United States of Kennedy: "The Bay of Pigs"

iHeartPodcasts | November 17, 2025
Hosts: George Civeris & Julia Claire
Guest: Dr. Steven Wilkinson (Chairman, International Institute for the Study of Cuba)

Main Theme

This episode delves into the infamous Bay of Pigs invasion of April 1961, examining it as a defining humiliation of the Kennedy presidency and a consequential flashpoint in US-Cuba relations. With expert insights from Dr. Steven Wilkinson, the hosts dissect how a covert US-led operation to topple Fidel Castro dramatically failed—shaping Cold War tensions and the Kennedy legacy.

Key Discussion Points & Insights

Setting the Stage: Revolutionary Cuba & US Policy (05:10–09:18)

• Post-revolution Cuba: Castro-led government embarks on sweeping social changes: agrarian reform, literacy campaigns, cultural and healthcare reforms.
• Flight of the elite: Wealthy and upper-middle-class Cubans flee, mostly to the US.
• US-Cuban relations: Rapidly sour after US imposes sanctions; Cuba moves closer to the USSR for economic survival.

  "The government's carrying out a series of reforms... The country is in a state of flux, and the upper classes and the middle classes have largely begun to leave the island." — Dr. Wilkinson (05:10)

• Nationalization triggers US wrath: Castro’s move to seize US refineries after US companies refuse to process Soviet oil is a "cardinal sin" (08:10).

Eisenhower Origins & CIA Covert Planning (09:18–14:27)

• Popular Castro: Initially celebrated in the US for overthrowing Batista and is welcomed by liberals.
• Bad blood with Nixon: Vice President Nixon, after a frosty and suspicious meeting, becomes convinced Castro must be ousted.

  "Nixon, as you know, was a very vehement anti-communist and took the decision after meeting Castro that Castro was a dangerous communist and had to be gotten rid of." — Dr. Wilkinson (11:34)

• Plausible deniability: The CIA is ordered to keep US involvement hidden, drawing on the Guatemala coup playbook; secrecy proves impossible.

The Kennedy Dilemma: Inheriting—and Retooling—Disaster (21:40–27:11)

• Political corner: Kennedy must appear tough on communism yet is skeptical of inherited covert plans; wants to distance US from coup tactics.
• Internal conflict: Advisers urge caution, fearing a reversal of goodwill via the Alliance for Progress initiative.

  "You can’t do both things. You can’t be trying to be kind and at the same time do something like this.” — Dr. Wilkinson (24:24)

• CIA manipulations: The agency oversells the project, insisting Castro is unpopular and Cubans will rise up against him.
• Reluctant green light: Kennedy allows the invasion but restricts overt US military support—setting the stage for failure.

The Plan Evolves: Logistics, Secrecy, and Poor Intelligence (29:38–38:01)

• Planned in Trinidad: Chosen for anti-Castro sentiment and potential for "legitimate" government installation.
• Switched to the Bay of Pigs: After Castro quashes nearby counter-revolutionaries, the ill-suited, impoverished, and staunchly pro-Castro local community at Bay of Pigs becomes the destination.

  "They were 100% behind Castro... they had formed a militia to defend the country." — Dr. Wilkinson (33:40)

• Secret's out: Family connections, media leaks (notably the New York Times), and loose lips doom any real operational stealth.

  "Kennedy actually said Castro doesn’t need any spies when he’s got the New York Times." — Dr. Wilkinson (38:01)

Execution: A Botched Invasion (43:20–57:38)

• Initial bombardment: A CIA-arranged false-flag air attack falls flat, with Cubans quickly identifying the ruse.

  "[Adlai Stevenson] is the guy that is given the job of going to the UN ... the Cubans basically blow him out of the water because they point out... it’s a fake." — Dr. Wilkinson (49:03)

• Kennedy calls off further airstrikes: After Stevenson embarrassingly presents fake pilots at the UN and protests.
• Failed landings: The community is well-prepared, and Castro’s regime preemptively neutralizes any anti-government element through mass detentions.

