This chapter focuses on the primary protagonists in a diversity culture shift and the ongoing evolution and challenges of the Chief Diversity Officer (CDO) role. It highlights the emergence of pluralistic and culturally responsive leadership models and accents the increasing role of faculty governance as a countervailing force in championing diversity change. The chapter overviews the critical components of organizational learning theory that undergird a diversity culture shift. The landscape for diversity poses substantial challenges on college campuses due to structural contrasts: the co-existence of a centralized administrative hierarchy and decentralized units comprised of divisions, colleges, schools, and departments. In higher education, leadership emanates from the president to the provost, executive officers, deans, department heads, and chairs. The chapter also introduces a case study of the University of Tennessee at Knoxville (UTK) that provides a startling example of the intrusion of conservative legislators in the area of diversity within public institutions.