I will show how the kenotic idea of ascending and descending is prevalent in both Augustine’s Confessions and Dostoevsky’s The Brothers Karamazov. I will be using St. Augustine’s Confessions and Fyodor Dostoevsky’s The Brothers Karamazov because both of these works document well the theological idea of kenosis. The kenotic idea in these works will be shown to link the two authors together, which is new to scholarship since Dostoevsky’s Orthodox East was so closed off to Augustine’s Latin West. By tracing the idea of kenosis, I will be able to show how Dostoevsky was influenced by the work and ideas of Augustine. This will be difficult to do since Dostoevsky only alluded to Augustine in his writing, however Dostoevsky’s relationship with Vladimir Soloviev will be shown to be important because Soloviev was acquainted with Augustine and would have been Dostoevsky’s link to Augustine. The topic of kenosis falls within the larger area of theological anthropology, which is the study of the creation, nature, fall and destiny of humanity in relation to God. Kenoticism offers the master key to the theological meaning of The Brothers Karamazov, and I believe this key was garnered from Augustine. Not only does Dostoevsky shed light on the genre known as conversion narrative in general with his work, but his use of kenoticism also shows deep affinities with Augustine, which I will explore.