The son of a jockey, he began riding as a young boy, turning professional in his home country where he rode successfully until emigrating to Toronto, Ontario in 1994.
In 1990 he became the youngest jockey to win the prestigious Barbados Gold Cup at just 16 years, 9 months on his mount Vardar.
Among his other notable wins, he rode Numerous Times to victory in the $1 million 2001 Woodbine Mile and Exciting Story in that same year's Metropolitan Handicap at Belmont Park in New York.
In 2008 he won his fifth riding title at Woodbine Racetrack and was voted the Sovereign Award for Outstanding Jockey for a record-tying sixth time.
The award recognizes jockeys who are Canadian-born, Canadian-raised, or a regular in the country for more than five years, who have made significant contributions to the sport of thoroughbred horse racing.