carter Roy]

Hand in the death of Marilyn Monroe. While certain cases are stronger than others, there are some assassination plots the US Government can no longer deny. After decades of secrecy. The JFK files, aka an archive of over 6 million assassinated related documents, photos and motion pictures have been declassified and released to the public in batches by the National Archives over the last several years. Inside these files, there is verifiable evidence.

[Co-host or Narrator]

To show that the CIA has been implicated in attempts on a number of global leaders, including Patrice Lumumba, the Prime Minister of the Democratic Republic of the Congo, Rafael Trulillo, the President of the.

[Carter Roy]

Dominican Republic, and most notably, Fidel Castro, the leader of Cuba. During his reign, Castro was one of.

[Co-host or Narrator]

The most hunted men on the planet.

[Carter Roy]

He embodied what many governments considered the threat of communist expansion into the Western Hemisphere. The White House in particular, became fixated on him and the influence he could have.

[Co-host or Narrator]

According to Cuban officials, throughout the leader's lifetime, there were an estimated 600 attempts to assassinate him. How many were the CIA actually responsible for?

[Carter Roy]

And how far were they willing to go to take down Cuba's charismatic new leader? Welcome to Conspiracy Theories, a Spotify podcast. I'm Carter Roy. New episodes come out every Wednesday. You can watch our episodes and more on our new YouTube channel Onspiracy Theories podcast and be sure to check us out on Instagram. He conspiracypod. Stay with us.

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[Co-host or Narrator]

Fidel Castro arrives in New York City just as summer settles into fall.

[Carter Roy]

It's September 1960 and the 34 year old Prime Minister of Cuba is here to attend the United Nations General assembly and give a highly anticipated speech. It's almost surprising to see him on US soil just shy of two years into his reign. Castro's current relationship with the White House is strained, to say the least.

[Co-host or Narrator]

They did originally recognize his leadership despite.

[Carter Roy]

Having the previous president in their pocket for so many years. But once Castro began making policy decisions they disagreed with and started publicly aligning with the Soviet Union, the US quickly withdrew any support.

[Co-host or Narrator]

After overthrowing Cuban dictator Falencio Batista, Castro started redistributing land to the peasants who.

[Carter Roy]

Worked on it and barring foreigners from.

[Co-host or Narrator]

Owning land in Cuba at all. The state took control of all US.

[Carter Roy]

Companies and holdings and what many consider to be the final straw.

[Co-host or Narrator]

They began doing business with the Soviets.

[Carter Roy]

Which during the Cold War was considered a massive threat to the Americans. So by the time Castro is photographed gallivanting around New York in his iconic army fatigues, long beard and smoking a.

[Co-host or Narrator]

Cigar, he is already an unwelcome guest.

[Carter Roy]

Of the US government. But he really catches the world's attention.

[Co-host or Narrator]

When he and his team check into.

[Carter Roy]

The Hotel Theresa in Harlem. At this time, Harlem is the site of both state sanctioned poverty and violence and a hub for revolutionary activism.

[Co-host or Narrator]

Each day, hundreds of black Americans gather outside the window of Castro's corner suite overlooking 7th Avenue and 125th street, cheering him on. He did, after all, outlaw segregation in many public institutions in Cuba and and committed his new government to pursue racial equality.

[Carter Roy]

It's at this hotel that Castro meets with a number of radical black American.

[Co-host or Narrator]

Leaders and thinkers, including Malcolm X and Langston Hughes. While Eisenhower hosts a luncheon for Latin American leaders, Castro treats the hotel staff to a steak dinner. One photo shows him sitting around a dinner table with the bellhops and desk.

[Carter Roy]

Clerks, sitting still in uniform. His decision to spend this time in Harlem sends a clear message.

[Co-host or Narrator]

At the peak of the civil rights movement in the U.S. cuba sympathizes with.

[Carter Roy]

The black American struggle.

[Co-host or Narrator]

He seemingly wants the world to know.

[Carter Roy]

That and more specifically the US government, when he finally stands before the United Nations. His whole reason for the Triple Castro.

[Co-host or Narrator]

Gives the longest speech the assembly has heard to this day. He speaks for almost four and a.

[Carter Roy]

Half hours, mostly about the horrific impact of American policies on Latin America.

[Co-host or Narrator]

In the eyes of many, this is the speech that solidifies his position as.

