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| 1899-1920 | William S. Fitzgerald |
| 1906-1921 | William L. Clarke |
The Fitzgerald and Clarke Military Academy began as the Fitzgerald School in Trenton and was founded by William Stone Fitzgerald. A Webb School and Vanderbilt graduate, Fitzgerald taught at the New Mexico Military Institute and the Memphis University School before he was asked to open the boys’ school in Trenton. From 1899 to 1911, the school operated in Trenton.
William Clarke, another Webb and Vanderbilt graduate, joined the faculty in 1906 as associate headmaster, and the school became the Fitzgerald-Clarke School. The school moved to Tullahoma in 1911, and World War I prompted the school’s conversion to a military academy in 1918. In 1920, the school’s barracks burned, and Fitzgerald retired. The remainder of the school burned in 1921 and was not rebuilt.