The purpose of this exploratory study was to examine "pockets of success" through the voices of participant stakeholders in low socio-economic status urban high schools and communities to identify opportunities and structures that can improve post-secondary outcomes for students. Examining those pockets of success to rise above the dynamics that obstruct pathways to success, and identifying opportunities for students to transcend their social, economic, and human condition, are the impetuses for the study. The study design is grounded in portraiture, created by Lawrence-Lightfoot and Hoffman-Davis (1997), to detail the intricate dynamics and relationships that exist in high schools. Portraiture steps outside of the traditional boundaries of quantitative and qualitative research to converge narrative analysis with public discourse in a search for authenticity. Identifying what the participants value, how they create and promote opportunities for students, the school's role in rebuilding the surrounding community, and the community's priority for graduates, provided the groundwork. The review of the literature reconstructs the term "opportunity" in the context of the urban high school, aligning it with the moral purposes of education. It traces the history of educational and social justice barriers for minority students, outlines the impact of leadership decision-making on the evolution of the urban high school, and addresses increasing the capacity of schools to create opportunities for students to succeed. Participants revealed the foundations for success, challenges and goals toward success, conduits to facilitate that success, and collaborations required to build an agenda to couple school-based stakeholders, civic groups, and national organizations to the creation of a national platform to improve outcomes for urban public high school students in disenfranchised communities. [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.]