[Carter Roy]

An outspoken opponent of the U.S. government. By the time he's on a plane back to Havana, the damage is done. Just four months later, President Dwight D. Eisenhower severs all diplomatic relations with Cuba.

[Co-host or Narrator]

And the CIA's plans to assassinate Fidel.

[Carter Roy]

Castro have already been set in motion.

[Co-host or Narrator]

Back when 19 year old Castro entered the University of Havana's law School in 1945, he began what he calls acquiring a revolutionary conscience.

[Carter Roy]

This was his first experience engaging with Marxist literature and going to demonstrations, although he claims he didn't explicitly identify as a communist at the time.

[Co-host or Narrator]

After receiving his degree, he worked as a civil rights lawyer representing the poor. Then in 1952, he ran for Congress as a candidate for the opposing orthodox party.

[Carter Roy]

The election, however, was interrupted by a.

[Co-host or Narrator]

Coup staged by then right wing president Fulencio Batista.

[Carter Roy]

In the following years, Castro embarked on a campaign of guerrilla warfare against Batista. He led a rogue army in opposition to the dictator. His image as a revolutionary leader taking shape globally. Castro began cheating deaf early on in his political career. As he struggled against Batista's forces, he was reported dead at least twice by local media. The first report was after a failed uprising at a military barracks where hundreds perished, but he ultimately survived. The second came after he briefly sought exile in Mexico before returning in full.

[Co-host or Narrator]

Force in a boat filled with guerrilla fighters. Where Batista had Castro outnumbered. Castro was strategic and fearless.

[Carter Roy]

He was ready to die for his cause and so were his comrades.

[Co-host or Narrator]

Just after midnight on New Year's Day 1959, as rebel forces descended on the city, Batista fled from the dark Havana airport to seek exile in the Dominican.

[Carter Roy]

Republic and eventually Portugal. Days later, Castro rode into the city and took his new position as the leader of Cuba. In the months to come, officials from the previous regime were ceremoniously executed before Castro's tribunals. The world watched the grainy black and white news footage as hundreds were killed by firing squad. Castro claimed those being executed were murderers of the lower classes. He said their deaths were necessary for revolution and that the US had hardly.

[Co-host or Narrator]

Cared when Batista tortured and executed thousands of his own opponents.

[Carter Roy]

The world looked at Cuba in a totally different light than it had just months before. Prior to the Cuban Revolution 1950s, Havana was infamous as a playground for America's rich and famous. The opulent nightlife, exciting music scene, beautiful people.

[Co-host or Narrator]

But this illusion of glamorous tourism in Cuba was largely orchestrated by the Cuban government and the Mafia. The mob used dirty money from America and funneled it into Cuba so they could build casinos, hotels and nightclubs. And corrupt Cuban leader Fulencio Batista didn't.

[Carter Roy]

Ask too many questions so long as his regime was reaping the financial rewards.

[Co-host or Narrator]

That meant the Mafia could bend local.

[Carter Roy]

Politics to their will. Without having to deal with consequences from US authorities.

[Co-host or Narrator]

It created the illusion that Havana was a place where anything could happen. Gambling, sex, work, Americans and Europeans doing the mambo.

[Carter Roy]

Soon it was a destination for the.

[Co-host or Narrator]

Likes of Frank Sinatra, Eartha Kitt and.

[Carter Roy]

John F. Kennedy to really let loose and free their inhibitions. This becomes such a distinct period in Cuba's history, it even makes its way.

[Co-host or Narrator]

Into The Godfather Part 2. On a rooftop in Havana, a group.

[Carter Roy]

Of Italian American mob bosses triumphantly cut.

[Co-host or Narrator]

Pieces from a cake shaped like Cuba.

[Carter Roy]

Some real symbolism going on here. This was their domain now.

[Co-host or Narrator]

But as the wealthy got wealthier, there was increasing unrest amongst the Cuban population. The masses faced a crisis of hunger.

[Carter Roy]

Illiteracy and immense poverty.

[Co-host or Narrator]

To Castro and his followers, the mob and the US government were co conspirators.

[Carter Roy]

In the exploitation of Cuba. So once Castro rose to power in 1959, they both had to go.

[Co-host or Narrator]

As truckloads of Castro's soldiers rushed through the streets of Havana, ready to stake their claim on the city, hotels and casinos were some of their primary targets. They represented the opulent wealth that stole resources away from the country's poorest and most vulnerable.

