This paper explores Haskalah (Jewish Enlightenment) literature representations of the Orient. Focusing on key Haskalah figures—Isaac Euchel, Solomon Löwisohn, and Abraham Mapu—the article asks how the discursive presence of the Orient influenced Haskalah literature’s definition of modernity and secularity, and provides a comprehensive analysis of the various literary tropes and figures (such as the beautiful, the sublime, oriental despotism, paganism) used by maskilic authors for either coping with or repressing the Orient in their work. The article argues that modern Hebrew literature’s embrace of humanistic western culture is highly ambivalent, and that the regnant historiography of Hebrew literature did not address this ambivalence properly. The  history of modern Hebrew letters is viewed less as a modern framework for overcoming or containing the rivals of modernity and enlightenment (among others, the Orient) and more as an uneven field, fraught with contradictory expressions of religious, exilic, and oriental resistance to the secularist and Eurocentric stance, that still dominate the study of Hebrew literary history.