To Live and Die in Chicago: 7 Prohibition Era Gangsters Who Met a Violent End in the Windy City

To Live and Die in Chicago: 7 Prohibition Era Gangsters Who Met a Violent End in the Windy City

Patrick Lynch - June 25, 2017

The city of Chicago was home to some of America’s most notorious gangsters. The violence escalated with an all-out gang war between the North Side and the South Side. Names such as Dean O’Banion, Al Capone, Hymie Weiss, Johnny Torrio and many others became infamous around the city as they bootlegged and murdered their way to a fortune. However, the fates of a large majority of these gangsters served proof that ‘crime doesn’t pay.’ While Al Capone survived the bloody feuds of the 1920s and 1930s, he was one of the few major criminal figures that didn’t meet his maker at the point of a gun. In this piece, I look at 7 of the most notorious gangsters to live and die in Chicago.

1 – Dean O’Banion

Dean O’Banion was born in Illinois on July 8, 1892, and is considered as the first great gangster of Chicago’s North Side. Although the newspapers of the era spelled his first name as ‘Dion,’ he always used ‘Dean.’ His family moved to Chicago from the town of Maroa in 1901 after his mother died. The O’Banions settled in an Irish area called Kilgubbin, also known as ‘Little Hell’ due to the high level of crime. O’Banion was not only a violent gangster, but he was also an excellent singer and had a genuine love of floral arrangement.

To Live and Die in Chicago: 7 Prohibition Era Gangsters Who Met a Violent End in the Windy City
Dean O Banion. Den of Geek

He joined the Little Hell gang as a youth and met Hymie Weiss, Vincent Drucci, and George Moran who would help him found the North Side Gang later in life. O’Banion was known for his mischievous sense of humor and regularly played jokes on his gang friends. He earned the name ‘gimpy’ after an accident where a car he was sitting on stalled and rolled backward. He fell, and the vehicle ran him over, and although he was lucky to survive, his left leg was one inch shorter than the right, so he walked with a limp until his death.

Like every other gangster, O’Banion began his criminal career with petty thieving. He served 3 months in a correctional facility in 1909 for stealing stamps, and in 1911, he received a short prison sentence for assault with a blackjack and possession of deadly weapons. Despite leading one of the city’s biggest gangs later in life, this was the last time he ever went to prison.

He started an extremely successful bootlegging operation in 1920 and earned up to $1 million a year selling liquor at his peak. His gang became known for committing major heists including the theft of $100,000 worth of Canadian whiskey and stealing 1,750 barrels of whiskey from Sibly Distillery. By now, O’Banion faced fierce competition from the South Side Gang led by Johnny Torrio.

O’Banion’s gang started to hijack the Genna Brothers’ liquor shipments, and in February 1924, he tried to frame Capone and Torrio for the murder of John Duffy, a North Side ‘hanger-on’. In fact, it was O’Banion’s crew who killed Duffy. The final straw for Torrio came when O’Banion sold his rights to the Sieben Brewery to the South Side Leader for $500,000. The police raided the brewery on the night of O’Banion’s last shipment and arrested him, Torrio and several others. O’Banion got off lightly as it was his first arrest for breaching Prohibition laws. Meanwhile, Torrio was indicted, and his one-time partner refused to give him the money back.

Torrio knew he had been double-crossed and ordered a hit on O’Banion. It transpired that the North Side Gang leader gained knowledge of the raid and used the information to steal from Torrio. On November 3, 1924, during a meeting with Al Capone and a few other important criminal figures, O’Banion refused to wipe out a debt owed by Angelo Genna as an act of good faith. Instead, he called Genna and demanded his money back. Mike Merlo and the Unione Siciliana refused to sanction the murder of O’Banion but when Merlo died on November 8, O’Banion’s days were numbered.

Torrio ordered the hit almost immediately after Merlo’s death, and on November 10, 1924, O’Banion was busy clipping chrysanthemums in his flower shop. His bodyguard was hung-over and was not available to protect his boss. Frankie Yale, Torrio and two of Capone’s gunmen entered the shop and shot O’Banion 6 times. He received a lavish funeral estimated to have cost over $100,000.

To Live and Die in Chicago: 7 Prohibition Era Gangsters Who Met a Violent End in the Windy City
The Genna Brothers. National Crime Syndicate

2 – Angelo Genna

‘Bloody Angelo’ Genna was born in Sicily, Italy on February 3, 1898, and moved to Chicago in 1914 to join brothers. There was a total of six brothers involved in the Genna Crime Family, but Angelo was the most violent. The Genna’s aligned themselves with a Sicilian Mafia boss named Anthony D’Andrea who ran for the important position of alderman of the city’s 19th Ward which included Little Italy.

