 Di Maggio was born in San Giuseppe Jato, a town in the province of Palermo and was initiated in 1981 in the local Mafia family, headed by Bernardo Brusca.He was involved in the elimination of Rosario Riccobono and 14 other men of Riccobono’s Mafia clan in November 1982 during the Second Mafia War (In 2001, he received an 11 year prison sentence, which took into account his testimonies as government witness).When the capo-famiglia of San Giuseppe Jato, Bernardo Brusca, a member of the Sicilian Mafia Commission went to prison and his son Giovanni Brusca was banished to Linosa, Di Maggio became acting head of the family.