[Carter Roy]

Castro's army destroyed, ransacked and totally took over many of these establishments. The mob was not pleased. And the CIA would use that fact to their advantage. The notorious gangsters were the perfect cover. Who wanted Castro gone more than the mob? Reeling from the loss of some of their most lucrative assets, the government was.

[Co-host or Narrator]

Too concerned about what the American public.

[Carter Roy]

Would think if they found out the CIA's murderous plans.

[Co-host or Narrator]

So they decided to seek out the.

[Carter Roy]

Enemy of their enemy for help.

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[Carter Roy]

By August 1960, the CIA had already determined they were looking for some outside help to take what they described as co quote gangster type action. AKA they wanted some mafiosos to do their dirty work without raising suspicion. The mission? According to one CIA document, the liquidation of Fidel Castro. They had their eyes on two big time gangsters in particular. Sam Giancana and Johnny Roselli. Both worked under Al Capone as young men, but as they reached the peak of their careers, they ran their own multi million dollar mafia empires. Roselli, who was their eyes and ears in Los Angeles and Vegas, was known as Handsome Johnny for his Hollywood good looks and irresistible charisma. Giancana was the unpredictable mobster who operated out of Chicago and had long dreamed of expanding their empire into Latin America. On a balmy September night in Miami, one week after Castro arrives in New York, the two mafiosos meet with a CIA middleman at the Fontainebleau Hotel. Over drinks, the middleman reveals the CIA's ploy to take out Castro and that they're willing to pay them $150,000 to get the job done. But the two mobsters decline.

[Co-host or Narrator]

No, no, they'll do it for free. They apparently claim it has something to do with patriotism.

[Carter Roy]

But odds are it has more to do with their own shuttered casinos scattered across Savannah.

[Co-host or Narrator]

Plus, they figure working with the feds would guarantee them a much needed get.

[Carter Roy]

Out of jail free card at some point down the line.

[Co-host or Narrator]

The mob boss only requirement?

[Carter Roy]

They didn't think it wise to use firearms as their weapon of choice. That would almost certainly be a death wish for whoever pulled the trigger.

[Co-host or Narrator]

Instead, Giancana suggests a pill that could easily be slipped into Castro's food or drink.

[Carter Roy]

The CIA agrees and develops a pill.

[Co-host or Narrator]

That they describe in an official document as having rapid solubility, high lethal content, and little or no traceability.

[Carter Roy]

To execute their plan, the two gangsters enlist the help of a crooked Chicago cop, Richard Kane, a fluent Spanish speaker who knows his way around Cuba.

[Co-host or Narrator]

Kane is also on Giancana's payroll, so.

[Carter Roy]

The men know they can count on his loyalty. In the fall of 1960, under the dark of night, Cain sneaks into Cuba with the help of a mystery woman, thought to be one of Castro's mistresses, who is in on the plan. Once they finally get into Castro's vicinity, they apparently can't figure out a feasible way to poison him. According to Kane, the woman is captured and later executed. He somehow manages to narrowly escape. Despite Giancana and Roselli's deadly reputations.

[Co-host or Narrator]

This was just the start of their many botched attempts they launch commando missions from Florida that fizzle out.

[Carter Roy]

Either bad luck or bad timing, or.

[Co-host or Narrator]

Their fighters are caught on Cuban shores.

[Carter Roy]

And jailed or executed. Roselli himself goes on a mission to Cuba.

[Co-host or Narrator]

He has to save himself from a sinking boat after a Cuban patrol boat attacks, riddling it with bullet holes. But even after several years, they can never get close enough to reach their target.

[Carter Roy]

Then, when President John F. Kennedy is assassinated in 1963, the CIA's ploy against Castro is put on ice. President Lyndon B. Johnson apparently tells the CIA it's time to get out of the cloak and dagger business.

[Co-host or Narrator]

So the gangsters return to their lives and act like nothing ever happened.

[Carter Roy]

Or at least that's what they're supposed to do. Roselli eventually gets into trouble with the FBI when they uncover a card playing scheme he's running out of the Friars Club in Beverly Hills. A ruse that involves spies looking through peepholes in the ceiling at each of the players cards.

[Co-host or Narrator]

He assumes he's golden, given that get out of jail free card he'd earned from working with the CIA.

