No culture associates individual worth with a career like the United States. For juvenile offenders, in particular offenders with disabilities, this presents a significant challenge. In addition, the requirements that have been imposed on all education through the No Child Left Behind Act (NCLB; 2001) make programming that is consistent with the needs of the juveniles with disabilities population a major challenge. The authors propose the development of a career-based model that is consistent with best practice and in line with the requirements of NCLB. A comprehensive model based upon a vocational assessment designed to determine the aptitude and interest of each student is the basis for the development of a career pathway for each youth. Programming to provide the needed skill development in the areas of vocational, literacy, and adjustment skills, as well as transition or aftercare services that include advanced vocational preparation, health, welfare, and mental health services are all vital needs in the development of a successful program. The authors discuss the political, training, and financial realities associated with this needed paradigmatic change.