20 Infamous Gangsters from Chicago

A photo of John Dilinger by FBI – Wikimedia commons

20 Infamous Gangsters from Chicago

Chicago, a city with a notorious history of organized crime, has been home to several infamous gangsters who have left an indelible mark on the city’s criminal underworld. These nefarious individuals were known for their ruthless tactics, engaging in activities such as bootlegging, gambling, and prostitution, which allowed them to establish and maintain their criminal empires.

Perhaps the most infamous of these gangsters was Al Capone, the leader of the Chicago Outfit, an organized crime syndicate that exerted tremendous control over the city’s criminal enterprises. Capone’s notoriety was due to his involvement in numerous violent incidents, as well as his ability to evade criminal prosecution for many years.

John Dillinger was another notorious gangster who achieved legendary status due to his daring bank robberies during the Great Depression. He was labelled as “Public Enemy No. 1” by the FBI, a designation that cemented his status as one of the most wanted criminals in the United States.

The North Side Gang, led by Bugs Moran, was a rival of Capone’s Chicago Outfit and was involved in a brutal gang war during the Prohibition era. Frank Nitti, a top lieutenant of Capone, took over as the head of the Chicago Outfit after Capone was imprisoned and was known for his ruthless tactics.

Other infamous gangsters in Chicago included Tony Accardo, a high-ranking member of the Chicago Outfit who avoided criminal prosecution and was involved in organized crime for over five decades, and Sam Giancana, a leading member of the Chicago Outfit who had connections to political figures and was rumoured be involved in the assassination of President John F. Kennedy. In the article are twenty infamous gangsters from Chicago.

1. James Marcello

James J. Marcello, an infamous crime boss, was known by multiple aliases such as “Little Jimmy“, “Jimmy Light“, and “Jimmy the Man“. During the 1980s, 1990s, and early 2000s, he served as a front boss for the Chicago Outfit criminal organization. Although he was identified as a figurehead by organized crime observers during that period, the day-to-day operations of the organization were run by John “No Nose” DiFronzo, Joseph “Joey the Clown” Lombardo, Joseph “Joe the Builder” Andriacchi, and Angelo J. LaPietra.

2. Michael Sarno

Michael Sarno is an American mobster who has been identified as the alleged, current leader of the Cicero street crew, in the Chicago Outfit criminal organization. On February 8, 2012, Sarno was sentenced to 25 years in prison on charges of racketeering. Sarno was identified in the indictment as being a mob money collector of extortion payments and juice loans and as the owner of a tavern in Cicero, Illinois.

On February 7, 1990, Sarno was one of 20 Chicago mobsters named in a 42-count indictment alleging racketeering. Sarno was jailed immediately but in an unusual move, was furloughed for several hours the following weekend to get married. Among the other defendants charged with various crimes in the same indictment were Chicago Outfit leaders Harry Aleman and Rocco Infelice.

3. Louis Marino

Louis Marino was a crime boss for the Chicago Outfit criminal organization. He was identified in a July 1986 Chicago Tribune article as an enforcer and driver for longtime Chicago mob boss Ernest Rocco Infelise. In September 1986, Marino was identified as a lieutenant of Chicago Outfit boss Joseph Ferriola, and recently elevated to be boss of the Outfit’s gambling operation in McHenry County, Illinois.

Marino was identified in court during the “Family Secrets” mob trial” in Chicago in 2007 by Chicago Outfit turncoat Nicholas Calabrese as having been one of several mobsters in the room during the fatal 1986 beatings of Chicago mobsters Anthony Spilotro and Michael Spilotro, whose murders were fictionalized in the 1995 film Casino. Marino has never been charged with the Spilotros’ murders; however, the only person ever convicted of participating in the murders is imprisoned Chicago mob boss James Marcello.

