Charles Nicoletti was born on December 3, 1916, in Chicago, Illinois. His parents, Philip Nicoletti and Grace Alessi, were immigrants from Santa Caterina Villarmosa, Sicily. The family settled in the Near West Side of Chicago, a gritty, working-class neighborhood known for poverty and crime. Nicoletti grew up in a household strained by alcoholism and violence. At just 12 years old, he fatally shot his father in an incident ruled as self-defense after his father—reportedly drunk and enraged—chased him with a knife. Charles grabbed a gun from his father’s room and shot him four times. The Cook County coroner cleared him two days later, marking a dark start to a violent life.

Nicoletti dropped out of school in the eighth grade and found his place among the Forty-Two Gang—a street gang that served as a training ground for future mob enforcers. Among his peers were soon-to-be-notorious mobsters like Sam Giancana, Sam "Teets" Battaglia, Lew Farrell, and Tony "Mad Sam" DeStefano. His early association with these men set the foundation for his later recruitment into the Chicago Outfit, the city’s dominant organized crime syndicate.

As Nicoletti matured, his capacity for violence and his icy detachment made him a natural fit for more serious underworld assignments. By the late 1950s, he was known as one of the Outfit’s top contract killers, feared even by other hitmen. His calm demeanor, professional precision, and loyalty earned him the nickname “Chuckie the Typewriter,” referring to how quickly and efficiently he could “type out” hits with his weapon.

By the time Nicoletti reached his prime, he had become one of the most feared enforcers under Chicago mob boss Sam Giancana. Alongside fellow hitman Felix "Milwaukee Phil" Alderisio, Nicoletti carried out a series of mob hits that drew attention from local police and the FBI alike. The pair even had a custom-built “hitmobile”—a car with hidden compartments for weapons and dimmable lights. When police found them one night sitting inside this modified vehicle, they claimed they were “just waiting for a friend.”

One of the most gruesome stories associated with Nicoletti occurred in 1962. Alongside Alderisio, Tony “The Ant” Spilotro, and Carlo “Duke” Olandese, he participated in the kidnapping and torture of 24-year-old Billy McCarthy. McCarthy and his associate, Jimmy Miraglia, had murdered two Outfit members without permission. The crew captured McCarthy and tortured him with an industrial vise until his eye was forced from its socket—at which point he confessed the name of his partner. Both men were then executed. Spilotro later bragged to fellow mobster Frank Cullotta that Nicoletti didn’t flinch during the torture and even calmly ate pasta as McCarthy’s eye popped out—earning Nicoletti a reputation as truly “heartless.”

Despite pressure from law enforcement, Nicoletti never turned informant. FBI Agent William Roemer once attempted to flip him, but Nicoletti only offered vague employment details and never cooperated further. Although there were rumors in mob circles that he might’ve flipped later in life, nothing was ever confirmed.

Nicoletti’s name resurfaced in conspiracy theories surrounding the assassination of President John F. Kennedy. In a 2010 Playboy article, inmate James Files claimed that Nicoletti was involved in the JFK hit, along with Files and Chauncey Holt. While widely disputed, the theory gained traction in alternative circles and fueled speculation that Nicoletti’s later death was a cover-up to silence him.

On March 29, 1977, Nicoletti was found dead in his Oldsmobile outside the Golden Horns Restaurant in Northlake, Illinois. He had been shot three times in the back of the head while waiting in the parking lot. Strangely, his car’s engine remained running and eventually overheated, sparking a fire that led to false reports of a car bombing. He was rushed to Northlake Community Hospital but died a few hours later.

At the time of his murder, Nicoletti was reportedly scheduled to testify before the House Select Committee on Assassinations—a chilling coincidence, as another scheduled witness, George de Mohrenschildt, also died the same day. Former FBI Agent Roemer suspected fellow Outfit enforcer Harry Aleman as the gunman, although no one was ever formally charged.

Nicoletti was buried at Mount Carmel Cemetery in Hillside, Illinois—a graveyard known for housing many of Chicago’s most infamous mob figures.