As a relatively recent phenomenon, the increasing overrepresentation of Aboriginal persons in both the child welfare and criminal justice systems is of critical importance to the field of social work. As social control systems, how do social workers contribute to or mitigate against overrepresentation as contemporary colonialism? What can social work professionals who themselves have been through these systems add to our social work discourse? A sample of fifteen Aboriginal social workers who had as youth been in either one or both of these systems were interviewed with respect to: what they found was helpful or unhelpful in their interactions as youth with social workers, why they subsequently chose social work as a career, the supports and barriers they encountered along their career path, and the difference their experiences had for their own professional practice. Using structural social work theory, overrepresentation as a contemporary colonializing process was re-conceptualised as structural violence. Institutional Ethnography (IE) and Hermeneutic Phenomenology were used to explore how these neo-liberal ruling relations are produced, maintained, and potentially deconstructed. The findings from this unique population have implications for decolonizing social work practice, education, and research.