Providing students who are involved in the juvenile justice system with an appropriate education has the potential to improve their academic, behavior, and post-school outcomes. Giving these students access to quality teachers is an important and necessary component of the educational process. The purposes of this study were to identify the initial reasons juvenile justice teachers entered their profession, examine the relationship between those reasons and their job satisfaction, and explore how teacher demographics influenced their profession selection. In total, 486 (n = 486) juvenile justice teachers across three states participated in the study. Results suggest that a majority of the teachers entered the field for both personal reasons and better employment opportunities, with the latter being more important to them. In addition, where teachers work influences how satisfied they are with their job. Teachers in short-term facilities were more satisfied as compared with those in long-term facilities. Findings are discussed in relationship to recruiting and retaining juvenile justice teachers.