The study evaluates the relationship between middle school principals' leadership characteristics and academic achievement of African American male students in grades 6, 7, and 8 in a large urban school district. Academic achievement is typically defined as the cognitive knowledge, skills, and abilities that are measured by achievement tests. The level of academic achievement that students attain by eighth grade has a larger impact on their college and career readiness by the time they graduate from high school than anything that happens academically in high school (ACT, 2008). Scores from the 2009 New York State English Language Arts exam were used to assess students' academic achievement. A sample of New York City middle school principals (n = 95) participated in a mixed-method study to investigate whether there are identifiable characteristics in their leadership styles that help Black males obtain academic success in English Language Arts. The principals were administered the Leadership Behavior Description Questionnaire (LBDQ) survey. Each principal completed his or her respective survey to ascertain his or her leadership characteristics. Data was collected during a three-week survey period. After the quantitative data was collected and analyzed, five (5) randomly selected principals from the sample group were chosen to interview and shadow seeking qualitative data using Marzano's 21 Leadership Responsibilities from "Balanced leadership: What 30 years of research tells us about the effect of leadership on student achievement" (Waters, Marzano, & McNulty, 2003). This study was conducted to determine if there are characteristics that middle school principals have that create opportunities for academic achievement of African American male students. Obtaining knowledge about positive correlating factors could help lower the educational achievement gap for Black males, increase high school graduation rates, and improve their college-readiness future. [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/en-US/products/dissertations/individuals.shtml.]