From exploding cigars to poisoned milkshakes: CIA’s 634 failed assassination attempts on Fidel Castro

(For Nicholás Maduro)

These efforts began shortly after Castro’s 1959 revolution and persisted under US presidents from Dwight Eisenhower to Richard Nixon (who oversaw 184 attempts), often involving Cuban exiles with CIA support.

Key failed plots include:

Exploding cigars and toxins: A cigar rigged to explode during Castro’s UN visit in New York; another contaminated with botulinum toxin (never delivered; Castro quit smoking in 1985).

Poison via a lover: A former girlfriend recruited by the CIA hid poison pills in her cold-cream jar, but they melted. Castro, suspecting her, offered his own pistol, but she couldn’t proceed.

Underwater traps: Explosive-filled Caribbean molluscs painted brightly to lure Castro while scuba diving (abandoned); a diving suit infected with a fungus to cause debilitating skin disease (also scrapped).

Other gadgets and poisons: Bacterial agents in tea or coffee; a toxic fountain-pen; botulin-laced chocolate milkshake at the Havana Hilton; an LSD aerosol to spray near Castro during a broadcast for public humiliation.

High-profile timings: On the day of John F. Kennedy’s 1963 assassination, a CIA agent was sent with a poison pen-syringe to kill Castro.

Later plots: In 2000, 200lb of explosives planted under a podium in Panama (foiled by Castro’s security; plotters, including CIA operative Luis Posada, jailed but pardoned; Posada denied involvement in a 1976 Cuban airliner bombing that killed 78).

Additional attempts: A sniper caught at the University of Havana; a grenade at a baseball game; mafia outsourcing (angered by lost Cuban casinos); the 1961 Bay of Pigs invasion aimed to kill Castro, Raúl Castro, and Che Guevara.

The obsession rivaled the hunt for Osama bin Laden, with former US diplomat Wayne Smith likening Cuba’s effect on American administrations to a full moon on werewolves.

Castro’s security measures doubled, constant movement, gift scrutiny thwarted them all. He famously wore a “moral vest” instead of bullet-proof gear and joked about declining a Galápagos turtle gift, noting pets die after attachment, alluding to his own endurance.

Fabian Escalante, retired head of Cuba’s secret service, documented these in his book Executive Action: 634 Ways to Kill Castro. https://www.amazon.com/Executive-Action-Fidel-Castro-Secret/dp/1920888721

After several unsuccessful attempts, US eventually shifted to a trade embargo to oust him