This essay draws attention to the Prison Reentry Industry’s potential to create unprecedented employment opportunities for formerly incarcerated individuals. Situated at the intersection of money, programming, and state-sponsored surveillance, the Prison Reentry Industry (PRI) is notable for its implication in prolonging and deepening people’s entrenchment in the criminal justice/reentry matrix; however, the burgeoning of a “reentry industry” also ensures the growth of employment positions tailored perfectly to the experiences of formerly incarcerated individuals. The PRI’s production of significant employment opportunities for certain members of the formerly incarcerated population turns social science research on incarceration and employment on its head. It is by now almost conventional wisdom that a criminal history stands as a barrier to employment, but the PRI’s potential to create a substantial job market for formerly incarcerated people may engender an extraordinary outcome in which a criminal record represents for some, the factor leading to entrée into the ranks of the employed.