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Episode 90: JFK vs the CIA: The Battle for Cuba (Ep 1)

Air Date: October 12, 2025
Hosts: David McCloskey (former CIA analyst, spy novelist), Gordon Corera (veteran security correspondent)

Overview

In this first episode of a six-part series, McCloskey and Corera launch a deep exploration of the fraught and fateful relationship between President John F. Kennedy’s White House and the CIA, with Cuba as their battlefield. Through detailed storytelling and vivid historical context, the hosts unpack how Cold War intrigue, covert action, and government-mob collusion intertwined—and how these dark currents ultimately shaped American politics, culture, and enduring conspiracy theories around JFK’s assassination.

Key Themes and Episode Structure

• The Explosive Relationship: JFK, the CIA, and the mission to overthrow Castro
• Setting the Stage: Pre-revolutionary Cuba—American playground, mob haven
• Castro’s Rise: Nationalism, radicalism, and the anti-American pivot
• America’s Dilemma: From cautious engagement to covert action and regime change
• The CIA in the 1950s: WASPish elites, unchecked power, and the birth of covert operations
• Seeds of Conspiracy: How Cold War schemes morphed into enduring public suspicion

Detailed Summary & Discussion Points

The Stakes: Cuba Becomes Washington’s Obsession

• [00:56] David McCloskey: “Cuba itself is really quickly going to become the Kennedy administration’s top priority.”
• The episode opens with archival audio on JFK’s death, setting a somber tone of historical consequence.
• The hosts highlight Cuba as the unexpected “epicenter” of Cold War rivalry, capturing Kennedy’s, the CIA’s, and the mob’s competing interests.

Setting the Tone: The Godfather II Parallel

• The hosts dramatize a scene from The Godfather Part II to underscore real-life collusion between the US government, exiled mobsters, and intelligence agencies targeting Castro.
  • [03:56] David McCloskey: “All these mobsters have been shoved out of Havana, lost all their money, and...they’re finding that they have an overlapping interest with the United States government and with the Central Intelligence Agency to stick it to Fidel Castro.”

Cuba Before Castro: The American-Mob Playground

• Geographical proximity: Cuba is only 90 miles from Key West, a fundamental factor in US foreign policy fears ([11:45]).
• Historical control: Extensive political and economic domination by the US since the Spanish-American War.
• Mob influence: Havana in the 1950s rivaled Las Vegas as a hub for American mob bosses, casinos, and vice.
  • [15:50] David McCloskey: “The Batista regime has struck a deal with the American mob...it’s a symbiotic relationship between the regime and the mob.”
  • [16:51] Gordon Carrera: “It’s a kind of playground for the mob, isn’t it...a decadent, particularly Havana in the 50s, in which it is pretty wild.”
• Cultural iconography: The mob’s power, debauchery, and celebrity allure made Havana “the actual Las Vegas of the 1950s” ([17:10]).

Batista, Corruption, and the Cuban Grievance

• US-backed dictator Fulgencio Batista is portrayed as “fabulously corrupt,” pocketing millions, and maintaining power through violence and mob money ([15:32], [15:50]).
• The reality of “Yankee exploitation” and economic hardship sows deep anti-American resentment and primes the island for revolution ([19:53]).

Castro’s Biography and Revolutionary Charisma

• Early life as a nationalist, shaped by direct experience of American corporate dominance ([22:58]).
• [24:28] Gordon Carrera notes: Castro was more a nationalist and anti-imperialist than a committed communist at first.
• Prison, exile, alliance with Che Guevara, and a daring return to lead a successful guerrilla war against Batista ([28:30]).
• [28:54] David McCloskey: “He is remarkably charismatic. He is a force of nature. He is a gifted orator and somebody that people want to follow.”

Washington’s Initial Ambivalence Towards Castro

• On gaining power, Castro becomes an American media darling—embraced even by elements of the counterculture ([32:22]).
• [32:33] David McCloskey: “Spring of 1959...you might have given them a costume Fidel beard made from treated dog or fox hair. That was a common novelty item in America.”
• CIA officers initially doubt that Castro is truly a communist, reflecting confusion within the US government ([33:51]).

The Turn: Nationalization, Mob Fury, Rising Tensions

• As Castro nationalizes US assets and kicks out the mob, he gains potent enemies among American business, organized crime, and anti-communist officials.
• The US policy quietly shifts, culminating in a State Department strategy to “encourage and coalesce opposition” to Castro while avoiding open intervention ([39:29]).

