The application of Thomistic Aristotelian principles to contemporary constitutionalism has involved many shifts and transformations: from postwar Christian democracy to post-liberalism. In order to evaluate these changing assessments, the article discusses and compares the work of Pierre Manent and John Milbank who provide a useful long term historical perspective on the relevant issues. The article explores how Manet’s emphasis on the theologico-political problem seems inescapable in one form of another in appraising the origin, development and the future of the liberal regime as well as any possible alternatives. Nevertheless, Milbank’s work points to more fruitful post-liberal institutional forms capable of sustaining an Aristotelian conception of political association. Despite this, the theologico-political problem arguably still affects how such political structures are to be thought and developed with tensions involving the realization of cardinal and supernatural virtues intrinsic to the balances that need to be struck.