Riley is First Woman to Lead Sailing Team

Dawn Riley can handle a jib or a spinnaker, just like any other sailor. The difference, however, is this deckhand also balances her boat’s books.

Riley, the first woman to head an America’s Cup team in the history of that yachting competition, also works in the middle of the crew of 16 on her yacht, “America True.”

But why is the boss in the middle of the boat instead of up front?

“Because,” she said, “I don’t have enough brain cells to steer the boat and the syndicate.”

Riley is an accomplished sailor, the only American to sail in two Whitbread Round-the-World races and two America’s Cups. A two-time winner of the Santa Maria Cup, she’s now involved in the challenge of a lifetime. It’s not the first time.

“I was the only woman on the 1992 team,” she said. “That was unique, an unbelievable experience. I was a rookie. It was my first America’s Cup. Everything was new. I got to sail with the best in the world. Occasionally, there were days when I felt I didn’t fit in. There was a lot of pressure.”

America3 won the Cup that year and three years later, Riley was back in the boat, this time as captain of an all-women’s crew in the 1995 Cup competition, won by New Zealand.

Now, Riley has a bigger stake in the challenge. Beyond her responsibilities on the crew, she’s also in charge of the money side of this operation.

The price tag is $20 million, a considerable sum until Riley puts the figure in relative terms.

“What do you get for $20 million in the NBA?” She said. “A couple of players? We’ve got a new boat, a training boat, 16 on the crew and between 22 and 30 persons on the overall sailing team.”

Liz Baylis works alongside Riley on the boat and is amazed by the boss’ energy.

“She’s cool, a very determined person,” Baylis said. “She’s tough. She gets the job done and she’s not afraid to dig in. It’s not like she’s the CEO and above all this. I’ve seen some of them, when the boat hits the dock, off they go. Whatever needs to be done, she does it.

“I’ve sailed against her and she’s always the last person off the boat. It’s amazing to think with so many things to be responsible for that she has so much energy.”

There are three other American teams as well as challengers from Italy, Japan, Spain, France, Switzerland and Australia.

They will begin elimination races in October to pick a challenger for the Cup series beginning Feb. 19. Riley wants it to be her yacht, which is on its way to Auckland, New Zealand.

She will follow next month.

“By Oct. 18, it’ll be time to put your boat where your mouth is,” she said. “We have a realistic chance. We have the boat. We’re confident in the design. We have plenty of time to get ready. We know our plan. Right now, we’re finalizing the sailing team. We’ll be in the water pretty much every day, off one day in 10. It’s all very positive. The next step is to be first across the finish line.”

Riley sailed at Michigan State, where she was captain of the crew, a trailblazer at a time when there were very few woman skippers and none assembling America’s Cup challengers.

Sometimes, in the midst of all the detail work involved in organizing this massive operation, Riley, 34, allows herself a moment to think about her own private fantasy.

“I want to be a housewife,” she said. “I want to do gardening outside a house with a picket fence and a dog.”

Then she paused.

“Not really,” she said. “What I want to do is be in the water and win the Cup.”