Before the Brown v. Board of Education (1954) case, Black schools were led by Black principals, who were community leaders and role models held in high regard (Tillman, 2004b). However, this image and perception of the Black male principal began to vanish after the Brown v. Board of Education case decision to integrate schools (James, 1970). This qualitative research study focused on the lived experiences of Black male principals in urban settings. The researcher aimed to hear the voices of Black male principals and learn about leadership from their perspectives, including the context for these principals' challenges, barriers, and supports that contribute to success. This study was conducted using semi-structured interviews, direct observations, and document reviews with five Black male principals who were randomly sampled from the Ohio Department of Education list of Black male principals in urban Ohio. Critical Race Theory, African American Male Theory, and Transformational Leadership Theory were used as frameworks to understand the lived experiences of Black male principals. The results of the study yielded 10 important findings: (1) Pathways for Success; (2) Challenges Poverty/Support; (3) Instructional Leaders; (4) Challenges leading White Staff; (5) Trust; (6) Mentors; (7) Innovation/Finances; (8) Macroaggression; (9) Code-Switching; and (10) Black Male Identity. The voices of Black male principals are shared throughout the study. Implications from this study will benefit educational leaders, school districts, aspiring Black male principals and graduate programs of study in higher education. [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.]