There is a recurrent conflict concerning law and judgment in the Catholic tradition. The tension between the manner in which just punitive judgments are to be rendered and the possibility of judging justly, if at all, is found frequently in Scripture and in Church history. This paper will give an overview of the dynamics of this tension in Scripture and in the significant disparities between natural law and more voluntarisitic theories of law in the Middle Ages. It will then present current Catholic Social Teaching on this topic and offer suggestions as how to insights from the tradition may help clarify some of the problems in contemporary debates over the nature of law and the dynamics of sentencing. Law, judgment, and punishment exacted for violations of law are matters of utmost importance in any society. They are also moral and spiritual issues with deep roots in Catholic theology. This essay will survey some of the principal ways these topics have been understood in the Catholic tradition. It will first provide a brief overview of the phenomena of hyper-retribution and mass incarceration in contemporary criminal justice, then proceed to a synopsis of three distinct strands in the Catholic tradition dealing with law and judgment: (1) Scripture and the moral quandary induced in those who judge; (2) natural law, its avowal of the divine legitimacy of positive law and its mechanism of judgment for malefactors; and (3) elements of nominalism and "purely penal law" that in many instances present law primarily as an exercise of power and control rather than a mirror of the mind of God. This will be followed by a summary of recent Church teaching in which a coherent synthesis of these once disparate of the dilemmas being faced in the areas of criminal jurisprudence and punishment. Finally, some suggestions will be offered as to how the topics raised in this essay might be investigated in the context of Catholic higher education.