
From bank robbers and hitmen to mobsters and politicians, these are the most notorious and curious Chicago gangsters from the Prohibition era
Written by Brent DiCrescenzo & Adam Selzer
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Chicago mobsters of the 1920s have become a sort of "Pirates of the Caribbean" for our city. There are gangster tours, a Tommy Gun's dinner theater, speakeasies that are no longer speakeasies, and we once had a sports team called the Chicago Hitmen. So it's easy to gloss over the fact that these murderous lawbreakers introduced the world to concepts like the drive-by shooting. The Prohibition-era criminal is romanticized in gangster movies and pop music. And, yeah, some of them in hindsight seem particularly silly and curious, despite being evil, with their goofy hats and names like "Willie Potatoes" and "Cockeyed Louie." The Irish North Side Gang and South Side Italian Chicago Outfit waged bloody war on what is now our doorsteps and doughnut shops. Here, we rank the 17 most notorious killers, thieves, bootleggers and, yes, politicians that continue to fascinate us.
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17.Frank "The Enforcer" Nitti
An underling and eventual puppet successor to Al Capone, Nitti ran the Outfit's bootlegging operations, channeling whiskey from Canada into Chicago speakeasies. In The Untouchables, Kevin Costner threw him off a roof, an in other films he has been portrayed by Sylvester Stallone and Stanley Tucci. In reality, he was softer and bureaucratic, pushing the mobsters into polical coercion, extorting money from Hollywood studios. In name he took over for Capone, though others ran the show. His survival is testament. Severe claustrophobia led him to commit suicide in a rail yard rather than face prison.
16.John "Papa Johnny" Torrio
An opera enthusiast sometimes known as "Johnny the Fox," Torrio was the man who brought Capone in from Brooklyn. He was the one who really built the empire Capone ended up in charge of. He worked hard to keep gangs from fighting, but when a gang working for him was blamed for the death of Dean O'Banion,original head of the North Side Gang, North Siders took revenge by shooting Torrio outside of his house in January 1925. He miraculously survived and was smart enough to retire and get out of town while the getting was good.
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15."Diamond Joe" Esposito
Esposito grew from a Black Hand extortionist and bootlegger in Little Italy to the elected Republican head of the 19th Ward. (And people say our politicians today are corrupt.) A sort of talent scout for the Outfit, Esposito brought Paul Ricca,Frank Nitti and Jack McGurn into the mob.Not to be confused with the close friend of Elvis Presley with the same name, this Diamond Joe ended up with five shotgun shells in him.
14.Vincent "The Schemer" Drucci
First making the news after taking daring leap over the Michigan Avenue bridge while it was being raised during a car chase, Drucci was known for coming up with zany schemes such as running for mayor and going to London to steal the crown jewels. His favorite trick was to dress as a priest and mess with people on the street. He was killed by the cops in 1927.
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13.Louis "Two Gun" Alterie
Obsessed with the Wild West, Alterie never went without a pair of Colt 45 pistols in holsters at his side, hence his nickname. A thug for Dean O'Banion, the temperamental hitman challenged rival gang members to a shootout on State Street and once punched a horse in the face. He pretended to be insane as a defense, but probably was. I mean, look at that hat. It's like being executed by the Arby's logo.
12.Jack "Machine Gun" McGurn
One of Capone's top hitmen, McGurn (born in Sicily asVincenzo Gibaldi)actuallymay not have been the shooter at the famous St. Valentine's Day Massacre (it's one of those cases where there's a new theory every six months), but local gangsters certainly blamed him for it. When he was eventually shot down himself in a Milwaukee Avenue bowling alley in 1936, the killers left a valentine at his feet reading "You've lost your job, you've lost your dough / Your jewels and car and handsome houses / But things could still be worse, you know / At least you haven't lost your trousers!"
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11.The Genna Brothers
The Genna Brothers officially worked for John Torrio, but wanted to branch out. They're generally blamed for having killed O'Banion and starting the gang war. By the time Tony Genna was shot to death outside of a Grand Avenue grocery store in July 1925, he was so unpopula no one's sure which gang killed him. A couple of his brothers had already been killed that year.
10.Frank McErlane
One of the early adopters of the Tommy Gun, McErlane went insane in 1931 and was found shooting up an empty street that he thought was full of ghosts. When he died the next year, one anonymous gangster said, "I don't remember that he ever did anything good in his life. I don't believe he had a friend left."
