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Caldwell attended State on a four-year football scholarship. State was one of the first whites to play on a previous all black football team. He played four years as a pulling guard from 1954 to 1957.
After leaving college, Caldwell played semi-pro football for a Charleston team. He also assisted in organizing the Nitro Midget Football League, where he was head coach of one of the teams, Union Boiler, for 16 years.
He also organized the Nitro Independent Baseball team, where he coached and played for several years. Additionally, Caldwell volunteered his time for several years working with the Capitol City Striders Track and Field Club.
