This paper reviews the work of four early radical educators: the cultural nationalist Rabindranath Tagore (1861-1941), Asia's first Nobel Laureate; Bertrand Russell (1872-1970), Cambridge mathematician and philosopher; the Irish educationalist and insurgent Patrick Pearse (1879-1916) and Leonard Elmhirst (1893-1975), co-founder of Dartington Hall school in England. Each represents a type of radicalism that is particular to his own era but resonates in twentieth-century educational provision and policy. Each articulated his political vision through the establishment of a school and all contributed to modern pedagogical practice. The paper argues that ideological and methodological similarities not only compel us to consider them as radical founders, whose ideas are in many ways identical, but to identify them as pivotal theorists in early conceptualisations of education as dissent and disengagement, as a means of decoupling thought and habit from the mainstream of educational practice, colonial imposition or curricular conservatism. In particular, the paper concentrates upon the work of the Irish educationalist and political radical Patrick Pearse and, employing his educational writings and practice as a template for dissension, demonstrates that it was both typical of and reflected the wider tone of early formulations of education as dissent.