This study examines the impact that My Other Brother (MOB) has on college Black male students in the MOB community organization. In critically examining the narratives of 12 first generation college Black male students in MOB: This study utilizes Tupac Shakur's construct of Thug Life as a theoretical and analytical lens in assessing how Black males in the MOB program navigate processes of alienation. Navigating processes of alienation was placed in context with four critical stages in alignment with Thug Life: These stages emphasized, 1) MOB students' recognition of racism/inequality on an individual level; 2) a recognition of structural level inequality of which they are members of a community of oppressed; 3) a recognition of pride and solidarity in communal struggle; 4) a recognition of political praxis to resist structural racism/dehumanization through education as a function of Black male success. Success was defined based on the following salient concepts expressed by students: 1) Students gaining a heightened sense of confidence and racial pride resulting in students asserting themselves in all educational spaces and life; 2) Students resisting white cultural norms of respectability politics and being affirmed in their "true self" Black identity; 3) Students taking up roles of justice and community leadership in engaging the larger Black community via programming and mentoring K-12 Black youth of the community; 4) Students taking command over their education and their life aspirations. Overall, MOB students feel that they can do whatever they want to do in life: college graduation and access to professional opportunities, entrepreneurship, or community engagement. These outcomes, especially the community and justice component, were grounded in the tenants of Tupac's Thug Life theoretical lens. [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.]