4. Johnny Torrio

John Donato Torrio was an Italian-born-American mobster who helped build the Chicago Outfit in the 1920s later inherited by his protégé Al Capone. Torrio proposed a National Crime Syndicate in the 1930s and later became an adviser to Lucky Luciano and his Luciano crime family.

Crime journalist Herbert Asbury affirmed that as an organizer and administrator of underworld affairs, Johnny Torrio was unsurpassed in the annals of American crime. Herbert added that he was probably the nearest thing to a real mastermind that this country has yet produced.

5. Frank Nitti

Frank Ralph Nitto known as Frank Nitti, was an Italian-American organized crime figure based in Chicago. The first cousin and bodyguard of Al Capone, Nitti was in charge of all money flowing through the operation. Nitti later succeeded Capone as acting boss of the Chicago Outfit.

Frank Nitti, notorious for his role in organized crime, passed away on March 19, 1943, at the mature age of 57. His final resting place is Mount Carmel Cemetery in Hillside, Illinois, yet the burial of a suicide in a Catholic cemetery remains a controversial subject. Nitti’s grave is situated to the left of the primary Roosevelt Road entrance, approximately 50 feet (15 m) from the gate.

Meanwhile, to the right of the gate, lies the family plot, housing the final resting place of Al Capone, which is distinguished by a 6-foot (180 cm) white monument stone. In the same vicinity, located directly up from the entrance gate, are the graves of Dean O’Banion and Hymie Weiss, both members of the North Side Gang, who were slain by the Chicago Outfit under Capone’s rule.

6. Louis Campagna

Louis “Little New York” Campagna was an American gangster and mobster and a high-ranking member of the Chicago Outfit for over three decades. As a teenager, he joined New York’s infamous Five Points Gang of Manhattan. One of Campagna’s gang associates was future Chicago Outfit boss Al Capone.

In 1919, Campagna was convicted of robbing an Illinois bank and sent to the Pontiac Reformatory in Pontiac, Illinois. In April 1924, Campagna was paroled but was returned to the reformatory six months later for a parole violation. After his final release in November 1924, Campagna returned to New York.

7. Sam Battaglia

Salvatore Joseph “Sam” Battaglia was an American mobster and high-level member of the Chicago Outfit criminal organization. Battaglia was born in Chicago, Illinois. At age 16, Battaglia joined bosses Johnny Torrio and Al Capone in the Chicago Outfit at the start of the gang war against the mostly Irish North Side Gang, which was underboss Dean O’Banion.

By the late 1930s, Battaglia had become a high-ranking member of the Outfit and a formidable loan shark.[citation needed] Debtors behind in their payments would be brought to Battaglia in the back room of the Casa Madrid restaurant, in Chicago, where they would be severely beaten or killed. Supposedly Battaglia’s nickname “Teets” came from one such encounter.

8. Jackie Cerone

John Philip Cerone was nicknamed Jackie the Lackey. He was an American mobster and boss of the Chicago Outfit during the late 1960s. He was the younger brother of mobster Frank “Skippy” Cerone, father of lawyer John Peter Cerone, and husband to the late Clara Cerone. He was born to John Cerone Sr. and Rose Valant.

Cerone was part of the enforcer team that tortured and murdered loan shark William “Action” Jackson. As an Outfit enforcer, Cerone was arrested over 20 times on charges including armed robbery, bookmaking, illegal gambling, and embezzlement. Cerone became boss of the Outfit following the semi-retirements of Accardo and Joey “Doves” Aiuppa.

9. John DiFronzo

John DiFronzo was nicknamed No Nose. He was an American mobster and the reputed former boss of the Chicago Outfit. DiFronzo, a former enforcer and caporegime, first appeared with a criminal record in 1949. He got the nickname “No Nose” because he sliced off part of his nose while jumping through a window during a 1949 clothing store burglary. Reportedly, the police gave him back the missing part which was almost perfectly restored.

