Opposite: America True during the 2000 Louis Vuitton Cup in Auckland where she finished 5th. As well as raising the team’s mostly private funding, CEO Dawn Riley assembled an extraordinary sailing group with John Cutler driving alongside names like Buddy Melges, Jeff Madrigali, Liz Baylis, Katie Pettibone and Leslie Egnot – who steered Mighty Mary (above) in San Diego five years earlier. The 1995 all-women crew backed by Bill Koch benefited from the legacy of Koch’s enormous 1992 defender programme and Mighty Mary defeated Dennis Conner’s Stars&Stripes in the first race of the defender trials and eventually came within one race of the finals; actually they ‘won’ their semi-final before the series was unexpectedly extended to keep the Stars&Stripes team in the competition…
Trimming beginnings One key mentor was Tim Woodhouse, the longtime owner of Hood Sails. She first met him when he came aboard the boat she was sailing on a freezing cold day. ‘I was miserable, wearing hardware store yellow foulweather gear that ripped. But he was impressed with my trimming, and that next year I was racing and working for him. That was a beginning, a huge point. He was a character…’ The next big moment came after Dawn
agreed to run two boats at once. ‘My owner said, “We’re going to have you run Lunatic in the Great Lakes and Trader on the east coast. We’ll fly you back and forth.” And I was like, “Oh, great!” Of course, in reality, I was doing double the work for the same amount of money… but it was still cool.’ The connections she made in the active
east coast sailing community led to more opportunities. She started a list of useful contacts; ‘The good engine repair people in Charleston, South Carolina… that kind of stuff. At one point I thought I was going to create a boat captain’s guide, for how to get anything fixed anywhere – remember, there was no internet.’ Dawn graduated in the middle of a
recession, so instead of an advertising job she continued working as a pro sailor. Decades later she admits that her own school of hard knocks was much less organised than the school she runs now. ‘Oakcliff is a single answer to how to become a professional.’ In the late 1980s she learned there
would be a women’s team in the 1989 Whitbread. Shortly after sending Tracy Edwards a fax, ‘I had a very expensive phone call from St Thomas, where I was racing on [the IOR Maxi] Matador… and she’s like, “Oh, I love Matador, come over to England afterwards.”’ Dawn flew straight from St Thomas to England, a climactic shock after a winter in Florida and the Caribbean. (Living in her van on South Beach could be an article in itself… though for a very different type of magazine.) I ask Dawn what she thinks of Maiden
the movie. ‘I thought the film was really good, and it showed the struggle and it showed the time. The only thing they stretched is trying to make Tracy go from a troubled kid who ran away to sea into the world’s best sailor. She was legitimately one of the best navigators, man or woman,
at that time. But she wasn’t the best sailor.’ Racing around the world increased
Dawn’s sailing ambitions; the only question was… which path? ‘Should I do an Olympic campaign in the Europe, or should I do an America’s Cup? ‘I realised right away that I could make
money in the America’s Cup, and I would have to spend money to campaign for the Olympics.’ (This still true reality has now inspired an Oakcliff-run Olympic training programme.) When a try-out with Dennis Conner’s
team for the 1992 America’s Cup didn’t work out she called Gary Jobson, who was in charge of Bill Koch’s America3
team.
That earned her another try-out – how- ever, she thought it was an interview. ‘Gary still gives me shit occasionally,
– only the second woman to play a racing SEAHORSE 55
because I showed up with my nails done, wearing earrings and my best pair of khakis. And they’re like, “No, dude, we’re going sailing.” So I changed in the parking lot.’ To this day Jobson teases her: ‘That’s the first time I ever sailed with a racer with nail polish and earrings!’ Despite her inappropriate attire Dawn earned a spot on the America3
sailing team
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