At age thirteen, Shaun Bridgmohan's family emigrated to the United States, settling in South Florida where he developed an interest in horse racing. 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 the of 1998 year which was his breakout year as the winner of the Eclipse Award for Outstanding Apprentice Jockey. On December 22, 2007 he again won six races on a single card, this time at Fair Grounds Race Course in New Orleans, Louisiana.