In Oakcliff Sailing Center’s main building near Oyster Bay Harbor on New York’s Long Island, a half-dozen employees, students and volunteers are bustling around the office, organizing upcoming regattas and other events. In the adjacent maintenance shop, a staffer is finishing a fiberglass repair to the bow of a catamaran shattered in a collision. Upstairs in a new dormitory, eight young sailors are holding a “debrief” on how they might have performed better in a race in Newport, Rhode Island, the previous weekend. Across the street in Oakcliff’s boatyard, another staffer rolls touch-up paint onto a 40-foot sloop.

And hustling back and forth between all of this summer weekday activity — and keeping tabs on all of it — is Dawn Riley, one of the world’s most famous sailors and the founding executive director of Oakcliff.

Modest beginnings

The first American to be part of four America’s Cup teams, Riley, 51, was initially hired as a consultant by the family of Bryan Lawrence. Her job was to help figure out how to turn the family’s large collection of boats into a foundation that could train people in match racing — one boat against another, as in the America’s Cup, as opposed to fleet racing. The goal was to raise the United States’ low profile in international sailing competitions.

Lawrence, 73, is a successful investor with homes in Manhattan and on Centre Island, across the harbor from the Oakcliff compound. “We have a partnership that at any particular time owns half or more of 30 companies, all in the energy business,” he says in a rare interview.

Known almost universally by his nickname “Hunt,” Lawrence likes to buy sailboats — sometimes entire flotillas at once. “I grew up sailing on the South Shore in Babylon [New York],” he says. “I was probably 8 when I got my first boat, a Beetle cat. I’ve always had boats.”

As Lawrence’s fleet grew, he and his family invited friends, and friends of friends, to sail at what they called Oak Cliff Yacht Club, named after Lawrence’s house. Seven years ago he had accumulated 67 craft.

“We had way too many boats,” he says. “And so we decided we ought to have at least one foundation. It turned out we have two: Oakcliff and the WaterFront Center.” (The latter, also in Oyster Bay, teaches basic sailing, rents kayaks and provides cruises on the historic oyster sloop Christeen.)

With Oakcliff, says Lawrence, “our goal is to put as many racing sailors on the water as possible, and that’s hundreds most weekends.”

Riley was a natural choice to make sense of the abundance of sailing craft. In 1992 she was the first woman to sail on an America’s Cup syndicate, crewing on winner America3. Three years later she was captain on America3, heading the first all-woman syndicate. 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 Cup. She also twice competed in the Whitbread Round the World Race.

When Oakcliff was officially launched in early 2010, Riley stuck around to run the operation. But she committed to stay only three years “because I knew how difficult it was going to be,” and she didn’t want to burn out.

Five years later, she’s still there because she relishes the challenges. Oakcliff has not only expanded in the number of people trained, but also in the scope of its offerings. Many say Oakcliff has become the biggest match racing training and regatta center in the country, if not the world, with 200 scheduled events annually.

And Riley and Lawrence have even bigger ambitions. They envision Oakcliff becoming a center for America’s Cup catamaran training to get more American sailors aboard the boats. Oakcliff acquired two foiling Nacra 20s last year as the first step toward that goal.

“In the past five years,” Riley says, “we organized what was here, then we started expanding. We added an Olympic training program, we added an additional 18 match racing events per year, we have added boatbuilding facilities, and the biggest expansion was gutting old, old office space and building a 5,000-square-foot dormitory for up to 40 sailors.”

The original concept for Oakcliff was to provide only training, but the foundation has been sponsoring regattas, including four national championships this year. “Which is yet another thing we have added that wasn’t in the plan,” Riley says.

Big goals

“When we started, there were only two U.S. sailors ranked in the top 100 match racers, which was a travesty,” Lawrence says, steering his favorite boat, Caper, a 56-foot Rhodes sloop built in 1957, in one of Oakcliff’s Thursday evening classic yacht races. “Now there are 15. A large part of that growth is Oakcliff. We have the largest collection of match race boats in the world. There are people who didn’t know how to sail three or four years ago who are now sought-after crew, which is quite remarkable. But the result we want is more U.S. sailors ranked internationally.”

Jack Gierhart, immediate past president of Portsmouth, Rhode Island-based US Sailing, the organization that oversees competitive sailing in the United States, says “they’re a really strong pathway to get younger kids and adults into professional sailing. They continue to host a range of match racing events. And you’re starting to see some of those graduates migrate onto bigger boats that are involved in international competition.

“They stepped up big time to support the Olympic sailing program,” Gierhart adds, last year becoming an official training center with 24 boats in three classes: the Nacra 17 catamaran and the 49er and the 49er FX skiffs (eight boats in each class, purchased by Lawrence). “It’s going to take some time to see the full results, but they’re certainly producing some good sailors.”

