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Dawn Riley (born July 21, 1964) is an American sailor, and a pioneer in the sport of sailboat racing. She sailed in three America's Cup races and two Whitbread Round the World races, and was the first American to accomplish this feat. She was the watch captain on Maiden, the first all-women's entry in the Whitbread race, and was the team captain of the first all-women's team in the America's Cup. She later established the America True Foundation to encourage youth participation in sailing. Since 2010 she has run Oakcliff Sailing dedicated to Building American Leaders Through Sailing