Charles "Chuckie" Nicoletti, also known as "The Typewriter" (December 3, 1916 - March 29, 1977), was a top Chicago Outfit hitman under Outfit boss Sam "Mooney" Giancana before and after Giancana's rise and fall.
Growing up in a poor, dysfunctional family in Chicago, at 13 years of age Nicoletti killed his own father Philip Nicoletti, a Sicilian immigrant and drunkard who was attacking his own wife; the young Nicoletti was found not guilty of justifiable homicide. Having dropped out of school in the eighth grade, Nicoletti soon joined the "Forty-Two Gang." By the 1930s, this Chicago street gang had so many adept criminals that it became a sort of farm team for the Chicago Outfit. The gang's members included such future Outfit heavyweights as Giancana, Sam "Teets" Battaglia, "Lew Farrell," "Mad Sam" DeStefano and William "Willie Potatoes" Daddano.
By the late 1950s, along with Felix Alderisio, Nicoletti was one of the most feared triggermen in Chicago and was drawing attention from the Federal Bureau of Investigation and the Chicago police. A number of times Nicoletti and Alderisio teamed up for a "hit," including one occasion on which they were discovered by police sitting on the floor in a car later dubbed "the hitmobile," by reporters. This car had special compartments where guns were stored and special switches to turn lights off at certain times. When questioned by police the two said they were "... waiting for a friend."
In 1962, Nicoletti took part in an infamous torture case. He, Alderisio and Anthony Spilotro, known as "Tony the Ant", had kidnapped Billy McCarthy, a thug who had killed two Outfit associates with a friend. The three men started torturing McCarthy to find out the name of his accomplice. Spilotro had placed the man's head in an industrial vice and started squeezing it tighter and tighter. Suddenly, McCarthy's eye popped completely out of its socket. At that point, he revealed his accomplice's name; then both men were killed. Years later, Tony Spilotro told this story to his friend Frank Cullotta. Spilotro was impressed by Nicoletti's reaction to the gory scene: "Boy, this is a heartless guy. He was eating pasta when Billy's eye popped out." This torture scene was re-enacted in Martin Scorsese's 1995 film, Casino.
In the 1960s, Nicoletti was questioned by two FBI Agents, including agent William F. Roemer, to see if they could develop Nicoletti as an informant against his Outfit loyalties. According to Roemer, Nicoletti gave him the names of several car dealerships he worked at and was very cordial; apparently, all the employment leads checked out. But Nicoletti never flipped and never talked to the FBI again, though there was eventually talk in Chicago that Nicoletti did flip.
During his career as a hitman, it has been alleged that Nicoletti was involved in as many as 20 mob hits. It has also been alleged by a number of sources that Nicoletti was involved in the assassination of President John F. Kennedy.
On March 29, 1977, Nicoletti received three .38 slugs to the back of his head while waiting in his Oldsmobile in a suburban Northlake, Illinois, restaurant parking lot. He was brought to the hospital where he died six hours later. Nicoletti's car was never turned off, and consequently overheated and started on fire. Some said that Nicoletti was murdered in retaliation for a hit on a Milwaukee, Wisconsin mob leader, but this is probably a false lead; while Milwaukee has its own mob (at the time of Nicoletti's death, probably headed by Frank Balistrieri), it's long been subservient to Chicago's orders, and if Nicoletti had killed anyone in the Milwaukee mob, it would've been ordered by Chicago. Another theory is that Outfit boss Joseph "Joey Doves" Aiuppa believed that Nicoletti had become an informant and ordered the hit. But the real reason for Nicoletti's murder remains unclear.
Nicoletti was due to appear before the House Select Committee on Assassinations at the time of his death. Chauncey Holt, allegedly the old tramp in the infamous JFK assassination "Three Tramps" photo, claims that he drove Nicoletti into Dallas from Licavoli Grace Ranch on the morning of the JFK assassination.