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By the turn of the 20th century, Samuel Hildreth had expanded his New York operations and owned the largest racing stables at the Fair Grounds Race Course in New Orleans. That year, he appointed former outlaw Frank James as his betting commissioner at the track. Among the horses Hildreth owned was Fitz Herbert (b. 1906) who won the Brooklyn Handicap, Suburban Handicap, and the Jerome Handicap en route to being voted the Horse of the Year in 1909, and again in 1910. Another of his horses, King James, won other important races in 1909, including the Metropolitan Handicap, Sheepshead Bay Handicap, and the California Handicap, and went on to win the Brooklyn Handicap in 1910. In 1909, Hildreth also won his second Belmont Stakes with his own horse, Joe Maddon, and went on to capture the first of three consecutive leading owner and trainer honors in the United States.