Lawrence calls Caldwell one of the greatest newspaper editors the South ever produced. He was fearless and absolutely fair in his work to all parties. He began as a printer's devil in his hometown of Statesville and later edited the Statesville Landmark for twelve years. When David A. Tompkins, a Charlotte industrialist and developer, offered him a partnership and editorship of his paper which later became the Charlotte Observer, Caldwell demanded and got complete autonomy in his role as editor. As an editor, his writings played an important part in forming opinion through the state.