This work examines four of the greatest theological and literary minds of the Christian tradition - Jesus, Augustine, Dante, and Flannery O'Connor - in a way that makes their prophetic and poetic challenge to our sinfulness accessible and relevant to the modern Christian. These thinkers offer timeless criticisms of four of the greatest and most flawed societies of all time - Israel, Rome, Medieval Europe, and America - and they do so in a way that raises their critiques out of the particular historical context and render them relevant today. To show this current relevance, the reader is given a twofold analysis of each figure. The author first focuses on two sins that they believe pervade and degrade society and the individuals in it, and then the two actions that they offer as the shocking, redemptive alternatives. The second half of each chapter guides readers through serious study, reflection, and prayer on three specific texts.. This unique approach demonstrates how these sins are still a part of our lives today, and how their alternatives can become a part of our lives through analysis, introspection, and prayer. All of these thinkers connect social and political ills with much deeper theological and anthropological analysis, so that their conclusions cannot be discounted as 'signs of the times', or the way people thought 'back then' about a particular problem (e.g. war, racism, corruption, etc.) that is now supposedly past: if their descriptions of the sickness in human nature were ever accurate, then they are always accurate and relevant, and demand our attention as the profound calls for personal and societal introspection and change that they really are. By offering the reader serious analysis as well as practical application, these calls for personal devotion and change are accessible to the modern Christian, so that intellectually as well as spiritually, the redemptive truth of these writings can begin to set them free, as well as encouraging them to pursue further texts on the subject.