The term "freethinking" originated in the 17th century to describe inquiry into beliefs which were accepted unquestioningly. Feminists such as Mary Wolstonecraft, abolitionists like Frederick Douglass, and novelists such as Mark Twain and Zora Neal Hurston are among the many who dared to simultaneously challenge religious dogma, patriarchal convention and racialized boundaries. But today the concept has been appropriated by the alt-right. A broad spectrum ranging from hardened white supremacists to those with more centrist tendencies have developed a discourse that objects to any form of antiracism on the grounds that it runs counter to individualism and freethought. In this essay we suggest that this critique from the alt-right should not be dismissed. Rather, it should be the impetus to revitalize the connections between antiracism and the principles of freethinking. We map out some of the history in which these connections were previously established; the reason the connection was weakened, and the principles by which the confluence could be restored. We recount some initial experiments using educational technologies to support this framework.