Contrary to customary genealogical study in which one hopes to elevate oneself through lauding the accomplishments of one’s ancestors, radical or reparative genealogy encourages us to engage such a pilgrimage to learn about the specific harms committed by one’s ancestors. It is an invaluable step toward undertaking efforts of repair. It uses one’s ancestral history to understand more deeply one’s ancestors’ contributions to oppression, to extend the circle of one’s empathy and compassion, and to live into possibilities of repair. Lotte Lieb-Dula defines reparative genealogy with respect to slavery as “the act of researching our heritage, acknowledging our connection to slavery, and daylighting the history of those our ancestors enslaved.” It is a path that importantly includes seeing more clearly how some of our own life choices continue to work against the well-being of people of color. In this chapter, the author grounds her discussion of reparative genealogy in her own ancestors’ involvement in chattel slavery. She outlines her method of using her ancestors’ lives as portals to parts of U.S. history related to colonialism and chattel slavery In doing so, she shares with white readers history they are least likely to know and demonstrates how their own reparative genealogy can be a path to racial reparations.