Leo James Caldwell was born in Durham in 1903. He was the son of Mr. and Mrs. J. H. Caldwell, and had three brothers and sisters.
Leo attended R. J. Reynolds High School during its first full year of operation. He played four years of varsity football, and was the captain of the 1922 basketball team. Leo was tragically killed during a football game in 1923. Reynolds was playing Charlotte, and Caldwell punted the ball which was caught by a Charlotte player who was running it toward a sure score when Caldwell tackled the Charlotte player. But Caldwell was thrown down and he hit the ground hard, causing a broken neck and instant death.
His death was devastating to the players and the spectators, and the entire community. Superintendent R. H. Latham cancelled the remainder of the 1923 football season. A memorial fund was established, and funds contributed would be used for worthy students in need of money for either high school or college, named the Leo Caldwell Memorial Student Loan Fund. Contributions were made by individuals, clubs and other civic organizations, and student organizations. The Winston-Salem polo club donated the ticket sales from a polo match. When the fund contribution time was nearing an end, the total raised was about $5,000.
At the 1924 graduation exercises, a portrait of Leo Caldwell was presented to the school by Charles Norfleet, to be hung either in the school or in the new gym. The Caldwell family announced that they were establishing a medal called the Leo Caldwell Medal, which would be awarded to the student who most nearly exemplified the qualities of character possessed by Leo Caldwell. And, a bronze tablet was installed over the entrance to the new gym in his memory, in 1927.
Photo courtesy of Forsyth County Public Library Photograph Collection.