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Lt. Clinton Dillard Castleberry, Jr. was a football player in the 1940s.

Castleberry showed extraordinary ability as a Georgia Tech "pony" back, standing at only 5'9" and weighing only 155 lbs. In high school, he played for Boys High in Atlanta, where he averaged 171 rushing yards per game and scored 102 points. In 1942, freshmen were ruled eligible to play varsity ball as rosters were drained by the World War II. This allowed Castleberry to display his spectacular prowess on the football field. Against national power Navy, Castleberry led Tech to a 21-0 blowout on October 24, 1942 in Annapolis that was broadcast worldwide via the Armed Forces Radio Network. On October 3, 1942, Georgia Tech beat Notre Dame for the first time since 1928, especially impressive as the game was played in South Bend and Notre Dame had not lost a game in two years. Castleberry led Georgia Tech in both passing and rushing yards, even after Notre Dame Head Coach Frank Leahy had been warned by a scout that Castleberry was "the most dangerous runner in America."

Georgia Tech started the season 9-0 and climbed to a top five national ranking. During that ninth win, Castleberry injured his knee in a hard-fought 20-7 win over Florida in Atlanta. Despite the injury, Castleberry played in the final two games of the season, but not quite at full speed. Tech lost their last game of the season 34-0 against Georgia, who shared a portion of the National Championship that season with Ohio State and Wisconsin. On New Year's Day, Tech traveled to the Cotton Bowl, losing a tight game with Texas, 14-7. Castleberry's injury improved for the bowl game, yet he was still not quite a hundred percent.

Castleberry finished third in the Heisman trophy voting for the season, behind winner Frank Sinkwich and Paul Governali, both seniors. This was the highest a freshman had ever placed in the Heisman voting. Castleberry's number 19 is the only football jersey Georgia Tech has ever retired.

After the 1942 season was over, Castleberry enlisted in Army Air Corps and planned to return to play football at Georgia Tech after the War. During World War II, he co-piloted a B-26 Marauder bomber known as "Dream Girl" and was stationed in Africa. In the early morning hours of 7 November 1944, Lt. Castleberry took off from Roberts Field in Liberia with another B-26 to continue a ferrying run up the coast toward Dakar, Senegal. Neither of the two planes were ever seen again, despite an extensive six-day search involving American and British search crews. On 23 November 1944, all crew members were officially re-classified from MIA to KNB (killed, no body).