Racism pervades the criminal legal system, influencing everything from who police stop and search, to who prosecutors charge, to what punishments courts apply. The Supreme Court’s fixation on colorblind application of the Constitution gives judges license to disregard the role race plays in the criminal legal system, and all too often, they do. Yet Chief Judge Roger L. Gregory challenges the facially race-neutral reasoning of criminal justice actors, often applying ostensibly colorblind scrutiny to achieve a color-conscious jurisprudence. Nor is he afraid of engaging directly in a frank discussion of the racial realities of America, rebuking those within the system who would treat Blackness as synonymous with crime. Judge Gregory’s jurisprudence can—and frequently does—serve as a model for judges in other circuits who are working to enact the vision of a color-conscious Constitution.