The Greatest Kentucky Derby Upsets

When Giacomo charged across the finish line in the 2005 Kentucky Derby at odds of 50-1, the select few who had bet him to win received a whopping $102 for having the luck or audacity to pick him. Giacomo's shocking win earned him a spot in The Greatest Kentucky Derby Upsets, which explores the tales of some of the Derby's most improbable victors. In 1904 Elwood became the first starter owned by a woman, one Laska Durnell, who failed to tell her trainer husband she had even nominated the colt. In between Elwood's winning and Giacomo's, Donerail returned a record price that still stands, Sir Barton made the Derby his first victory, Dark Star defeated the seemingly invincible Native Dancer, Iron Liege capitalized on a rival jockey's miscue, Canonero II went from laughing stock to hero, and Genuine Risk won one for the girls.