Charles "Chuckie" Nicoletti(real surname Nicoletto or Nicoletta) was a Sicilian mobster and made member of the so-called Chicago Outfit. At first sight, he was a very good looking guy with a gold front tooth and smooth dresser but in reality he represented a real-life bogeyman that struck fear in the hearts of his victims and fellow mobsters. Nicoletti never had any problems with race, religion or nationality, so he made money for everyone and with anyone who had the skills for it. He also didn’t have feelings for another man’s life even if it was a woman or a member from his own family. He was known for saying “Hey, hitting a broad is that same as hitting a man…only she’s got tits and pussy. Who the fuck cares?! A guy is not there to screw her, he’s there to do a fuckin’ job”. Nicoletti left a big mark in mafia’s history, followed by true or false urban legends, as the participant in some of the main bloody events and in the end he left this world with a little touch of mystery. There’s not much info out there about his criminal or personal life, so ill try to portrait his life story as the best I can.

Everything started in 1903 when Sicilian population from Europe in great numbers began arriving to Chicago. In the beginning of the 20th century, the Italian gangs were the most numerous and later became the most powerful ones. Back than the South/West Side was considered as the center of the Italian population in Chicago. There were areas such as "Little Hell" or “Little Sicily”, where many Italian or the so-called Black Hand gangs operated at the “Death Corner" of Oak & Cleveland street. Filippo (Philip) Nicoletti and Grazia (Grace) Nicoletti (born Alessi) were natives of Santa Caterina Villarmosa, Sicily and one day they decided to leave their homeland and hard conditions and head to the new land of opportunities, the United States of America. The Nicolettis arrived in Chicago in 1907 and settled in an apartment at 737 Campbell Avenue on Near West Side. While in Chicago, they brought two children to this world. The first one was Philip Jr., born in 1914 and two years later, they brought another child Charles, who was born on December 3, 1916. Charles or Chuckie as he was known, grew in a hard conditions because he lived in impoverished and dysfunctional family. His father, who worked as a teamster, was a heavy drinker and very abusive man. When little Chuckie started attending public school, after classes he was forced to stay on the streets because Philip Sr. abused his family on daily basis. In other words, Chuckie was forced to run away from home because he couldn’t stand the bloody sight of his mother and brother getting beaten on the floor and the daily threats and punches that he received from his own father. While on the streets of Chicago, during his free time, young Chuckie saw the poverty and violence that occurred around him. It was a very poor and dirty area. The people around him lived in very hard conditions which forced them into the criminal life. The huge Italian families squeezed mainly between Taylor and Mather streets. It was a place filled with filthy criminals, disgusting brothels and saloons. Brawls and bloody battles between the residents was a daily routine. So by living in these conditions, some of the kids like Chuckie started to reach to each other and formed small criminal gangs. It was the only way to survive the hard conditions in and out of their homes. Most of these young boys ran from their homes, slept in abandoned cars or locals or beneath back porches and also survived by stealing food from vendors and pickpocketing. Like Philip Sr. most of the parents didn’t care about their children because they had bigger problems of their own, so the street gangs were the only families for these kids. They learned how to organize themselves and started surviving in their own style.

During the mid 1920’s one of the most prominent juvenile gangs on Chicago’s West Side were the 42's. They were characterized by the youthfulness of its members and the average age was between 16 and 23. The so-called Patch area was the gang’s territory. All of these boys had criminal records in juvenile and boys courts and their only "school" was a reformatory named St. Charles. The gang’s usual headquarters was Mary's Restaurant or Bonfiglio's Pool Hall on Taylor Street. Their types of crimes differ with their age, for example the older gang members were mostly involved in robbery and stick ups and the younger ones were mostly involved in larceny. Legend goes that the gang came to the name "42's" from one of the "more literate" gang members who recounted the story of Ali Baba and the forty thieves.

As time passed by they became known around the neighbourhood and kids like Chuckie Nicoletti started having a strange mixture of awe and respect for the gang. The 42's started making the newspaper headlines and were noticed by the big time gangsters. During the 1920’s the main and most important figures on Chicago’s West Side were the Italian and Jewish gangsters who ruled with an iron fists and commanded respect around the neighbourhoods. It was the time of Prohibition and the streets of Chicago were filled with dead bodies because of the competition that was going on among these criminals. First the young boys would do anything for two bits, a beer or a cigarette but later the gangsters started to throw money at these boys thus making them their "farm teams" for their dirty work. The young boys would do everything to impress the gangsters so soon they graduated in high profile murders, bombings and vice enterprises.

