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

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

Patrick Lynch - June 25, 2017

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.

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