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After graduating from jockey school in California, Nakatani began his riding career at Caliente in Mexico in the fall of 1988, winning his first race there aboard Blue King in a dead heat.  He moved to Southern California in April 1989 and became the leading apprentice rider that year and has won meet titles at Santa Anita, Hollywood, and Del Mar.  He won his 3,000th race on May 29, 2006, when he guided Shakin N Dancin to victory in the ninth race at Hollywood Park.

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