  “When the invasion started... Castro ordered the Committees for the Defense of the Revolution to make citizens arrests of every single person they suspected might be supportive of the Americans.” — Dr. Wilkinson (47:02)

• Logistical nightmares: Coral reefs, mis-timed airstrikes (due to time zone errors), and the well-defended, swampland landing zone doom the brigade.
• Rapid defeat: Within 72 hours, the invading force is battered, cut off, and surrenders; about 200 killed, 1,200 taken prisoner.

Aftermath & Historic Legacy (57:38–75:12)

• Captured exiles traded for supplies: Castro negotiates their release in exchange for baby food and medicine.
• Dueling narratives:
  • Cuban perspective: "First defeat of Yankee imperialism"—site now memorialized, veterans honored as heroes.
  • Cuban exile/American perspective: Seen as betrayal by Kennedy and the US government. Veterans of Brigade 2506 often blame the CIA now, but Kennedy’s public acceptance of blame shaped the popular narrative.
• Long-term impacts: The disaster cements hostility and hardlines on both sides, producing ripple effects through Cuban-American activism (including involvement in Watergate and anti-Castro terrorism).

  “For the Communist Party in Cuba and the supporters of the revolution, this is a very, very proud moment in their history... whereas, of course, in Miami, this is remembered as a betrayal of great magnitude by the American government.” — Dr. Wilkinson (64:44)

• Enduring chill: Relations remain strained, with US-Cuba antagonism persisting through decades.

  “...this breakdown of the relationship between the United States and Cuba ... is a very, very important event in creating that division.” — Dr. Wilkinson (68:08)

Notable Quotes & Memorable Moments

• On the era’s failed secrecy:
  "You can’t train 1,500 Cubans secretly because they’re going to communicate with their family and their families are going to talk to other people.” — Dr. Wilkinson (38:06)

• On Kennedy’s balancing act and the CIA’s duplicity:
  “[The CIA] lied to Kennedy ... they told Kennedy that, 'Oh, this thing will be okay, these people will land and the Cubans hate Fidel Castro.' ... And Kennedy, more or less, told the CIA, 'Well, if that’s the case, go ahead, but it’s you guys that are gonna have to do it. Don’t expect support from us.'" — Dr. Wilkinson (24:40)

• Describing the disastrous landing:
  “They thought it was seaweed or something and it was a very sharp coral reef. So immediately they had to get off the vessels earlier than they normally would and walk in the water and carry whatever they could on their back.” — George Severis (61:52)

• Summing up the complete failure:
  “I mean, yeah, what could go wrong seemed to go wrong partly through bad luck, mismanagement, hubris ... It was that rare thing in history, the perfect failure, this kind of oxymoronic expression.” — Dr. Wilkinson (63:02)

• On the Cuban and Cuban-American memory:
  “In Cuba, this is the first victory of Yankee imperialism in the Western Hemisphere... Whereas, of course, in Miami, this is remembered as a betrayal of great magnitude by the American government.” — Dr. Wilkinson (64:44)

• Reflections on cultural ties despite politics:
  “Cubans love American culture...The national drink of Cuba is called a Cuba Libre and it's a mixture of rum and Coca-Cola, for God's sake. What more do you need?” — Dr. Wilkinson (75:22)

Important Timestamps

• Cuba’s post-revolution transformation: 05:10–09:18
• Eisenhower and origins of the Bay of Pigs plot: 09:18–14:27
• Kennedy’s initial position and the CIA’s sales job: 21:40–27:11
• Trinidad plan and switch to Bay of Pigs: 29:45–37:11
• Media leaks & failed secrecy: 38:01–39:31
• Execution of the invasion & three days of fighting: 53:23–57:38
• Aftermath, prisoner swap, and legacy: 57:38–75:12

Summary

This episode expertly weaves together the policy history, operational comedy of errors, and long-term consequences of the Bay of Pigs debacle. Listeners will understand how a Cold War attempt at regime change, rooted in arrogance, poor intelligence, and institutional inertia, became a legendary failure—one that not only haunted Kennedy but also fundamentally altered the US-Cuba relationship for generations. Dr. Wilkinson’s expertise and the hosts’ sharp commentary make the political drama vivid and relevant, highlighting both the human and historic dimensions of the story.