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Gioe became a high ranking lieutenant for the Outfit, specializing in extortion and blackmail, under Frank "The Enforcer" Nitti after Al Capone's 1931 tax evasion conviction. In 1936, Gioe went to Des Moines, Iowa to expand syndicate operations. He eventually returned to Chicago, leaving underboss Louis "Cock-Eyed Louie" Fratto in control of the Des Moines operations. During the mid-1930s, Gioe, Paul "The Waiter" Ricca and Louis "Little New York" Campagna, began financially supporting extortion operations by Willie Morris Bioff and George Brown against Hollywood movie studios. In exchange for annual payoffs to the Outfit, the mob-controlled projectionist unions would refrain from labor strikes and disruptions.
In the late 1930s, the extortion racket was busted by law enforcement. On March 18, 1943 Gioe, Ricca, and Campagna were indicted for extortion; Bioff and Browne agreed to testify against them. On December 31, 1941, Gioe was convicted of extortion and sentenced to ten years in prison. Gioe was later paroled (along with the other syndicate members) in 1947, despite protests from Senator Estes Kefauver. Upon his release, Gioe became second to Ricca and Campagna as the top Chicago syndicate leader.
On August 18, 1954, Charles Gioe was shot to death by mafia soldiers controlled by Joseph "Joey" Glimco after he accidentally interfered in a dispute Glimco was having with a contractor building a Howard Johnson's restaurant.
- May, Allan. "The Guileless Gangster." Crime Magazine. April 2000; Smith, Sandy. "Glimco Sought for Quizzing in Gioe's Slaying." Chicago Daily Tribune. August 20, 1954.
- Crime Magazine: The Guileless Gangster by Allan May
- American Mafia.com: Charles “Cherry Nose” Gioe by Allen May