The most prominent gangsters on the West Side at the time were Joseph “Diamond Joe” Esposito and the Sicilian Genna crime family. Diamond Joe besides paying bonds and using them as soldiers for his dirty work like extortion, he also used to employ them in legitimate businesses, like selling sugar. As for the Gennas, they taught these young criminals in making illicit moonshine and selling it. But the Bloody Gennas were also known for carrying a crucifix in one pocket and a gun in the other, so they used these young kids in many murder plots and also bombings. But beside these two criminal factions, the most powerful one was the Capone faction, headed by the most famous Italian mobster around the world Alphonse Caponi a.k.a. Al Capone. During that period, almost every Italian kid that was thrown on the cold streets of Chicago idolized Capone and his nature of crime.

So in his own little mind, Chuckie Nicoletti saw the daily act of violence and criminal activities as natural thing and together mixed with the domestic violence and the old Sicilian mentality, he decided to defend his own honour. Chuckie started hanging around with the local young hoodlums from his neighbourhood and learned the way of the street. He knew that being a tough guy was the only way to stop his father and his violent temper. So when Philip Sr. was at work or getting drunk at some of the local bars, Chuckie was playing target practise with his father’s gun. He stood in front of a mirror with the gun and imagined himself as the local big shots that he saw them every day. He often raised the gun and imagined his father begging for mercy on his knees in front of him. Suddenly Chuckie realised that if one day all hell break loose, he can stop the daily terror with that “beautiful” gun.

On February 25, 1929 at 7:30 pm Philip Sr. came home very drunk and with many abusive thoughts on his mind towards his own family. He started beating his own wife Grace like never before. The poor woman’s screams were heard all around the neighbourhood. Young Chuckie came to the kitchen and started punching his father and begged him to stop. That enraged Philip Sr. so much that he took a knife, pointed to his son and threatened to kill him. Chuckie, pursued by his drunken father, ran into the bedroom and took the gun which was in a bureau drawer and pointed it in Philip’s direction. Even with that, Philip Sr. didn’t stop so Chuckie was forced to close his eyes, squeezed the trigger and the gun went off. When he opened his eyes, his father laid on the floor, chocking in his own blood and in matter of seconds his heart stopped. At first Chuckie’s blood froze and felt a sudden feeling of great fear and horror. After a while the fear was gone, because the evil beast that tortured him and the rest of the family was now also gone forever. When he saw his mother crying over her husband’s dead body, Chuckie felt very confused. He thought to himself, “Why she’s crying?”, “What kind of love is this?”. That’s when he wrongfully realized that no matter what kind of violence was committed over the people or human kind, they will still obey you and cry for you. In other words, Chuckie Nicoletti “made his bones” when he was only 12 years old. After the shooting someone called the cops from the 23rd precinct and they arrived just to see the 39 year old Philip Sr. lying dead on the floor with his wife crying beside him and Chuckie with the gun in his hand standing in the corner of the room. The cops calmly approached Chuckie and took the gun from his hand. It was obvious who took the shot so Chuckie was taken to the police office for questioning. Only two days later on February 27, the Cook County Coroner’s Office cleared Charles Nicoletti of his father’s death. Chuckie was exonerated and also commended for protecting his family because he was threatened by his drunk and knife-wielding father who caused Chuckie to do the intentional homicide. Now every youngster in the hood was scared of little Nicoletti because he managed to kill his own blood. He became known for his brutal force and also became destined for underworld recruitment.

