This paper explores the reception of Dewey's ideas on democracy and education in Latin America from the beginning of the twentieth century through the "long 1960s" (1958–1974). The analysis is framed by a dynamic interplay between the local, regional, and supranational. To bring empirical specificity to Dewey's "translations," the author discusses Dewey's uptake in two political settings, in 1920s Chile and post-revolutionary Mexico, and two cases of Christian adaptation of Dewey's theories. The long 1960s signaled an epistemic shift in conceptions of education and social transformation. Dewey was not embraced while Paulo Freire and Ivan Illich became the referents.