Educational engagement and advocacy of parents is a central priority for increasing the academic performance of African American male students at risk of academic underachievement. This research explored six types of parental involvement in education to evaluate which ways of engagement have the best relationships with African American male students. The purpose of this proposed qualitative research was to describe the persistent academic achievement gap among African American students. A grounded theoretical approach was used to explore parents' ability to advocate in their children's education through the lens of administrators and educators. The theoretical framework for research used Epstein's six step model for parental involvement and addresses obstacles in which African American parents face in correlation to their child's school and how those obstacles can prevent parents from advocating in their child's educational achievements. Collected data of educators and administrators were analyzed in detail to provide information on how educators view parental involvement of African American male students. Themes revealed in relation to the research questions were determined to support findings that uncover explicable reasons for parental disengagement. Findings also suggested the impact of lack of parental involvement. The limitations and delimitations of the research were addressed to fulfill a broader understanding of the gap in this research. Recommendations and suggestions were provided for further research 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.]