Salvatore "Sam" Giancana (1908 -1975) began his criminal career in the "42 Gang," a group of criminally-inclined teens that eventually morphed into the Chicago Outfit. From street thief, he graduated to wheel man and eventually to trigger man. In the mid-1950s, Outfit boss Tony Accardo handed the reins of leadership to "Momo." It's said that Giancana had a key role in making JFK President and later planning his assassination. He also worked secretly for the CIA. His romance with wholesome singer Phyllis McGuire put him on the front pages -- and the bad graces of his Outfit peers. Giancana was assassinated in his Oak Park home by an unknown assailant days before he was scheduled to testify before Congress about the CIA's involvement in an attempted overthrow of Castro's Cuban government.
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