The Rest Is Classified – Episode 93: JFK vs the CIA: Bay of Pigs (Ep 4)

Date: October 21, 2025
Hosts: David McCloskey (former CIA analyst, novelist) & Gordon Corera (security correspondent)

Overview

This episode dives deep into the covert planning, mishaps, and ultimately doomed execution behind the Bay of Pigs invasion—a CIA-led operation aimed at overthrowing Fidel Castro's regime in Cuba in April 1961. Framed by the power struggle and mistrust between President John F. Kennedy and the CIA, McCloskey and Corera unpack the intelligence failures, political dynamics, and the persistent role of secrecy, misinformation, and media leaks. The narrative advances towards the brink of invasion, dramatizing the chaos, indecision, and mounting sense of disaster as the operation nears its fateful landing.

Key Discussion Points and Insights

1. Setting the Stage: US, JFK, and the CIA vs. Castro

• JFK’s Approach: Kennedy viewed Cuba as a top priority, expecting the CIA to handle "the business of the Cold War" with limited US interference (00:50).
• CIA's Attitude: The CIA appeared to think it could manipulate JFK into giving last-minute military support to guarantee the operation’s success (13:16).
• Dissent and Secrecy: Despite unanimous advisor votes (in public), Kennedy’s administration was privately divided, with no clear, shared strategy (11:00).

2. Cuban Awareness & The Role of Journalists

• Castro’s Vigilance: By April 1961, Castro was well aware the US was preparing to strike. His security apparatus in Cuba and among exiles in Miami was robust, having been strengthened by Soviet KGB advisors (03:17–09:47).
• Journalistic Leaks: An investigative reporter, Ted Zolk, uncovers imminent invasion plans and nearly blows the operation’s cover in the New York Times (04:06–06:48). Though the story was partially suppressed, its appearance in the press both enrages JFK and confirms what Castro already suspected.

“I can’t believe what I’m reading. Castro doesn’t need agents over here. All he has to do is read our papers.”
— David McCloskey, quoting Kennedy's reaction to the Times article (06:48)

• Soviet Role: While there's speculation the Soviets told Castro the invasion date, it’s unclear; Castro was already on high alert (07:29).

3. The Ill-Fated Planning and Frayed Nerves

• Loss of Surprise: Strategic surprise was lost due to media leaks and infiltration by Castro’s agents among the exiles (09:47), leaving only tactical details undisclosed.
• Internal CIA Dismay: Senior CIA planners, notably Jake Esterline and Dickie Bissell, began expressing deep worry, privately calling the operation “a terrible disaster” in the making (11:16).

“Everything that could go wrong does.”
— David McCloskey (01:15)

• Kennedy’s Cold Feet: JFK continuously pressured the CIA to scale the invasion down, particularly air support, signaling his reluctance for overt US involvement (14:31).

4. Red Lines and Political Constraints

• JFK’s Public Commitment: In an April press conference, JFK set a hard public red line: “There will not be under any conditions an intervention in Cuba by the United States Armed forces.” (15:05)
• Difficult Choices: By hedging and limiting military involvement, Kennedy boxed himself in, reducing his options if the operation failed (16:04).

“You publicly box yourself in...you’re suddenly reducing the intimidatory effect you might be able to have.”
— Gordon Corera (16:04)

5. The Crucial Airstrikes Dilemma

• Underpowered Attacks: Originally planned as 16 B-26 bombers, JFK unexpectedly cut the first airstrike to only 8 planes, miscommunicating and underestimating the importance of air superiority (18:59–19:35).
• CIA’s Sins of Omission: Bissell failed to insist to JFK that destroying Castro’s Air Force was essential. The lack of forceful advocacy by CIA leaders at critical junctures emerges as a theme (19:35).

“Most of Dickie Bissell’s sins...are sins of omission. He should have said, ‘This plan doesn’t work unless we destroy Castro’s air force.’”
— David McCloskey (19:35)

• Rube Goldberg Cover Stories: The CIA’s effort to disguise the airstrikes as Cuban pilot defections—complete with staged landings in Miami—quickly unraveled under journalist scrutiny (27:32–30:17).

“Pesky journalists...refuse to tow the company line.”
— David McCloskey (29:11)

6. Collapsing Covert Stories & UN Embarrassment

• Adlai Stevenson's Fury: US Ambassador Adlai Stevenson, fed bad CIA cover stories, is humiliated at the UN and furious when he realizes he’s been lied to (32:14).

