The African American population has faced adversity in the United States in many ways since the arrival of their first known ancestors in Jamestown in 1619. This narrative of systemic oppression creates obstacles and challenges for this people group even today. Using a transcendental phenomenological approach, the researcher, who has a long history of collaborating with the justice-involved, sought to explore the lived experience of African American male youth in the years preceding juvenile probation supervision. As a prospective counselor educator, the researcher was interested in how this study would inform counselors-in-training and supervisees who would serve this unique demographic group. Results reveal complex adversity across multiple ecological systems within the participants' lives prior to adjudication. Results also uncover how the participants experienced these challenges in the home, family relationships, school, and their communities. Implications for counselor education, public policy modifications, and future research are discussed in the study. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]