The long-standing rumor that the CIA recruited American mobsters to assassinate Fidel Castro has persisted for decades, but author and mob historian Eric Dezenhall says the story is filled with more mythology than fact—and that the Kennedy administration did not start it. The initiative actually began under President Dwight Eisenhower. The CIA reached out to operative Robert Maheu, who in turn contacted Johnny Roselli of the Los Angeles underworld, Santo Trafficante of Florida, and Chicago Outfit boss Sam Giancana. The pitch was direct: the CIA knew the mob wanted its Havana casinos back, so would they help eliminate Castro?
Dezenhall, author of “Wiseguys and the White House,” challenges the assumption that mobsters believed they would ever regain their casinos. The most powerful mob figures in Havana before the Cuban Revolution were Meyer Lansky and Santo Trafficante Jr. , and Dezenhall says both knew nothing about the CIA recruitment plan and considered it foolish. Lansky had previously put a contract on Castro, but by the time the CIA operation was underway, he was back in South Florida suffering from serious heart problems and unaware of the scheme.
Trafficante later claimed in life that no one ever approached him about the plot. Dezenhall suggests the mob’s real motivation was avoiding federal prosecution. The Kefauver and McClellan Committee hearings had put organized crime under intense scrutiny, and Robert and John F. Kennedy were deeply involved in those prosecutions.
The mobsters wanted the government off their backs and hoped cooperating with the CIA would provide leverage. The efforts themselves were largely ineffective. According to Dezenhall, there were seven or eight attempts, ranging from absurd schemes like placing poison powder on Castro’s shoes to shooting attempts and smuggling firearms into Cuba. Roselli ran weapons and materials from Florida into Cuba, but nothing succeeded.
Dezenhall believes the mob did not give the operation its full effort. He also notes that the mob was not a single unified organization. When Giancana returned to the Chicago Outfit, his partners including Accardo and Murray Humphreys thought the CIA involvement was stupid and wanted no part of it, ultimately telling Giancana the risk was on him. When John F.
Kennedy took office, the intensity increased. Dezenhall describes both Kennedy brothers as absolutely fanatical about killing Castro, with Bobby Kennedy a rabid anti-communist who was fixated on the threat just 90 miles off the American coast. The CIA operation outlasted the Eisenhower administration, and the Kennedys inherited it. The FBI eventually informed Bobby Kennedy that mobsters had been recruited for the plot, and his reaction was explosive.
He hated the mob and demanded an explanation. According to Dezenhall, the CIA essentially told Kennedy that if he wanted Castro dead, they had to use the kind of people who do that kind of work. Kennedy responded that he never wanted to hear that gangsters had been recruited, insisting instead that Cubans be used for the job. Dezenhall points out the contradiction: if you want someone murdered, the pool of acceptable candidates is inherently limited.
Dezenhall argues that prominent CIA officials who later spoke about the operation overwhelmingly insisted that the Kennedy brothers knew exactly what was happening. He says John F. Kennedy himself floated the idea of killing Castro in conversations with people around him. While the documentation stops short of showing the Kennedys on record approving the mob involvement, Dezenhall accepts the testimony of former CIA directors that the Kennedys wanted Castro out of the way.
The later fates of the mob figures involved have fueled further conspiracy theories, particularly the deaths of Giancana and Roselli within a year of each other in 1975. Dezenhall rejects the theory that the CIA or the mob killed JFK, calling such ideas preposterous. He argues the two mobsters were killed because they were aging men in poor health who had begun talking to the government. The fear was not that they would testify about Kennedy’s assassination, Dezenhall says.
Rather, it was that they were cooperating with congressional investigators. He explains the mob logic: if a soldier tells his boss he is talking to the government but swears he is only discussing unrelated matters, the boss cannot take that risk. The response was better safe than sorry. Roselli had spoken to Congress, and there was discussion of grand jury testimony.
Giancana may not have testified before a grand jury, but congressional testimony was the real threat—especially given that Congress had put these men on the map in the first place after the 1957 Apalachin conference. Dezenhall believes Roselli was genuinely running materials into Cuba, but he doubts the mob ever sent its own men on the ground to attempt the shooting themselves. It was too risky. Trafficante, he says, was reportedly given poison to pass along to someone who could reach Castro, but apparently flushed it down the toilet instead.
The mob’s real goals, Dezenhall argues, were freedom from prosecution and having dirt on the government. The relationship gave them leverage: if you are a mob boss facing trial, it helps to know that the FBI has been in bed with you. J. Edgar Hoover was initially unaware of the operation.
He learned of it through a separate investigation involving bugs planted in the Las Vegas hotel room of Giancana’s girlfriend, singer Phyllis McGuire, and her other boyfriend, comedian Dan Rowan. When the FBI traced the bugging, they uncovered the role of Robert Maheu, the same operative who had brought the mob into the CIA plot. Hoover then went to Bobby Kennedy with the revelation that mobsters were being used in the administration’s anti-Castro efforts. Dezenhall describes Kennedy as shocked in the manner of a rich kid, unable to accept that the people doing the work would be the kind of men he despised.
The operation, he says, reflected a naive belief that the job could get done without getting one’s hands dirty.