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On Watch - Ben Cesare

Ben CesareAs of this issue, the helm at WindCheck is in the sure hands of Ben Cesare, an affable and accomplished sailor who acquired the magazine last month from co-founders Anne Hannan and Christopher Gill, who launched ‘The Magazine by and for Long Island Sound Sailors’ in 2002. “I grew up on Southfield Point, on the west side of Stamford Harbor in Connecticut, until I was eight,” says Ben, who resides in nearby Norwalk. “There was a tiny community beach where Dad kept the dinghy leaning against the seawall and a Rhodes 19 moored off the beach. That is when I started sailing, and though the memories are fuzzy, I do remember overnights on the Rhodes with the family. Later in childhood, my parents got a Menemsha 24, which seemed like superyacht in comparison.”

“I do have crystal clear memories of Dad taking my older brother, Ed, and I out on the Cape Dory 14 in the winter for tours of Stamford Harbor,” Ben recalls. “I got to steer while Dad and Ed manned the two sets of sweeps, and we went fast! Especially memorable was going up the West Branch, where the sewage treatment plant yielded all kinds of goodies for us to poke at with the oars. Then we would go ashore on one of the grassy islands in the harbor and cook hot dogs and drink cocoa. Not sure what Mom thought of those excursions but from then on, I have had a love for the water.”

“We moved to Norwalk, and my first solo sailing was in the Dyer Dhows at Norwalk Yacht Club’s junior program. My first boat was a very slow Blue Jay that my parents bought for me before getting me my first Laser when I was 13. It was bright red/orange. I think I astounded them, and might have hurt Dad’s feelings, when I sold it and added my own lawn mowing money to get a better one that was white (better for starts) when I was 14.”

“My most significant sailing mentor was David Powlison. He was responsible for not only my but also my friend Scott MacLeod’s questionable use of 10,000 hours apiece on this sport. Scott and I would rig up and sail outside of junior program hours to practice. Dave (Sailing World Contributing Editor) lived across the harbor, with his Laser on a dock in front of his house. He took us under his wing and taught us how to ‘spar’ – spending long periods going in a straight line working on speed, and then equally long periods working on boat handling. His was the white Laser that I ultimately bought. Dave’s generosity yielded a great singlehanded career for Scott in Lasers and Finns, and got me hooked as well.”

“Since then, I have had the good fortune to participate in so many aspects of this sport with all kinds of great sailors, mostly here in the Northeast. From college sailing at BU to match racing, offshore racing and one-design keelboat racing, I never really had to travel further than Miami to access some of the best sailing competition in the world. I have enjoyed sailing all over the country and overseas, but it really is hard to beat what we have right here in the Northeast for cruising, racing or just ‘messing about’ on the water.”

Ben has also had the opportunity to work in the sailing industry in between corporate jobs. “I had six years of coaching experience, teaching both juniors and adults, by the time I was two years out of college,” he says. “Then I got the chance (with aforementioned childhood friend, Scott) to form a business whose mission was to transform the sport of match race sailing into a professional tour with – then radical – rule and format changes to make it commercially viable. It was a ton of not very profitable work, but it has proved very satisfying to this day as many of the changes we made are standard operating procedure now. Another very memorable sailing ‘job’ was the opportunity to coach Carol Cronin, Liz Filter and Nancy Haberland during their successful bid to represent the United States in the Yngling at the 2004 Olympic Games in Athens. It was so much fun to watch a team succeed by focusing on improving every day, until improvement for its own sake became the goal and the end results ‘just happen.’”

“The point is,” Ben continues, “I believe positive change can be made to practically anything. We often lament the changes or swings in participation for almost all the things we love. But my main concern about raising my ten-year-old son, Matt, is not how well he does in Optimist racing. My hope is that he knows and enjoys how to ‘hand, reef and steer.’ In this day and age, that translates to being able to swim, kayak, SUP, drive a powerboat well, fish, wakeboard, surf, navigate, sail offshore, race one-designs, hopefully foil, and maybe some kiteboarding (foiling, of course), but above all, become a true waterman. Largely because of where we live, and the weekends he spends on the water with his family and friends, he is well on his way!”

“So to help others on that journey, my goal is that WindCheck carry on as not only a beloved steward of this great community but to also expand it, attracting others to not only enjoy our traditions but to help push our interests and those of our kids into new and exciting ways to enjoy the gift of Sailing the Northeast!”


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  • Paul
    commented 2018-03-07 11:12:10 -0500
    Congratulations Ben, wishing you and your team every success going forward. It has been a delight to work with Ann and we wish her well. Paul & Sherrie Norton – SlipSure
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