High Master, St Paul's School.

Bailey had previously lectured in medieval history at the University of Cambridge (1986-99), and returned to academic life in 2010 as a Visiting Fellow of All Souls College, Oxford (2010), and then as Professor of Later Medieval History at the University of East Anglia.
In 2019 he will deliver the James Ford Lectures in British History at the University of Oxford. His main outside interest is sport, having played Minor Counties cricket for Suffolk, captaining the side between 1989 and 1991, and winning seven caps for England in rugby.