Highlands High School

Wes Caldwell is in his sixth year as Athletic Director at Highlands High School, where he brings a strong foundation of experience as both a student-athlete and athletic administrator. A Lexington, Kentucky native and graduate of Lexington Catholic High School, Wes was a standout multi-sport athlete—earning letters in football, baseball, and basketball—and finishing his high school career as the school’s all-time leading receiver with 159 catches, 2,601 yards, and 38 touchdowns. He went on to compete as a two-sport athlete at Middle Tennessee State University, playing both football and baseball at the Division I level. After his collegiate playing career, Wes gained valuable coaching and administrative experience through internships at Lexington Catholic and MTSU, as well as a graduate assistant role and wide receivers coaching position at Bethel University. He holds a bachelor’s degree in Organizational Communication from MTSU and a master’s degree in Recreation and Sports Administration from Western Kentucky University. Wes is dedicated to building on Highlands’ rich athletic tradition, supporting student-athletes both on and off the field, and fostering a culture of excellence across all sports programs.