Notable Quote

• [46:48] David McCloskey (quoting Dulles):
  “What is the CIA? ...It’s the State Department for unfriendly countries.”
  (An encapsulation of the CIA’s covert-action ethos.)

Introducing the 1950s CIA: Culture, Power, and Agency

• Elites in charge: Led by Allen Dulles and staffed by Yale/Bullingdon types, the CIA is portrayed as a clubby, energetic old-boys’ network with minimal oversight.
  • [40:17] Corera’s skeptical sighs: “A deep state endures.”
  • [43:28] Corera: “There is this sense in which Allen Dulles is emblematic of a certain type of American elite and a certain view of the world and of what the CIA should do.”
• Unchecked authority: Congress offers little interference; executive branch directs policy.
• Mission: Roll back communism covertly, not through open war—using coups, subversion, and assassination as tools.
• Rapid growth: By the end of the 1950s, the agency is “sprawling” both in real estate and influence ([49:47]).

Shifting Towards Regime Change

• The State Department’s covert directive leads the CIA into plotting against Castro, even as agency assessments lag in calling him a communist ([51:29]).
• Enter Richard “Dickie” Bissell—a quintessentially elite, energetic CIA operator, becomes the architect of anti-Castro covert action.
  • [54:37] McCloskey: “He’s full of manic energy...a PhD who could win a bar fight.”
• Assassination discussions: By late 1959, Bissell formally suggests considering “elimination” of Castro; Dulles tones it down to “removal” ([57:31]).
  • The seeds for the CIA’s involvement in plots against Castro are sown, a thread that will later reappear in JFK conspiracy theories.

Notable Quotes and Memorable Moments

| Timestamp | Quote | Speaker |
|:---:|---|---|
| 03:56 | “What better way...than to read from the Godfather Part 2...It sets the tone for this, this whole series about this insane chapter in the Agency's history.” | McCloskey | | 08:59 | “So much of the talk about what the CIA could do is shaped by what’s come out through the stories related to JFK.” | Carrera | | 15:50 | “The Batista regime has struck a deal with the American mob...a symbiotic relationship between the regime and the mob.” | McCloskey | | 24:28 | “He’s primarily a nationalist at this point, isn’t he, rather than a communist?” | Carrera | | 32:33 | “If you were looking for a great party gift to give someone, you might have given them a costume Fidel beard...” | McCloskey | | 46:48 | “What is the CIA? ...It’s the State Department for unfriendly countries.” | McCloskey (quoting Dulles) | | 54:37 | “He’s full of manic energy...a PhD who could win a bar fight.” | McCloskey (on Bissell) |

Timestamps for Major Segments

• 00:56–04:55 — Setting the Series: Why Cuba? Godfather II analogy
• 11:45–21:53 — The pre-revolutionary Cuba: US dominance, mob rule, economic background
• 22:58–28:30 — Castro’s emergence, background, and revolutionary victory
• 29:38–35:21 — US confusion: How do we handle Castro? The “cool” rebel; business losses and growing hostility
• 39:29–46:47 — US policy shift: Quiet regime change, CIA empowerment
• 46:47–54:37 — CIA of the 1950s: Personnel, mission, lack of oversight, growth
• 54:37–58:58 — Richard Bissell and the move toward covert action and assassination plots

Tone & Style

• Conversational and witty, yet precise: The hosts blend narrative history with wry asides and references to pop culture.
• Insider’s insight: McCloskey lends first-hand CIA experience; Corera offers journalistic skepticism.
• Directly engaging the audience: Frequent invitations to question official narratives and explore deeper conspiracy theories.

Closing & What’s Next

The episode concludes with the hosts teeing up the coming installments: the disastrous Bay of Pigs invasion, the unraveling of US-Cuba relations, and a descent into the assassination plots and cover-ups that forever changed American history.

[58:58] Gordon Carrera: “So there, with plans for elimination or removal of Fidel Castro and his beard by the CIA, we’re going to leave it. Next time: join us as we look at how those plans evolve and lead to what is, I think, David, one of the greatest catastrophes for the CIA with the Bay of Pigs invasion…”

For Further Exploration

• Exclusive miniseries for Declassified Club members delving into the JFK assassination and related theories, featuring guest Anthony “The Mooch” Scaramucci.
• Book recommendation: Havana Nocturne by T.J. English for a deeper dive into the Havana mob scene.

Summary prepared for listeners new to the podcast or this series, highlighting all major themes, events, and characters in the episode—while capturing the spirit, tone, and texture of the hosts' discussion. Advertisements, audio distractions, and non-content sections have been omitted for clarity.