For several decades historians have struggled with the dynamics of cross-cultural contact and the creation of perceptions of the Other. Detailed studies of the image formed by Europeans of the Islamicate World during the pre-modern period, with a few exceptions, rarely analyze why and how these representations were formed. Through the analysis of Jesuit missionary correspondence made during the middle of the seventeenth century, this paper will present the variables that affected the development of Jesuit attitudes toward the people and environment of Greater Syria. This paper will also reveal these projections were contingent on the form of communication: personal letters, annual reports, and published works. Each of these modes of communication reflected degrees of detachment and embellishment to suit the audience. Where the letters sent to the Superior General in Rome typically disclosed the chronology of events that influenced the course of the missions, the reports (sent to the provincial hierarchy and were circulated throughout the Jesuit colleges) conveyed in flowing narrative a more subjective and theatrical rendition of their experience. Comparing the letters of the missionaries to their annual reports reveals their capacity for objectivity and the realities of the relationships they developed, as a means of wading through common tropes about Southwest Asia and Ottoman society in general articulated in the reports. In writing for a public audience, the Jesuits show how the form of communication influenced the methods and language used to describe Ottoman-Syrian society. Yet, the paper also considers that while the Jesuits had pre-conceived notions of Syria, their constructions of Syrian society were also influenced as much by local factors as their ideologically-driven stereotypes. These local factors, mixed with the violence of strongmen and the Jesuits failure to affect conversions to Catholicism, filled the pages of their reports with apocalyptic visions and made heroes of holy men.