The Rest Is Classified – Episode 92

JFK vs the CIA: Raising Hell in Havana (Ep 3)

Date: October 19, 2025
Hosts: David McClarsky (former CIA analyst, novelist), Gordon Corera (veteran security correspondent)

Episode Overview

In this gripping episode, David and Gordon delve into the fraught relationship between President John F. Kennedy and the CIA during the lead-up to the infamous Bay of Pigs invasion. They explore the spiraling strategy, the intelligence community’s internal dysfunction, the mounting political pressure, and the high-stakes calculations that would both define Kennedy’s presidency and sow the seeds for decades of conspiracies surrounding his assassination. Drawing on original CIA documents, behind-the-scenes analysis, and sharp-witted banter, the hosts unravel how plans for Cuba became bungled, and whether they unwittingly—or purposefully—boxed a U.S. president into an impossible decision.

Key Discussion Points & Insights

1. Historical Context & Power Struggle

• Bay of Pigs Plan Origins: The show opens with a dramatic reading from a declassified CIA memo outlining early planning for an amphibious invasion of Cuba by exiles, copyrighted by covert airstrikes—setting the scene for the high-risk gambit (03:33).
• Kennedy Inherits the Mess: Upon taking office, JFK keeps Allen Dulles (CIA) and J. Edgar Hoover (FBI) on, shaping “a presidency built on continuity but loaded with Cold War baggage” (08:57). The pressure to act on Cuba is immediate—Cuba “quickly becomes the Kennedy administration’s top priority” (01:57, 12:24).
• Kennedy’s View of the CIA: Far from being anti-agency, early JFK is “fascinated” and even “enamored with the swashbuckling cold warriors at Langley,” particularly Dickie Bissell, described by Kennedy as “a man-eating shark” (10:24).

2. Planning the Invasion: Idealism Meets Reality

• Problematic Assumptions: The CIA and White House policymakers expect a “quick collapse of Castro’s regime” following an exile invasion (15:24). Gordon warns these echo “the hubris of later regime-change disasters, like Iraq in 2003” (15:24).
• Analysts vs. Operations: There is a “stovepiping” of intelligence—CIA analysts and covert operators are “entirely separate organizations at this point in time,” leading to intelligence silos and groupthink (16:20).
• Operational Issues:
  • Brigade 2506 suffers resignations and poor morale (“a few hundred of those very precious exile brigade members abruptly resign,” 21:42). The CIA, instead of reassessing, waters down recruiting standards, prioritizing “numbers over combat experience” (22:47).
  • Training conditions are harsh and unglamorous: “Happy Valley,” the main Guatemalan camp, is “definite prison vibes…infested with scorpions” (19:32).

3. Political Pressures, Urgency & False Choices

• Racing Against the Clock: Fear of Soviet arms arriving in Cuba and the impending rainy season funnel the plans into a “use it or lose it” scenario (25:00). Both the CIA and Kennedy's advisors insist time is running out.
• JFK’s Dilemma: Kennedy is stuck with “two bad choices”—scrap the plan and look weak, or risk a “public disaster” (30:41). JFK “is boxed in, perhaps by his own rhetoric during the campaign, perhaps by the CIA’s briefing” (32:16).

4. Flawed Decision-Making & Groupthink

• Shallow Policy Process: The National Security Advisor, Bundy, and JFK are “abysmally unprepared and shallowly engaged,” missing key details and failing to ask “penetrating questions” (27:03).
• Downplaying Risks:
  • Pentagon reviews are “supportive on the surface,” but “fair chance” is later defined as a mere 30% chance of success—never communicated directly to JFK (29:27).
  • Even more damning, a report notes only “15% chance of achieving surprise”—buried in a paragraph, not the executive summary (38:52).
  • No one forcefully voices skepticism: “People who harbored real skepticism…did not speak up clearly when they had the opportunity” (38:55).

Notable quote:

"If someone says to you, 'Oh, there's a fair chance this plan works,' if you're a candidate, you'll go, okay, that's pretty good. But if someone says there's a 30% chance this plan works, that feels very different."
— Gordon Corera (30:00)

5. Kennedy Tries to Minimize American Involvement

• Relentless 'Dialing Down': JFK repeatedly asks the CIA to make the operation “quieter”—to the point of being almost covertly invisible, which ironically undermines its chances of success (34:51, 40:32).
• Critical Flaw with the Bay of Pigs landing site:
  • Moving to Bay of Pigs eliminates the “escape hatch” into the mountains for the exile force—“if you get stuck, there is no escape. That’s a really, really big downside.” (42:48)
  • The optics: “How can we have a victorious landing force at a place called the Bay of Pigs?” (44:00)
• CIA and Kennedy 'talking past each other'—the agency never says, “If we tone it down, it means it doesn’t work. So which do you want?” (41:45).

