The main research question guiding this dissertation study is, How can we understand the conditions that make possible the cultural construction of difference as it relates to Puerto Rico’s students at the turn of the twentieth century? In answering this question, I have considered the idea of ‘conditions’ as the articulation of epistemological principles of education reforms and curricular plans that aimed to define and (re)define who the Puerto Rican child was, and was to become at the turn of the twentieth century. The construction of these epistemological principles and ontological objects of schooling relied upon a particular set of discourses about race, intelligence, hygiene, and morality. These discourses were part of a ‘grid’ in which several historical trajectories converged and circulated to construct and administer Puerto Rico’s students as the objects of schooling. I have also analyzed the idea of ‘cultural constructions’ as the discourses and discursive formations embodied in the systems of ‘reason’ that governed Puerto Rico’s education and society; and the methods for inscribing such beliefs of what could be ‘seen’ or acted upon in Puerto Rico’s schooling. These all become part of a cultural thesis that discursively creates the ‘reason’ about particular modes of knowledge and being. In my study, the cultural theses ultimately become about the idea(l)s of civic progress and the fear of creating a barren cosmopolitan. Lastly, I have critically examined the idea of ‘difference’ as both a discursive marker that ‘makes’ a particular idea and ‘type’ of being intelligible; but also, as an ordering practice that collapses and (re)inscribes these distinctions of “Self” and “Other” within the processes of differentiation. The interdisciplinary nature of my work lends itself to studying constructions of difference across various academic fields including Curriculum Studies, History, Postcolonial Studies, Indigenous Studies, Latinx Studies, Puerto Rican Studies, Caribbean Studies, Transnational Studies, and Legal Studies.