Mohamed Enani, one of the Arab world's most significant translators, was also a prolific writer on translation theory. Though he—like most practitioners of translation—often expressed a skeptical attitude towards translation theory per se, he admired theoretical perspectives on translation which depart from dry linguistic approaches to view translation as a human activity that cannot be separated from its sociocultural context. For example, he believed in the Functional theories of  Reiss and Vermeer, which put emphasis on the nature of the text type as well as the purpose of translating, making them the main factors which should be taken into consideration during both the process of translation as well as assessing a translation. This paper investigates Enani's translation theory as expressed in his books and as applied in his actual translations in light of Reiss and Vermeer's Functional theory, in an attempt to highlight similarities and differences between Enani's views and Reiss and Vermeer's views. This study argues that Enani's theoretical assumptions are generally in line with those of Reiss and Vermeer. Enani's literary translations, however, occasionally depart from his theoretical belief in a way that shows that decision making in translation is not a straightforward process, but one in which various factors come into play, including changes in the translator's view of his/her own role as well as changes in his/her conceptualization of  the target readers