This dissertation explores four events in which Joseph Ratzinger (now Pope Benedict XVI) attempts to address the modern and post-modern worlds. I demonstrate that his treatments of the relationship between reason and revelation, the Enlightenment's legacy, universal values, identity, and pluralism are engaged with a similar set of concepts addressed in the communitarian critique's initial reaction to the notion of the original position advanced in John Rawls's A Theory of Justice and the libertarian spirit of Robert Nozick's Anarchy, State, and Utopia. I posit that at the heart of this critique, as well as in Ratzinger's works analyzed here, is the concept of liberal entitlement as generated from Locke and other social contractors, and that bound up with this are a challenge against philosophic obsolescence and the absences of humility and obligation. It is through these three themes--humility, obligation, and obsolescence--that Ratzinger's political teaching and his own communitarian thought emerge in his writings. Particular attention is paid to the communitarian critique's discussion of the narrative method and the importance of identity, as they offer potential solutions for Ratzinger's desire for creating a non-coercive sense of civic obligation through a salient European identity and correcting the breakdown of common moral reference points in the West. This study ultimately explores where these select works by Ratzinger fit within this dialogue, and where they do not, as well as how they are situated within "garden variety" communitarianism of political theory and the Catholic Church's anti-liberal history. In doing so, Ratzinger's own communitarian thought takes shape.