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This qualitative study uses a culturally relevant resilience framework to examine the developmental outcomes of Latino and Black boys participating in an extended graduate support program at two urban Catholic independent NativityMiguel middle schools. It examines the mentoring approaches used to challenge and support the students to succeed in high school and beyond and develop as leaders and change agents. We analyze interviews with graduates, examining the differences in outcomes and mentoring processes provided. Outcomes examined include students’ academic, social, and leadership development and development as “men for others.” The authors aim to engage session participants in a discussion of best practices that increase the likelihood of academic and professional success of urban Latino and Black students placed at risk.