The present contribution delves into an ancient enigma rooted in the history of Syriac monasticism, aiming to propose a potentially definitive solution regarding the identity of the monk John of Apamea, a prominent figure in Eastern Christian spirituality. Esteemed scholars such as Hausherr, De Halleux, Strothmann, and Lavenant have offered their perspectives on this historical puzzle, presenting contrasting interpretations. One perspective suggests that John of Apamea represents a singular individual, a Gnostic with Origenist inclinations. This monk, known as a master of monks, covertly concealed his heretical beliefs and later faced condemnation by the East Syrian ecclesiastical authorities, long after his teachings had faded. In contrast, another viewpoint argues for the distinction of three distinct figures. Firstly, an orthodox author from the early 5th-century can be associated with a portion of the corpus attributed to John the Solitary. Secondly, an Origenist monk bearing the same name of John of Apamea emerges, linked to Stephen Bar Sudaili and recognized as an opponent of Philoxenus of Mabbug during the late 5th and early 6th centuries. Lastly, an enigmatic Messalian monk from the 8th century, also named John of Apamea, remains shrouded in historical obscurity. Through a comprehensive reassessment of the available sources, this study proposes an alternative solution, positing the existence of two distinct historical figures: the early 5th-century author and the Origenist monk from the late 5th to early 6th centuries. These individuals were later merged, through a scholastic synthesis with heresiological elements, into a single fictional character who was condemned by Timothy i, the East Syrian Patriarch of the Church of the East at Baghdad. The objective of this investigation is to outline the primary factors contributing to the construction of this fictional figure during Timothy's time, which subsequently gained canonical recognition within the ecclesiastical memory of both the East Syrian and Syro-Orthodox churches. [ABSTRACT FROM AUTHOR]