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Although Latino men strive for college, they trail other groups in matriculation and completion. High school guidance counselors are well positioned with college-going information to improve this reality, yet many leave Latinos college aspirations to happenstance. This study utilized qualitative narrative inquiry and Hipolito-Delgado and Lee’s (2007) empowerment theory as a framework to answer the following research question: How do guidance counselors and other key institutional agents (dis)empower Latino men to access college-going information and matriculate to a selective public flagship institution? Findings teach us participants enjoyed either clear pathways or faced prohibitive roadblocks through the actions of powerful gatekeepers. Implications for policy, practice, and research are followed by recommendations for creating a more equitable, consistent, and systemic college pathways.