During the 5th-6th century multiple clashes of theological debate engulfed the Roman empire after the heated council controversies of Ephesus and Chalcedon. The aftermath sparked factions and formulated alliances dependent on their hermeneutical and dogmatic positions. This study inquires Narsai of Nisbis and Jacob of Serugh who are characterized by the late-antique’s drama and compares their hermeneutical backgrounds in relation to their beliefs.