On April 1, 1924, Torrio gang members Frank Capone and Charles Fischetti had a quarrel with the police which resulted with the death of Capone.

On April 4, 1927, North Side gangster Vincent Drucci was also killed by the cops while being arrested.

December 13, 1925, William “Three Fingered Jack” White shot and killed Policeman Edward Pflaume of Forest Park. White was a close associate to the Capone mob and later the Outfit.

In 1923, Joe Montana murdered Detective Lawrence E. Harnett during a liquor raid. Montana worked for his father Joe Sr. and also for Diamond Joe Esposito.

On June 13, 1925, Mike “The Devil” Genna was killed by the cops because of a previous shootout. Mike and two of his associates were in a shootout with the Northsiders and killed two police officers during the process. Story goes that the cops managed to shoot Genna in the leg, while badly wounding him and later he died in an ambulance after he kicked an officer in the face who tried to question him

On December 31, 1931, Sam "Teets" Battaglia and George Busk shot police detective Martin Joyce and patrolman John Maier