This work examines four of the greatest theological and literary minds of the Christian tradition, including 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. In addition, they do so in a way that raises their critiques out of the particular historical context and renders them relevant today.