Conspiracy Theories

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

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.

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.’”

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.”

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]

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.”