The aim of this essay is to explore the democratizing contribution of John Dewey's educational proposal, while also examining the political weakening that emerges in his thought, stemming from his emphasis on the individual’s interaction with their environment. The central hypothesis argues that Dewey’s educational perspective, by focusing on a communicative and individualistic pragmatism, contributes to the erosion of the historical-political dimension of education. This shift is evident in Dewey’s epistemological reliance on the immediacy of the subject-environment interaction, in conjunction with the rise of a biopsychological and behavioral teaching, shaped by the political structures of the second half of the 20th century. The essay aims to highlight the danger of erasing history through the adoption of a pragmatic stance in education and to engage with its current political effects. In this way, it underscores the hybrid nature of Dewey’s principles, which oscillate between democratic aspirations and technocratic individuation. Finally, the essay seeks to present an alternative educational approach, anchored in historical knowledge and teaching, with stronger collective commitments and a focus on social transformation.