This paper describes a therapeutic mentoring program involving 150 children over a period of three years. The program is operated from an outpatient clinic, in this case using psychodynamic supportive therapy delivered in the home as a clinical hub for high-risk families referred by child welfare, juvenile justice, or courts. This program is part of Massachusetts Children's Behavioral Health Initiative (CBHI, 2013). This model of therapeutic mentoring requires all youth be involved with individual or family therapy and that the technique is designed to stabilize aggressive behavior in the community and begin to develop lasting social skills that can be sustainable in the community as a protective factor against poverty, social deviance and violence. The process of mentoring is viewed as an adjunct to therapy and a concrete way to practice mentalizing while learning to engage in a positive community activity.