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HERALD 1262517
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DECEMBER 27, 2024 - JANUARY 2, 2025
VOL. 71 NO. 1
HERALD PERSON OF THE YEAR DAWN RILEY
Skippering O.B. to a better tomorrow What’s INSIDE
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Dawn Riley is the 2024 Oyster Bay Herald Person of the Year By WILL SHEELINE
Dawn Riley’s life has always been connected to the water. From her early days sailing on the Great Lakes with her family to her groundbreaking achievements in competitive sailing, Riley’s journey is one of resilience, leadership, and a passion for community. As the executive director of Oakcliff Sailing in Oyster Bay, she has dedicated the past 15 years to mentoring the next generation of sailors and fostering a deeper connection to the community, and the water making her the Herald 2024 Person of the Year. Born in Michigan and raised near Detroit, Riley’s love for sailing began with a transformative family voyage when she was 12 years old. “We sailed for a year on our cruising boat from the Great Lakes to Maine, e’ve Florida, the Bahamas, the Virgin Islands, Grenada and back,” the Bayville always resident recalled. “It was critical to shapbeen about ing who I am.” collaboration That formative experience set the stage for a lifelong dedication to the and giving back. sport. Riley, 60, attended Michigan State DAWN RILEY University, working on and around boats to finance her education. Upon graduation, a recession made finding a traditional job difficult, so she returned to her nautical roots. What began as a practical choice, soon became a defining career as Riley broke barriers and achieved historic milestones in sailing. In 1990, she was part of Maiden, the first all-women’s team to compete in the grueling Whitbread Round the World Race. “The reason to do an all-women’s team is because the guys aren’t letting you, so you’re being shut out,” Riley said. “It’s just like in business. If you have all men on a company board it’s going to be a slow, difficult road for women to get in. As soon as you start getting three or four women in positions of power, then the floodgates open.” The journey was chronicled in the acclaimed 2018 documentary “Maiden,” which followed the team’s tenacity and success. Riley continued to blaze trails, becoming the first woman to compete in the America’s Cup in 1992 — and winning it. She then led an all-women’s America’s Cup team in 1995 and later served as CEO and team captain of America True, a co-ed team that competed in New Zealand in 2000. Riley also authored
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“Taking the Helm,” chronicling her experiences and insights into leadership and teamwork. Despite these achievements, Riley emphasizes that her focus has always been on collaboration rather than exclusivity. “Mixed teams in America are really the way to go,” Riley explained. “In most sailing, its equal and it’s just about skill.” In 2007, Riley served as general manager for the French America’s Cup team, based in Valencia, Spain. She was at the height of her professional sailing career when she was approached to consult for the Waterfront Center in Oyster Bay. That project led to the creation of Oakcliff Sailing, a nonprofit organization dedicated to raising the caliber of sailing and sailors, and Riley found herself drawn to a new challenge. “They used guilt to keep me here,” Riley jokingly explained. “I’d designed such a great program; they said I had to be the executive director.” Though initially reluctant, Riley embraced the role, and Oakcliff has since become a cornerstone of the Oyster Bay community. Under Riley’s leadership, Oakcliff Sailing has grown into a world-class training and resource center for aspiring sailors, Continued on page 2 Courtesy Dawn Riley
Dawn Riley, left, works alongside community members like Jeannie Marks of Oyster Babies for the annual Holiday Market and Stroll.