The Rest Is Classified: "JFK vs the CIA: Death in Dallas" (Ep 6)

Podcast: The Rest Is Classified
Hosts: David McCloskey & Gordon Corera
Date: October 29, 2025
Episode: 95

Episode Overview

This episode dives deep into the tumultuous relationship between President John F. Kennedy and the CIA in the years leading up to his assassination, focusing primarily on the secret US campaign against Fidel Castro's Cuba. Drawing on stories of botched invasions, wacky assassination plots, bureaucratic infighting, and the rise of institutional distrust, McCloskey and Corera unpack how shadowy CIA operations, organized crime, and Cold War paranoia helped create a climate ripe for conspiracy theories following JFK’s murder. The episode frames the history as an origin story for modern American suspicion of intelligence agencies—and sets up an exclusive miniseries on JFK assassination conspiracies.

Key Discussion Points & Insights

1. Setting the Scene: Bay of Pigs Aftermath & Kennedy’s Cuba Obsession

• Kennedy’s Doggedness Post-Bay of Pigs
  • Despite the Bay of Pigs fiasco, the Kennedys remain obsessively committed to Castro's downfall. "If you were expecting the Kennedy brothers to just sort of let Castro go after Bay of Pigs...you're wrong." (David McCloskey, 05:56)
• Bobby Kennedy’s Role
  • RFK becomes the White House’s hands-on Cuba chief, managing mid-level CIA and Pentagon officers, blurring lines between policy, law, and covert action.
• CIA’s Resilience
  • While the agency faces a shakeup (Dulles and Bissell exit, Helms and McCone ascend), many mid-level players persist, ensuring broad continuity rather than fundamental reform.

2. Operation Mongoose: Sabotage, Schemes, and Saboteurs

• Lansdale, The “Can-Do” Covert Operator
  • Brigadier General Edward Lansdale leads the interagency Operation Mongoose, designed to unseat Castro through sabotage, psychological operations, and insurgency.
  • "Lansdale...kind of a notorious figure. He's got a reputation as a can do covert action specialist...he is made chief of an interagency task force..." (McCloskey, 11:24)
• Absurd & Desperate Plans
  • Routine sabotage missions are joined by almost comic schemes—from airdropping airline tickets (Operation Freeride), to "toilet paper with pictures of Fidel and Khrushchev," to perhaps the most infamous, “Illumination by Submarine” to frighten superstitious Cubans using star shells on All Souls’ Day (15:05–17:14).
  • "It's a rite of passage...you have to come up with an insane idea, and you have to put that idea on paper for the historical record..." (McCloskey, 15:32)
• Operation Northwoods
  • Some dark proposals, like staging attacks on Americans to justify war (Operation Northwoods), never get adopted, but demonstrate the intense pressure on the CIA to deliver quick results.

3. Mob Connections and Poisonous Plots

• Mafia Hitmen Enter the Fray
  • The CIA, desperate, partners with organized crime figures like Johnny Roselli and Sam Giancana to kill Castro—mainly by poisoning him.
  • As one effort fizzles, Bill Harvey (legendary if erratic CIA man) whittles the mafia plot to just Roselli; attempts to poison Castro’s favorite chocolate shake fail spectacularly due to mishaps (24:27).
• The CIA’s “Navy”
  • The agency’s Miami station swells to one of the world’s largest, and it operates so many boats that “the agency may have controlled the third largest navy in the Caribbean” (McCloskey, 27:08).

4. The Cuban Missile Crisis & New Restraints

• The Crisis Explodes (30:03)
  • Missiles spotted on Cuba force JFK to choose between invasion (pushed by the military) and diplomatic brinkmanship. He chooses the latter, learning from prior missteps:

    "He could have taken that opportunity to...get rid of Castro. But he’s learned to be skeptical and back away from the most aggressive option..." (Corera, 31:37)

• Operation Shut Down
  • With 40,000 Soviet troops now in Cuba, the White House clamps down on sabotage and invasion attempts.

    "RFK goes to Mongoose, goes to the CIA and basically says, shut down the Cuba operations." (McCloskey, 33:03)

• Rogue Operations
  • Bill Harvey disobeys, running an infiltration during the missile crisis, infuriating RFK and ending Harvey’s CIA career.

