It sounds like a gag from a Peter Sellers comedy, but exploding cigars really were one of the methods the CIA considered while plotting to assassinate Cuban President Fidel Castro. The United States has regularly engaged in regime change throughout its history, and Castro – after establishing a Communist government just under 100 miles from its border – was a particularly irritating thorn in the nation’s side.
It’s unknown exactly how many times the CIA tried to eliminate Castro, but one of Castro’s security officers estimated that there were 634 attempts on Castro’s life. Many of these were conventional assassination plots, like a 1963 plan to shoot Castro with a sniper rifle at the University of Havana, or a plan to throw grenades at Castro while he attended a baseball game, or a 2000 plot to plant explosives under a podium where Castro was due to give a speech.
But when conventional plans failed, the CIA was more than willing to think outside the box. Many of these plans tried to take advantage of Castro’s personal life. Multiple plans involved his love of cigars, like the plot to plant explosives in a cigar that Castro would smoke, or a 1961 plot to lace a box of his favorite cigars with botulinum. Since Castro was an avid scuba diver, the CIA considered poisoning his diving suit, or giving him an exploding seashell. The CIA found a seashell large enough to hide a lethal amount of explosives, painted it to make it stand out, and tried to leave it in a swimming spot where a curious Castro would find it.
There were also plans to take him out with a poisoned fountain pen and a poisoned milkshake. (The milkshake plot apparently came the closest to success.) At one point, the CIA sent one of Castro’s former lovers to take him out. She hid poison pills in a jar of cold cream, but they melted. Castro supposedly guessed that she wanted to end his life, and offered his pistol to let her finish the job, but she couldn’t work up the nerve.
After the exploding cigar plot failed, the CIA again tried to slip Castro a cigar, this time laced with LSD. The hope was that Castro would start tripping during an interview and ruin his reputation. Castro dodged that one, too.
