The Doctrine of Discovery, viewed through the lens of six hundred years of international law, has shaped Chile’s legal history, from Diego de Almagro’s first footprint in the north to its later claim to part of Patagonia and Antarctica. A comparative law examination of the Doctrine’s long history in Latin America demonstrates that the European acquisition of Chile was founded on what can be considered today to be feudal, religious, racial, and ethnocentric justifications. The adaptation of many of the Doctrine’s elements into the Chilean government’s own domestic policies over the past two hundred years has had profound implications for its Indigenous peoples. Chile’s attempts to create a more positive and equal future for its citizens, just as the efforts of settler societies such as Spain, Portugal, England, and the United States, must begin with an enlightened recognition of this history. Only then can serious efforts to eradicate the vestiges of this doctrine from international law provide resolution of deeply-rooted issues in a place of justice and healing.