Paulo Freire's philosophy of education, popularized via his magnum opus, "The Pedagogy of the Oppressed" (2000 [1970]) 'shocked' the world, sort of constructively, with its trenchant, au courant and futuristic meditations on the onto-epistemological lives of the marginalized in Latin America, and by elliptical extension, across the world. The central tenets of Freire's thought as reflectively (and reflexively) acting upon the world to transform it, are as current today as these were in the late 1960s, majorly because of the subjectively active ways it interacts with our onto-epistemological locations and intentions. It is in appreciating such durable temporality about his philosophy that one can sense, indeed, thickly discern it trans-spatial and transcultural connections with the humanist African philosophy of Ubuntu and it educational foundations. Ubuntu in its across-Africa readings, represents both a practical and aspirational humanization of all people (more popularly, perceiving and practicing our personhoods through the personhoods of others) with the potential outcome, in the words of Desmond Tutu (in Battle, 2009), of the cessation of inter-people conflict and oppression. With these perspectives and prospects from Freire and Ubuntu, the intersecting subsets of the two are, I argue, thickly important with analytically discernible onto-epistemological and pedagogical connections and operations.