This paper is about the depiction of the “East” and the representations of the “Easterners” in the works by Ottoman author Cenap Şahabettin. Cenap was not only an intellectual but also a representative of the state bureaucracy. After finishing his education in Istanbul and Paris, Cenap became a dermatologist, and was appointed public health officer in Egypt, and consequently in Iraq. Cenap’s works on the Arab lands were published when the Ottomans were trying to adapt a modernist colonial approach towards their provinces, as opposed to their older governing practice. Paradoxically, although the Ottoman Empire placed itself among European states, it fell into a dichotomy by conceding the prejudices many European intellectuals had towards the “East”. The Ottomans overcame the paradox of seeing themselves both as hard-working, powerful, constitutionalist “Westerners”, and lazy, weak, despotic “Easterners”, by projecting the second set of adjectives onto their provinces. Cenap wrote that people of the “East” deserved despotic rulers, since they lacked the ability to reason freely. Besides using the discussion of Eastern despotism to legitimize the Ottoman presence in the area, he also mentioned the economic backwardness of the Easterners, and concluded that they needed to be modernized, but lacked the means to do so. Cenap asserted that western countries were not good candidates for modernizing the region. He cleverly notes down the developments brought by the Ottomans and emphasizes that Ottomans were not only the sole proper candidate for modernizing them, but also a good one. Nourished by the works of Edward Said, Ussama Makdisi and Jale Parla, the paper takes a semiotic approach in evaluating Cenap’s works, and compares Cenap›s attitude with that of the western travelers, attempting to provide a broader picture.