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This paper shows that translating cultural and ideological issues, in general, and those of Orientalism in particular, is not an easy task. It also investigates the what might be viewed by the researcher as main innovative translation strategies adopted by Kamal Abu Deeb in translating Edward W. Said's Orientalism into Arabic. The difficulties in translating the book lie both in the nature of the topic of Orientalism as well as in Arabic which may be unfamiliar with some English linguistic terms. This is not a shortcoming of Arabic; a language once considered a successful means of transferring old civilizations and from which modem western civilization benefited. The paper selects and analyzes some examples taken from Edward Said's Orientalism together with Abu Deeb's translation to show some main courageous strategies adopted by Abu Deeb in translating such a work. These strategies betray some translation problems, which are not easy for average translators to overcome. In other words, the paper aims at pinpointing the main strategies adopted in the present paper for the sake of translators, teachers of translation, theorists and researchers alike.