This paper first observes some of the most striking aspects of the oldest Near Eastern translations of the collection of stories known in Arabic and Turkish as the Kalilah wa Dimnah, and Kelile ve Dimne (KD) respectively. This is followed by a discussion on (a) the earliest known translation of KD (by Kul Mesud) into Western (Old Anatolian) Turkish in the 14th century, which was identified in the late 19th century but has only recently been the subject of a full scholarly study and (b) the need for descriptive research particularly on the medieval rewrites belonging to the formative period in the Ottoman-Turkish literary tradition.