The persistent inequalities in urban public education in the U.S. that have left far too many Black and Hispanic male students behind with respect to academic skill development, high school graduation, and college success have led Catholic groups to provide alternative secondary school models to advance the academic and career success of urban students. One of these initiatives is the NativityMiguel model school, the first of which opened in New York City in 1971. The present study examines the lived experience, with respect to benefits of this education on the subsequent academic and career successes, of male graduates of two of these schools, one for African American, or Black, students and one for Mexican American students in different parts of the country. Analyses of interviews with 37 graduates showed that they benefitted from the schools' approach to academic skill development and the building of resilience, leadership, and a commitment to service in the context of a community that continued to support the development of resilience after middle school graduation. Differences in aspects of the two programs are examined along with the implications for making use of the schools' initiatives on a larger scale.