Webb was a standout multi-sport athlete at Pasadena High School during the late 1950s, earning nearly a dozen varsity letters in football, basketball, baseball, and track. He played on some of Pasadena ISD's most esteemed teams and later earned a football scholarship.

As a three-season starter in football, he was twice named All-District and helped the Eagles reach the 1958 state championship game. On the basketball court, he was a member of the 1958 district championship team, while in baseball, he earned All-District recognition twice. He also contributed to the track team's state title in 1957.

After playing football at Rice and Lamar, Webb returned to Pasadena High to coach. He led the baseball team to the state finals in 1968 and continued his coaching career at Tomball High and Lamar.