In 1999, Santos won the coveted George Woolf Memorial Jockey Award (since 1950, presented annually to the thoroughbred horseracing jockey in North America who demonstrates high standards of personal and professional conduct both on and off the racetrack); the Award has long been considered a very high honor, for the winning jockey is selected by his peers. Santos also won the 2003 ESPY Awards as the foremost jockey in the United States. He has long been a favorite of aficionados of the sport and is one of the best-liked and most respected jockeys in it.