This article critically assesses the works of Paul Monroe, Isaac L. Kandel, and the International Institute at the Teachers College, Columbia University, in the early twentieth century. Drawing on Edward Said's notion of contrapuntal reading, it presents a different account of their legacies that foregrounds the colonial and imperial realities of the time as constitutively significant to the early formation of the field and the comparative education knowledge generated during this period. In doing so, the article unsettles the comforting ways in which the founding histories of the field have been narrated by the historians. By illuminating their deep colonial/imperial entanglements during the early formative period, this article invites readers to reflect on how the particular historical and geopolitical context within which we operate sets limits on what knowledge we produce, and today, when the relationship between our scholarship and international development agencies are closer than ever.