Leestown Middle School first opened as an elementary school in 1958. Henrietta Harris was the first principal, and she supervised 11 classrooms and a total of 350 students. On Jan. 2, 1961 Leestown became a junior high school.
Through the years, Leestown has undergone several structural changes. Built as two separate buildings connected by a breezeway, a wing was added in 1963 that connected the buildings and included the gymnasium and front foyer. In the spring of 1984, a second floor was added to the building.
During the tenure of Principal Luther Jones (1961-66), Leestown became the first public junior high in Kentucky to be inducted into the Southern Association of Colleges and Schools.
During the 1990-91 school year under the guidance of Principal Rafael Cordoves, Leestown became a true middle school serving students in the sixth, seventh, and eighth grades. On March 27, 2000 the library was dedicated to honor Cordoves for his service to Leestown (pictured at right).
Between 2008 and 2010, under the leadership of Principal Jennifer Kendall, Leestown underwent a complete renovation with additional classroom space, new administrative offices, and a state-of-the-art library media center. Kendall also oversaw the creation of the Pre-Engineering Program in 2010.
In 2012, Cynthia Lawson was selected as principal. She was influential in creating and implementing a student-centered program called the Leestown Way. This program was successful in creating a supportive school learning environment. Under Lawson’s leadership, Leestown increased enrollment, expanded the Pre-Engineering Program, and improved overall student achievement as evidenced by large gains in state test scores.
Lawson retired in 2017, and the School-Based Decision Making Council selected former Associate Principal Joe D. Gibson as the new principal of Leestown Middle School.