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Born in Hagerstown, Maryland, Dutrow is the son of the late Dick Dutrow, a long time Mid-Atlantic trainer, who had 3,665 career victories at the time of his death in Feb. 2000. His brothers Tony and Chip also are trainers. The Dutrow brothers went to the barns with their father as young children and Rick began working as an assistant to his father at the age of 16.

Dutrow went out on his own in the late 1990s when his father left New York to return to Maryland. Things were not easy at first; he had no money and was living in a tack room at Aqueduct. His stable consisted of one horse, Churkin, whom he had claimed for $16,000. Dutrow's career began to take off in 2000. His lone stakes winner that year was Stalwart Member, who was owned by commodities trader Sanford Goldfarb. Goldfarb, leading owner by wins in New York in 2001, ’02 and ’03, was the main force in propelling Dutrow’s numbers skyward.

Dutrow’s career reached a pinnacle in 2008 with two champions, Big Brown, the year’s best 3-year-old male, and Benny The Bull, the year's best sprinter. Big Brown’s dominance of his division featured wins in the Kentucky Derby, despite drawing post 20, and Preakness. Unfortunately, he failed to fire in the Belmont and was pulled up by jockey Kent Desormeaux. Following the debacle in the Belmont Stakes, Big Brown returned to the winner’s circle with a victory in the G1 Haskell Invitational and the Monmouth Stakes on turf, but was retired in early October, prior to the Breeders’ Cup Classic .“Anyone who gets to live through anything as exciting as I have with Big Brown is living a very good life,” Dutrow said.

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