D’Andrea narrowly lost the election to John Powers in 1921 which angered the Genna family. By now, they had already gained a reputation as they had been involved in bootlegging since 1919. In March 1921, Angelo murdered one of Powers’ precinct captains, Paolo Labriola, probably on the orders of D’Andrea. It was the middle of the violent Alderman Wars, and two months later, D’Andrea was murdered outside of his apartment building.

Meanwhile, a witness claimed to have seen Angelo murder Labriola, and he stood trial. However, another man claimed that the witness was paid to lie about Angelo’s presence at the scene, so the case was eventually dismissed. Nicola Maggio was a close friend of the Genna family, but she was murdered, apparently by a man named Paul Notte. In typical fashion, Angelo retaliated in kind by shooting Notte on March 16, 1922. Notte identified Angelo as his killer while he lay on his deathbed. Although he did not name Angelo, Notte told a detective that it was the youngest of the Genna brothers.

Once again, Angelo walked free; this time because there was doubt over Notte’s mental state since he had been given medication before his death. Angelo was eventually sentenced to one year in prison for intimidating a waitress. After serving his time in Leavenworth, Angelo returned to Chicago intent on making money and avoiding violence if possible. However, his criminal activities ultimately led to his death. The Genna Family continued to sell bootleg liquor much to the chagrin of Dean O’Banion.

Angelo lost a lot of money at one of O’Banion’s casinos and instead of waiving the debt as a professional courtesy like Al Capone suggested, O’Banion spoke to Angelo on the phone and demanded that he paid his debt. The personal insult angered the Genna family, and Torrio agreed that they should kill O’Banion. On November 10, 1924, three hit men performed the deed.

The North Side Gang under Hymie Weiss demanded vengeance and went after the Genna brothers, Torrio and Capone. On May 26, 1925, Angelo was shot by three North Side Gang members and died in hospital. As he lay dying, he refused to name his shooters. Mike Genna was killed by police a few weeks later while Anthony Genna was murdered by the North Side Gang a couple of months later. Angelo’s brother-in-law, Henry Spignoli, was killed the following year, so the rest of the Genna’s returned to Sicily.

To Live and Die in Chicago: 7 Prohibition Era Gangsters Who Met a Violent End in the Windy City
Hymie Weiss. Ampoleagle

3 – Hymie Weiss

Born as Henry Wojciechowski in Poland in 1898, Weiss rose to prominence as the leader of a North Side Gang in Chicago during the prohibition era. He helped establish the gang with Dean O’Banion and George Moran, and they were in direct competition with Al Capone. Weiss’ reputation for violence preceded him, and he was apparently the only gangster that Capone feared.

Weiss’ family moved to America when he was young, and they lived on Chicago’s North Side. As a youth, he messed up a burglary and knocked over a fragrance shelf, so the police mocked the teen by dubbing him ‘The Perfume Burglar.’ Weiss befriended O’Banion when they were both teenagers, and they eventually set up their gang with Moran and controlled bootlegging and a number of other illegal activities in their area of the city.

He was known for his explosive temper. When police questioned his brother Fred on his whereabouts in 1926, Fred said that the only time he saw him in the last 20 years was in 1920 when Hymie shot him. On other occasions, when photographers tried to take his picture, Weiss would threaten to kill them. When O’Banion was murdered in 1924, Weiss swore to get revenge on Al Capone and his gang and declared war.

On January 25, 1925, Weiss and his men were suspected of shooting at Al Capone’s limousine outside of a restaurant on the city’s South Side, but their target wasn’t even there. He was also suspected of involvement in the murder of Angelo Genna on May 26, 1925. Capone survived a near miss on September 20, 1926, when Weiss’ men opened fire on him and his bodyguard Frank Rio as they ate at the Hawthorne Hotel. The assassination attempt persuaded Capone to attempt a truce with Weiss. However, he refused to meet Weiss’ demands to hand over the men that killed O’Banion.

A week later on October 11, 1926, Weiss and four of his men were seen at the Jury Selection process for the murder trial of Joe Saltis. Weiss was probably looking to forge an alliance and looked to bribe the jury to ensure the acquittal of Saltis. As the five men crossed the street to enter the same flower shop where O’Banion was murdered, two hidden gunmen opened fire with a shotgun and machine gun. Weiss and one of his bodyguards died in the attack. Jack McGurn was suspected of involvement in the attack and in the age old tradition of ‘settling scores,’ the North Side Gang did not allow him to get away with it although it took many years for them to gain revenge.

To Live and Die in Chicago: 7 Prohibition Era Gangsters Who Met a Violent End in the Windy City
Jack McGurn in 1930. Deadly Valentines

4 – Jack McGurn

McGurn received the ‘Machine Gun’ designation before George Kelly but his real name was Vincenzo Gibaldi, and he was born in Sicily in 1902. His family moved to the United States when he was just four years of age, and they lived in the Brooklyn slums. McGurn moved to Chicago aged 14 and became a boxer a couple of years later. He changed his name to ‘Battling’ Jack McGurn because pugilists with Irish sounding names received better bookings and payment.

