While at West Point, Charles Leonard was a swimmer and runner. This, combined with his marksmanship training, led him to the pentathlon. At the 1936 Olympics, Leonard won the silver by taking a seventh place in running, a sixth in swimming, and a first in shooting with a perfect score – the only time this has ever occurred in international competition. Had there been a team event in 1936, Leonard, with Al Starbird and Fred Weber, would have won that competition. Leonard spent his entire military career in the infantry. He taught military science and tactics at West Point before retiring from the army in 1967 as a major general. His decorations included the Distinguished Service Medal and the Legion of Merit.