Chesterfield Smith is from central Florida. His father had been a schoolteacher and then opened an electrical appliance shop near Arcadia, when electric power became available for the remote areas. The business failed during the twenties and the family traveled around wherever his father could find work. When they returned to Arcadia, Chesterfield finished high school graduating at the top of his class. He enrolls at the University of Florida where he would be a student for one semester and then take the next off to earn money.