Winston Thompson
Known for being one of the hardest working jockeys in New England, the 27-year veteran earned his fifth riding title in 2008. Won the 2007 Mystery Jet Stakes aboard Lily s Goldmine The Jamaican native swept leading rider honors at Suffolk Downs from 2004 through 2006 Had one of the best days of his career on June 18, 2005, winning six races on the Suffolk Downs program, including a victory in the $50,000 Old Ironsides Stakes on Miesque’s Approval for Hall of Fame trainer Bill Mott. Miesque’s Approval went on to win the Breeders’ Cup Mile and the Eclipse Award for top turf male in 2006 Thompson learned his race riding in a formal jockey training school, attending educational programs that are required for aspiring riders in his native country. He won his first race in 1983 at Caymans Park in Jamaica and was the leading apprentice in Jamaica in 1984 before coming to the U. S. two years later. Thompson had riding stints in New Jersey, Florida and West Virginia before coming to New England in 1988. He has been a fixture in Boston since…Was the leading rider at the 1995 Suffolk Downs Autumn meet…In 2000, had one of the most memorable days of his career, winning the $250,000 James B. Moseley Breeders’ Cup Handicap aboard King Roller. In 2009, he finished second in the jockey standings with 95 wins. He spent the winter riding at Laurel Park.