Infamous Chicago mafia hit man Charles (Chuckie the Typewriter) Nicoletti was slain 40 years ago this week in a suburban Windy City restaurant parking lot. The 60-year old Nicoletti, a top hit man under multiple Outfit bosses, but particularly close to Sam (Momo) Giancana and Felix (Milwaukee Phil) Alderesio, died a suspect in dozens of gangland murders and on the verge of indictment on a slew of racketeering charges according to media reports at the time.

Chuckie Nicoletti was shot to death as he sat behind the wheel of his Oldsmobile in the parking lot of the Golden Horns Restaurant in Northlake, Illinois on March 29, 1977. He was felled with three bullets to the back of the head. The Olds overheated and caught fire before authorities reached the scene. Nicoletti died shortly thereafter at a nearby hospital.

Nicoletti and Milwaukee Phil Alderesio were partners-in-crime and made up a vicious tandem of mob executioners in the 1950s and 1960s. Alderesio was boss of the Outfit from 1967 until he was incarcerated in 1969. Milwaukee Phil succumbed to cancer behind bars in the fall of 1971.

Nicoletti’s killing capped a near two-year purge of Outfit heavyweights possibly tied to the 1963 assassination of U.S. President John F. Kennedy and the attempted assassination of Communist Cuban dictator Fidel Castro. Giancana was murdered inside his suburban Chicago home in May 1975, a decade removed from being the Outfit’s day-to-day boss. The Chicago mob’s longtime rep in California, John (Handsome Johnny) Roselli, got clipped less than three months later, found stuffed in an oil drum floating in Biscayne Bay in Miami, Florida.

Chuckie Nicoletti

Giancana and Nicoletti became acquainted as youngsters when they were both members of the 42 Gang on Chicago’s Westside. The 42 Gang served as a breeding ground for a number of future Outfit leaders. Roselli, Giancana and Nicoletti had all been subpoenaed to testify before a U.S. Congressional committee investigating ties between the CIA and the mob and the reputed partnership’s alleged role in the Kennedy and Castro plots.

Convicted felon James Files fingered Nicoletti and Roselli as co-conspirators in the Kennedy assassination in a Playboy Magazine article from 2010. Files claims to have driven Nicoletti from Chicago to Texas in the hours preceding Kennedy being shot in his Presidential motorcade driving through the streets of Dallas on November 22, 1963 and that him and Nicoletti were two of the shooters.

When he was 12 years old, Nicoletti shot and killed his own father in a murder ruled a justifiable homicide due to the fact that the elder Nicoletti was brutally beating his mom. At the time of his own murder, he was being eyed in a homicide probe out of Milwaukee, Wisconsin — the 1975 gangland slaying of Milwaukee mobster Augie Maniaci, a suspected FBI informant.

Some in law enforcement tab fellow notorious deceased Chicago Outfit hit man Harry (The Hook) Aleman as the prime person of interest in the Nicoletti murder inquiry. Aleman died of lung cancer in prison in 2010 on an unrelated first-degree homicide conviction


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