After his father’s death, two years later in 1931, Nicoletti dropped out of school in the 8th grade and at the age of 14 went for the street life. He joined and became one of the youngest members of the 42 gang. His bloody reputation, as a kid who had the guts to kill his own father, preceded him so no one dared to challenge him. He was a quiet kid with a cold look in his eyes that obeyed every order given by his superiors in the gang. Chucky burglarized many stores and sold the merchandise on the street corners, knocked over cigar stores, held up nightclubs but his main activity was stealing cars. The 42’s were held responsible for about 80 percent of the auto thefts in Chicago at the time. They sold the cars at prices from $75 to $200 per car-Fords $75, Buick or Chrysler for $150, a Peerless and Packard for $200. During the early 1930’s many older members of the gang, like the Battaglia brothers, started working for the former Capone gang, which was now known as the Chicago Outfit. One of their most prominent members and one time leader of the gang Sam “Mooney” Giancana was the first and closest to the Outfit’s big shots. Giancana was the main guy who later brought many members of his old gang into the organization by implicating them in many criminal activities which were executed on behalf of the Outfit. The main Capone member and one of the “fathers” of the newly formed Chicago mob that took “care” of these young boys was Felice DeLucia aka Paul “The Waiter” Ricca. Ricca knew the 42’s since the days when he also worked for Diamond Joe Esposito so he understood their roots and criminal nature and also knew how to exploit it. The 42’s looked at Ricca as their god and idol and they had enormous respect for him. He paid them well and gave them the opportunity to become bigger in the underworld. The ones that obeyed his rules and requests were invited to the upper circles but the ones that failed were severely punished.


Young Paul Ricca

Through the connections with other various gangs around Chicago, the Outfit started forming its own small army of young ruthless criminals. By now Ricca was one of the top guys in the Outfit so the other captains that belonged to Ricca’s West Side Crew oversaw these “young turks”. Old timers like Lawrence Mangano, James Belcastro and Sylvester Agoglia belonged to an area known as Taylor Street, and they brought dozens of these young guys into the Outfit. So these gangsters can be considered as the creators of the infamous Taylor Street crew. Many of the new fellas specialized in extortion, gambling operations, kidnappings and above all murders. Former 42’s like the Battaglia brothers and Sam Giancana worked as one of the Outfit’s kidnapping and murder teams. They were held as a special breed of young killers, who were called by members of the hierarchy or by the bosses themselves. By the age of 17, Nicoletti, and other younger crooks, worked as a chauffeurs, burglars, car thieves and messengers for the Outfit. In 1934 Nicoletti was arrested on charges for conspiracy and burglary and was sent to trial. He received 1 year probation and a $5,000 fine. The fine was paid by his criminal connections and now his allegiance fully belonged to the Chicago Outfit.


Young Sam Giancana


One of the Battaglia brothers, Sam “Teets” Battaglia

During the mid 1930’s Nicoletti developed a reputation as a loyal guy among his fellow gangsters. Also with his charm he had a large number of females around him and besides sex, Nicoletti also used them for hiding his weapons under their skirts and also as lookouts during his criminal activities. By now Nicoletti’s mother Grace re-married with another man named Paul Tergo. Tergo was no different than her previous deceased husband, because he was always in and out of the county jail. Looks like Grace Nicoletti always had a thing for tough guys. In fact Tergo was an old associate of the Capone gang and also of the new criminal administration. To tell you the truth, there’s not even a slice of info out there about this guy, but I am totally sure for one thing that Tergo played a key role in bringing his stepson into the upper circles of the Chicago mob. Years later Tergo was sent to prison and later was deported to Italy. The exact dates are not known. Also in 1940, Charles Nicoletti decided to expand his family by entering a marriage with a young beautiful girl named Agnes Raimondi. Agnes was one year older than Chuckie and later they brought one son to this world. Together they moved into an apartment at 2745 West Lexington.

While his family was growing steady, Chuckie’s illegal activities were also growing. By the late 30’s and early 40’s, the Outfit’s main racket was gambling, so Chuckie got involved in bookmaking at the race tracks and was also involved in numerous card games. During the process he established many connections with other up and coming mobsters in Chicago. By now one of his closest and oldest associates was Ernest Sansone, a former bootlegger and ex-convict. Together they ran bookmaking operations, car theft operations, placed vending machines and later got involved in another illegal venture, like narcotics. They robbed local pharmacies over opium and morphine and they also sold heroin packages to drug addicts. There’s a legend that the Chicago Outfit had a long standing rule against narcotics but that’s not true. Even since the early 30’s the Chicago crime family made connections with the New York faction under Charles “Lucky” Luciano and entered in the drug business. Any kind of profits, especially from narcotics, are welcomed in the mob world. But the thing was in those days, that if anyone got caught by the cops dealing narcotics, the punishment was death. But the reality was, not everyone. Since almost everyone was involved in that business, sometimes the bosses used that rule as the “main” reason to kill their members or associates that didn’t fit in their own world. But that wasn’t the case with Chuckie Nicoletti because the rising star Sam Giancana was his sponsor. In May 10, 1943, Nicoletti and Sansone were arrested by the Chicago police for peddling narcotics. On May 13, Nicoletti was sent to Midland, Michigan to serve 18 months in custody of the Attorney General.