6. Conspiracy Theories & Motives for Murder

• Was the CIA Setting JFK Up?: Gordon, donning his “tinfoil hat,” shares the theory that CIA wanted the invasion to fail to force US military intervention. David firmly pushes back: “I love that theory. It just doesn’t comport with the facts. That’s the problem with all good theories” (47:03).
• Mob and Castro Assassination Plots:
  • The other track is wild—Mafia bosses are paid to kill Castro, using “poison cigars,” “toxin pills,” and even “fungus-coated diving suits.” Most attempts are comically unsuccessful:

  "They test it on actual guinea pigs. But the guinea pigs, Gordon, survive. And the cigars...did not kill the guinea pig."
  — David (53:52)

  • Mob connections backfire, involving the FBI due to a bugging incident over a girlfriend (50:04).
  • This establishes the “credible motive for Castro to try to kill Kennedy”—he knows the US is coming for him (57:10).

7. Final Push and Climax: The Eve of the Invasion

• Decision Time: 4 April 1961: Kennedy, after Easter weekend (and likely a pep talk from his father), decides to launch the operation. At the critical briefing, “not one person spoke against it”—a textbook case of groupthink (60:00).
• Kennedy Still Unsure: Even as the plan is finalized, JFK keeps “tinkering,” suggesting infiltrating men in smaller units—“a troubling sign for Bissell or any of the military planners.” The question now isn’t if the invasion will happen, but how (61:55).

Most Memorable Moments & Quotes

• On the dynamic between policy and reality:

  "It kind of doesn't matter at that point if the analysts are saying, well, Assad's got a bunch of staying power. You've been handed covert action guidance from the White House—you have to do it."
  — David (17:35)

• On military review of the exile brigade:

  “The soldiers receive really high marks. But buried in that report...the operation would fail without the element of surprise, and achieving surprise had only a 15% chance of success.”
  — David (38:50)

• On CIA-planning logic:

  “Dulles and Dickie Bissell draw the exact opposite lesson from this kind of semi-mutiny... We need to move faster before this whole thing falls apart.”
  — David (22:19)

• On the risk of groupthink:

  "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."
  — David (61:21)

Timestamps of Key Segments

• 01:57 — Cuba becomes Kennedy’s immediate top priority
• 03:33 — Readout from the original CIA Cuba Task Force memo
• 08:57 — Kennedy decides to keep Dulles and Hoover
• 12:24 — Kennedy’s enthusiasm for CIA and covert action expansion
• 22:19 — Training camp turmoil, rushed decisions, shifting selection standards
• 27:03 — Critique of JFK’s policy process and lack of tough questioning
• 30:00 — “Fair chance” Pentagon report on invasion success
• 38:50 — Buried military assessment: only 15% chance of achieving surprise
• 40:32 — The myth of a low-cost failure and the disappearance of the “escape hatch”
• 42:48 — Landing site switch: why Bay of Pigs is both brilliant and terrible
• 47:03 — “CIA set it up to fail?” Conspiracy theory (and swift debunking)
• 53:52 — CIA testing poison cigars on guinea pigs (comedic failure)
• 57:10 — Castro’s motive to try to kill JFK
• 60:00 — The fatal briefing: everyone says yes, no dissent
• 61:55 — Kennedy’s last-minute tinkering; groupthink; invasion imminent

Language & Tone

True to form, the hosts combine sharp historical insight, wry humor, and a skeptical but clear-eyed approach to both documentation and conspiracy. They banter affectionately (“You seem quite excited by this failure. As your cousin across the Atlantic—deeply disturbing…”), are candid about their limited sympathies for anyone (“dealing with exiles…is never that clean, is it?”), and quote both primary sources and intelligence lingo with playfulness and gravity in equal measure.

For New Listeners

This episode offers an in-depth, accessible dissection of one of the 20th century’s most consequential intelligence failures. It clearly lays out the flawed mechanics, personalities, and cultural myths that led to disaster, while engaging with the grander, darker question: could this covert conflict have provided a motive for murder on both sides of the Straits of Florida? Whether you’re new to Cold War history or a veteran conspiracy sleuth, you’ll come away both wiser and more skeptical of “the official story.”

End of Summary.