In 1923, Scalise immigrated to Chicago due to his troubles with the law in Castelvetrano, Sicily. Shortly after arriving to Chicago, Scalise found employment with the gangs at Taylor street. While working for the Gennas, Scalise met Albert Anselmi who ultimately became his mentor and best friend. Both men remain to this day, the prime suspects in the November 1924 murder of Dean O'Banion, boss of Chicago's North Side Gang. Following the death of O'Banion, the two secretly left the Gennas for Al Capone's Chicago Outfit.
On June 23, 1925, Anselmi and Scalise, along with Mike Genna, ambushed North Siders George "Bugs" Moran and Vincent "The Schemer" Drucci in The Patch. Only wounding Drucci, the shooters were spotted and pursued by a detective squad on Western Avenue, The gangsters were overtaken at the corner of Western and 60th street where they began shooting at the police. During the shootout, two officers, Harold Olsen and Charles Walsh, were killed. Anselmi and Scalise were bound over trial. Both were found guilty of the manslaughter of Officer Walsh and were sentenced to 14 years in prison. In December of 1926 both Anselmi and Scalise were granted retrial for the Walsh murder and in January were released from prison. In June of 1927, the two were acquitted and Capone threw them a grand party. In 1929, Anselmi and Scalise were arrested and charged in the St. Valentine's Day Massacre case. However, both were released due to lack of evidence.
In the morning of May 8, 1929, the bodies of John Scalise, Albert Anselmi, and Joseph Gunta were discovered near Hammond, Indiana. All three were severely beaten and shot to death. Initially, it was suspected that the North Side gang killed the three in retaliation of the St. Valentine's Day massacre, but this theory was discounted when informants stated that the three men were lured to a banquet with their Sicilian friends and, while trying to break up a fight that was staged for their benefit, were themselves attacked and killed. Scalise's body was shipped back to Castelvetrano, Sicily for burial.
Years later, a rumor emerged that Al Capone discovered Scalise, Anselmi, and Gunta were conspiring with a rival mobster Joe Aiello to betray him. Capone refused to believe this when his bodyguard, Frank Rio, initially told him. Capone staged an argument with Rio in front of Anselmi and Scalise and slapped his bodyguard, who left the room. Moments later, the two tracked down Rio and told him their plans to betray Capone. Once Capone was confirmed of the treachery, he threw a dinner in their honor. During the dinner, Capone beat the three men with a baseball bat and on the brink of their deaths, two or three gunmen stepped in to finish the job.
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