 Before becoming a jockey, and while still in school, he worked at a Florida racetrack as a hot walker, groom, and as an exercise rider.After graduating from high school he pursued a riding career and in August 1997 earned his first win at Calder Race Course.Six months later on February 15, 1998 he won six races on a single card at Aqueduct Racetrack in Queens, New York, finishing 1998, which was his breakout year, as the winner of the Eclipse Award for Outstanding Apprentice Jockey.