He stayed away from gang-related activity until 1923 when his stepfather was murdered by extortionists from the Black Hand gang. Apparently, the three killers mocked the victim by saying he was a “nickel and dimer.” McGurn took swift and brutal revenge by killing all three men; he left a nickel in the hands of each of the victims. This act later became his trademark. Al Capone learned of McGurn’s deeds and was so impressed that he hired him as an enforcer. McGurn had probably come to the mob boss’ attention when he was a boxer because he was on the Outfit’s payroll before the murders.

It is strongly suggested that he was one of the two gunmen that killed Hymie Weiss in 1926. Further evidence of McGurn’s violent tendencies is seen in his brutal attempted murder of a singer/comedian called Joe E. Lewis. McGurn had part ownership of a speakeasy jazz club on Bugs Moran’s territory. The club’s manager, Danny Cohen, gave McGurn money to try and ‘persuade’ Lewis to perform as the singer was one of the city’s most popular entertainers. When Lewis refused, McGurn cut off part of his tongue and slit his throat. Lewis somehow survived and resumed his career, but he never reached his previous heights again.

While McGurn is believed to have helped plan the St. Valentine’s Day Massacre in 1929, his role in the crime was never proven. In 1930, McGurn had the dubious honor of being named #4 on the Chicago Crime Commission’s Public Enemies list. This unwanted attention resulted in McGurn’s isolation from other gangs as no one wanted to be associated with him. He was arrested at the Olympia Fields Country Club in 1933 when he was taking part in a golf tournament.

In 1936, the once powerful McGurn was practically broke and friendless. He was an easy target for the three hit men who approached him in a bowling alley in Chicago and opened fire on February 15. He was killed instantly in what was probably long overdue retribution for the Valentine’s Day Massacre and/or the murder of Weiss. It is likely that Moran ordered the hit which may have been carried out by James Gusenberg, the brother of two of the victims of the massacre.

To Live and Die in Chicago: 7 Prohibition Era Gangsters Who Met a Violent End in the Windy City
Giacomo Colosimo. Timeout

5 – Giacomo Colosimo

Also known as ‘Big Jim’ or ‘Diamond Jim,’ Giacomo Colosimo was born in Calabria, Italy on February 16, 1878. He moved to America in 1895 and began by trying to earn an honest living. He shined shoes and sold newspapers but soon decided that petty crime such as pickpocketing was more to his liking. He opened a brothel with his wife in 1902, and most sources suggest that he became the leader of a gang called the Chicago Outfit at around this time. He was also involved with an Italian gang called the Black Hand.

While Colosimo worked legitimately as a street sweeper and then a foreman, his illegal activities were bringing in real money. His brothel was a huge success and attracted the attention of two key politicians in the city. With their assistance, he soon rose to prominence in the underworld and ran up to 200 brothels. He was also involved in racketeering and gambling.

Despite his power, Colosimo was still threatened by the Black Hand gang who threatened to kill him if he didn’t give them money. Colosimo was frightened and paid up, but the gang continued to extort money. He turned to his nephew, Johnny Torrio, for assistance and Torrio murdered the Black Hand members that turned up to collect the next payment. Torrio continued to take care of his boss’ problems, but the two men soon fell out when the Prohibition era started. While Torrio wanted to make money from selling illegal booze, Colosimo didn’t want to draw attention to his many businesses.

The relationship between them completely fell apart when Colosimo divorced Torrio’s aunt and married a 19-year old singer in 1920. Torrio was irate and decided to kill his one-time boss. On May 11, 1920, Torrio arranged a meeting with Colosimo regarding a bootlegging shipment to one of Big Jim’s restaurants. Once Colosimo arrived and realized there was no shipment, he turned around to leave but was shot dead by a gunman hiding in a coatroom. Frankie Yale is widely believed to be the killer though some historians believe it was Al Capone. Torrio took control of the Outfit and eventually handed over the reins to Capone.

To Live and Die in Chicago: 7 Prohibition Era Gangsters Who Met a Violent End in the Windy City
Announcement of Drucci’s death in Newspaper. historical news

6 – Vincent Drucci

Born Vincent D’Ambrosio in Chicago in 1898, this Sicilian-American mobster gained notoriety as a member of the city’s North Side Gang. He served in the Navy for a while, but when he returned home, he resorted to petty crime such as breaking open telephone boxes to steal money. Drucci eventually graduated to the big leagues when he became friends with Dean O’Banion. He earned the sobriquet ‘schemer’ because of his propensity to come up with new and ingenious ways of robbing banks, performing kidnappings and other innovative forms of criminal activity.

