From Poison Pills to Cigars: How the CIA Tried to Assassinate Fidel Castro

Former Cuban President Fidel Castro died at the age of 90 from natural causes. But few people know that the revolutionary leader survived not 10 or 20, but more than 600 assassination attempts. For nearly half a century, attempts to kill Cuba’s most iconic leader have relied on spies, mafia hitmen, James Bond-style assassination weapons and other methods that might seem like something out of an Ian Fleming novel.

Now, a new docuseries, Mafia Spies, streaming on Paramount+, reveals how the CIA actually worked with the Mafia to orchestrate Castro’s assassination. It’s based on a book of the same name, written by Thomas Maier.

The intricate storylines and large company of politicians, gangsters, spies, revolutionaries and entertainers are explored in the six episodes of Mafia Spies.

Castro was the newly appointed Prime Minister of Cuba and the CIA, then led by Allen Dulles, wanted to overthrow him.

To assassinate Castro, the CIA recruited organized criminal figures, Sam Giancana and John Roselli of the Chicago Outfit, through an intermediary named Robert Maheu, a lawyer and businessman.

Interestingly, the Mafia had its own motives for letting Castro go, as Havana’s casinos were no longer a haven for them when he took power in 1959.

The series highlights the failed invasion of Cuba at the Bay of Pigs in 1961, the Cuban Missile Crisis in 1962 and the assassination of US President John F. Kennedy in 1963.

To achieve their goals, the CIA and its Mafia allies used everything from poison tablets to a deadly “honey pot” that involved a woman to murder and seduce.

Maier’s book is based largely on documents about the Kennedy assassination, which the National Archives published in batches in 2017 and 2018.

The JFK archives reveal that despite their deadly reputation, Giancana and Roselli, the Mafia duo, failed to kill Castro.

A potential assassin in Havana was given poison tablets by the CIA, but got cold feet before he tampered with Castro’s food.

The Church Committee, a Senate committee that documented intelligence abuses in the mid-1970s, alleges that the cigar scam, perhaps the best-known attempt to assassinate Castro, began in 1960.

According to the commission’s investigation, an official was handed a box of Castro’s favorite cigars, along with instructions to inject them with a deadly poison. The cigars were tainted with a botulinum toxin so potent that ingestion would cause death. It is not clear from the documents whether any attempt was made to give Castro the cigars.

Castro was fond of diving, so it should come as no surprise that the CIA investigated the possibility of creating an explosive shell to assassinate him during one of his forays.

According to the Church Committee report, in 1963 Desmond Fitzgerald, the head of the (anti-Castro CIA) Task Force, ordered his assistant to find out if it was possible to place a detonating shell at a spot where Castro often dove.

Other failed commando operations in Florida have been attributed to bad luck or bad timing.

CIA-trained fighters who raided the Cuban coast in night raids were often captured and sometimes killed by firing squad.

The JFK papers also reveal how Castro’s own network of double agents and associates in Florida thwarted CIA operations and helped protect the communist leader.

A few conspirators who had ties to the two gangsters betrayed them for personal gain.