Since the implementation of the legislation of the Elementary and Secondary Education Act and Title I there is one group to which the achievement gap has widened: the Black male. Not only are Black males are in the lowest percentage on every marker of educational success (Kirp, 2010). Black males lead the percentages for every negative educational marker. The Black male demographic is choosing to go to the back door without being told, despite the efforts being made to even the proverbial educational playing field. This widening gap between Black males and other demographics, especially in Title I schools, laid the framework for this study. The purpose of this study was to identify Title I initiatives through the perspectives of the Title I stakeholders, which include school administrators, district personnel, and educators in Leon County, Florida Title I schools, and what effect those identified Title I initiatives are having on Black male achievement (Gupta & Oboler, 2001; Tyler, 2016). This study chose to focus on the defining of the Title I initiatives through the perspectives of Title I stakeholders, then use those Title I stakeholders to gauge whether those Title I initiatives are influencing Black male academic achievement. This study applied a qualitative methodology using an explanatory case study. This explanatory case study utilized a series of semi-structured interviews with fifteen Title I stakeholders in a school district in the Florida Panhandle. The study found that the effectiveness of Title I initiatives on Black male achievement is inconsistent and heavily dependent upon school level implementation. The perspectives of fifteen Title I stakeholders demonstrated that despite the existence of sporadic Black male achievement based on many school-based initiatives, it has minimal impact on wholistic Black male achievement This is due to the existence of many inhibiting factors which were identified as: lack of parental involvement, lack of autonomy, Black male apathy, and disenfranchisement and ignorance of the needs of and programing for Black 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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]