In the 50's, the CIA tried to assassinate Fidel Castro by slipping an exploding cigar into his private supply

In the late 1950s under Dwight D. Eisenhower’s presidential administration and in the early 1960s under John F. Kennedy’s, the CIA had been brainstorming and implementing plots to assassinate Fidel Castro, going as far as enlisting the help of mafia leaders such as Johnny Roselliand Santo Trafficante, Jr. to assist in carrying out their plans. Many assassination ideas were floated by the CIA in the covert operation which was dubbed “Operation Mongoose.” The most infamous was the CIA’s alleged plot to capitalize on Castro’s well known love of cigars by slipping into his supply a very real and lethal “exploding cigar.” A November 4, 1967 Saturday Evening Postarticle reported that during Castro’s visit to the United Nations in 1966 a CIA agent approached New York City police chief inspector Michael J. Murphy with a plan to get Castro to smoke an exploding cigar.

While numerous sources state the exploding cigar plot as fact, at least one source asserts it to be simply a myth, and another, mere supermarket tabloid fodder. Another suggests that the story does have its origins in the CIA, but that it was never seriously proposed by them as a plot. Rather, the plot was made up by the CIA as an intentionally “silly” idea to feed to those questioning them about their plans for Castro, in order to deflect scrutiny from more serious areas of inquiry.

Whether true or not, the CIA’s exploding cigar assassination plot inspired the cover of the October, 1963 issue (#82) of Mad Magazine. The cover bears the headline, “You’ll Get a BANG out of this issue of Mad Magazine”, and features a painting by Norman Mingo depicting Castro in the act of lighting a cigar wrapped with a cigar band on which is drawn Alfred E. Neuman with his fingers plugging his ears, awaiting the explosion. An exploding cigar is also featured on the poster for the Channel 4 British Documentary, 638 Ways to Kill Castro, which shows Castro with a cigar in his mouth that has a fuse projecting from the end and a lit match approaching. An exploding cigar was tested on a season 2 episode of Deadliest Warrior, KGB vs. CIA. The cigar completely destroyed the upper and lower jaw of a gel head but was determined to be very unreliable due to its timed fuse and small explosive payload.