In the O. Henry short story, “After 20 Years,” the diamond stickpin is a symbol. It’s a symbol of the wealth and affluence that Jimmy’s friend went off to seek and found. It’s also symbolic of the “diamond in the rough” philosophy. Both youth started out as a diamond in the rough. Life and life experiences honed and polished them into what they became. Diamond Jim became a common criminal like a diamond that looks good on the outside but has lots of occlusions when one looks closer. Jimmy on the other hand allowed life to hone and polish him into a strong and upright citizen with good morals and values.