For more than two decades, the diagnostic and cultural insights of psychological jurisprudence (PJ) have informed social theory, clinical practice, and public policy. As a form of heterodox criticism, PJ probes the relationship between human agency and social structure, and it examines how both are informed by and co-produce extant reality. This article explores the utility of PJ—especially as a basis to reconfigure the problem of crime, to redefine institutional responses to it, and to reconceive the process of desistance. To accomplish this objective, the article addresses two issues. First, it explains how the diagnostic and cultural footing of PJ functions as philosophical critique concerning the subject of crime. Second, it demonstrates how this critique represents the grounding of an ethic with considerable relevance for developing a normative theory of trans-desistance. The article concludes by suggesting how the normative dimensions of trans-desistance portend dynamic change for future criminal justice practice and mental health treatment.