Podcast Summary: The Rest Is Classified – Episode 94

JFK vs the CIA: The Mafia Plot (Ep 5)
Air Date: October 27, 2025
Hosts: David McCloskey & Gordon Corera

Overview

This episode takes a deep dive into the catastrophic Bay of Pigs invasion, focusing on the tangled relationship between President John F. Kennedy and the CIA. Through riveting historical detail and sharp analysis, McCloskey and Corera break down how a clandestine operation intended to spark revolt in Castro's Cuba unravelled into disaster—spawning a bitter blame-game inside Washington and hardening JFK’s resolve on both Cuba and Vietnam. Along the way, they explore the personal, political, and bureaucratic fallout from the failed mission and set the stage for the final confrontation between Kennedy, Castro, and the intelligence community.

Key Discussion Points & Insights

1. Setting the Scene: JFK, the CIA, and Cuba

• Escalating Priorities: Cuba rockets to the top of Kennedy’s foreign-policy concerns immediately after his inauguration, with the Bay of Pigs intended as a display of American covert might.
  • "Kennedy really looks to the CIA to get the business of the Cold War done." (David McCloskey, 03:12)
• Operation Plan: The CIA-backed exile Brigade 2506 would land at Bay of Pigs, hold a narrow beachhead, and spark a popular uprising against Castro.
  • The site was chosen for its defensive swamps—not as a springboard for a march to Havana (06:55–10:23).
  • "It is a beautiful area... looks like the kind of place you might want to plop a beach resort down. But the plan..." (David McCloskey, 07:22)

2. The Catastrophic Landing: Everything Goes Wrong

• Key Failures:
  • Coral Disaster: CIA analysts wrongly concluded there was no coral; landing troops had to disembark far from shore, slowed by jagged rocks.
    • "Those imagery analyst eggheads back in D.C. screwed up." (David, 13:10)
  • Local Interference: Nighttime fiesta lights up the beach; accidental signals alert Cuban militia and trigger early firefights (14:13).
  • Operational Disasters:
    • Rusty winches alert everyone with noise; half the landing craft are lost or unusable; precious supplies are stranded.
    • "Even if the coral hadn't been there, you've lost 6 of your 8 landing craft..." (David, 17:29)
• Crucial Lack of Air Cover:
  • Kennedy, determined not to use overt US military force, repeatedly refuses to authorize direct air support.
    • "JFK is just doing what he said he would—no direct military intervention." (Gordon, 21:30)

3. Castro's Blitz & Collapse of the Brigade

• Castro's Tactical Response:
  • Receives word of the landing at 2:30 AM; swiftly scrambles air power to strike at the landing ships, not just the men on the beach (22:13).
  • Massive losses as the Houston and Rio Escondido ships are destroyed, cutting off supplies and marooning Brigade units far from their objectives.
    • "The Houston's hit...some are killed by sharks, some drowned." (David, 23:15)
• Doctrinal Failure:
  • Air support confusion: Brigade’s B26 bombers, disguised like Castro’s own, sow friendly-fire risks and are hamstrung by fuel limitations.
  • CIA on the ground realizes within hours the plan is doomed; desperate requests for US military aid are denied (26:09).

4. Personalities & Politics in Crisis

• Castro's Showmanship:
  • Arrives at the front, takes command, and uses victory for propaganda and political consolidation (27:06).
• Inside Washington:
  • Oval Office mired in gloom as news spreads globally, with US embassies worldwide besieged by protests (37:31).
  • JFK’s private anguish and public calculation are juxtaposed—he contemplates moving Bobby Kennedy to run the CIA and starts preparing to lay blame (41:12).
    • "Already kind of scapegoating them...we have to deal with the CIA." (David, 41:35)
• Brigadistas’ Desperation:
  • Repeated, frantic appeals for promised support go unanswered.
    • "Do not see any friendly air cover, as you promised. Need jet support immediately." (Pepe San Roman’s message, 1:25 PM, David, 41:35)