[Carter Roy]

But once he realizes they aren't planning on helping him out, he threatens to go public with the entire assassination plot. When he and Giancana are asked to testify before the senate about the CIA's wrongdoings, both men turn up dead. Roselli's body is found in a metal.

[Co-host or Narrator]

Barrel dumped in a waterway near the Fontainebleau Hotel in Miami.

[Carter Roy]

If you remember, that's where they originally hatched their plan to kill Castro. Giancana is shot to death in his Chicago home.

[Co-host or Narrator]

Files show the police suspect another Mafioso is responsible for the murders of both.

[Carter Roy]

Men, though some believe the CIA had involvement. But the CIA still wants to eliminate Castro. The whole Mafia plan wasn't as fruitful as they thought.

[Co-host or Narrator]

So the CIA has to take a different approach.

[Carter Roy]

They use all the intel they have on Castro to figure out how to get close to him so they have a better shot at killing him. They look closely at his habits so they can wield them against him. He smokes cigars, so they toy with.

[Co-host or Narrator]

Poisoning one of them.

[Carter Roy]

But then he quit smoking. He loves chocolate milkshakes, so they hire.

[Co-host or Narrator]

A cook to poison his evening treat.

[Carter Roy]

But the cook can't go through with it.

[Co-host or Narrator]

They eventually turn to Castro's love life.

[Carter Roy]

How much closer can you get? Marita Lorenz was 19 years old when she met 32 year old Castro. The young German woman worked with her father on luxury ships sailing around the world. In February 1959, they happened to dock in Havana it should be noted that Marita has long been considered the patron.

[Co-host or Narrator]

Saint of conspiracy buffs, which means she.

[Carter Roy]

Has shared plenty of unbelievable stories about Castro over the years in both the press and testifying in front of a judge.

[Co-host or Narrator]

Many of her claims have been supported.

[Carter Roy]

While others have been totally disproven. So it's impossible to tell which stories are fiction and and which are the truth. According to Marita, a boat full of.

[Co-host or Narrator]

30 armed men approached her ship while.

[Carter Roy]

Her father was taking a nap. At first she thought they were going to take over their ship, but then.

[Co-host or Narrator]

One of the men politely asked her if he could come aboard.

[Carter Roy]

She asked his name. It was of course, Fidel Castro. There was an immediate attraction between them and they had a brief love affair.

[Co-host or Narrator]

Marita claims that Castro later got her.

[Carter Roy]

Pregnant, and when she was about seven months in, someone drugged her glass of milk. When she woke up, she was no longer pregnant. That's when Marita decided to move to Florida, where she got involved with anti Castro militants. Due to its close proximity to Cuba.

[Co-host or Narrator]

Thousands of wealthy Cubans fled to Florida.

[Carter Roy]

During the revolution to avoid persecution. Miami became a major hub for the anti Castro movement and also where the CIA decided to set up headquarters for their operation to help overthrow the Cuban government. In Miami, Morita is introduced to CIA agent and future Watergate burglar Frank Sturgess. Are there any conspiracy theories not involved here?

[Co-host or Narrator]

He approaches her about returning to Havana and eventually convinces her to consider killing.

[Carter Roy]

Castro on behalf behalf of the US Government. And based on their history, she has more than a few reasons to do it. The plan goes something like this. Merida Lorenz would join Castro at his hotel in Cuba.

[Co-host or Narrator]

There they would talk, reconnect, maybe order room service and enjoy a meal together. Then she would slip the two botulism toxin pills the CIA gave her into.

[Carter Roy]

His food or drink, and that would be that.

[Co-host or Narrator]

This all had to happen before a televised speech he was giving that evening.

[Carter Roy]

That way, if Castro didn't show up.

[Co-host or Narrator]

The CIA would know right away that the plan worked.

[Carter Roy]

That's how things were supposed to go. From Marita's account of the events that day in 1960, she lands in Havana.

[Co-host or Narrator]

And hops in a jeep that drives her straight to the Hilton Hotel, where.

[Carter Roy]

Castro and his regime set up a command post. In the Continental Suite, she greets the.

[Co-host or Narrator]

Workers at the front desk and walks right past them upstairs to suite 2408.

[Carter Roy]

Then she waits. When Castro finally arrives, the plan seems.

[Co-host or Narrator]

To go forward as planned, except Marita.

