He did serve time in prison 1930-31 for burglary and was behind bars once again in 1939-42. Those sentences helped earn him notice among the big-time Chicago Mafiosi.
In 1933, he became bodyguard for Tony Accardo. In 1948, with Accardo then the big boss, he graduated to the position of the family's primary enforcer. By 1950, he was specializing in gambling and associating with Hollywood stars. When Accardo began losing a battle with the Internal Revenue Service, he turned the Family operations over to Giancana.
Giancana is believed to have had connections with the Kennedy family and to have assisted in John F. Kennedy's Presidential election in 1960. Some sources have claimed that Giancana and Kennedy shared mistresses and passed information to each other through their women.
It appears Giancana may have good reason to feel that he was betrayed by the Kennedy Administration, as Attorney General Robert Kennedy put enormous legal pressure on the Chicago crime lord. Giancana eventually fled the United States for Mexico in 1966, turning the Family back over to Accardo but continuing to participate from a distance.
U.S. authorities convinced Mexico to shove Giancana back across the border in 1974. Aging and in declining health, he was ordered to appear before a Senate panel in July 1975.
Just five days before his appearance, on June 19, 1975, an unknown gunman ended Sam Giancana's life. Police found a bullet entry wound in the back of his head and several more in his mouth. Clearly some of Giancana's associates believed he was in no condition to take a fall and do jail time at that point. (The same argument John Gotti used to justify the assassination of Paul Castellano.)
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