Sam Giancana was a famous and powerful mafioso and boss of the Chicago Outfit from 1957-66. Originally nicknamed "Mooney", when he became Boss, Giancana shortened it to "Momo", which stood for "More Money". Born in Chicago's "Little Italy," Sam Giancana was arrested more than 70 times in his life, but was imprisoned only twice.
Giancana started his criminal career in the 1920s on Chicago's West Side as a member of a violent street gang called "The 42s". He soon developed a reputation for being an excellent getaway driver, high earner and vicious killer. These qualities got him noticed by the successor to Al Capone, Frank "The Enforcer" Nitti. It is widely reputed Giancana and other mobsters had been recruited by the CIA during the waning days of the Eisenhower administration to assassinate Cuban dictator Fidel Castro, who had taken power in January 1959. Giancana was himself reported to have said that the CIA and the Mafia are "different sides of the same coin." It is also widely reputed that at roughly the same time Joseph P. Kennedy recruited Giancana to help mobilize labor union voter and financial support behind his son, Massachusetts Senator John F. Kennedy in the latter's bid to secure the Democratic nomination for the 1960 Presidential election.
There are also strong suggestions that during his presidency, JFK maintained close links with Giancana and the Chicago Mafia as he continued the practice of covertly using the Mafia in a bid to assassinate Castro. The two men also shared the same lover, Los Angeles socialite Judith Campbell who also apparently acted as a courier between the two men, passing money and information.
Giancana was forced to step down as Mafia boss in 1966 because of his greed (refusing to share the profits of his Latin American gambling operations--a major violation of Mafia protocol) excessively high-profile personal behavior (openly associating with various popular entertainers like singers Phyllis McGuire and Frank Sinatra) and serious legal problems, serious enough to have had the FBI place Giancana under close, intense and relentless surveillance. In response to these setbacks, the dethroned Giancana spent the next seven years (1967-74) in exile in Cuernavaca, Mexico until the Mexican government (under pressure from the US Justice Department) had him deported to the United States. Returning to Chicago, Giancana was assassinated on 19 June 1975 in the basement of his home in Oak Park, Illinois (which had been under close FBI and Chicago Police observation) shortly before he was to appear before a Senate committee investigating CIA and Mafia links to plots to kill Castro.
The unknown assassin shot Giancana in the head seven times with a silenced .22 caliber handgun. Although some suspected the CIA was responsible for the shooting (as Giancana had a somewhat troubled history with the agency), CIA Director William Colby was quoted as saying, "We had nothing to do with it." Many researchers believe Colby's claim as it seems much more likely that Giancana's onetime friend and Chicago Mafia boss Joseph "Joey Doves" Aiuppa ordered the hit on the disgraced "Momo" because he had become too talkative and Aiuppa feared Giancana would reveal everything he knew about Chicago mob operations (including Giancana's alleged complicity in orchestrating the JFK assassination) during his upcoming Senate committee appearance.