This qualitative study of first-generation, low-income urban Latino male college students considers their transition experience and success in various higher education institutions. Schlossberg's theory of mattering and marginality is used as a lens to explore how these students navigate the college environment and build relationships with campus agents. The findings focus on the students' motivations to attend college, the importance of the college environment, the impact of mentorship, and feelings of mattering as a result of relationships with campus peers and professional staff. The authors offer implications and program recommendations for student affairs professionals to better support and understand Latino male students at their institutions.