90. JFK vs the CIA: The Battle for Cuba (Ep 1)

The Rest Is Classified

Goalhanger

History

4.6 • 732 Ratings

🗓️ 12 October 2025

⏱️ 61 minutes

🔗️ Recording | iTunes | RSS

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Summary

“I think that Senator Kennedy's policies and recommendations for the handling of the Castro regime are probably the most dangerously irresponsible recommendations that he's made during the course of this campaign.” That was Richard Nixon, in the final presidential debate of 1960, targeting John F. Kennedy's stance on Cuba. Fidel Castro has seized power, transforming Cuba, a former “playground” for American mobsters and corporations, into a nationalist state opposing the US. The Eisenhower administration, determined to oust him, tasks the CIA to destabilise and replace the regime. Join Gordon and David as they introduce the formidable figures at the heart of this confrontation: the charismatic and increasingly communist-aligned Castro, and the brilliant, manic CIA Deputy Director for Plans, Dickie Bissell. Discover the CIA's initial ludicrous ideas - from drug-laced food to a plan to make Castro's beard fall out - and the dangerous decision to subcontract a deadly task: a plot to "eliminate" Fidel, with the American Mafia. ------------------- Join The Declassified Club: Start your free trial at ⁠⁠therestisclassified.com⁠⁠ - go deeper into the world of espionage with exclusive Q&As, interviews with top intelligence insiders, quarterly livestreams, ad-free listening, early access to episodes and live show tickets, and weekly deep dives into original spy stories. Members also get curated reading lists, special book discounts, prize draws, and access to our private chat community. To sign up to the free newsletter, go to: ⁠⁠https://mailchi.mp/goalhanger.com/tric-free-newsletter-sign-up⁠ ⁠ ------------------- Order a signed edition of Gordon's latest book, The Spy in the Archive, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠via this link.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Order a signed edition of David's latest book, The Seventh Floor, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠via this link.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ------------------- Email: [email protected] Twitter: ⁠⁠⁠⁠⁠⁠⁠@triclassified⁠⁠⁠⁠⁠⁠⁠ Video Editor: Nathan Copelin Social Producer: Emma Jackson Producer: Becki Hills Senior Producer: Dom Johnson Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0	For exclusive interviews, bonus episodes, ad-free listening, early access to series,
0:09.0	first look at live show tickets, a weekly newsletter, and discounted books,
0:13.1	join the Declassified Club at the Rest is Classified.com.
0:17.3	From Dallas, Texas, the flash apparently official President Kennedy died at 1 p.m. Central Standard Time.
0:26.6	Cuba itself is really quickly going to become the Kennedy administration's top priority.
0:33.1	The next four years are going to be difficult and challenging years for us all.
0:38.3	At the end of the day, the U.S. is facing off against this tiny island.
0:42.3	How could you lose?
0:45.3	Castro will tell the General Assembly, the United States is seeking to overthrow him.
0:50.3	Kennedy really looks to the CIA to get the business of the Cold War done.
0:55.3	Castro and his fellow dictators may rule nations. They do not rule people.
1:00.8	The CIA were kind of playing, Jennifer K.
1:05.1	In the eyes of some CIA trained militants, Kennedy had become a traitor to the cause.
1:11.3	B-26 bombers of the Cuban Exile Air Force attack Castro's airfield.
1:15.9	Everything that could go wrong does.
1:18.2	Out of ammunition, men fighting in water, if no help given, Blue Beach lost.
1:24.4	The airstrike has humiliated the United States before the world.
1:28.3	Were you ever offered money to assassinate President Kennedy?
1:32.3	Directly on numerous occasions.
1:35.3	It is clear that the forces of communism are not to be underestimated in Cuba or anywhere else in the world.
1:48.0	It's like a nightmare.
1:53.0	It's something you think, well, I'll wake up tomorrow and it's not true. Can you see it, Dominic? It's our future. Cuba. 90 miles away, no goddamn justice department. No FBI.
	...

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