Dick Chastain became the head football coach at Carroll High School in Ozark, Alabama in 1974. His two teams finished with a combined 6-14 record. In 1976 he moved over to Ariton High School for the next eight seasons.

After his first two teams went 4-16 he turned the Ariton program around. Chastains last five teams finished 56-13 with five area titles and five playoff appearances. His last three teams went 29-1 in the regular season.

Following the 1983 season he accepted the head coaching job at W.S. Neal High School in East Brewton. Chastain would remain with the Blue Eagles for four years and produce a 15-27 record.

In 1988 he took over the football program at Samson for the next six seasons. Coach Chastains overall football record is 111-102 in 20 years as a head coach. His teams won seven area championships and qualified for the playoffs a total of ten times.