Young Charles Nicoletti

The same year, on December 30th, 1943 a Federal Grand Jury returned a guilty verdict against the West Side boss and head of the Outfit Paul Ricca in the Hollywood extortion case and was sentenced to 10 years in prison. The top layer of the Chicago leadership was changed. Now the acting boss became Tony Accardo and at the same time Nicoletti’s sponsor Sam Giancana started climbing up the ladder. Nicoletti heard about the great news and impatiently waited to get out of jail and to make some real cash. On December 24, 1944 Nicoletti was released from prison and went back to Chicago. He was greeted by his old friends from back in the days, who by now were in the upper circles of the Chicago Outfit. Nicoletti was ready to kill anyone for his old friends and also expected to get big rewards. During this time Nicoletti met with another up and coming mobster, future partner and mentor named Felice Alderizio aka Felix “Milwaukee Phil” Alderisio.

Felix Alderisio was born in 1912 in Yonkers, New York and was 4 years older than Nicoletti. As a teenager, Alderisio left New York and went to Milwaukee to compete as an amateur boxer under the moniker “Milwaukee Phil”. His career as a boxer was short lived but it became very profitable because he met a lot of mobsters and his ability with his fists served him very well for the next profession that he had chosen. In 1930 he came to Chicago, he had no home so he lived on the streets and one day was arrested for vagrancy. According to Chicago police records, Alderlisio first was arrested in Wheaton, Illinois in 1933 on suspicion of car theft. There’s no information if his parents were dead or he was chased out of their home. At the age of 18, Alderisio started moping around the Lexington Hotel, which was the headquarters for the Capone gang, hoping to get some kind of job. One day he got lucky, and I mean very lucky, because one of his older cousins, also former boxer, Luigi Fratto aka Louis “"Cock-eyed"” Fratto was already working for the Capone mob and was riding high. Young Fratto was already working with other youngsters like Sam Giancana and Sam Battaglia so he brought Alderisio into the former 42 gang. He was also introduced to another young brutal hoodlum named Marshall Caifano. Caifano, with the association of his older brother Leonard, helped Alderisio and himself to rise steadily through the ranks during the Great Depression and Alderisio soon gained a reputation for brutality. By the end of the decade, Alderisio also worked under the Jewish boss of the non-Italian faction Jake "Greasy Thumb" Guzik, who was the Outfit's financial expert and prostitution overlord. The prostitution racket is very monstrous business and Alderisio was the right guy for it. He started gathering and kidnapping young girls, forcing them in to lives of prostitution. To succeed in doing that, Alderisio gave them high quantities of booze thus making them alcoholics and at the same time he also gave them narcotics. He also worked as Guzik’s bagman, delivering payoffs and messages to Chicago judges, police officials and also other Outfit bosses. So beside his enforcer skills, Alderisio also gained knowledge for making the big buck. In 1936 he was convicted for violation of the federal internal laws and was placed on a years probation. Later he also became a liaison between the Chicago Outfit and the Milwaukee mob because of his previous connections.


Alderisio’s cousin Lou Fratto

So during the late 1940’s the Alderisio-Nicoletti deadly combine became just one of the many ruthless hit teams and money making machines under the auspices of the Chicago Outfit. Both consider killing as a profession and earned the name as “button men”. They became the most vile and bloodthirsty individuals who enforced the rule of the Outfit’s "justice". They even had protection from their higher-ups in case they were caught by the cops. “Connection guys” like Jake Guzik or Murray “Curley” Humphreys hired the best lawyers for their defence and in some cases they used their police contacts and the duo walked free. For example, during political elections, kidnappings or murder was used very often and it wasn’t only for competing between the candidates but it was mainly for the Outfit’s benefit. At the beginning, the street gangs were the politicians heritage and they used them for many favours and own purposes. The head-knocking tactics of the gangsters were very useful for the rival candidates. But in time, the gangsters grew more powerful than the politicians. So during this period it was the time when the mob decided who’s going to win the elections and who’s not. The ones that opposed the Outfit, ended up with a bullet in their heads.


