John Scalise, born Giovanni Scalise in 1900 in Castelvetrano, Sicily, immigrated to the United States and quickly became embedded in the criminal underworld of Prohibition-era Chicago. Little is known about his early life before joining organized crime, but by the early 1920s, he was deeply involved with the Genna brothers, a Sicilian crime family that had a stronghold in Chicago’s Little Italy. While working with the Gennas, he formed a close bond with fellow Sicilian immigrant Albert Anselmi.

John Scalise, alongside his trusted partner Albert Anselmi, was one of Al Capone’s deadliest hitmen during Prohibition-era Chicago. After defecting from the Genna crime family, the duo became key players in the orchestration of Dean O’Banion’s assassination on November 10, 1924.

On June 13, 1925, Scalise, Anselmi, and Mike Genna ambushed North Side bosses George “Bugs” Moran and Vincent “The Schemer” Drucci. The assault led to a chaotic, high‑speed chase that ended at Western and 60th Street, turning into a fire‑fight where two police officers, Harold Olsen and Charles Walsh, were killed and a third was wounded. Genna was gunned down, while Scalise and Anselmi were captured after fleeing onto a streetcar.

They were eventually tried—not for murder, but for the manslaughter of Officer Walsh—receiving 14-year sentences. Yet, their trial included dark undercurrents: private "collectors" were sent around The Patch to fund their defense, sparking further murders among their own network. After these tumultuous months, both Scalise and Anselmi were acquitted in a retrial in June 1927, setting off celebrations characterized by legend’s tell of champagne corks being shot like guns.

In the infamous Saint Valentine's Day Massacre of 1929, although Scalise and Anselmi were arrested and charged along with others, they were released immediately at their arraignment on March 8, 1929 for lack of evidence—again escaping justice despite widespread suspicion.

On May 8, 1929, the bodies of Scalise, Anselmi, and mob boss Joseph Giunta were discovered on a deserted road near Hammond, Indiana—brutally beaten, shot to death, and in Scalise’s case, cruelly disfigured, with one of his gunshot wounds removing his pinky finger. Mob lore holds that Capone himself orchestrated the killings. Secretly informed of Scalise and Anselmi’s alleged plot with rival Joe Aiello and Giunta to betray him, Capone lured them to a fake celebratory dinner—only to strike them down with a baseball bat before his men sealed the execution with gunfire.