This chapter traces the rigorous intellectual work of philosopher-pedagogues José de la Luz y Caballero, Félix Varela y Morales, and Enrique José Varona, demonstrating their shared anti-authoritarian pedagogy, exemplified not only in how they transformed the teaching of philosophy and science at the University of Havana, but also in their liberal and republican views of politics and their model roles as public intellectuals engaged in the righting of social ills. The analysis demonstrates that the three men’s philosophical and pedagogical arguments were modernizing and progressive for their time and might therefore appear to challenge the class and racial interests supporting the tyrannical regime imposed by Spain on the island. At the same time, the chapter complicates this view of their contributions to education and philosophy with examples of their periodic blind spots with regard to authoritarian abuses around them or their failures to speak out against such abuses.