The purpose of this discussion is to explore how the educational and social philosophy of John Dewey offers insight for those involved in education evolution in emerging economies, with a particular emphasis on nurturing leaders who are capable of recognizing and responding effectively to the challenges of a globalized economy now and for the next century. Dewey offers comprehensive critiques of the interlocking systems of oppression that are present not only in the educational system but also in the workplace and expanding economic system, along with systematic pedagogical strategies for overcoming identified hurdles. To demonstrate application of these insights, we will focus specifically on the implementation of Deweyan theory in an elementary educational system in today's Haiti through a case study involving l'Ecole de Choix (the School of Choice). After explaining the genesis of the school's relationship to Dewey, the discussion unpacks Dewey's diagnosis of the challenges facing both leadership and education within his social context. The analysis then examines the central features of Dewey's pedagogical vision within that historical context. To illustrate their continuing relevance to a current social environment that finds remarkable parallels with Dewey's own, we detail the ecosystem, inspiration, history, vision, design, structure, and examples of Dewey-based influences in an educational institution in rural Haiti. We then conclude with implications for educational research and practice that respond to complex challenges in emerging economies.