Lawrence Cremin gained prominence as an educational leader in the 1960s and early 1970s. Much of his efforts were at Teachers College where he was Chair of the Department of Social and Philosophical Foundations of Education from 1958 to 1974 and Director of the Institute of Philosophy and Politics of Education from 1965 to 1974. He also worked on a number of committees in the expanding federal government, in a number of private foundation boards, and in the development of various academic institutions. As his scholarly reputation grew, so did his administrative stature. In his work diary, he reflected on the tension he experienced between scholarship and leadership, and how that tension played out in his own professional ambition. This chapter examines Cremin’s development in and reflections on administrative leadership in this period and the way that his leadership reflected his liberal.