It was still dark when the sound of alarm clocks filled the Oakcliff bunkhouse in Oyster Bay, NY. Staff and graduates gathered in the office fidgeting in their seats as they waited. It had finally arrived, the day we’d all been waiting for: Tryouts & Training with American Magic, New York Yacht Club’s challenge for the 36th America’s Cup.

NYYC American Magic Grinder Luke Payne helms a Match 40 with a crew of Oakcliff trainees in a tight battle against fellow grinder Joe Spooner on the third day of training. © Francis George/Oakcliff Sailing

A black SUV pulled into the driveway emblazoned with the American Magic logo on the side. One by one, juggernauts of the sailing world walked through the door casually sipping their morning coffees. The first one was Ryan West, Head of Athletic Performance for the team; he worked for Softbank Team Japan in the last edition of the America’s Cup. Next was Andrew Campbell, a Helmsman/Tactician for the team; previously he was a sailor for Oracle Team USA and a Laser sailor at the 2008 Olympics. A bit later to arrive was James Lyne, the Team Coach: a self-professed winning addict who regularly coaches America’s Cup and Volvo Ocean Race sailors.

We rose in deference to their arrival and introduced ourselves. There’s a certain sense of awe you get when you meet America’s Cup sailors on such a human level; they were still drowsy like we were, still shrugging off the morning chill…still just people.

When the training began, it was like the floodgates of sailing and athletic knowledge had been swung wide open. Ryan coached each and every one of us through the strength tests, which consisted of max bench press reps at 165 lbs and max body weight pull-ups. Andrew joined Ryan to give shouts of encouragement when we approached failure: “Don’t give up!” “You’ve got one more in you!” “Keep going!” They treated us just like their teammates.

Later on, James gave us a debrief after doing match racing drills and practice races in the Swedish Match 40s. We were left nearly speechless after the most detailed analysis of boat handling and trim we’d ever witnessed. James uses a custom program he developed that uses an image of a sailboat to analyze the rig and sail trim with staggering precision.

The next day was even more awe inspiring. A few more members of the team arrived including Terry Hutchinson himself, the Team Skipper/Executive Director and a veteran of four America’s Cup campaigns. He came with two of the team’s grinders: Luke Payne, formerly a sailor on Softbank Team Japan, and Joe Spooner, who won the Cup twice with Oracle Team USA.

The Oakcliff team broke up into three crews and headed out to the boats for some more drills and practice races. Terry, Luke, Joe and Andrew rotated through positions on the boats. They focused on coaching but also enjoyed some healthy competition amongst themselves (with some more competitive than others!)

At the end of the day we gathered in the Oakcliff bunkhouse for a family-style dinner prepared by none other than Dawn Riley, Executive Director of Oakcliff Sailing. We happily chowed down on a delicious arugula salad and meat-lover’s pasta that was topped with fresh burrata. Each of us naturally gravitated towards our favorite sailors. There was a little bit of competition for seats at the tables but we all got our turns. We swapped stories about our sailing adventures and bonded over the thing that has brought us all together: a love of the game.

By the fourth and last day, most of the team had returned to Newport but Joe, Luke and James remained. It was the sunniest day all week but also the windiest and coldest. Before we went out on the water, we had a special session in which we had 90 seconds or less to answer the question, “Why do you want to be in the America’s Cup?” We didn’t know this was coming, but Dawn had prepared us well. She helped each of us write an “elevator pitch” before the training session started. One by one, we stood up in front of the group and told these three America’s Cup sailors why we want to make it to their level.

They also opened up and shared their stories with us. Most of us had watched interviews or read about them in the magazines, but to hear them tell their stories in the flesh was priceless. They were honest and raw. They told us about the moments of success that drove them forward, and the painful moments of failure where they almost gave up. Some of them even got choked up as they recalled those critical forks in the road where their lives could have gone in a totally different direction.

When one of us asked Joe what winning the Cup was like, he cocked his head to the side with a pensive look. A moment later a grin spread ear-to-ear across his face. He simply said, “Yeah…winning is good.” The hairs on my arms stood up. There was something about that smile I’ll never forget. It brought me back to my childhood, to those small moments of triumph like riding a bike without training wheels for the first time. It was that rare form of joy, the purest kind that only comes at the end of a long road riddled with setbacks, hard work, and sacrifice. It was the smile of a dream come true.

Alex “Firefly” Lulewicz, a 2018 Sapling Graduate, does his bench press test with the guidance of Coach Ryan West and takes the high score for the Oakcliff crew. © Francis George/Oakcliff Sailing

The week of training was just the beginning of an ongoing partnership between Oakcliff Sailing and New York Yacht Club American Magic. They have evaluated all of the candidates who participated in the first session and are helping top candidates develop a training regimen and set goals to strive for. They want to continue to train and inspire the next generation of American sailors. These training opportunities are exclusively for graduates of Oakcliff’s programs. If you are interested in applying, you can find more information at or you can email the Training Program Director at

Francis George is Oakcliff Sailing’s MarComm Manager.