Ludovico Di Ambrosio, better known as "Vincent Drucci" was born in Chicago, IL to John and Rose Di Amrosia, both Italian immigrants. There is very little known about Drucci's childhood other than he was close friends with Dean O'Banion. After being honorably discharged from the US Navy, Drucci returned to Chicago and started robbing telephone coin boxes until he was caught by the North Siders. Shortly after, he was invited to join the North Side Gang. Here he gained the nickname "The Schemer" for his inventive and detailed plans for committing bank robberies, kidnappings, and other crimes. Always creative, he once allegedly eluded police pursuit by leaping his car over a bridge just as it was raising to allow passage of a boat.
The greatest rival to the North Side Gang was the South Side Gang. On January 25, 1925, Drucci, Weiss, and George Moran ambushed Johnny Torrio, lieutenant to Al Capone, shooting at Capone's car but failing to kill him. Two days later, Drucci and a couple other North siders attacked Torrio outside his home only injuring him. Between May and November 1925, Drucci was a suspect in 3 murders and was himself wounded. On May 25, Weiss, Drucci, and Moran were believed to be the gunmen who killed Angelo Genna. In retaliation, Moran and Drucci were surprised when Scalise and Anselmi started shooting at Moran's car injuring Drucci. A month later, Drucci was thought to be one of the two shooters who killed Tony Genna. Drucci's killing spree ended in November when he fatally wounded Samuzzo Amatuna in a barbershop. On August 10, 1926 Drucci and Weiss were ambushed by two South Side gunmen; both men left uninjured. In retaliation, the North Side Gang conducted a massive raid on the hotel that Capone owned and lived in. Although shaken up by the attack, Capone was unhurt.
On October 11, South Side gunmen succeeded in killing Hymie Weiss outside of Holy Name Cathedral. Therefore, Drucci
and Moran assumed leadership of the North Side Gang. After Weiss' shooting, Drucci and Moran attended a peace conference with all of the Chicago gangs, including the South Siders. Although Moran wanted to continue fighting, Drucci persuaded him into accepting a ceasefire. However, on April 3, 1927 Drucci ransacked the office belonging to an alderman aligned with the South Side gang. Thus, the Chief of the Chicago Police Department ordered his men to arrest every North Side gang member in sight. The next day, two police officers stopped Drucci and two other North Side Gang members. When they discovered Drucci was carrying a firearm, they arrested him. Four police officers were assigned to escort Drucci and the other North Side gang members to the courthouse. While waiting to enter the vehicle, Drucci began arguing with the arresting police officer, Dan Healy. Their argument continued and escalated when the two entered the police vehicle. Allegedly, Drucci lunged for Healy's firearm forcing Healy to fire his weapon four times hitting Drucci in the arm, leg, and abdomen. Because of his injuries, Drucci died on the way to the hospital. On April 7th, Drucci, a veteran of the Navy, was buried with full military honors. Drucci's lawyer was waiting at the courthouse when he heard the news of his client's demise. He demanded that Healy be arrested for murder. After hearing the testimonies of Detective Healy and other witnesses, the Coroner's jury ruled the killing a justifiable homicide.