Eraly mugshot of Alderisio

In the October 1948 political election, William John Granata the Republican candidate was running against State Representative James Adduci. Aducci was a close associate of the Chicago mob and even some investigators considered him a made member. Story goes that John and his brother Rep. Peter Granata, had refused to trade votes that they controlled on the West Side for the benefit of the Outfit. So on October 8, John Granata was returning home when an armed assassin with a meat cleaver crept from behind on him as he entered the building. Granata was found with his skull split wide open and was pronounced dead at the Henrotin Hospital. Charles Nicoletti was questioned about the murder but there was no evidence to hold him so they let him go. Police Captain William Drury was a tough cop who arrested a lot of mob thugs and worked to expose corruption in the Chicago Police Department. In June 1944 he was suspended from the police department for "failing to suppress citywide gambling" but in reality, this was likely a revenge move by the mob for framing mobsters in many murder cases. Later he became a crime reporter for the Chicago Herald-American and the Miami Daily News. In 1950, when Senator Carey Kefauver launched an investigation into organized crime and Drury provided written and oral testimony. So on September 25, 1950, his wife received a call at their home that William's request for police protection has been granted. He was to call back at 7:00pm. Ealier that day, Drury arrived home and parked in his garage around 6:45pm. A shot rang out and his wife ran out to the garage as a black car sped west in the alley. Drury was dead from a close-range shotgun blast. There were many suspects questioned about the murder, like Marshal Caifano or the so-called “Three Doms”( North Side mob enforcers Dom Nuccio, Dom DiBella, Dom Brancato) but few days later the cops received an anonymous phone called saying that Fat Leonard Caifano, Sam Marcelli and Charles Nicoletti were the hit team on Drury. Two years later, in 1952 Charles Gross was a politician who wanted to become a Republican Committeeman in the 31st Ward. He was putting on a good campaign but didn’t want any shady people around him. So Felix Alderisio sent another hitman named Lenny Patrick to warn the politician and also gave him an offer to retire. But Gross ignored them so on February 6, 1952 he was blown away by seven shotgun blasts outside his Kedzie Avenue home allegedly by two men. The only witness was Mrs. Julia Jankowski and she told the cops that after the shooting a big, black car sped past her followed by another car. She also described two men as 30 to 35 years old in the first car and other two men as 25 to 28 years old in the second car. Later she was taken she to the bureau of identification to study pictures of known hoodlums. On February 25 1952, 35 year old Chuckie Nicoletti was arrested and questioned by Lt. John Golden of the police homicide division regarding the murder. He apparently was cleared of any connection with it by a lie detector, and later was released on $25 bond on a disorderly conduct charge. These are only some of the many examples, where the Outfit actually controlled every part of the government and politics in Chicago and they even owned the politician’s lives. That’s why I always said that the 1950’s was THE golden era for the Chicago crime family and mobsters like Nicoletti played major part in creating it.


Nicoletti questioned about the murder of Charles Gross

By now the Outfit’s boss Paul Ricca was out of jail but he had a problem. He was forbidden by the government to associate with any of his known criminal cohorts so now he had to pull the strings from the shadows. Also his loyal companion from the old days Tony Accardo had problems of his own with the government. Both, Accardo and Ricca had many new tax trials on their way. Also in March 1954 Accardo almost received a bullet from an unknown assassin during a meeting in a car with Sam Giancana, Jackie Cerone and Sam Battaglia. The reason was that some of the old bosses started to get nervous because of the ambitious young turks who were making more money and with money, comes power and that left a sour taste in the mouths of some of the old big shots. Now Ricca and Accardo became a little bit more paranoid both from the pressure of their old companions and the pressure from the government. They realised that the well known old guard had to go and it was time for the faithful “new blood” to take over the reigns, which according to them was a very smart move. But was it really the smartest thing to do?


Outfit royalty Paul Ricca