5. Final Assassination Plots & Conspiratorial Webs

• Enter Desmond Fitzgerald—and the Exploding Seashell
  • New leadership (Des Fitzgerald) brings new, equally eccentric assassination ideas—like the “exploding seashell” intended for Castro while scuba diving (37:32).
• Operation AM/LASH
  • The CIA tries to recruit Rolando Cubela, a Cuban military officer, as a coup plotter/assassin. He’s ultimately supplied with a poison-injecting pen on November 22, 1963—the very day JFK is killed in Dallas (43:52–44:55).
  • "The pen...which the CIA hopes will finally put an end to Fidel Castro, is delivered to Cubella on When else? November 22nd of 1963." (McCloskey, 44:27)

6. The JFK Assassination: Chaos, Conspiracies, and Institutional Distrust

• The Shooting in Dallas (44:55)
  • Detailed recounting of the events in Dallas:

    "At 12:30pm, JFK...is riding in an open top motorcade...three shots are fired...He is rushed to Parkland Hospital and declared dead by 1pm..." (McCloskey, 44:55)

• Seeds of Suspicion
  • Oswald’s bizarre biography (defection to USSR, pro-Cuba activities, Mexico City trip) and the presence of Agency/Mafia enemies feed speculation.
  • The Warren Commission, notably featuring ex-CIA chief Allen Dulles, finds Oswald acted alone, but leaves a legacy of suspicion:

    "The official record...is not trusted by the majority of Americans and at one point in the late 90s was not trusted by 80% of Americans." (McCloskey, 48:51)

  • This period, hosts argue, marks the beginning of mass American distrust in institutions, fueled by CIA secrecy and unsavory covert actions.

Notable Quotes & Moments (w/Timestamps)

• "The heat's actually going to get turned up after the US failure"
  Gordon Corera, 05:34
• "It's basically a rite of passage...you have to come up with an insane idea."
  David McCloskey, 15:32
• Operation Northwoods:

  "Operation Northwoods, which was to create pretexts that would provide justification for US military intervention in Cuba...carrying out a terror campaign in the Miami area that could be blamed on Castro."
  David McCloskey, 19:59

• On the JFK assassination’s aftermath:

  "Case closed, right?... That's the thing is...case is absolutely not closed in the minds of most Americans."
  David McCloskey & Gordon Corera, 46:45–46:49

• On distrust as an enduring legacy:

  "I think the Warren Commission...riddled with politics and problems and conspiracies of its own...this distrust of institutions, this distrust of the Central Intelligence Agency...the seeds of that distrust start in this period."
  David McCloskey, 48:51–50:29

• On why conspiracies flourish:

  "People are going to want to look for answers...because of this history with the CIA and because...Lee Harvey Oswald has this kind of curious background, there’s going to be layers of secrecy ...and so we'll have more time...to explore who we really think did kill Kennedy."
  Gordon Corera, 50:29–51:49

• On Bobby Kennedy’s private doubts:

  "...in the wake of the assassination, Bobby Kennedy asks McCone if the CIA did it. Bobby Kennedy wonders if it could have been the Cubans...these are not zany ideas. These are hypotheses...held by senior officials."
  McCloskey, 51:49

• Historical moment:

  "The flash apparently official President Kennedy died at 1pm Central Standard Time."
  News Interjection, 02:19

Structural Timestamps for Important Segments

• [05:15]: Aftermath of Bay of Pigs & the Cuba Project
• [08:02–12:20]: CIA leadership reshuffles; rise of Operation Mongoose
• [15:05–19:59]: Absurd and illegal covert ops, pressure on the CIA, Operation Northwoods
• [21:27–27:46]: The Mafia connection and failed assassination attempts
• [30:03–34:01]: Cuban Missile Crisis changes the rules; Bill Harvey's rogue ops explode
• [36:33–38:10]: Fitzgerald's "exploding seashell" and CIA's persistence
• [40:15–44:30]: Recruiting Cuban military for assassination; the poison pen
• [44:55–46:45]: JFK's assassination—minute-by-minute account
• [48:17–50:29]: The Warren Commission, birth of institutional distrust
• [51:49–53:25]: Bobby Kennedy’s suspicions and the shadow of Vietnam

Episode Tone & Takeaways

The conversation is sharp, occasionally sardonic, and deeply informed—deliberately painting the era's covert actions as a tragicomic spiral: from promising idealism to desperate, sometimes ludicrous plotting. The hosts blend spy-thriller drama with sober historical analysis, never shying from the moral and political aftershocks.

Main Takeaways:

• The anti-Castro crusade epitomized the perils of unrestrained covert action, and the Kennedy administration’s entanglement with the CIA left a legacy of operational chaos and political suspicion.
• Failures, secrecy, and bizarre assassination attempts seeded modern conspiracism and deep suspicion of American institutions.
• The shadowy intersection of government, organized crime, and Cold War paranoia continues to fascinate, and the official story retains more doubters than believers.

For more on JFK assassination conspiracies and the CIA, the hosts tease a members-only miniseries available at the show's website.