In 1950, DiFronzo served two years in prison for burglary. DiFronzo was a suspect in the unsolved 1952 murder of Charles Gross, a West Side politician with suspected ties to organized crime. He was a member of the Three Minute Gang and identified as a member of a loansharking operation along with former Chicago police officers Albert Sarno and Chris Cardi in 1964.

10. Peter DiFronzo

DiFronzo was a made member and the caporegime of the Elmwood Park Crew within the Chicago Outfit. In 1965, he was sentenced to 10 years at Leavenworth Prison after he and two Outfit affiliates robbed a warehouse in Forest View, Illinois, of cigarettes, razor blades, and ladies hosiery. He was featured in William F. Roemer Jr’s War of the Godfathers: The Bloody Confrontation Between the Chicago and New York Families for Control of Las Vegas in 1990.

His wife, Josephine, was part owner of D&P Trucking, located in Chicago, Illinois, though authorities believe it was DiFronzo and his brothers Joe and John that ran the enterprise. DiFronzo was also supposedly active in some of the Outfit’s racketeering schemes. DiFronzo’s name appeared on a 2002 FBI list as a potential threat to the life of Nick Calabrese, a star witness in Operation Family Secrets under federal protection.

11. Joseph Ferriola

Joseph Ferriola was also known as, “Joe Nagall,” “Mr Clean” and “Oscar,”. He was an American mobster who was boss of the Chicago Outfit, from 1985 to 1988, after Joseph Aiuppa and John Cerone went to prison for skimming Las Vegas casino profits. Joseph Anthony Ferriola came from Chicago’s Near West Side. He was the father of one son, Nicholas Ferriola who followed his father into organized crime.

Ferriola began his career as a protégé of the late mobster Leonard “Fat Lennie” Caifano.Fat Lennie was Marshall Joseph Caifano’s brother. In 1970, Ferriola and four other mobsters were convicted for conspiring to operate an interstate gambling ring. He was sentenced to five years in federal prison but only served about three years.

He later became one of the Outfit’s top enforcers, working in particular as an enforcer for Sam Giancana. A 1989 article in the Chicago Tribune reported that federal agents had described Ferriola as a “cold-blooded terrorist” and as one of the most feared men in the mob.

12. Leonard Caifano

Leonard Caifano’ nicknamed “Fat Lennie” was a prominent figure in the world of organized crime, and was known for his imposing physique, as indicated by his moniker “Fat Lennie.” Caifano was a member of the Chicago Outfit during the 1960s and was involved in various criminal activities such as loan sharking, extortion, and murder. He was known for his ruthless demeanour and was considered one of the most violent enforcers in the organization’s history.

Caifano was also a suspect in numerous homicides, but he was never convicted of any crimes due to his skill in evading law enforcement and his connections to powerful figures. Despite his infamous reputation, Caifano was admired by many for his street smarts, resourcefulness, and unwavering loyalty to the Outfit.

13. Nicholas Ferriola

Nicholas Ferriola was a notorious figure in the criminal underworld. He was a high-ranking member of the Chicago Outfit during the late 20th century. He was known for his astute business acumen and involvement in various illegal enterprises, including gambling, extortion, and drug trafficking. Ferriola was also rumoured to have been involved in numerous homicides and was widely feared for his ruthlessness and willingness to use violence to protect his interests.

Despite his criminal activities, Ferriola was respected within the organization for his leadership skills and his ability to manage complex criminal operations. However, his career was cut short when he was gunned down in a hail of bullets in 1989, reportedly as a result of internal disputes within the Outfit. His death was a significant blow to the organization, and it marked the beginning of a period of instability and decline for the Chicago Outfit.

14. Joseph Aiuppa

Joseph Aiuppa, a prominent figure in the world of organized crime, was a high-ranking member of the Chicago Outfit during the mid-20th century. He was known for his shrewd business sense and his involvement in various illicit activities, including extortion, gambling, and loan sharking. Aiuppa was also rumoured to have been involved in numerous violent crimes, but he was never convicted of any charges due to his skill in evading law enforcement and his connections to powerful figures.

