In this Article, written in connection with a symposium honoring Chief Judge Roger L. Gregory’s twenty years on the bench, I place Judge Gregory’s jurisprudence within the tradition of African-American political thought. I suggest that, at bottom, Judge Gregory has a leveling-up jurisprudence that seeks to interpret the Constitution in a way that ensures the least well-off in society are granted the same rights as the most privileged. This brand of democratic theorizing approximates a mainstream position by Black political theorists optimistically seeking to have the least well-off integrated into a fully equal society. By comparing and contrasting his work with other legal and political thinkers in this tradition, I sketch an example of how Judge Gregory uses his role in the judiciary to help shape an America that lives up to the ideals expressed in its founding documents.