Beginning in the mid-1990s, Florida hotelier Mr. Harris Rosen focused his philanthropic efforts on the creation of the Tangelo Park Program, an initiative that intentionally coupled free preschool with a full-ride scholarship for a public college, university, or vocational school in the state. The Tangelo Park Program has become a national model of how private citizens can positively impact their communities by addressing the root causes of poverty, despair, and social disintegration. This study utilized archival records and one-on-one stakeholder interviews with divergent voices to explore four research questions: how the program built social capital, how the assets-based approach developed self-interest and collective interest, how the program contributed to student- and neighborhood-level outcomes, and what are the best practices that emerged from the program’s first 25 years. The findings can inform other communities in the customization and implementation of their whole-child programs. The findings reveal that efforts to cultivate social capital must begin with the buy-in of the community’s residents, institutions, and formal and informal leaders. Grassroots social capital-building requires trustworthiness and follow through, purposeful listening, a neighborhood presence, and respect for the will of the community. Recognizing cultural norms and mores is fundamental to successful interactions. Engaging families as partners in their children’s education is paramount, and encourages the prosocial behaviors of cooperation and shared decision-making. This program was the impetus for children in Tangelo Park internalizing their potential for success, thus resulting in high school and college graduation rates that far outpace the state and nation. The program’s $7:$1 return on investment as measured by degree completion and a reduction in crime is indicative of the transformation that defines this urban neighborhood.