© Francis George/Oakcliff Sailing

A graduate of the Shorthanded Offshore Acorn program at Oakcliff Sailing in Oyster Bay, New York, Catherine “Cat” Chimney is back at the high performance training center on Long Island Sound with one of the coolest jobs in the sport…and she may be a future Olympic medalist.

“I’ve been a wharf rat since I was born,” says Cat, whose very first sailboat race was frostbiting at Seawanhaka Corinthian Yacht Club with her father Ed Chimney, a longtime Oakcliff supporter and a graduate of the High Performance Acorn program. “There was what seemed like a mountain of prep work to get the little Dyer Dink race-ready. We had to make a new rudder and centerboard from scratch, and Clam needed to be painted and all the rails varnished. We applied for special dispensation from the SCYC frostbiting race committee to put two people in a Dyer, and finished second for the season.”

“I got an Optimist for Christmas when I was nine, and slept in it that night under the tree. Spring came and I hatched a plan to sail around the world via the Hudson River to my grandmother’s house on Lake Erie. After two years of junior sailing at Mentor Harbor Yachting Club, I was overly confident about my journey. I calculated the amount of Honey Nut Cheerios I needed to put in my water ballast tanks, then hooked the Optimist up to my bicycle and put a letter in the mailbox to Grandma, telling her I was coming. Of course, I hit a dilemma as my moral compass said I was not allowed to cross the street…and certainly not allowed to go sailing by myself. Arriving at the dock and weighing up the consequences of my actions, I decided to walk the boat back up the hill, hide it in the yard and eat my Cheerios at home. This covert operation was a success until three days later when Grandma got my letter and phoned my parents…I was busted.”

Cat cites Seawanhaka Corinthian YC Past Commodore Ian McCurdy as an important mentor. “He did a lot with the SCYC Junior Club to develop racing and positive keelboat practices,” she recalls. “Many of those lessons I was able to apply onboard their family yacht Selkie. The McCurdy & Rhodes 44 was a good boat to learn proper winch etiquette, dip pole jibes, sail changes, and of course maintenance practices.”

Focusing on the Laser Radial during high school and her early college years, Cat got out on as many boats as possible. “After ‘hitchhiking’ with my Laser to Florida for Miami OCR,” she says, “I decided to spend more time sailing and moved to Auckland, New Zealand in 2006 to pursue my Chemical and Materials Engineering degree. I was lucky enough to be able to compete in the 420 World Championships, the Oceania and European Laser Circuit before attending two Laser Radial World Championships. I went on to work in heavy industry, managing Project and Product Development.”

While she was in New Zealand, Cat also dabbled in windsurfing, kiteboarding and foiling. “After living in New Zealand for twelve years and the UK for two, [Oakcliff Executive Director] Dawn Riley convinced me to move halfway around the world for the third time in my life, back to Oyster Bay to live, work and train at Oakcliff,” she says. “As Technical Specialist & Rigger, I am responsible for the fleet management of our eight Swedish Match 40s and six Melges 24s. I project manage their race readiness, the breakdowns, and the preventative maintenance schedule in addition to the rigging requirements of all the other boats Oakcliff operates. I’ve recently taken on mentoring two graduates on our Class40 for shorthanded racing.”

“There are two driving components of Oakcliff: the staff and the trainees. As staff, I have the freedom of creative problem solving. Being a non-profit, we’re a ‘waste not, want not’ work environment. Our motto is ‘shop at home before buying anything.’ For example, a carbon rod may start its life here as a tiller extension, turn into a spray extender, and end up as a running light mount. We have some trainees that come back season after season. Seeing their skill set expand and problem-solving skills mature under our Training Program Director Ethan Johnson and the team is very rewarding. No two days here are ever the same. With staff and trainees living onsite, trainees can get involved with staff projects at any time.”

In 2019, Cat and Ethan Johnson won the inaugural Oakcliff Melges 24 Doublehanded Distance Race, a 120-mile jaunt around Long Island Sound. “Rounding Falkner as the sun came up with four competitors on our hip was breathtaking,” she enthuses. “Ethan and I believe 80% of success offshore is on-shore preparation. We’d prepared the boat well, and had a good sleep management and nutrition plan. Plus, a little Taylor Swift playing boosted morale when there was no wind!”

Oakcliff is leading the charge to place Americans atop the podium in the Mixed Two-Person Keelboat Offshore event at the 2024 Olympics, and Cat is planning a campaign. “The new format has sparked my adventurous spirit, and I’ve been very lucky to have people supporting my Olympic dream,” she says. “CFOforaDay has supported my doublehanded sailing since the end of last year and are continuing to support me now.”

“Whenever you’re visiting Oakcliff,” says Cat, “say ‘Hi’ to Zoe Waffles, our in-house pet therapist and Labrador mascot who’s been on nearly every boat we own. She has two passports and has travelled from New Zealand to Australia to Dubai to the UK, and now resides at Oakcliff. Her escapades are well documented on her Instagram page @zoewaffles.” ■

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