Jose Santos first raced horses at the Club Hípico de Concepción in his native Chile, following in the footsteps of his father and three of his seven brothers, and in Colombia before moving to the United States in 1984. There he was the top money-winning jockey four years in a row, from 1986 through 1989, winning the 1988 Eclipse Award for Outstanding Jockey in the United States; Santos was at the top of the sport during those years. He won seven Breeders' Cup races and won the 1999 Belmont Stakes aboard Lemon Drop Kid. He won the 2003 Kentucky Derby and Preakness Stakes with Funny Cide but missed winning the Triple Crown of Thoroughbred Racing after finishing third in the Belmont Stakes. More recently, Santos has said that Funny Cide was not the greatest horse he ever rode but certainly was his personal favorite.