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9.Giacomo "Big Jim" Colosimo
The proto-pimp, Colosimo earned the moniker "Diamond Jim" for his white suits and diamond rings, pins and jewelry. The prostitution kingpin oversaw around 200 brothels, including the Four Deuces at Wabash and Cermak in the Near South Side. Up the street, where his restaurant and clubColosimo's Cafe sat, is nowTommy Gun's Garage, a 1920s gangster-themed dinner theater.
8.Frank and Peter Gusenberg
Contract killers under the employ of the North Side Gang, brothers "Goosey" and Frank left bullet holes all over the city. Wearing brown overalls, Peter casually emptied an entire 100 round chamber of Tommy gun ammo into the Hawthorne Hotel, Capone's Cicero hub. The younger Frank was the only survivor of the St. Valentine's Day Massacre, despite being riddled with 14 bullets. In the hospital, cops asked who shot him. "Nobody shot me," he replied.
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7.Hymie Weiss
One of the "board of governors" who took over for O'Banion in the North Side Gang, Weiss was considered "the only man Capone fearerd." The Polish born mobster was shot in 1926 outside of Holy Name Cathedral, right across the street from O'Banion's flower shop, a year after his old boss was killed. Legend has it that a hole in the cornerstone of the church is one of the bullet holes. It's probably not true, but the cornerstone was shot up pretty badly that day.
6.Paul "The Waiter" Ricca
Know as "The Waiter" due to his start in Diamond Joe Esposito's restaurant, Ricca outlasted everyone on this list, running the Outfit after Capone. Under his oversight, the mob moved from narcotics and prostituion to grander schemes like labor racketeering and extorting movie studios in Hollywood. He lived until 1972.
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5.George "Bugs" Moran
After taking over the North Side Gang (as everyone else capable of running it was dead by then), Moran was presumably the target of the St. Valentine's Day Massacre in 1929. He wasn't in the garage that day. One of the pioneers of "drive-by" shootings, Moran lived until 1957, when he died in prison.
4.Dean O'Banion
Original head of the Prohibition era North Side Gang, O'Banion got his start as a singing waiter in a tavern where the Kerryman now resides (it was a punk club called O'Banion's in the 1980s) and ran a flower shop on State Street as a day job. The great gang war of the 1920s really got underway after he was shot in the flower shop in November 1924. By this time, the gangsters were already being romanticized; a Tribuneheadline read "O'Banion Gang Like Pirates of Olden Days - Beer Trucks Their Gold Ships."
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3.Lester Joseph "Baby Face" Nelson
As a nascent mobster, Nelson stole tires, drove bootlegging trucks and mugged the wife ofWilliam “Big Bill” Thompson, the mayor of Chicago (she's the one who compared his face to that of a baby). That was not his only high-profile target. In 1930, he invaded the home of magazine bigwigCharles M. Richter, tying him up with adhesive tape. After serving some time in the clink, he hooked up with Dillinger. After the deaths of Dillinger and Pretty Boy Floyd, Nelson rocketed up the charts to be Public Enemy No. 1, until being gunned by federal agents at the age of 25 and dying in a Wilmette safehouse.
2.John Dillinger
Though he was an Indiana native who robbed banks in seemingly every Midwestern state but Illinois, Dillinger is forever linked with Chicago. The charismatic criminal hid out in Uptown and eventually met his end outside the Biograph Theater on Lincoln (now home to Victory Gardens). He became something of a rock star—the Johnny Depp of his time, say, but with armed robberies instead of box office bombs—through his ruthless activity. When Cook County put his corpse on display to the public (yeah, they used to do that), 15,000 people lined up to see him.
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1.Alphonse Gabriel "Al" Capone
Because he's become more of a cartoon character or Halloween costume in our modern era, it's easy to overlook the fact that he caused a gargantuan amount of death and pain for our city. He was the pioneer of the mobster as pop star, as sharp with his PR tactics as his bootlegging. While battling the North Side Gang for control of the underworld, he opened soup kitchens and strutted around town in custom suits, chomping cigars and sipping Templeton Rye. Every mobster cliche today is in some way due to him.
