According to a former Cuban intelligence official, CIA assassination attempts got pretty weird during the Cold War. The target: Fidel Castro. The weapon: A delicious milkshake. Though it didn’t work, the milkshake was apparently the closest the U.S. came in over 600 attempts on Castro’s life.
Here is the story of the poisonous milkshake, and some of the curious ways they tried to kill Castro.
The end of the Cold War lifted the curtain on all sorts of strange, often brilliant stories that went on during the mid-to-late 20th century. From seeing who could dig the deepest hole in the world, to the Soviet war hero who drank American Coca-Cola disguised as vodka, the competing superpowers inadvertently provided us with a number of Great Big Stories.
This is the one about a deadly milkshake, the Central Intelligence Agency and an elaborate plan to kill Cuban leader Fidel Castro. It all sounds so utterly inconceivable, it’s hard to imagine that this really happened, or that it was a fairly close call. As well as the CIA and Fidel Castro, the story involves American mobsters and a malfunctioning poison capsule.

The year was 1963 and the CIA turned to the mob to help slip the poison into a milkshake. It was reported they offered $150,000 for the hit, planning to use Castro’s love of ice cream against him.
Every lunchtime, Castro would enjoy a milkshake at the Havana Libre Hotel. One of the mob assassins hid a poison capsule in the freezer, yet when the waiter they’d enlisted to help them went to retrieve it, he found it had already ripped open.
“That moment was the closest the CIA got to assassinating Fidel,” the retired state security general Fabian Escalante told Reuters.

It was not the only time the CIA tried to exploit one of Castro’s favorite treats. The Cuban leader was known to enjoy a cigar, and therefore the US agency tried a poisoned cigar and even an exploding cigar. Both attempts were thwarted. Other attempts were chemical powder sprinkled on his boot that would cause his beard to fall out, an exploding shell near where he was fishing, and a poisonous scuba diving wetsuit.
Read More: The Soviet war hero who drank Coca-Cola disguised as vodka
There were, of course, more conventional methods as well. Escalante revealed car ambushes and grenade attacks, including one at a baseball game.
In the end, Castro survived all the assassination attempts against him. He became one of the longest-serving rulers in the world, and died at the age of 90, in November 2016.
