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A very high point in Berry's long career came on December 10, 2010, when he won with all seven of his mounts on the program at Remington Park. The sweep - a night after he rode five winners - matched the North American record of seven wins without a loss on a card shared by Tim Moccasin and Richard DePass. Berry got his start galloping horses for his father, Bob Berry, a bloodstock dealer, and in the beginning of his racing career rode Quarter Horses before switching completely to Thoroughbreds in the early 1980s. A top rider on the Arkansas, Oklahoma, Texas circuit, Berry is a 13-time riding champ at Remington Park. He won the 2011 Oaklawn title with 18 more wins than defending champ Terry Thompson. Two of those victories came in stakes aboard Win Willy.

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