The problem addressed in this study was the ineffectiveness of federally implemented college and career readiness programs to ensure that at-risk African American male students are adequately prepared for academic and career success. Academic performance for at-risk African American males in high schools is significantly lower than their peers. In addition, the U.S. workforce is suffering due to a shortage of qualified workers who are equipped to enter the workforce upon graduation. Furthermore, the purpose of this qualitative case study was to determine alumni and teachers' perceptions of college and career readiness programs, and their usefulness in preparing students to enter a postsecondary institution or the workforce upon graduations for high school. A sample size of 10 alumni students and 5 teachers within the same school was used to conduct this study. Data related to participants' perceptions of college and career readiness was collected using interviews and open-ended questionnaires and were analyzed using a qualitative data analysis software (NVivo). The findings from the study generated seven themes which were connected to the alumni and teachers' perceptions and experiences with college and career readiness programs and factors that impacted their success. Findings from this study included participants having mixed feelings about the overall effectiveness of college and career readiness programs. The implications from this study included the need for improvement in the programs by implementing more African American male teachers, providing equitable access to college and the workforce, utilizing restorative discipline, and providing diversity training for teachers. Overall, this research provided insight on the effectiveness of college and career readiness initiatives with the intent of influencing educational leaders to explore more ways to further develop these programs which can greatly impact the future of at-risk African American male students. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]