This article utilizes Gloria Ladson-Billings' notion of educational debt in order to explore the historical, economic, and cultural politics of education reform under George W. Bush and Barack Obama. It tracks the No Child Left Behind Act across a number of fields in order to claim that Bush's expansion of the educational debt should be understood as both an exacerbation of systemic inequality as well as the erosion of the democratic purposes of public education. In conclusion, the article forecasts ahead to the future of the educational debt under the Obama administration by looking at the policies implemented in Chicago under former Chicago Public Schools chief executive, and now current secretary of education, Arne Duncan. The authors contend that the sociopolitical infrastructure of Bush's No Child Left Behind presents a fundamental challenge to progressive educational reform under an Obama administration. (Contains 6 notes.)