This essay revisits college presidents during the early 1960s to investigate the long history of how academic leaders manage racial unrest on college campuses. Throughout time, the concept of a welcoming and inclusive climate for black students on majority-white campuses has functioned as an illusion alongside the prevailing reality of racism on and off American campuses. In turn, this essay exhibits how political structures, as well as university hierarchy, have shaped academic leaders' approach to social change in higher education. Therefore, this work demonstrates the need to reevaluate higher education history as a lens for understanding the current American sociopolitical context that shapes present-day academic leaders and their challenges of addressing racism on college campuses. In summary, this work renders a richer and more nuanced understanding of the complexities college presidents, students, and campus stakeholders, such as governors and boards of trustees, face to provide equal and meaningful educational opportunities to all students.