Despite his criminal activities, Aiuppa was respected within the organization for his leadership skills and his ability to manage complex criminal enterprises. However, his career was eventually cut short when he was forced to flee the country to avoid prosecution, eventually settling in Mexico, where he remained until he died in 1997. Aiuppa’s legacy as one of the most powerful and influential figures in the Chicago Outfit has endured to this day, cementing his place in the annals of organized crime history.

15. Anthony Zizzo

Anthony Zizzo is also known as Little Tony and Little Toes. He was an American mobster who was the underboss of the Chicago Outfit. Unfortunately, Anthony disappeared on 31 August 2006. He was last seen outside a Melrose Park restaurant where his car was found after a missing person report was made by his wife. He is presumed murdered, although the FBI is also considering the possibility he went into hiding.

Theories on why Zizzo may have been targeted include fears he might testify against the Outfit as well as an ongoing feud with powerful captain Michael Sarno, whom he was supervising. At the time of his disappearance, law enforcement believed Zizzo was the underboss of the Chicago Outfit as he was third in command in the 1990s.

16. Joseph Andriacchi

Joseph Andriacchi is a Chicago area resident and convicted criminal, considered by that city’s Crime Commission to be a high-ranking member of the Outfit, the city’s LCN organization. Andriacchi was one of several reputed mobsters ordered to appear before a federal grand jury after the May 17, 1992, bombing of a car outside the home of a daughter of Leonard Patrick, who was in the process of testifying against several known mobsters.

17. Antonio Lombardo

Antonio Tony the Scourge was an Italian-born American mobster. He was consigliere to Al Capone, and later the President of the Unione Siciliana. In September 1917 he was involved in the killing of Cleveland Police Officer Elmer Glaefke. A long-time Mafia associate, Lombardo became Al Capone’s advisor after John Torrio retired in 1925.

Lombardo tried unsuccessfully to negotiate peace between the Chicago Outfit and the North Side Gang during the four-year gang war, suggesting that Capone surrender supposed Dean O’Banion assassins Albert Anselmi and John Scalise, which Capone refused.

18. Paul Ricca

Paul De Lucia was also known as Paul Ricca. He was an Italian-American mobster who served as the nominal or de facto leader of the Chicago Outfit for 40 years. In 1958 he was named the country’s most important criminal by a Senate crime investigating subcommittee. By age 17, he worked for organized crime in Naples (Camorra). In 1915, he stabbed Emilio Parrillo to death on Mafia orders.

Ricca later claimed that he killed Parillo for breaking an engagement with his sister.
In 1917, Ricca was convicted of murder, serving two years in prison. Once released from prison, Ricca killed Vincenzo Capasso, who had testified against him in the Parillo trial, by slitting his throat. Ricca died on October 11, 1972.

19. Angelo J. LaPietra

Angelo J.  LaPietra “The Hook” was a Chicago mobster and member of the Chicago Outfit, involved in extensive loansharking operations in the city’s First Ward during the 1970s and 1980s. He earned his nickname “The Hook” due to the way he murdered his victims—those that did not, or could not pay up.
He would take his victim, bound and gagged, hang him on a meat hook, and then torture him to death with a blow torch. The torch would not be the cause of death. The victims most often died from suffocation.

20. Al Tornabene

Alfonso Al the Pizza Man Tornabene was a Chicago-area resident who was reported by several newspapers to have been a high-ranking member of the Chicago Outfit crime organization. Tornabene began his career in the Outfit as a bookie. However, he never had a criminal record of any kind. He was a long-time member of the Chicago Heights Street Crew.

Subsequently, Tornabene was identified as having helped to run the Chicago Outfit while its then-boss, James Marcello, was imprisoned between 1992 and 2003. Tornabene died on May 17, 2009, at MacNeal Hospital in Berwyn, Illinois of complications related to peptic ulcer disease.