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FAQs
Who was a famous gangster in Chicago during Prohibition? ›
Al Capone, byname of Alphonse Capone, also called Scarface, (born January 17, 1899, Brooklyn, New York, U.S.—died January 25, 1947, Palm Island, Miami Beach, Florida), American Prohibition-era gangster, who dominated organized crime in Chicago from 1925 to 1931 and became perhaps the most famous gangster in the United ...
Who were the biggest Prohibition gangsters? ›Al Capone, Mob boss in Chicago, is the most infamous gangster and bootlegger of the Prohibition era.
What are some famous criminals from the Prohibition era? ›- Louis Campagna.
- Al Capone.
- Frank Capone.
- Ralph Capone.
- Robert Carey (gangster)
- Anthony Carfano.
- Silvestro Carollo.
- William Colbeck (gangster)
Most of the gangster haunts have long since been razed, and city officials and residents have put the Prohibition-era crime and corruption well behind them. But Al Capone may still be the city's most famous citizen -- a notoriety perhaps now shared by former Chicago Bulls superstar Michael Jordan.
Who was the most ruthless gangster? ›...
Albert Anastasia | |
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Service/branch | U.S. Army |
Years of service | 1942–1944 |
Its investigators were called prohibition agents, or more colloquially 'Prohis' /ˈproʊhiː/. Its most famous agent was Eliot Ness.
Who was the main leader of Prohibition? ›In October 1919, Congress put forth the National Prohibition Act, which provided guidelines for the federal enforcement of Prohibition. Championed by Representative Andrew Volstead of Minnesota, the chairman of the House Judiciary Committee, the legislation was more commonly known as the Volstead Act.
Who gained the most from Prohibition? ›The prohibition movement achieved initial successes at the local and state levels. It was most successful in rural southern and western states, and less successful in more urban states. By the early 20th century, prohibition was a national movement.
Who was the biggest gangster of all time? ›Al Capone is perhaps the most notorious gangster of all time, and also one of the richest. During prohibition, Capone controlled the illegal alcohol, prostitution and gambling rackets in Chicago which brought in $100 million a year at its prime.
What is Chicago Mobs of the Twenties? ›Chicago Mobs of the Twenties was a book published in New York on Earth in the year 1992. It detailed life in the city of Chicago during the 1920s when the conventional government had broken down and crime families had taken over.
Who were the biggest gangsters of the 1920s? ›
Rival gangs led by the powerful Al “Scarface” Capone and the hot-headed George “Bugs” Moran turned the city streets into a virtual war zone with their gangland clashes. By 1926, more than 12,000 murders were taking place every year across America.
Who is the head of the Chicago outfit today? ›The current reputed boss of the Outfit since 1996 is John DiFronzo who took control when Carlisi was convicted of mob racketeering, loansharking, and arson. At the current age of 87 (2016) he has still eluded authorities.
Who was the serial killer in Chicago? ›John Wayne Gacy (March 17, 1942 – May 10, 1994) was an American serial killer and sex offender who raped, tortured, and murdered at least 33 young men and boys in Norwood Park Township, Illinois, a suburb of Chicago.
Who was the most respected gangster? ›1. Al Capone (1899-1947) Earning the nicknames Scarface, Big Al, Big Boy, and Snorky, Alphonse Gabriel Capone was born in New York.
What is a mobsters wife called? ›molls. A woman who's the companion or conspirator to a gangster can be called a moll. One of the most famous molls was Bonnie Parker, of the criminal duo Bonnie and Clyde.
Who is the most powerful mobster today? ›With the deaths of Bernardo Provenzano in 2016 and Salvatore Riina in 2017, Messina Denaro was seen as the unchallenged boss of all bosses within the Mafia. After 30 years on the run, he was arrested on 16 January 2023 near a private clinic in Sicily's capital, Palermo.
Who was the father of prohibition? ›Under the fiery leadership of Portland's Neal Dow - known internationally as the "Father of Prohibition" - Maine approved a total ban on the manufacture and sale of liquor in 1851. This so-called "Maine Law" remained in effect, in one form or another, until the repeal of National Prohibition in 1934.
How did gangsters get rich from prohibition? ›Organized crime emerged because of Prohibition, as it gave gangsters another racketeering operation. Mobsters made millions of dollars every year from bootlegging and running thousands of speakeasies.
