In Chapter 2, I trace the trajectory of Augustine’s psychagogic project throughout book 1. Based on a close reading of the preface, I argue that Augustine sets up City of God as a work designed to teach his readers to see the world anew: not simply as it fits into the Roman story but as it fits into God’s story: the story of the two cities. I then trace this endeavor throughout the rest of book 1, showing how he presents facets of the Roman perspective as distortions generated by amor sui. Approaching his response to the sack of Rome in this light, I find that Augustine is especially sensitive to the way in which pride has fostered judgmentalism amongst the Romans. Playing with Roman conceptions of friendship, civilization, and the prerogatives of empire, he highlights the way in which pride has vitiated their culture, creating customs all too marked by amor sui. In order to combat these distortions, Augustine models a stance of compassion rooted in humility and points to amor Dei as the source of true cultural renewal. In this way, I argue, he begins the process of correcting his readers’ distorted vision.