Born in Bagheria, Sicily, Aiello was one of 10 boys in his family. In July 1907, Aiello immigrated to the United States to join various members who were already there. The Aiello family set up a number of businesses in both New York and Chicago. They became importers of groceries such as olive oil, cheeses, and sugar. Aiello was the co-owner of a cheese importing business alongside a fellow Sicilian, "The Scourge" Antonio Lombardo. The Aiello's also opened a bakery and a confectionery shop. With the enactment of Prohibition and beginning of bootlegging, the sugar import business brought the family into contact with organized crime. In Chicago, the Aiello family began supplying sugar to gangs illegally distilling spirits, a territory previously occupied by the Genna family, a Sicilian-Ameri