The purpose of this study was to investigate the generational transference of community cultural wealth and how this valuable commodity impacts student navigation of higher education, persistence, and attainment through individual experiences, backgrounds, and interactions. Most research on Black student success in higher education reflects the deficit of historically marginalized communities, this study however is coupled with the notion that family and community nurture such a deep sense of value that can only be replenished and never replaced embedding the notion that failure is not an option. This community cultural wealth encompasses the tenets of aspirational, navigational, social, familial, resistance, and linguistical capital breeding empowerment of persistence through the higher education journey regardless of the obstacles and barriers that are routinely positioned to hinder the generational progress of my family who have chosen to excel at all costs. The combination of social and legislatively political elements that began in slavery, emancipation, pre and post Reconstruction, Jim Crow, and the Civil Rights Era through the current state of civil unrest and social justice platforms, predictably, many Black students continued to encounter many of the same barriers and challenges that were initially designed to hinder the successful navigation of higher education. The value of storytelling is important because it brings context to the circumstance as the reader not only comprehends but also becomes part of the undocumented higher education experience as well as life that would empower and sustain future generations. The theoretical framework includes Critical Race Theory, the Cultural Wealth Model, and the history of Black families embodying community cultural wealth that bridges the gap in support needed by the students. The minimal existence of documented data detailing cultural capital is the result of both legal and social norms of the times that have existed to hinder progress of equity. This research will show that it is through generational transference of educational opportunity that community cultural wealth has been the mainstay of the Black community. [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.]