The Kennedy Administration and Organized Crime
When John Kennedy was inaugurated as President in 1961 his administration initiated a crackdown on organized crime spearheaded by his brother, Attorney General Robert F. Kennedy. The crackdown was largely focused on the relationship between organized crime and labor unions. At the same time, the CIA continued to conduct covert operations aimed at the assassination of Fidel Castro. During the Kennedy administration, the CIA planned or conducted forty-two separate attempts to kill Castro, and a significant number of them used Mafia members and associates.
In August 1961 the CIA contacted Johnny Roselli with an offer of $150,000 to kill Castro. Roselli was a longtime member of the Chicago Outfit, the Mafia organization descended from that of Al Capone. By the early 1960s Roselli was the mob’s chief representative in Las Vegas, and also served as a go-between for Sam Giancana and Santo Trafficante. Roselli was contacted by Robert Maheu, a former FBI official who had been recruited by the CIA. Roselli, Giancana, and Trafficante met with Maheu and were provided by the CIA with poisons to be secreted in Castro’s food by a girlfriend Castro shared unknowingly with Frank Sturgis.
The CIA and mobsters recruited several Cuban nationals to make attempts on Castro’s life, none successfully, over the remaining months of the Kennedy administration. By 1962 Roselli was operating a training base in the Florida Keys, paid for and secured by the CIA, where rifle teams were prepared in assassination techniques. Roselli worked directly for CIA officer William King Harvey, another former FBI agent who had resigned from the Bureau rather than accept demotion for violations of regulations stemming from his chronic heavy drinking.
By the 1970s, the US Senate was investigating CIA activities regarding Castro, and Roselli was called to testify before the Church Committee on CIA-Mafia plots to assassinate Castro. Sam Giancana was also called to appear before the committee but was shot and killed in his home only days before. Roselli testified and was scheduled to reappear in April of 1976. Before he could return to the committee he vanished.
The CIA connection with the Mafia through John Roselli and others was confirmed by the CIA itself in 1976, through the declassification of records which are known as the Family Jewels. John Roselli’s decomposed body was found in an oil drum that same year, floating in the waters near Miami. His murder has never been solved.