In 2000, Desormeaux won his second Kentucky Derby aboard Fusaichi Pegasus. The two combined to take the Wood Memorial Stakes and Jerome Handicap. "Probably the most talented horse I rode (was) Fusaichi Pegasus," he said in 2004. "What an amazing, amazing, animal that horse was." In 2001, Desormeaux decided to ride in Japan for three months. His son, Joshua, then age 2, had been born deaf and had recently received a "microphonic implant." Since Japan only has two racing days a week (compared to six in the United States), the move allowed Desormeaux to spend more time with his family. During this stint, he became the first foreign jockey to win a Classic race in Japan when he rode Lady Pastel to victory in the Yushun Himba (Japanese Oaks).