Dave Perry, an Oakcliff board member who chairs the US Sailing Match Racing Committee, says the foundation “has helped put match racing in the mainstream of sailboat racing in the U.S., where before it was very much a niche discipline and very difficult to do in the U.S.

“There weren’t that many events,” he explains. “As a result, not many American sailors did match racing, so they didn’t get on the ranking lists, and they didn’t get into the top regattas. What Oakcliff has done is create a match-racing hub and generated a lot of match-racing activity.”

Riley modeled the Oakcliff operation on an America’s Cup syndicate, instituting regimens of grueling physical training and the long hours on the water needed to persevere in competitive sailing. In addition to racing instruction, it has branched out to teach boatbuilding and repair, as well as industry management skills, such as budgeting and provisioning for offshore races.

Riley and Lawrence are proud of their alumni. Two young men who sailed on the foundation’s offshore racing team, Charlie Enright and Mark Towill, won the last leg of the recent Volvo Ocean Race around the world on Team Alvamedica. They are already fundraising for the next race, with help from Oakcliff.

Another veteran, Jeff MacFarlane, two years ago was ranked No. 1 in the world in the Mini Class for single-handed ocean crossings. “I don’t think an American has ever been No. 1 ranked before,” Riley says.

In five years, Oakcliff has grown from a budget of just over $1 million and 30 boats to 86 boats and a budget of about $2 million. The foundation also does a lot of fundraising. It has no members but does ask people who sail regularly to become supporters, with a minimum annual contribution of $500. There are about 300 of them so far, and Cold Spring Harbor Laboratory last year signed on as a corporate sponsor.

Despite program growth, the staff has grown modestly from five to seven, Riley says. At the end of her third year, her health suffered because of the workload, so she’s planning to beef up the staff. She wants to hire a shore manager who has worked on an America’s Cup campaign or similar event, and have more than one training manager because “you can’t work that hard for that long.” With additional staff, she says, “I think I’ll be around for a while.”

The latest addition at Oakcliff is the 5,000-square-foot dormitory. It fills a need Riley identified when she first came to Oyster Bay as a consultant. “The primary issue that I saw was housing” — a lack of owned or rental space for visiting students and sailors. “When you normally have a regatta, you end up borrowing and begging for space and buying air mattresses,” Riley says. She wanted something more concrete.

Riley helped design, build and furnish the dormitory. She kept the cost below $300,000 by enlisting volunteers to augment contractors, buying used appliances and taking shortcuts, such as cutting and sewing the curtains herself.

The new space can accommodate about 20 visitors on a regular basis and twice that for big events. “Now we cannot only house people who come for a match racing event, which is amazing,” Riley says, “but also Olympic athletes,” who began arriving last fall to prepare to compete in the Games in Rio de Janeiro next summer.

“We have now — and it will get better — the best facility to train racing sailors in the world,” Lawrence says “One of the reasons there are so many New Zealanders in the America’s Cup was a program they started in Auckland more than two decades ago. What we’re doing is modeled a lot on that program. And New Zealand sailors who have come through that program recently say we have better facilities than they have there.”

In addition to the new dorm, the facilities include the insulated plastic-sheeting-over-metal-frame “Taj” — the repair and boatbuilding shed nicknamed by the Lawrences because Riley says it’s luxurious, with its heated floor and high-tech ventilation system to avoid air currents and dust that can ruin fiberglass work.

Lawrence calls it a natural outgrowth of the sailing program. “We had to take care of the classic boats and rebuild some of them,” he says. Once the capability to do repair work had been developed, the next logical step was to build boats from scratch, so Oakcliff obtained a set of molds to build the Ker 11.5, a 37-foot offshore-capable raceboat.

And that’s the plan starting next year or the year after with the Ker 11.5 molds. The foundation already owns one Ker 11.5, and Lawrence wants to start building others for racing.

The rate of expansion “is more than I expected,” Lawrence says. “But now we can do more.”

The future of sailing

“My goal for next year,” says Riley, “is not to add anything and do everything that we’re already doing perfectly. Hunt’s goal is to continue to change the world. We’ll figure it out.”

Despite all the work, Riley says she does get some water time that isn’t on a chase boat, including a regatta she sailed in Nantucket, Massachusetts, last year.

Riley says she’s unsure how long she’ll stay at Oakcliff but won’t be leaving to sail in another America’s Cup. “What I would like to do is manage the entire event because it’s the only thing I haven’t done,” she says.

With Oakcliff running smoothly under Riley’s direction, Lawrence can continue to focus on what he likes to do: sailing and buying sailboats and the occasional powerboat, including a Grand Banks 49 Eastbay, which he purchased last year. 

Whatever boat Lawrence is aboard, when he looks around Oyster Bay Harbor and sees the Oakcliff fleet spread out before him, he’s very proud of his creation. “Think about it — this is the future of sailing,” he says.

This article originally appeared in the October 2015 issue.