The Rest Is Classified – “Did Fidel Castro Kill JFK?”

Podcast: The Rest Is Classified
Hosts: David McCloskey (Former CIA Analyst & Spy Novelist), Gordon Corera (Veteran Security Correspondent)
Episode Date: October 31, 2025
Episode Type: Special Declassified Club Members-Only
Theme: Investigating whether Fidel Castro and Cuba were behind the assassination of President John F. Kennedy through connections to Lee Harvey Oswald and covert intelligence operations.

Overview

In this special Declassified Club episode, David McCloskey and Gordon Corera explore the “Cuba-Castro” theory about JFK’s assassination. Building on their previous examinations of mob and CIA “deep state” conspiracy theories, this episode scrutinizes whether Fidel Castro, motivated by repeated CIA assassination attempts against him, chose to strike first by leveraging Lee Harvey Oswald. The hosts unpack intelligence reports, defectors’ testimonies, pivotal threats, and the mysterious events surrounding Oswald’s movements just before Kennedy’s assassination.

Key Discussion Points & Insights

1. Setting the Stage: The CIA’s Cuba Conundrum and Motive

• Cuban Embassy Encounters
  Gordon Corera introduces a perspective from a former CIA officer (via Brian Littell’s book), suggesting that while Cubans may not have explicitly recruited Oswald to kill Kennedy, they exposed him to intense propaganda and revolutionary fervor that “planted the seed” for the assassination in his mind.

  “The trabajo politico would have agitated him, given him new even violent impulses. This…is where Oswald got the idea for the assassination.”
  (Corera quoting, 00:24)

• The Series’ Arc
  They remind listeners this is the final episode in a trilogy dissecting JFK assassination theories, this time focusing on the possibility that Oswald acted at Cuba’s behest, as opposed to for the mob or a “deep state” faction.
  (01:27)

2. Castro’s Strong Motive: Decades of Assassination Attempts

• Direct Motive From U.S. Plots
  McCloskey details the CIA and Kennedy administration’s repeated (and sometimes bizarre) attempts to kill Castro—including the infamous “poisoned milkshake” plot. He underscores Cuban intelligence’s full awareness of these plots, citing defectors and the former CIA Cuba Task force chief, Bill Harvey.

  “Castro believed that he had actually prevented 30 plus assassinations on his person… He’s specifically aware of plots to take his life.”
  (McCloskey, 03:05)

3. Castro’s Rare Public Threat to U.S. Leaders

• The Brazilian Embassy Episode
  In September 1963, Castro gives a pointed warning to journalist Daniel Harker:

  “US Leaders should think that if they are aiding terrorist plans to eliminate Cuban leaders, they themselves will not be safe.”
  (Castro quoted by McCloskey, 05:11)

  • This is notable as “probably the first time he’s directly threatened American leaders.”

• Link to Lee Harvey Oswald
  That article, “Castro Blasts Raids on Cuba Says US Leaders imperiled by aid to Rebels”, appears in Oswald’s local paper.

  “It’s very likely that Oswald would have read that article. I mean he’s, he’s obsessed with Cuba.”
  (McCloskey, 06:05)

4. The Pivotal Mexico City Visit

• A Mysterious Diplomatic Odyssey
  Three weeks after reading the article (late September 1963), Oswald travels to Mexico City, visiting both the Cuban and Soviet embassies.

  "Three weeks after reading an article about Castro threatening American leaders, Oswald is meeting with Cubans in Mexico City."
  (McCloskey, 08:30)

  • The CIA is heavily surveilling these diplomatic posts, signaling their importance.
  • The historical record of these Mexico City contacts is “an absolute mess,” full of gaps and ambiguities—even suggesting lost or manipulated evidence.

5. New Evidence & the Double Agent Dilemma

• Ongoing CIA Operations: Project “A.M. Lash”
  During this period, the CIA presses forward with new plots to kill Castro and explores coup options with Cuban insiders, especially a source codenamed “A.M. Lash”—actually a military officer named Cubella.
• Double Agent Intrigue
  McCloskey raises evidence from defectors that Cubella might have been a Castro “dangle” (double agent), meaning the CIA may have been manipulated into exposing its own operations.

  “Testimony… suggests that this source, A.M. Lash… may have actually been a double agent, a dangle by Castro, and that the CIA took the bait.”
  (McCloskey, 08:59)

Notable Quotes & Memorable Moments

• Motivation and Consequences:

  “Kennedy, the CIA, Bobby, had been behind numerous plots to kill Fidel… there’s some solid motive on that front.”
  (McCloskey, 03:05)

• Open Threats:

  “US Leaders should think that if they are aiding terrorist plans to eliminate Cuban leaders, they themselves will not be safe.”
  (Castro quote, relayed by McCloskey, 05:11)

• Oswald’s Obsession:

  "It’s very likely that Oswald would have read that article. I mean he’s, he’s obsessed with Cuba."
  (McCloskey, 06:05)

• Historical Uncertainty:

  “The historical record on this is an absolute mess.”
  (McCloskey, 07:50, discussing Mexico City visit coverups and confusion)

• Spycraft Irony:

  “Cubella may have actually been a double agent, a dangle by Castro, and that the CIA took the bait.”
  (McCloskey, 08:59)

Important Timestamps

• 00:24: Corera reads former CIA officer’s assessment; sets up Cuba theory intro.
• 03:05: McCloskey outlines CIA plots against Castro and Cuban awareness/motive.
• 05:11: McCloskey recounts Castro’s unprecedented threat and its publication in Oswald’s city.
• 06:05: Discussion of Oswald’s fascination with Cuba and likely exposure to Castro’s threat.
• 07:50: The enigma of the Mexico City visit.
• 08:59: McCloskey introduces the double-agent hypothesis (Cubella as Castro’s dangle).

Episode Tone & Delivery

The hosts sustain a measured, deeply sourced, and investigative style, layering intelligence community details with the flavor and unpredictability of Cold War spycraft. There’s professional skepticism, admissions of uncertainty, and a willingness to challenge established narratives—perfect for listeners fascinated by real-world espionage’s tangled motives and ambiguous evidence.

For listeners, this episode delivers a meticulously argued, source-rich exploration of the theory that Cuba—if not operationally responsible—may have indirectly shaped Oswald’s path to Dallas, all while threading in first-hand intelligence disclosures and hard-won historical nuance.