As the machine of mass incarceration continues down its destructive path, ever-increasing numbers of formerly incarcerated citizens have been released back into society. Convict Criminology (CC) was created out of the societal chaos produced by these events. This article presents an ever-expanding CC perspective—over two decades since its founding. The article begins with a journey into the field’s dynamic past. It then examines the present, delineating examples of the multiple pathways individuals have taken to align with the spirit and goals of CC. Next, this article addresses claims regarding the lack of diversity in CC and explains how a heterogeneous membership currently exists within the group. The article’s final sections undertake further development of a theoretical model of CC, discuss current ideological debates within CC, and demonstrate how the field has grown. The article concludes by summarizing the benefits of CC to ex-convicts, criminology and society, at large, and then outlines tasks that need to be addressed in the future.