5. The Final Collapse

• "One Last Stand":
  • Ammunition gone, supplies lost, and men fighting in waist-deep water.
  • Castro’s encirclement ends in retreat, destruction of equipment, and dissolution into the swamps.
    • "I can't wait for you." (Pepe San Roman’s final message, 49:22)
• Aftermath:
  • In Cuba, defeat consolidates Castro’s power and justifies a police state. Brigadistas face years in brutal captivity.
  • In the US, the CIA is pilloried, and Kennedy is wracked with guilt but resolves to redouble efforts against Castro and in Vietnam.
  • "We not only look like imperialists, we look like stupid, ineffectual imperialists, which is worst of all." (White House aide journal, quoted by David, 51:27)

6. Blame, Scapegoating, and the Shadow War

• The Blame Game:
  • Kennedy and his aides quietly feed the narrative that the CIA, especially Allen Dulles, botched and oversold the plan.
    • "If this was Britain, I'd resign, and you would remain. But...you and Alan Dulles have to go and I remain." (JFK to CIA's Bissell, 55:07)
  • Dulles and CIA leaders counter in their memoirs that Kennedy failed to supply crucial air support.
  • Maxwell Taylor’s official report blames CIA for "sins of omission" and lack of candor (60:25).
• Enduring Lesson:
  • The CIA, with no natural constituency, is an easy scapegoat for failed covert action (58:07).
  • The episode foreshadows mounting White House–CIA tension—a thread that runs straight toward the ensuing assassination conspiracies.

7. Consequences: Foreign & Domestic Policy

• Cuba:
  • The survivors of Brigade 2506 are eventually traded for medical aid and returned to Miami—against JFK's hope that they'd reclaim Havana (65:06).
• Kennedy’s Psyche & Vietnam:
  • Humiliated but unbowed, JFK commits to ousting Castro and instructs the Pentagon to escalate in Vietnam—signalling the larger wars to come.
  • "In pretty much immediate aftermath...JKF directs the Pentagon to create a presidential task force on Vietnam." (David, 53:44)
• CIA–White House Rift:
  • Seeds of deep mutual distrust are planted; both sides retreat into their own narratives as national and personal politics collide.

Notable Quotes & Memorable Moments

• On CIA hubris:
  • "Coral analysts have hugely failed." (David, 13:13)
• On Kennedy’s calculation:
  • "At every point up to this critical meeting, JFK has been essentially walking things back. Right, let’s get the boats further out. No air support. On and on..." (David, 39:08)
• On Castro’s propaganda victory:
  • "He’s beaten the Americans...he uses the Bay of Pigs as an excuse to tighten his grip inside Cuba." (David, 62:09)
• On the politics of blame:
  • "I think there is something evergreen here—which is the CIA...has no ability to defend itself from those kind of attacks. So it is a very helpful scapegoat..." (David, 58:07)

Key Timestamps

• 02:39–06:11: Setting up Kennedy, Cuba, and the Cold War context
• 06:55–14:13: The Bay of Pigs landing plan and first disastrous missteps (coral, fiesta, firefights)
• 16:25–18:00: Logistical failures and the air cover dilemma
• 21:16–26:09: JFK’s refusal to escalate and the resulting military catastrophe
• 27:06–34:38: Castro’s response and the unraveling on the beaches
• 37:03–41:35: White House crisis meetings and blame shifting begins
• 45:08–47:48: The abortive "one hour" air cover: lethal time-zone error (and finger-pointing)
• 49:22: End of the line for Brigade 2506—collapse and surrender
• 51:27–56:26: Political aftershocks, legacy, and the shaping of a dangerous new Kennedy doctrine

Tone & Style

Insightful, dramatic, occasionally wry—McCloskey and Corera sustain a gripping, sometimes darkly humorous narrative with sobering, poignant asides. The hosts blend deep research, sharp argument, and human moments of decision, confusion, and heartbreak.

Conclusion

This episode expertly unfurls the inside story of the Bay of Pigs fiasco, illuminating the complex interplay of covert action, leadership failure, and bureaucratic hubris. With clear-eyed skepticism for post-factum narratives, the hosts lay bare how the disaster not only solidified Kennedy’s enmity toward Castro but also redefined America’s global posture—and its secret war at home.

Next episode: The final act—how the Kennedy–Castro–CIA triangle leads inexorably toward November 1963 in Dallas...