This paper analyzes the work of Herbert M. Kliebard, not only as a curricular historian, but also as a curricular theorist. We focus on his approach to studying the history of education and curriculum as a methodological framework for understanding the purpose of education. Next, we explore two important curricular events in the 1930s: The Eight-Year Study and the social studies textbooks of Harold Rugg. While the 1930s were markedly different from today, most notably in terms of the demographic and educational contexts of the United States, our analysis points to ways that educational scholars in the 21st century might mobilize more Kliebardian insights in their work. In both sections, we build from Kliebard's discussion to explore ways in which massive poverty and economic precarity did not lead to the federal centralization of curriculum and school policy, but rather to a range of localized and radical curricular interventions and practices. We then draw from the sense of possibility at the core of Kliebard's work to show that even in the face of seemingly commonsense responses to the growing poverty of school-aged youth, multiple opportunities for resistance remain. We conclude with future directions for curriculum theory and curriculum studies to carve out critical spaces where transgressional and transformational scholarship remain inherently possible.