America's Cup vet runs an LI school for sailors

Late on a recent weekday afternoon, Dawn Riley deftly maneuvered an inflatable speedboat around four sailboats that were aggressively circling one another on Oyster Bay.

Very much in control, Riley yelled across the water with crisp, rapid-fire commands: "Tack! Tack! Tack!" she ordered, an instruction to turn with the wind coming across the bow. And "Don't tack, jibe!" for turning with the wind across the stern. And encouragement: "Nicely done!"

But when the sailors in some of the sloops bungled a maneuver, Riley kept her frustration mostly to herself. Stamping her feet on the floorboards of her chase boat, she groaned, "Oh, my God, they're killing me!"

She quickly brightened, adding, "They've already made a significant amount of progress" in just one or two afternoons on the bay.

Riley is extremely knowledgeable about sailboats and how to race them, and fiercely competitive while still adept at managing people. This will come as no surprise to those familiar with her and the sport. She is, after all, arguably the most famous female sailor ever as the first American to be part of four America's Cup teams.

But what many sailors don't know yet is that Riley has taken up residence on Long Island to run the new Oakcliff Sailing Center in Oyster Bay. She will be leading its effort to teach sailors how to become better racers -- at least until another Cup team comes calling for the next competition three years from now. 

A roundabout journey
How she got here is a story almost as interesting as Riley herself. It started with a financial whiz from Centre Island with a lifelong love of sailing who began accumulating boats until he owned 67. That's not a typo.

As Bryan Lawrence, who made a fortune in banking and investing, acquired his fleet, he and his family invited friends, and friends of friends, to sail with what they called Oak Cliff Yacht Club, after the name of Lawrence's house.

"It's quite a small navy," said Lawrence's son-in-law, David Halliwill of Manhattan. Driving the enterprise, he said, was Lawrence's "idea that just as he had been a young kid with talent, there would be young people on Long Island who might not have the opportunity to get out on the water."

Even as the private operation grew large and time-consuming, the family feared it was too much of a closed group and not training enough young sailors. "So we begin asking: 'How do we structure this? How do we open this up?' " Halliwill said. There was also a desire to fill a competitive niche -- one-on-one match sailing -- that yacht clubs and sailing schools weren't serving.

The answer was creation of a nonprofit foundation with a big name at the helm to train sailors who already had some experience. Oakcliff Sailing Center - which has a program unique in the Northeast -- opened Jan. 1 with Halliwill as board chairman and Riley, a friend of his who was initially hired last year as a consultant to oversee the transition, as executive director.

Riley, 45, was certainly the kind of big name the Lawrences had in mind. In 1992, she was the first woman to sail on an America's Cup team, crewing on winner America3.

Three years later she was captain on America3, heading the first all-woman team. In 2000, as captain of America True as well as chief executive of its support organization, Riley became the first woman to manage a Cup team.

Then from 2004 to 2007 she was general manager of Areva Challenge, the French team competing for the America's Cup. She also competed in two grueling Whitbread round-the-world sailing races. 

A lifelong sailor
The Detroit native who began sailing with her parents when she was a year old is also experienced in the nonprofit world. She served as president of the East Meadow-based Women's Sports Foundation, founded by Billie Jean King in 1974, and is on the board of US Sailing, the Rhode-Island based national governing body of the sport.

The goal of Oakcliff's training, Riley said during a pause in the hectic activity at the group's South Street compound, which is modeled on an America's Cup team headquarters, "is raising the level of sailors in the U.S. If some of our people go on and do the America's Cup, great."

Oakcliff teaches offshore cruising and boating industry skills, too, and if students just become better sailors or learn how to run a sailing-related business, Riley and Oakcliff will be pleased.

The 67 boats in the fleet include modern and classic boats used for match racing and fleet racing. The latter, in which all boats in a class compete simultaneously, is common at yacht clubs as well as in the Olympics. One-on-one match racing events, such as the America's Cup, are rarer, as are opportunities to train for them. So the chance to learn and practice match racing - along with the likes of Riley and her five full-time coaches, a staff that will be augmented by summer apprentices - is the attraction for many. 

Match racing mind-set
"It's a different aspect of the sport, and it brings a whole different set of challenges," Colin Fitzpatrick, 27, of Port Washington, who began sailing with Oak Cliff more than three years ago, said of match racing.

He called the new sailing center "a great opportunity to be able to come down and pay a nominal amount and sail with a lot of good people." And Riley, he added, is "a national name organizing and running the show."

The organization has a $2-million annual budget and relies on funding from the Lawrences and on donations. Anyone who sails more than twice as a guest is asked to become a "supporter" by donating at least $500 annually, and those with limited incomes can substitute labor for some of the cash.

In summer, supporters can sail almost every evening, and in winter they can attend classroom training. There are currently 220 supporters, a number Riley hopes to boost to 1,000 this summer as she also seeks to add large donors.

Sailors from around the country are starting to come to Oakcliff for training. And that doesn't surprise Gary Jobson, another America's Cup veteran and president of the 41,000-member US Sailing. He said the program is unlike any other in the Northeast. Plus, "Dawn Riley brings a lot to the table," he said. "She's an experienced manager. And Dawn has experience racing around the world. She's good with people."

Those qualities were evident when, after conferring with her coaches and consulting her laptop on the proper mix of three sailors for each of the four boats, Riley gathered everyone in the office and handed out their assignments.

After they were ferried out to the moored sloops, Riley used shouts and her whistle to lead the group through nonstop exercises, starting with sailing tight circles to practice tacking and jibing and moving on to race starts punctuated with shrill whistle blasts.

Some crews excelled. Of the others, she said, "They don't get it. Next week, I'm going to get on the boats" with the students.

By 7:30 p.m., it was getting dark. Riley blew her whistle again. "We're done," she yelled.

Not quite. Riley didn't let anyone go home until they had returned to the office for a detailed debriefing on what hadn't gone well out on the water.