This study investigates and analyzes Danville Regional Foundation’s (DRF) $5.4 million investment to support the Smart Beginnings Danville Pittsylvania County (“Smart Beginnings”) early childhood program. Findings are presented as an historical case study. The study applies the perspective of strategic philanthropy, paying particular attention to the elements of asset-based social policy and the context of the American South. The study uses qualitative methods including textual analysis of key internal and external documents as well as structured interviews with four participants deeply engaged in the conceptualization and execution of Smart Beginnings. Careful consideration of DRF’s investment in Smart Beginnings surfaces at least six questions that merit explicit consideration by philanthropic leaders when attempting to address issues of persistent inequity.