Who were the biggest Prohibition bootleggers? ›George Remus was the biggest bootlegger of the Prohibition era, but his reign was short-lived.
Who was the most famous bootlegger of the 1920s? ›Criminal competition for control of the illegal alcohol market was intense and violent. One of the most notorious mobsters, Al Capone, ruled Chicago with an iron fist.
What was Prohibition nickname? ›
The National Prohibition Act was informally known as the Volstead Act.
Did most people drink during prohibition? ›We find that alcohol consumption fell sharply at the beginning of Prohibition, to approximately 30 percent of its pre-Prohibition level. During the next several years, however, alcohol consumption increased sharply, to about 60-70 percent of its pre-Prohibition level.
What group was rich during selling alcohol prohibition? ›Today, the Bronfmans are still one of the richest families in North America, but they don't wield their clout of old. Patriarch Samuel Bronfman built up the family's fortune in Montreal by selling Canadian whiskey to the United States during Prohibition in the 1920s.
Who was prohibition a failure for? ›Not only did Prohibition fail, over the long-run, to decrease the overall consumption of liquor, it also failed to decrease taxpayer burden, the prison population, and public corruption.
Who is the biggest crime family in the world? ›The 'Ndrangheta have surpassed Sicily's famous Cosa Nostra to become the most powerful organised crime group in Italy and one of the largest in the world.
Who were two of Chicago's biggest gangsters? ›Johnny Torrio was the street gang leader and among the other members was Lucky Luciano, who would later attain his own notoriety. About 1920, at Torrio's invitation, Capone joined Torrio in Chicago where he had become an influential lieutenant in the Colosimo mob.
Does Chicago still have mobs? ›Despite a diminished crime syndicate in Chicago, the organization's bones are in place seven and a half decades after Capone's reign officially ended. However, 2022 has not been business-as-usual for the crime organization, according to Chicago mob expert and "The Chicago Outfit" author John Binder.
Where did gangsters hang out in Chicago? ›If The Green Mill is one of the most famous sites from Al Capone's Chicago, then the Exchequer Restaurant & Pub may be one of the most under-sung. Located below the 'L' tracks near the Adams/Wabash station, this family-owned restaurant was the site of a Capone-run speakeasy during Prohibition.
Who was one of the most notorious gangsters from Chicago during the 1920s? ›Al Capone. Al Capone, also called Scarface, was a major gangster during the Prohibition era in Chicago. He was eventually prosecuted and convicted for tax evasion in 1931. He was sentenced to 11 years in federal prison and served 8 before he was released.
Who was the oldest mobster? ›Who were 3 famous gangsters from 1920? ›
The 1920s plays host to many other organized criminals with expensive suits and flashy names. The 20's most famous gangsters were: "Scarface" Capone, "Lucky" Luciano, "Bugs" Moran (AKA Jack "Legs" Diamond), and "Dutch" Schultz.
Who was the biggest gangster in Chicago in the 1920s? ›Chicago, Illinois, has a long history of organized crime and was famously home to the American mafia figure Al Capone.
Who was the most famous bootlegger during Prohibition? ›Al Capone became one of the most successful racketeers in Chicago. He owned thousands of speakeasies. He led illegal brewery, distillery, and distribution operations and made tens of millions of dollars each year throughout Prohibition.
Was Al Capone around during Prohibition? ›Born in 1899 in Brooklyn, New York, to poor immigrant parents, Al Capone went on to become the most infamous gangster in American history. In 1920 during the height of Prohibition, Capone's multi-million dollar Chicago operation in bootlegging, prostitution and gambling dominated the organized crime scene.
Who was the most famous Prohibition agent? ›Its investigators were called prohibition agents, or more colloquially 'Prohis' /ˈproʊhiː/. Its most famous agent was Eliot Ness.
Who was the biggest supporter of Prohibition? ›The Anti-Saloon League, with strong support from Protestants and other Christian denominations, spearheaded the drive for nationwide prohibition. In fact, the Anti-Saloon League was the most powerful political pressure group in US history—no other organization had ever managed to alter the nation's Constitution.
Who was the best known most feared American gangster in the 1920s? ›Rival gangs led by the powerful Al “Scarface” Capone and the hot-headed George “Bugs” Moran turned the city streets into a virtual war zone with their gangland clashes. By 1926, more than 12,000 murders were taking place every year across America.