|1870-1926||W.R. “Old Sawney” Webb, Sr.|
|1874-1916||John M. Webb, Co-Principal|
|1926-1953||W.R. “Son Will” Webb, Co-Principal|
|1953-1959||G. Webb Follin, Sr., Co-Principal|
|1959-1963||John Lewis Morgan, Principal|
|1963-1970||Henry O. Whiteside, Sr., Principal|
|1970-1973||Kenneth F. Stuckey, Principal|
|1973-1978||Gary M. Jones, President|
|1977-1989||Jackson E. Heffner, Headmaster|
|1989-2005||A. Jon Frere, Headmaster|
|2005-2009||Albert R. Cauz, Head of School|
|2009-2010||Gordon E. Bondurant, Interim Head of School|
|2010-present||Ray Broadhead, Head of School|
There was in [John Webb] the perfect combination of saintly character, deep learning and the gift of imparting it.
—Edwin Mims, Professor Emeritus at Vanderbilt University, Webb School class of 1888
The Webb School and Vanderbilt have always had a close relationship. One of the oldest schools, founded in 1870, the Webb School had been known as the Culleoka Institute. When William Robert “Old Sawney” Webb took principalship in 1870, he renamed the school. His brother John joined him in 1874. Webb School was intended from its inception to be a preparatory school, not a university or college like many other schools at the time, and it prepared boys for Vanderbilt almost from the beginning. Webb School graduated its first class in 1874, the year Vanderbilt opened, and these boys formed part of Vanderbilt’s first freshman class.
The school was often held up as a standard for prep school education by Vanderbilt University administration and faculty, and many Webb School graduates went on to establish prep schools of their own after leaving Vanderbilt. The Webb School moved from Culleoka to Bell Buckle, where it still operates, in 1886. The school is both a day and boarding school, and while female students were always admitted as day students, the first female boarding students were not admitted until 1973.
Edwin Mims’ quote from “W.R. Webb and John M. Webb, Tributes to Headmasters by Former Students” in Private Preparatory Schools for Boys in Tennessee by William O. Batts, 1957.