Born in England in 1931 of Irish immigrant parents and raised in Liverpool, Professor Oakley has vivid memories of the World War II wartime Blitz there and, while his elementary school was closed because of the bombing, of being homeschooled by his mother whose own education in a tiny village on the edge of Connemara had ended at the age of 14. That notwithstanding, she proved to be an effective, dedicated and demanding teacher and he was able to go on, first to Jesuit academic high school in Liverpool and then, via that route, to Oxford, where he graduated in 1953 with First Class Honours in the Honours School of Modern History. Awarded a Goldsmiths' Company's Commonwealth Traveling Research Scholarship, he spent the next two years studying Latin Palaeography and the history of Medieval Philosophy at the Pontifical Institute of Mediaeval Studies in Toronto. Oakley's graduate studies were interrupted by the need to return to England to serve for two years in the British Army, where he rose to the rank of lieutenant in the Royal Corps of Signals and was attached to the Commonwealth Communications Army Network. Having decided to return to North America, he completed his Ph.D. in History at Yale University in 1959 and spent the next two years teaching in the Yale History Department before taking up a similar position in the history department of Williams College in Massachusetts. There, for forty years, he taught medieval and early-modern history for the history department, as well as courses in the Interdepartmental History of Ideas major and in the Environmental Studies Program until his retirement from the faculty in 2002. Oakley's teaching work was punctuated by seventeen years of senior administrative service at Williams, first as Dean of the Faculty, then as President of the College, and later, 2002–03, as President of the American Council of Learned Societies in New York City—an interim appointment. A lifelong scholar, Oakley has held visiting research appointments at the Institute for Advanced Study at Princeton University, the National Humanities Center in North Carolina, and the Woodrow Wilson International Center for Scholars in Washington, D.C. During the academic year 1999-2000, he held the Sir Isaiah Berlin Visiting Professorship in the History of Ideas at Oxford University. Oakley has written extensively on topics pertaining to medieval and early modern intellectual and religious history and to American higher education, and is the co-editor of three volumes as well as the author of fifteen books. Prominent among the latter are his Omnipotence, Covenant and Order: An Excursion in the History of Ideas from Abelard to Leibniz, , Community of Learning: The American College and the Liberal Arts Tradition, and The Conciliarist Tradition: Constitutionalism in the Catholic Church 1300-1870, which was awarded the Roland H. Bainton Book Prize in 2004. For ten years, Oakley worked on a trilogy with the overall title of The Emergence of Western Political Thought in the Latin Middle Ages, published by Yale University Press between 2010 and 2015, and for which he received the 2016 Haskins Medal from the Medieval Academy of America. An honorary Fellow of Corpus Christi College, Oxford, he is also Fellow of the Medieval Academy of America and of the American Academy of Arts and Sciences. He holds honorary degrees, LL.D., L.H.D. and Litt.D., from Notre Dame, Northwestern University, Wesleyan University, Massachusetts College of Liberal Arts, Sacred Heart University, Amherst College, Bowdoin College, Southern Methodist University, and Williams College. Oakley has served for many years on the boards of various non-profit organizations in the arts and higher education, among them the Williamstown Theatre Festival, the Massachusetts Museum of Contemporary Art, the American Council of Learned Societies, the Sterling and Francine Clark Art Institute, and the National Humanities Center. Oakley currently serves as the Interim Director of the Sterling and Francine Clark Art Institute. He is married to the former Claire-Ann Lamenzo of Manchester, CT, a gifted fiber artist and dedicated horsewoman. They have four children—Deirdre, Christopher, Timothy, and Brian—and seven grandchildren; William, Charlotte, Ryann, Erin, Kevin and Joslyn Oakley.