[Carter Roy]

Has already changed her mind.

[Co-host or Narrator]

She claims as soon as she saw the outline of Havana from the plane.

[Carter Roy]

She knew she couldn't do it. But even if she had decided to carry out the attempt, she'd already ruined.

[Co-host or Narrator]

Her chances by storing the pills in a jar of cold cream. When she digs them out, she finds they're completely unusable.

[Carter Roy]

So she flushes them down the toilet.

[Co-host or Narrator]

But she can't shake the feeling of.

[Carter Roy]

What she almost did. Castro can tell her behavior is off. He asks her plainly, did you come here to kill me? Standing at the edge of the bed, looking down at him, she admits it.

[Co-host or Narrator]

He asks if the CIA center. She says, not really.

[Carter Roy]

I work for myself. But that's a lie.

[Co-host or Narrator]

It's then that Castro hands her his.45 and urges her to do it. He wants her to shoot him and get it over with. She cocks the gun and points it right at him. But he doesn't even flinch.

[Carter Roy]

Instead, he laughs and says, you can't kill me. Nobody can kill me. He just smiles and chomps on his cigar, knowing he has her all figured out.

[Co-host or Narrator]

That evening, his speech is televised as planned.

[Carter Roy]

And the CIA knows they have another failed plan on their hands. But they have already been cooking up their biggest attempt of all.

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[Carter Roy]

At a hidden outpost in the Florida swamplands, the CIA continues to train hundreds of Cuban exiles in combat.

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Under President Eisenhower, the CIA campaign to arm and facilitate a full scale invasion.

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Of Cuba in an attempt to take down Castro once and for all. Then, once Eisenhower leaves office, President John.

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F. Kennedy inherits his plans. So on April 17, 1961, this brigade launches their invasion, starting at a pretty.

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Isolated spot on the island's southern tip, known as the Bay of Pigs. From the start, it is an absolute disaster. Naturally, the CIA doesn't want the Cuban army to know they're coming.

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But they also don't realize there's a radio station on the beach and which picks up on their communications and broadcasts it to listeners all across Cuba. It doesn't take long for Castro and his troops to catch wind of what's going on.

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Plus, the CIA and exiles are already losing some of their force.

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A few of their ships sank because.

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Of unexpected coral reefs and some of their paratroopers landed in completely the wrong place. The element of surprise is gone and they've only got a fraction of the manpower they'd planned on. President Kennedy doesn't want a full on.

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War with Cuba, so he refuses to.

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Send in any backups. When Castro's army arrives, they trap the helpless brigade on the beach.

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The CIA and exiles surrender less than.

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24 hours after the invasion begins. Over 100 soldiers are killed and more than 1,000 taken prisoner. And Castro walks away totally unscathed. Although the whole invasion wasn't Kennedy's idea, the devastating blow is his to contend with as a young president new to office. To some he appears weak and inexperienced.

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He knows he has to do something about Castro.

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Shortly after the Bay of Pigs, he approves a covert campaign called Operation Mongoose. Their mission to do what they couldn't that day topple Castro's regime without inciting World War three.

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He decides that the only person he.

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Can trust to execute his plan is his brother Robert Kennedy, the Attorney General at the time. During a November of 1961 meeting at the White House, RFK scribbled down some notes about the operation. They said, my idea is to stir things up on the island with espionage, sabotage, general disorder, run and operated by Cubans themselves. Do not know if we will be successful in overthrowing Castro, but we have nothing to lose in my estimate. And stir things up they did. There is evidence of some of the CIA's more absurd assassination plots that never quite made it past the brainstorming phase.

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There was one plan that involved the CIA investing in a large collection of Caribbean mollusks. Castro was an avid diver, so they planned to pack a large mollusk with explosives so when he picked it up, it would detonate. Another would plant a diving suit and.

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Mask that were covered in a fungus that was meant to give him a debilitating skin infection. Then there was a pen that was.

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Concealed as a hypodermic needle so fine that he wouldn't even notice he was injected with poison.

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Poison. The Cuban official who was cooperating with the CIA learned they wanted him to.

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Use this device and was apparently unimpressed.

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With how unsophisticated it was. Plus, the day he was supposed to carry out this plan happened to be the same day John F. Kennedy was killed.

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There were also plots that weren't quite lethal, but instead targeted something else, his public Persona. One plot involved an aerosol of a.

