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.