Thirteen jockeys have won the Hollywood Gold Cup at least twice. Laffit Pincay won the stake nine times, starting when he was 23 and for the ninth time when he was 55. Bill Shoemaker won it eight times, and three riders − Shoemaker, George Woolf and Jerry Lambert − won it three straight years. But for some jockeys − the best in the business, even Hall of Famers − the Gold Cup was elusive. No better example than Chris McCarron, who tried unsuccessfully 19 times. For nine minutes one year, McCarron thought he finally had the Gold Cup won, until the stewards disqualified his horse.