Arkansas State University

Inducted in 1985, Caldwell was a three-sport athlete at Arkansas State. Caldwell was a four year letterwinner in baseball, one year letterwinner in basketball, and a three year letterwinner in football. As a quarterback from 1957-59, Caldwell led Arkansas State in total offense all three years including a career-high 1,281 total yards in 1959. That same season, Caldwell earned Honorable Mention All-America honors through the Associated Press. 

In 1959, Caldwell also led the Indians in rushing with 322 yards on the ground and five TD. He threw for nearly 2,000 yards in his career, including a career-high 959 yards in 1959 with 13 passing TD. 

Following his playing career, he returned as an assistant coach for Arkansas State in 1961.