In 1829, David Walker argued that emancipation from slavery would not be enough for justice and the moral uplift of former slaves. More recently, Derrick Bell argued that Brown v. Board of Education was no success at all and that racism is and will remain a permanent force in American society. If Walker and Bell are right, then emancipation from slavery was no more than a development of negative liberty at best, yet even one which was incomplete when we consider the forces of a culture of injustice. In my overarching project, in which I argue for understanding the moral requirements of a culture of justice, a deep and troubling challenge is evident at the outset. It questions the meaning of democratic ideals of justice and of emancipation in the face of hundreds of years of entrenched and harmful culture. Democracy implies a rejection of hierarchies of citizenship, yet the differential treatment of citizens is commonplace and foundational in a white supremacist culture. If American society is believed to be democratic, it is important to question the relationship of democracy to justice. If democracy is a way of life and a set of values, practices, and ideals, it is worth asking whether such ideals are truly meaningful in the real world of deeply entrenched cultural forces of injustice. To address these concerns, I argue that justice is best understood as a democratic and evolving regulative ideal. In making my case, I begin with a rejection of Rawlsian “ideal theory” while defending the pragmatic usefulness and value of ideals as guides for beliefs and behavior. I next offer reasons why we must see justice as democratic and hence as evolving. Finally, despite some flaws in John Dewey’s thoughts about race in America, I will conclude in agreement with his sober view that democratic ends cannot be achieved except by democratic means. In circumstances featuring a culture of injustice, therefore, a profound effort to reconstruct culture is necessary for any real progress to be achieved towards justice.