The growing body of literature on reparations consists primarily of articles showing that black reparations are consistent with various legal theories, promote racial justice, or further broader societal goals like eliminating poverty and promoting education. This article takes the distinct position of challenging reparations supporters to justify their confidence in the legal system to deliver meaningful reparations for slavery and segregation in light of the historic use of law as a means of instantiating white racial supremacy and the prospective individualistic approach to race adopted by contemporary judges and legislators. The article also challenges those who oppose reparations based on its supposed unfairness to contemporary citizens to explain how their position differs from that of past generations who opposed reparations and related legal efforts to redress racial injustices as unfair at that time. To support the challenge to reparations commentators, the article examines the historical framework of blacks’ relationship to the law through legislation and court rulings from 1619–1963. The article closes by presenting an alternative approach to reparations focused on building and strengthening black political, economic, and educational institutions.