Alderisio began his criminal career as a teenager during the Prohibition era. One of his early arrests was for vagrancy; he frequently waited outside Outfit boss Al Capone's Lexington Hotel headquarters in the hope of getting a job as a messenger. In the early 1930s, Alderisio's maternal cousin Louis Fratto brought Alderisio into the Outfit. Alderisio began working with Sam Battaglia and Marshall Caifano as an enforcer. Rising steadily through the ranks during the Great Depression, Alderisio soon gained a reputation for brutality. By the end of the decade, Alderisio was working under Jake Guzik, the Outfit's financial expert, as a bagman delivering payoffs to Chicago judges and police officials.