This chapter discusses the process of reconciliation between the Catholic Church and the Jewish people launched by Pope John XXIII in 1960. In order to heal the wounds left by a troubled history, the Church chose to proceed on a path of conciliatory gestures without any explicit request for forgiveness or apology. Some steps were unilateral pronouncements by the Church, others acts of engagement with the Jewish people and the State of Israel. This long, challenging process began at Vatican II in 1965 with the declaration NostraAetate, Part 4, proceeded via the establishment of diplomatic relations with Israel in 1994, and culminated in Pope John Paul II’s Millennium pilgrimage to Israel in 2000 when he inserted a prayer of repentance – teshuva in Hebrew – into Jerusalem’s Western Wall. This moving and original penitential gesture is analyzed within the context of Church thinking and the logic of the papal visit. Emphasis is placed on the pope’s deep personal commitment to fraternal ties with the Jewish people.