One of the top-earning jockeys in the sport today, Hall of Famer Mike Smith wore these black boots during his racing career and they show terrific use, as evidenced by the worn-out ankles. Both are signed by the man who rode Giacomo to the 2005 Kentucky Derby crown but the signatures are light (3/10). No one has won more Breeders' Cup races than Smith, who is a second-generation jockey.