The school appointed Marie Frisardi Cleary Letter to the editor. and Juanita Ponte as the first two women in its academic faculty in 1967. Cornelia Kelley was the school's first female headmaster, serving from 1998 until her retirement in 2007, after which Lynne Mooney Teta became headmaster. In 2016, Mooney Teta resigned amid a federal probe into racially charged incidents at the school. In 2017, Rachel Skerritt became the first person of color to serve as headmaster. Skerritt resigned at the conclusion of the 2021-22 school school year and was succeeded in the retitled position of Head of School by elementary principal and fellow Latin School alumnus Jason Gallagher.
