This paper uses Derrick Bell's interest convergence principle, which argues that whites will support racial justice efforts only if they believe they will see gains for themselves, to examine white philanthropic support of Black education in the postbellum South and in current school reforms. Using the concept of "bad" (or compromising) money to describe philanthropy's curtailment of Black self-determination and agency, this conceptual paper demonstrates how such philanthropy has promoted white capitalistic gain to the detriment of African American communities for decades. To build this claim, the author synthesizes key points from extant literature that address these topics. The paper links the application of the interest convergence principle to Black education issues of the past as a connection to and clarification of current market-based approaches said to remedy educational and racial inequity.