The Rest Is Classified
Episode 91: JFK vs the CIA: Killing Castro (Ep 2)
Date: October 14, 2025
Hosts: David McCloskey (former CIA analyst & spy novelist) & Gordon Corera (security correspondent)
Episode Overview
This episode explores the fraught relationship between President John F. Kennedy and the CIA as the United States becomes obsessed with toppling Fidel Castro. Using the Bay of Pigs as the centerpiece, hosts David McCloskey and Gordon Corera examine how covert operations, bureaucratic inertia, internal agency politics, and escalating Cold War tensions pushed the Kennedy administration and the CIA towards disaster—and, in the eyes of some, laid the groundwork for later conspiracy theories about Kennedy's assassination. The episode also delves into parallel CIA plots to assassinate Castro, including outlandish Mafia collaborations and poison schemes.
Key Discussion Points and Insights
1. Setting the Stage – Cuba as JFK’s Top Priority
[00:26, 01:00, 03:32]
- After Kennedy’s election, Cuba moves to the top of his agenda. Eisenhower’s quiet regime change policy is inherited but gains urgency.
- The CIA presents itself as the administration’s action arm in the Cold War. Kennedy and his brother, Robert, are fascinated by espionage culture—evidenced by their love of Bond novels and friendly relations with spy chiefs like Allen Dulles.
2. The Bay of Pigs: Planning, Delusions, and Warnings
[02:02 – 17:46]
- Early CIA memos envision a small Cuban exile force provoking a nationwide uprising—a plan Gordon calls "wobbly" and reminiscent of later misadventures like the Iraq War.
- Analytical rigor is lacking: operational teams are siloed from analysts who might have questioned Castro’s actual support and regime durability.
- The Pentagon provides only lukewarm endorsement—privately pegging the plan’s odds of success at “fair” (30%), but communicating the risk poorly:
"If someone says to you, oh, there's a fair chance this plan works... But if someone says there's a 30% chance this plan works, that feels very different." (C at [28:29])
- Internal urgency grows as the CIA rushes to expand its exile force, loosen recruitment standards, and leverage deteriorating camp conditions to justify speed.
3. Interagency Dynamics, Groupthink, and Political Traps
[17:46 – 37:00]
- The new administration is swept up by the plan’s momentum. Senior officials—often unconvinced—fail to voice objections or highlight risks.
- Kennedy’s input is described as “shallow” (citing Jim Raisenberger’s history), and the White House lacks rigorous independent evaluation. According to David:
"A lot of the people who harbored real skepticism... did not speak up... to steer it differently, or at least to make plain how risky this was to the President." (A at [35:36])
- Crucial changes are made to “tone down” the operation for deniability, stripping away elements like the “escape hatch” into the mountains—sometimes without fully briefing the President.
4. Conspiracy Theories: Did the CIA Set Up JFK?
[39:00 – 45:02]
- Gordon floats—but maintains distance from—theorist claims that the CIA manipulated Kennedy by presenting a doomed plan, hoping a failure would force his hand to commit U.S. forces. David is skeptical:
"I love that theory. It just doesn't comport with the facts." (A at [43:44])
- Both agree that the CIA earnestly pushed for more air assets and resources, underlining internal belief (however misguided) in the plan’s viability.
5. Final Decisions Under Duress: Political, Emotional, and Familial Pressure
[45:02 – 59:18]
- As the final decision looms, Kennedy weighs bad choices: kill the operation and appear weak, or proceed and risk debacle.
- Influences include unclear risk communication, doubts about local Cuban support, and alleged discussions with his father that steel JFK’s resolve.
- In a telling moment on March 28, 1961, aide Arthur Schlesinger asks JFK what he thinks of the invasion:
"I think about it as little as possible." (JFK quote, reported by Schlesinger at [45:58])
- The fateful 4 April meeting ends with no one dissenting due to groupthink—even as many present privately harbor reservations.
6. Poison Plots and the Mafia: The Parallel Assassination Track
[46:44 – 54:04]
- The wild, often inept, CIA-Mafia efforts to kill Castro run alongside the invasion planning. Poison cigars, toxins, and mob-whispered kill squads abound, but nothing comes close to success.
- Host David relates the story of poison-laced cigars tested (unsuccessfully) on guinea pigs, and Mafia-linked exile leaders tasked with distributing deadly pills—a parallel operation shrouded in operational chaos and secrecy.
- This context partially explains why Castro, too, may have developed motive for revenge against Kennedy:
"This is where you can start to build a really plausible case for Castro to have motive to try to kill Kennedy." (A at [53:51])
Notable Quotes & Memorable Moments
-
On the CIA’s hero status in JFK’s eyes:
"Kennedy in now this 60 plus years on kind of come interpreted the story and say, oh, you know, JFK had this kind of sour view of the Central Intelligence Agency, but when he takes office, I think it's not the case at all...they love the Bond novels. I think they see the CIA guys as being these kind of swashbuckling cold warriors."
(A at [08:53]) -
Comparing CIA optimism to Pentagon realism:
"The Joint Chiefs of Staff consider that timely execution of this plan has a fair chance of ultimate success... So what does fair mean? ...Fair like a 30% chance of success?"
(C at [27:54]) -
On the psychological trap of ‘toning it down’:
"At some point, if you're Bissell, you gotta say, if we tone it down, it means it doesn't work. So which one do you want? And that doesn't happen."
(A at [38:55]) -
JFK’s disengagement:
"Schlessinger...asked JFK, what do you think about this damned invasion? And Kennedy replied, I think about it as little as possible."
(C at [45:58]) -
On Mafia-CIA plotting absurdity:
"I don't know how they got a guinea pig to smoke a cigar... but the guinea pigs, they survive."
(A at [50:33]) -
The groupthink at the pivotal meeting:
"There are a lot of people in that room who later on are going to say they had serious doubts. Not one person spoke against it. No one in that meeting votes no."
(A at [58:02])
Timeline of Important Segments
- [00:26] – Cuba becomes top JFK priority; decision-making context set.
- [03:32] – CIA’s Bay of Pigs plan revealed, inheriting Eisenhower’s regime change agenda.
- [08:53] – Discussion of Kennedy’s infatuation with CIA culture.
- [16:40] – Pentagon questions CIA’s manpower and plan feasibility.
- [24:53] – Urgency grows as Soviet aid to Cuba threatens window for invasion.
- [27:54] – “Fair chance” evaluation by Pentagon; risk communication issues.
- [35:30] – Meeting where risks are downplayed and warnings buried.
- [39:00] – Landing site change to Bay of Pigs; deniability trumps tactical soundness.
- [43:44/45:02] – Conspiracy theory: CIA playing JFK? Hosts weigh evidence.
- [45:58] – JFK admits disengagement; “I think about it as little as possible.”
- [46:44] – Parallel mobster-poison plots against Castro and their operational absurdity.
- [53:51] – Castro’s possible motive for vengeance enters discussion.
- [58:02] – Fateful 4 April decision meeting: unanimous yes, no dissenting voices.
Conclusion
The episode meticulously chronicles how bureaucratic drift, political pressure, groupthink, and poor interagency dynamics led a willing, but distracted, President Kennedy to approve a deeply flawed operation in Cuba. McCloskey and Corera peel back the layers of history, showing how the seeds of confusion and mistrust between the White House and the CIA were sown—not just in operational disaster, but in the continuing shadow of conspiracy theories about Kennedy and Castro. Next time, the hosts will unpack the disastrous execution of the Bay of Pigs and the explosive aftermath.