Numerous Greek patristic writers read the Matthean and Lukan accounts of Christ’s words in Gethsemane as indicative of Christological aporias. These aporias are focused on Christ’s experience of fear, and emerge from a dialectic of hermeneutical commitments and moral-philosophical assumptions. This paper will unravel this dialectic in three authors, to highlight the contributions that Hellenistic and late antique philosophical traditions made to Christian exegesis, the problems raised by the psychophysiological assumptions embedded in those traditions, and the kinds of solutions Christian writers came to in their readings of Scripture. As early as Eusebius in the early Fourth century, Christians read Psalm 54:5-6 (LXX) prophetically and Christologically: “My heart was troubled within me, and death’s dread [δειλία τοῦ θανάτου] fell upon me. Fear and trembling [φόβος καὶ τρόμος] came upon me, and darkness covered me.” In commentaries on the Psalms and in commentaries on Matthew (as well as John’s Gospel), patristic authors applied these words to Christ’s prayer in Gethsemane, “Father, let this cup pass from me.” However, this language—especially that of δειλία—raised serious issues. In Stoic and Platonic moral psychology, fear is a natural (and thus not necessarily blameworthy) passion (πάθος φυσικόν), and its physical effects (heated blood, trembling, blushing, etc.) are not (at least not entirely) within rational control. However, moral education and cognitive training served to subject this “natural passion” to reason’s control (whether located in the Stoic ἡγεμονικόν, or the Platonic λογιστικόν). Thus, δειλία before death may be a sign of Christ’s humanity, but it implicates insufficient moral development, and a lack of preparation. After all, philosophy was, for Seneca and Epictetus as much as Plotinus and others, a “rehearsal for death.” Thus, Christian writers struggled to reconcile Christ’s apparent cowardice with his being the perfect human, the new Adam in whom all deficiencies are healed.