The story of American urban renewal is frequently reduced to a struggle between autocratic supporters of mass urban clearance and the admirable individuals and communities who resisted. Henry Stern Churchill (1893-1962), the focus of this thesis, was an early advocate and practitioner of urban renewal, who, by the end of his career, became a staunch critic of the practice. Churchill, therefore, upsets the dominant narrative of renewal, showing that it is not purely a story of good vs. evil, but rather one with dynamic figures who evolved over their careers. Churchill demonstrated a lifelong commitment to planning as a democratic practice. This manifested itself in numerous ways, from his work for the Roosevelt Administration’s Greenbelt Towns program to his housing reform advocacy with New York’s Housing Study Guild to, in the late 1950s, advising a community planning effort in Philadelphia’s Germantown neighborhood. Throughout Churchill’s career, he was in close contact with important figures in planning. Henry Mayer, Albert Wright, and Churchill were founding members of the Housing Study Guild, and they served in the same Greenbelt project. In New York, Churchill engaged in a public dispute with Robert Moses, accusing the latter of racial prejudice in the pages of The New York Times. In Philadelphia, to which he moved in the early 1950s, Churchill was the chief planner for the Eastwick renewal project. Finally, he corresponded with Jane Jacobs, offering advice and support as she fought against urban renewal in the West Village. Churchill, despite his liberalism, had a perspective that was, at times, exclusionary. In his community planning, he considered the community’s interest to be that which was represented by the leaders of its institutions, such as private schools, giving no place to the common resident. Moreover, Churchill, in his renewal consulting, exhibited racial bias in the identification of sites that he thought should be cleared. Henry Stern Churchill embodies the complexity of planning past and present. As such, his story provides instruction and caution to a discipline in continual evolution.