Mary Ann Sullivan (b. 1944) was born and raised in Charleston, South Carolina. She attended the College of Charleston and then the University of Georgia where she graduated with an M.A in Classics. Sullivan worked as a teacher for a few years and in 1976 joined the Mayor’s Office of the City of Charleston as a grant writer. She became Mayor Joseph P. Riley executive assistant and continued working with him until his retirement in 2016. In the interview, Sullivan remembers growing up in Charleston and the events that contributed to her early political interests. She also talks about her experiences working with Mayor Riley through critical moments in the history of the city such as the development of the Charleston Place, Hurricane Hugo, the annexations of Daniel Island and James Island, the Sofa Super Store fire and the Mother Emanuel massacre. Sullivan reflects about Riley’s leadership style and his inclusion of minorities in government. Finally, she talks about her decision to retire and her plans for the future.