Urban Scholars was founded at the University of Massachusetts Boston two decades ago as a pilot program with just 15 students. With support from the university, Boston Public Schools and various funders, this multicultural academic enrichment program has thrived. Remarkably, 98 percent of the low-income, first generation Boston students who complete the UMass Boston-based Urban Scholars program are accepted to a post secondary institution. In this article, the author explores how this "best practice" in college readiness is preparing city students for leadership positions.