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Chemical similar to lsd, which would be.

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Sprayed in his face at a radio.

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Station where he frequently broadcasted speeches in the hopes he would hallucinate on air and humiliate Himself.

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Another wanted to sprinkle thallium salt on his shoes so his famous wiry beard would fall out.

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But the attempts to destroy his pride, much like the attempts on his life, were unsuccessful. Even with all the new declassified files that have become available, the CIA made.

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Sure there was plausible deniability at every turn.

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So it's hard to say what the.

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Kennedys did and did not know.

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But one thing is for sure. There's definitely bad blood between Castro and JFK. After all of the CIA's attempts on.

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Castro's life, some believe that it was.

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The Cuban leader himself who helped orchestrate JFK's assassination. In September 1963, just two months before President Kennedy is shot and killed in.

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Dallas, Texas, Castro sits down for an interview with the Associated Press in Havana. He warns United States leaders should think that if they are aiding terrorist plots to eliminate Cuban leaders, they themselves will not be safe.

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In retrospect, some have interpreted that as an ominous threat against the US President.

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Castro, however, went on the record over a decade later to clarify it wasn't.

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Meant as a warning of retaliation. He actually meant that the US was setting a very serious, very negative precedent that surely could only come back to hurt them. However that may be. But there are some interesting connections between Castro and Lee Harvey Oswald, the man who shot jfk. Oswald, an American citizen, felt extremely connected to the Communist cause in Cuba. He spent years as a pro Castro advocate.

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On at least one occasion, he distributed leaflets that read Hands off Cuba as.

[Carter Roy]

A member of the Communist Fair Play for Cuba organization. In September 1963, Oswald visits the Cuban consulate in Mexico City to apply for a visa to enter Cuba, but is rejected. Just two months later, he assassinates Kennedy. Once Oswald's connection to Cuba is unearthed by the press, Castro knows that he'll receive blame for Kennedy's assassination. He meets with officials investigating Kennedy's murder.

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On a yacht off the coast of.

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Cuba just so he can try and clear his name. But the official investigation determines that it was in fact Oswald and Oswald alone who was responsible for the President's death. He himself was shot and killed shortly thereafter. While Castro's name was pretty much cleared.

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He knew he was still considered an.

[Carter Roy]

Enemy of the American government. In a rare interview with Vanity fair in their March 1994 issue, Castro said, it has been my fate to lead a life full of fascinating events and experiences at the age of 67. Acknowledging how many times he'd cheated death, he added, it's not my fault the CIA has failed to kill me even after five decades in power. The final attempt on Castro's life was as recent as 2000, but this time it wasn't the CIA. At a meeting of Latin American and European leaders in Panama, four Cuban exiles.

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Had planted explosives underneath the podium Castro.

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Would be speaking at, but his security caught it first. The men were convicted of public endangerment.

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But were ultimately pardoned.

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Castro was in power longer than any other national leader aside from Queen Elizabeth II. He outlasted 11 US presidents. And as many books and documentaries like to remind the world, he was said to have had over 600 assassination attempts on his life.

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He even somehow outlived several of the.

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Journalists who wrote his obituary for various newspapers. For decades, papers like the New York Times and the Miami Herald kept a draft of Castro's obituary ready to print at any moment. He was one of the biggest targets.

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In the world, after all.

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Journalists would update it as the years.

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Went on, but occasionally the original writer would have their own obituary published in.

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The paper before Castro's.

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The papers didn't have to officially publish.

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Castro's obit until 2016, when, against all odds and attempts, he died at the age of 90, peacefully in his sleep. Thank you for listening to Conspiracy Theories. We're here with a new episode every Wednesday.

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Be sure to check us out on instagram @the conspiracypod.

[Carter Roy]

If you're watching on Spotify, swipe up and give us your thoughts for more information on Fidel Castro. Amongst the many sources we used, we found Mafia the Inside Story of the CIA, Gangsters, JFK and Castro by Thomas Mayer. Extremely helpful to our research. Until next time, Remember, the truth isn't always the best story, and the official story isn't always the truth.

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This episode was written and researched by.

[Carter Roy]

Sarah Tardif, edited by Chelsea Wood Fact checked by Sophie Kemp, engineered by Sam Amazing mezquah and video edited and sound designed by Ryan Contra. I'm your host, Carter Roy.