Schooling can often function as a structure contributing to the reproduction of an American Dream of material and social success, but it can also reproduce an American nightmare of marginalization. Research studies have noted young men of color populate negative outcomes of academic achievement with trends of low test scores, overrepresentation in special education programs, and underrepresentation in gifted and talented programs, contributing toward higher rates of school failure, delinquency, and dropout with life outcomes involving poverty, despair, and legal punishment. This study is an exploration of how school rules and expectations impact the perceptions of low-income young men of color. To gain a deeper understanding of the ways research participants' perceptions were influenced by a suburban high school embedded within a middle/upper class white structure, I conducted a critical interpretive investigation. My theoretical lens is an examination of the American Dream ideology anchored within critical theories of marginalization, reproduction, and resistance. I collected data through interviews of nine low-income male students of color, observations in school hallways and the cafeteria, and a review of four school documents to understand the rules and expectations impacting research participants' school world. Student interviews and observations unveiled reasons for participants' negative perceptions of their school, entailing disconnected academic expectations, punitive disciplinary measures, and white favoritism. Research analysis suggests students resisted respect and insubordination school rules and expectations due to the school's inattention to their low-resourced backgrounds. Research participants also shared that their school prevented them from developing their own personal and occupational goals. Interviews further revealed students possessing a defeatist attitude, indicating a need for school supports to help students develop a more positive socioemotional and racial identity, while finding space for student voices to help shape equitable school policies and practices. [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.]