Bioff was born and briefly raised in a kosher Jewish household in Chicago, but his father kicked him out on the street when he was eight years old. Bioff soon became involved in criminal ventures, beginning with petty theft, then minor protection rackets and working his way up to pimping in Chicago's Levee vice district, of which he was later convicted in 1922. Bioff later worked for Harry and "Greasy Thumb" Jake Guzik where, through Guzik, Bioff met Al Capone and later "The Enforcer" Frank Nitti.