Cuban dictator Fidel Castro died over the weekend at age 90 of natural causes. That’s a remarkable achievement in and of itself—the Communist leader was a long-time declared enemy of the American government, which tried to kill him lots of times. He thwarted and survived them all.

The ol’ poisoned seashell

Castro enjoyed scuba diving in the Caribbean Sea off the coast of Cuba. That coast was also home to large-shelled Caribbean mollusks. According to declassified documents, at one point, the CIA rounded up hundreds of those mollusks with hopes of finding one with a shell large enough to stuff explosives into. Then it would be painted in bright colors and planted in an area Castro was known to go diving. The reasoning went that the shell would be so pretty that Castro would pick it up, and BOOM.

The ol’ poisoned diving suit

Another scuba-related death plot: The CIA wanted to smuggle into Castro’s possession a special diving suit. What made it special was that it would be lined with a fungus that would slowly infect Castro with a horribly painful skin disease.

The ol’ poisoned cigar

Castro loved cigars—after all, he had easy access to what are regarded as the finest cigars in the world: Cuban cigars. In 1960, a box of poisoned tobacco was whipped up, contaminated with botulinum toxin to be rolled into cigars, which Castro would smoke and then die almost immediately. While the cigars made their way into Cuba, the cigars never reached Castro himself.

The ol’ girlfriend-with-secret poison

In 1959, Castro’s former flame Marita Lorenz was recruited by the CIA to rekindle her romance with the dictator, and then use her access to kill him with poison pills. Lorenz smuggled them into Cuba inside of a jar of face cream…where the pills dissolved.

The ol’ poisoned milkshake

In the early 1960s, two unlikely parties came together to go after Castro. The CIA wanted to stop the Communist dictator, and so did the Mafia, because Castro had cracked down on organized crime on the island nation. The plan was to poison a milkshake and serve it up to Castro during a visit to the Havana Hilton. According to one report, the milkshake got spilled on the floor before it could be consumed by El Comandante.

The ol’ bundle of explosives

Not every assassination attempt on Castro was orchestrated by the U.S., and not all of them were clever. In 2000, a group of CIA-backed operatives conspired to place 200 pounds of explosives under a podium where Castro was supposed to speak during a visit to Panama. During a routine security check by Castro’s personal detail, the explosives were easily and quickly discovered.