Released from prison in 1943, Sam worked his way to the top of Chicago’s crime rackets. After Capone was jailed, Sam’s new boss Frank Nitti moved Capone’s outfit into labour racketeering, gambling, and loan sharking. It extended its tendrils to Milwaukee, Madison, Kansas City, Hollywood and other Californian cities, where the Outfit's control of labour unions gave it leverage over movie production.
But Sam, with his now familiar trademark of pork pie hat and dark shades didn’t get his hands on the helm of the powerful mafiosa outfit, heading its Chicago headquarters until as late as 1957.
During the early 1950s, it is alleged Sam pulled strings for the Kennedy family, getting a career-threatening marriage of Senator Jack Kennedy annulled, and all legal documents eradicated.
There are also strong suggestions that the CIA covertly used Giancana and the mob during the last days of the Eisenhower administration, in their attempt to assassinate Cuban dictator Fidel Castro who had taken power in January 1959. Giancana himself said that the CIA and the Mafia are "different sides of the same coin".
It is also alleged that Joseph P. Kennedy recruited Giancana to help influence labour union support behind his son, Massachusetts Senator John F. Kennedy, in the young man’s bid to secure the Democratic nomination for the 1960 Presidential election.
If the story is true, it was an ironic twist of fate that the eventual President JFK, together with his brother Robert Kennedy, turned against Giancana in order to dismantle the criminal underworld and imprison Giancana.
Could it therefore have been Giancana himself who backed the assassination of JFK due to this betrayal?
Years later it was discovered that Giancana and JFK had shared the same mistress, Los Angeles socialite, Judith Campbell, who acted as a go-between for the two men, in 1960.