Using critical theory and an analysis of missionary reports and documentation describing education in colonial Puerto Rico and Mexico, the authors cross borders and time periods to socially and historically situate Spanish colonial educational methodologies and their contemporary use in one low-income Latino community in urban Detroit, Michigan. By invoking associations from the colonial past to shed light on contemporary struggles, this study problematizes US educational reform initiatives such as high stakes testing and school turnaround policies. The authors found that when the playing field is not equal, such reform efforts are but another in a long line of colonial and neo-colonial methodologies that further disenfranchise Latino youth and push them out of school.