In this chapter, the project examines and evaluates the historical trajectory of apophasis as a negative theology in the Western intellectual tradition. The chapter consists of three parts. The first part of the chapter examines the Greek correlation with the notion of apophasis and tries to illustrate certain features of this method, followed by reviewing the strategy used by Heraclitus, Plato, and Aristotle. The chapter also is devoted to the study of Neo-Platonist philosophers such as Plotinus and Proclus. The father of Neo-Platonism and author of the Enneads, Plotinus (205–270), frequently spoke negatively of the One (the Good or God) and upheld that the theory of emanation revolves around the meaning of its title, as all things are derived from the first Reality without any definite will. According to Heraclitus, the essential logos was the unity of opposites and the presence of balanced conflict between them. Proclus uses wild human desire as a metaphor for the unknowability of the One. He radicalizes the destructive approach by discussing negation proper rather than abstraction. Like Plotinus, Proclus concludes that the entire corporeal Universe is only an expression of the “One” and is kept alive by it. Our examination of some of Plotinus’ and Proclus’ writings reveals that Neo-Platonism and the emerging Christian worldview have a lot in common. According to the final Neo-Platonist Dionysius, God is unnameable and beyond our comprehension. One way to describe Dionysius's use of apophasis is comparable to “constructive deconstruction.” The apophatic approaches to divine contemplation, which started with Heraclitus and were developed by Plato and Aristotle before ending with the Neo-Platonists, appear to overlap in the writings of the Cappadocian Fathers. There are many references to Plotinus and Proclus in the Cappadocian and Dionysian Corpus. It can be demonstrated that Mystical Theology precisely cites the latter. St. Irenaeus employs the dialectical language of transcendence and immanence by making a distinction between the nature or essence of God, wholly unknowable and incomprehensible, and his “energies,” which are revealed by the creation and sustenance of the material universe and by extension, humanity itself. The writings of the Cappadocian Fathers make it clear that there is an interaction between Platonic philosophy and Christianity. St. Basil recognizes that the legitimate object of worship is beyond the realm of human comprehension within the framework of the Christian life. The revelatory acts of God in creation are essentially pictorial depictions or symbols that never completely encapsulate or exhaust his ultimate essence. The writings of St. Gregory, who used Platonic and Neo-Platonic apophatic notions, provide a significant illustration of the Cappadocian tendency to expound upon Christian themes based solely upon scripture. Augustine of Hippo (354–430), the greatest of the early Christian theologians, in his emphasis on the importance of meaning and the desire for knowledge, considered the via negativa a preparatory method towards the positive understanding of God. God is the source of everything, including order, meaning, and events. Augustine will thus contend that reason and faith are the two paths leading to truth. For Augustine, belief is the first prerequisite for accepting God. The Cappadocian Fathers maintained the radical transcendence and mystery of the Godhead while affirming the incarnation of the Logos, or Word, in the world through their use of apophatic language.