This chapter begins with Eliano’s birth and early exposure to a world of cross-cultural exchange. Eliano was raised and educated by his grandfather, Elijah Levita, the famed scholar of Biblical Hebrew who collaborated with Christian Neo-Platonists and Kabbalists such as Marsilio Ficino and Cardinal Egidio da Viterbo. The chapter then turns to Eliano’s time as a merchant in Egypt with his father. Next, Eliano experienced, in quick succession, his older brother’s conversion to Catholicism and the death of Elijah Levita. Within two years, Eliano traveled to Venice, converted to Christianity, and entered the Society of Jesus. This chapter then unpacks Eliano’s first confrontation with his Jewish past when he returns to Venice en route to Egypt. Chapter 1 sets up the remainder of the book by unpacking the various ways in which Eliano’s Jewish youth and his confrontations with it as a Catholic informed his later missionary efforts: he was educated in philology and book printing; he traveled to Egypt and learned Arabic; his brother and the Jesuits welcomed him into their intellectual circle whereas other Jews did not.