This chapter offers a series of reflections on how to pursue new directions in critical criminal justice, by exploring the links between the moral grammar of criminal justice on the one hand, and a serious engagement with moral psychology on the other. In atypical fashion, this handbook chapter starts with an original discussion, leaving a broader engagement with literature and scholarship in criminal justice to its latter half. The first section explores the foundations for a moral psychology of criminal justice, which are further developed in the second and third sections through a dialogue with the work of Melanie Klein, which is then applied to a critical understanding of punishment. The fourth and final section then applies the conceptual framework developed in the paper to the field of criminal justice scholarship and practice. The chapter concludes by considering whether criminal justice can be considered within an emancipatory frame.