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One of the first known plots involved the CIA attempting to use poisoned pills to assassinate Fidel Castro. A pharmacist made the pills, which were planned to be smuggled into Havana and slipped into Castro's meals. However, the operatives failed to get close enough to carry out the plan.

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The CIA devised a plan to give Fidel Castro a cigar filled with explosives, hoping it would detonate when he lit it. This plan, however, never made it out of the planning stages.

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Knowing Castro's love for diving, the CIA considered sending him a contaminated diving suit laced with spores and toxins. The suit would have caused a deadly skin infection, but Castro never accepted the gift.

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The CIA recruited members of the mafia to help assassinate Fidel Castro. They offered mafia operatives over $150,000 to carry out poisoning during one of Castro's dining events. This attempt fell apart due to mistrust and operational failures.

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Another creative assassination attempt involved a handkerchief coated with botulinum toxin intended to infect Castro fatally. The plan, however, was abandoned before execution.

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As part of their psychological warfare strategy, the CIA tried to humiliate Fidel Castro by spraying his broadcasting studio with chemicals that would make him hallucinate and lose focus during live speeches.

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The CIA considered using LSD in a cigar, hoping that it would make Fidel Castro act irrationally during a televised speech. This psychological disruption plan was never implemented.

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One scheme involved an ink pen filled with a lethal toxin that would be handed to Fidel Castro at a meeting. The plan failed due to operational mishaps.