My story begins back in 1793 when November Caldwell was “gifted” to Helen Hogg Hooper (whose father-in-law, William Hooper, signed the Declaration of Independence), the wife of the first president of UNC–Chapel Hill, Joseph Caldwell. November Caldwell is my great-great-great-grandfather. Currently, I owe over six figures in student-loan debt to the very institution that enslaved my ancestors. We are at a particular place in the political history of our nation. White supremacy is morally corrupt. It requires that we deny the humanity of human beings for one reason or another. It is hard to stand up against white supremacy because folks who do are often ostracized from their families and communities. We have all been socialized to believe in white supremacy—it was one of our nation’s founding principles. In this essay I hope to break open a dialogue about the white supremacist hegemony institutionalized within our neoliberal university system. Connecting the past atrocities of slavery with actual educational experiences of the descendants of those who served the proslavery institutions has not been widely publicized or talked about. We must interrogate our history or we will be doomed to continue to repeat the horrific inhumane atrocities.