“The briefing for Adlai Stevenson contained the flavor but not the facts.”
— David McCloskey (32:16)

• Impending Disaster: As the first, insufficient airstrikes only partially destroy Castro’s planes, the CIA’s plan to finish the job with a second attack falters due to political hesitancy and State Department lobbying (37:34).

7. The 11th Hour Collapse: No Second Airstrike

• Decision Unravels: On the eve of invasion, confusion reigns—Deputy CIA Director Charles Cabell’s attempt to “double-check” airstrike approvals, along with furious cables from Stevenson, leads Secretary of State Rusk to re-raise doubts with JFK, who is “surprised” by the D-Day airstrike plan (41:03–43:41).
• Last-Minute Cancelation: Around 9:30pm before launch, JFK cancels the critical second airstrike until after a beachhead is established, a blow the CIA knows is fatal (44:17–45:47).
• CIA’s Missed Chance: Incredibly, CIA leaders Cabell and Bissell opt not to press their case directly with the President, letting the disastrous decision stand:

“Sins of omission...had an opportunity to weigh in with the President at the 11th hour...and inexplicably decided not to.”
— David McCloskey (48:23)

8. Towards the Beach: The Looming Fiasco

• Exile Brigade Sets Sail: With the operation now fatally compromised—due to loss of surprise, insufficient air support, and political wavering—the Cuban exile team heads to Cuba, the stage set for what history will call the Bay of Pigs disaster (34:16–35:29, 49:09).

“With the invasion task force primed to land..., let’s leave it and we’ll pick it up next time...this operation, with this air of doom hanging over it, unfolds in the coming hours.”
— Gordon Corera (49:09)

Notable Quotes & Memorable Moments

• “The CIA were kind of playing jfk.”
  — Gordon Corera (01:00)

• “Pesky journalists. This is going to be the part of the story I knew you would love, Gordon. The journalists coming in and shaping history.”
  — David McCloskey (03:17)

• “You can see why in the kind of exile community and why in some quarters they think at the end of the day, the US is facing off against this tiny island, Cuba. How could you lose?”
  — Gordon Corera (13:16)

• “Something has gone wrong. And all of the CIA planners had certainly taken the airstrikes and the condition of air superiority for granted. But...what matters most that night is the opinion of John F. Kennedy.”
  — David McCloskey (44:17)

Important Timestamps

• 00:26–01:18: Setting stakes—JFK, CIA, Castro, and the looming invasion.
• 03:17–07:29: Journalistic leaks, Castro’s counterintelligence, KGB involvement.
• 11:00–14:51: CIA planners panic; internal administration divisions; JFK’s red lines.
• 15:05–16:36: JFK’s press conference public commitment—no US troops in Cuba.
• 18:59–19:35: JFK unilaterally cuts bomber numbers in first strike.
• 27:32–30:17: CIA cover story about “defecting Cuban pilots” falls apart under media scrutiny.
• 32:14–33:49: Adlai Stevenson’s UN embarrassment.
• 35:16–37:34: Details of exile brigade flotilla; political interference halts planned airstrikes.
• 41:03–43:41: Deputy CIA Director’s intervention leads to confusion over authorizations.
• 44:17–48:23: Last-minute cancellation of key airstrikes and CIA’s missed opportunity to object.
• 49:09–end: Setting up for the disaster—next episode will cover what happens as the men land.

Tone & Style

• Conversational and lightly irreverent—David and Gordon banter, poke fun at "pesky journalists," critique CIA and government actors, and draw modern parallels (e.g., Biden and Ukraine, Colin Powell at the UN).
• Rich with period details ("made in Cuba" baseball caps, duck hunting camouflage, dilapidated plumbing on ships) and espionage lore.
• Nuanced criticism: The hosts repeatedly point out not just “who failed” but exactly how miscommunications, wishful thinking, and institutional pathologies doomed the plan.

Summary for Listeners

This episode brings you behind the curtain of the Bay of Pigs disaster—tracing the steady unraveling of the CIA’s plan, JFK’s no-win political calculus, and the fatal consequences of secrecy, half-truths, and “sins of omission.” With vivid storytelling and pointed analysis, McCloskey and Corera make clear how intelligence failures and political risk aversion combined to shape not just an infamous Cold War fiasco, but the very future of the American presidency’s relationship with its covert warriors. Next time: the beach landings, and the consequences, both personal and geopolitical, of the night everything went wrong.