The 18th Amendment was ratified in 1919 and took effect on January 16, 1920. It established the prohibition of the sale, transport, and distribution of alcohol in the United States. The Prohibition Era was a golden age for criminals such as the North Side Gang in Chicago who made a fortune by bootlegging booze. Drucci was a key member of the gang and worked alongside O’Banion. The South Side Gang, under Johnny Torrio, was the biggest rival of the North Side Gang and once O’Banion was gunned down in 1924, the violence escalated as the new gang leader, Hymie Weiss, carried out retaliatory attacks.

On January 25, 1925, Drucci was involved in the failed attempt at murdering Al Capone. Just two days later, he tried and failed to kill Torrio and soon after the South Side Gang leader came out of the hospital, he relinquished control to Al Capone. Not content with attacking rivals, Drucci helped murder North Side allies Angelo and Anthony Genna in the space of a couple of months. On November 13, he was part of a group that killed one of the Genna’s top gunmen, Samuzzo Amatuna. The killing took place in a barber shop, and the gang also kidnapped and murdered the shop owner.

Drucci’s activities ensured he was high on Capone’s hit list and the new South Side Gang leader was determined to squash the man he called the ‘bedbug.’ The first significant attempt on Drucci’s life occurred on August 10, 1926. He was with Weiss at the time, and neither man suffered injury. The duo survived another assassination attempt just five days later. They decided to retaliate and narrowly failed to murder Capone in a massive raid on the Cicero Hotel owned and lived in by the legendary gangster.

On October 11, Drucci became joint leader of the North Side Gang along with Bugs Moran when Weiss was murdered. Both sides called a peace conference soon afterward, and Drucci convinced Moran to agree to a ceasefire. It didn’t last long as Drucci ransacked the office of an alderman known to be an associate of the South Side Gang. It was a mistake as it prompted the chief of the Chicago Police Department to order the arrest of all North Side members on sight.

After surviving multiple attempts on his life from his rivals, it is perhaps ironic that Drucci died at the hands of the police, one of the few high-profile gangsters to die in this manner. On April 4, 1927, police officers spotted Drucci and two of his gang, and once they saw he was carrying a gun, they arrested him. Four officers were ordered to escort Drucci to the courthouse, but when Detective Dan Healy was putting the crime boss in the police car, Drucci swore at him and demanded that Healy let go of his arm.

Healy hit Drucci and brandished his gun. Instead of backing down, Drucci continued to taunt and threaten the detective. He said: “Take your gun off, and I’ll kick the hell out of you.” In an act of astonishing stupidity, Drucci tried to take the gun from Healy after hitting the detective, but Healy recovered and shot Drucci three times. The gangster died en route to the hospital. His funeral was a typically ostentatious affair with a $10,000 silver casket and $30,000 worth of flowers.

To Live and Die in Chicago: 7 Prohibition Era Gangsters Who Met a Violent End in the Windy City
Esposito hands out baskets of food to the poor of Chicago. Pinterest

7- Joe Esposito

‘Diamond’ Joe Esposito was born in Accera, Italy on April 28, 1872, although there is a suggestion that he was Sicilian. He was born as Giuseppe Esposito and moved to America. By the early 1900s, he was involved in one of the numerous street gangs that operated in Chicago’s Little Italy. After the Volstead Act was enacted, his firm, the 42 Gang, became embroiled in bootlegging and he enjoyed early success with the aid of the Genna Brothers.

Unlike the majority of gangsters of the era, Esposito enjoyed political success and became a Republican ward boss in Chicago’s 19th Ward. He used his influence to protect the Little Italy bootlegging gangs including the Gennas and the South Side Gang boss, Johnny Torrio. During the early 1920s, Esposito watched as several of his allies were murdered including fellow politician Antonio D’Andrea in 1921 and Angelo and Anthony Genna, both men died in 1925.

Despite his early association with the South Side Gang, Esposito soon found that the gang’s new leader, Al Capone, had political influence of his own, so the two men became fierce rivals. He became known as ‘Diamond’ Joe because of his love for flashy jewelry and extravagant clothing. His trademark was a $5,000 diamond ring, and a diamond belt buckle with his initials J.E engraved on it. Whatever favors he performed to procure the money for such fineries came back to haunt him because, on March 21, 1928, he was murdered outside his house in a drive-by shooting.

Esposito was apparently given a warning on the morning of his death, but it has long been assumed that his bodyguards were part of the assassination plot. Esposito was in the middle of a new political campaign; one where he hoped to become the Republican Ward Committeeman of the 25th Ward. He was standing outside his home when suddenly; his assassins drove past and opened fire. Even though both of Esposito’s bodyguards were standing beside him, neither man was hit. This is something of a surprise since Esposito was riddled with a total of 58 pellets and bullets from the combination of shotgun and revolver fire.