As the Race Program Director at Oakcliff Sailing in Oyster Bay, New York, Bill Simon has an essential role in the non-profit organization’s mission of putting American sailors atop podiums around the world and building American leaders through sailing.


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“I grew up in Port Washington and learned to sail from my father and friends,” says Bill, who lives in Port Washington near the house he grew up in. “We sailed off a local beach from when I was 7. My first boat was a Jigger, a 13-foot, round-bottom dinghy designed by Ralph Heinzerling, a local racing legend. For many years we rowed it out to our moored keelboat to race, and it remained in the family until my wife and I sold it last year in preparation for moving to Annapolis. I raced with my dad, Daniel, for about 40 years. Initially we had a Lightning, then an Ensign, and we moved to the Sonar Class. I learned to have fun while racing from Dad.”

“For about 20 years we raced Sonars in Manhasset Bay, where we race Saturdays and Sundays from May until October. At the height of the fleet we had 26 Sonars, most of which were drysailed out of Manhasset Bay Yacht Club. Along with my sailing partner Einar Haukeland and Dad, we worked our way up the fleet to be a competitive member of the class. I became the Captain of Fleet 11 and an International Sonar Class Vice President.”

Bill joined Oakcliff in 2010. “When I heard there was a high end coaching and training center two harbors over, I had to see how I could become involved. I made an appointment to meet with Executive Director Dawn Riley, and got some assignments that day. Dawn leads an extremely open management of Oakcliff. This style worked for Dawn on an America’s Cup team, and Oakcliff has grown incredibly following this model.”

“I schedule and run 25 high level regattas each year. These include about one third of the graded match racing events in the country, from local Grade 5s to the Oakcliff International which is a Grade 2 and the highest level event we host. As part of the management team, I also work on some financial responsibilities and feeding the sailors.”

“In September, we hosted the 3rd Annual Clagett/Oakcliff Match Race Clinic and Regatta, the only match race I’m aware of for sailors with adaptive needs. We had several past Paralympians, and coaches Dave Perry and David Dellenbaugh. It was very rewarding. We host the Triple Crown Series, comprising three regattas each year for the 49er, 49erFX, 470 Men and 470 Women Olympic classes and the foiling Nacra 17. There’s $100,000 of prize grants per class, so most U.S. Olympic hopefuls are here and international competitors are now coming as well. We’ve developed our own fleet race umpiring for these events.”

Oakcliff is renowned for its Acorn and Sapling training programs, created to prepare students for sailing industry careers. “The Acorns are two-week, high intensity specialist programs,” Bill explains. “Many times these are younger sailors, but frequently Acorns are 60-plus and want to improve their skills. Saplings spend several months here. They generally participate in all of the Acorn programming but also learn all functions, from working on boats to navigation, racing rules, tactics and sail trim, in much more detail. They sail everything from the foiling fleet to our Match 40s, Farr 40s, and our JV 66 Numbers. They race offshore and in all kinds of local races.”

“New York Yacht Club American Magic came to Oakcliff recently to offer tryouts to our staff and graduates for their America’s Cup team. We have foiling and high performance camps, and US Sailing recently ran a 49er and 49erFX camp here. We had five boats and 65 people in the Newport Bermuda Race this year, many teams in the Triple Crown Series, and we did all the medium distance races in the area. You cannot believe what Dawn can make happen in a week!”

A passionate match racer, Bill is the incoming Chairman of US Sailing’s Match Race Championship Committee and dedicated to growing the discipline in the U.S. and abroad. “I had only match raced a time or two in Manhasset Bay and really didn’t understand it until coming to Oakcliff. I learned from all the wonderful coaches we’ve had here. Match racing will make you a much better racer in all disciplines. It’s not unusual to do eight or ten races in a day. It’s quite aggressive, and you need to know the rules intimately. Your boat handling will get much better, and your boat-on-boat tactics will improve exponentially. Most importantly, you either win or lose each race. Combine this with group learning and camaraderie, and what’s not to love?”

Bill is the Regional Administrative Judge for Area B. “Oakcliff is a coaching and training center for race officials as well as sailors, and we run a full schedule of seminars in the off-season. At our judge, umpire and race officer seminars, we take people on the water to improve their skills. This year, with the help of Bruce Cook, Mary Savage and others we developed Protest Day, a one-day US Sailing seminar in which participants run seven or more protest hearings, with coaching from top judges to improve their techniques. US Sailing certifications are about helping volunteers improve their skills, and certified race officials are covered by US Sailing’s insurance while volunteering. It’s a great way to give back to the sport.”

Bill relishes “the feel of a tiller in your hand when you have a perfectly balanced boat and a great team of friends to sail with in 12 knots of breeze,” adding, “It is wonderful to see young sailors come to Oakcliff and mature as sailors and people.”

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