This article is based on an ethnographic study of a cottage for violent offenders in one state's maximum-security training school. Staff members working in the cottage were the institution's front line in its attempts to hold the youth accountable for their crimes while also trying to resocialize and rehabilitate young men who were growing up with few conforming role models. As such, cottage staff members were put in the difficult position of juggling their roles as corrections officers, counselors, and surrogate parents. To effectively do their job, they had to find ways to balance the rhetoric of rehabilitation with the punitive reality of daily life in the institution. This article details the juvenile justice career paths of the staff members in the cottage and provides a sociological analysis of the roles, responsibilities, and interactions of the staff members with each other and with the young men in their care.