Seeking the Daily Grind

With his head down and his hands dirty, one sailor muscles his way onto the American Magic sailing team

The time Sean O’Halloran was called into a meeting with American Magic skipper Terry Hutchinson and team coach James Lyne is one he won’t forget. O’Halloran had barely sat down on the couch when Hutchinson announced that they wanted him to be a part of the sailing team. “He just put it right out there,” O’Halloran says. “It was a huge relief and really exciting. I didn’t get that emotional at first but when I walked back to my car, I spent a few minutes just sitting there, breathing, letting it sink in.”

Now, let this sink in: The next America’s Cup will be sailed in Auckland in 2021, on flying 75-footers. They will be power-hungry machines fed by a team of grinders such as O’Halloran who willed his way into the most technical generation of Cup sailing. His is a story of determination and commitment.

He grew up in San Jose, California, where he learned to sail at summer camp at around the age of 12. When he joined his college sailing team, the sport became a major focus in his life. He earned a spot on the team through countless hours of studying videos of ­sailing technique. After graduation, O’Halloran went into the culinary industry, but sailing was never far from his thoughts. In 2015, he moved to Newport, Rhode Island, where he managed a bar and continued to seek more sailing experience. He landed a ride on a J/122 for Block Island Race Week, where he first learned about Oakcliff Sailing and how its Sapling program could turn his passion into a profession. He applied and was accepted in 2016.


One of his first assignments as a Sapling was running a mark boat for the America’s Cup World Series and helping the Artemis syndicate set up and break down its base. The best piece of advice he got, he says, “was to always ask yourself, am I being challenged?’ If the answer is no, you have to change something. If the answer is yes, then put your head down, work hard, and you will create the right opportunities.”

After the program, Oakcliff hired O’Halloran and gave him ample challenges: When he got comfortable with match racing, he became boat captain of one of Oakcliff’s Farr 40s, then started racing offshore. He then began doublehanded racing, which tested his knowledge of every position on the boat.

Onshore, he apprenticed in rigging, sail making and composites. He was always on the edge of his skill threshold.


A year and a half later, Oakcliff partnered with Vestas 11th Hour Racing to send two staff or graduates to every stopover of the 2017-2018 Volvo Ocean Race to work alongside the shore team. O’Halloran’s ticket got punched for the Cape Town stopover, where he spent two weeks working with the team.

Shortly after that, Oakcliff ­partnered with the New York YC’s America’s Cup challenger, American Magic, to host a week of training and tryouts for Oakcliff staff and graduates in fall 2018. They were tested on the water in match-racing drills and in the gym with a series of benchmark tests.

O’Halloran had been ­diligent with his fitness regimen, but this sparked a new level of dedication. He was pulling two sessions a day in the gym and sometimes sacrificing his lunch break to go for 6-mile runs.


By the time the American Magic team arrived, he was in the best shape of his life. He stood out amongst the candidates, so when they needed another set of hands to maintain their 38-foot test platform, and to drive a chase boat, his name came up. After the holidays, he headed south to join the team at its winter base in Pensacola, Florida.

When O’Halloran first arrived, he was facing the same fitness struggles that most people have after the holidays. “It was hard to get back into it at first,” he says. “Making the team as a grinder was still my main goal, but first I just wanted to get back in shape.”

grinding machine
Sean O’Halloran undergoes one of many benchmark fitness tests on the grinding machine at American Magic’s base in Portsmouth, Rhode Island. Amory Ross/American Magic

He had access to a ­meager gym with dumbbells, a few aerobic machines and a pool. It worked fine for cardio, but he needed to increase his strength and power. In the past, he’d had success exercising at CrossFit gyms, so he opened his phone and searched using three words: “CrossFit near me.”


He found Revolt Fitness. It had a shower and a 6 a.m. class, so he could work out and make it to work on time. The months that followed saw the most rigorous training schedule of his life. His days began at 5:15 a.m., and after the gym, he would head to work for a 7:30 a.m. start and finish as the sun was setting or later. Working on his strength in the morning freed up his ­evenings to focus on grinding.

He spent hours honing his technique to get every ounce of power out of each revolution of the handles. He’d end his days with a meal and go straight to bed to do it all over again.

“It was hard at times to keep motivated, especially after a long day out on the water, but I had to remind myself that this could change the course of my life,” O’Halloran says. “There are few things that have such a direct correlation between hard work and achieving the goal you’re striving for. Most jobs or promotions have other politics that come into play, but for me, the equation was simple: put my head down, put in the work and I have a very real chance to make the team.”

After he found his groove in the gym again, he spoke with Ryan West, American Magic’s head of athletic performance, to arrange another benchmark test.

O’Halloran’s girlfriend, Nora Hoefer, recalls talking to him one night after a grinding test that he had pushed further than he expected.

“He was proud of his progress but still wanted to push harder,” she says. “He told me, ‘I would love to be on the boat, but I just want to do what is best for the team.’ I remember thinking how selfless that statement was. He was working so incredibly hard on his own, but he was never driven by personal success or stature. He truly wanted to ­represent American Magic.”

Although O’Halloran performed well on the test, he still wasn’t hitting the marks. When the team returned to its base in Rhode Island, for the summer, he had a final opportunity to demonstrate he was up to the challenge. He took the fitness test again…and then he waited.

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When Hutchinson and Lyne called him into the office, he had no idea he was getting the nod for the sailing team. Later that night, O’Halloran called Hoefer: “I dropped it pretty casually and she started crying. I called my parents after. There was no announcement to the team so nobody really knew.”

Unsure if he could ­actually tell anyone about his new assignment, O’Halloran says he simply started showing up to the workouts and eventually word traveled down the grape vine. In the team’s gym in Portsmouth, he must now train for the Cup team’s most ­grueling assignment.

“The physical challenges of a grinder in the next America’s Cup are moving in the same direction they have been for the past few editions of the race,” West says. “You have to be able to sustain high output for a long period of time. The grinders need to be able to maintain near maximum-heart-rate work for 25 to 30 minutes or longer. That’s where O’Halloran really stands out. He’s got an engine; he can maintain high aerobic capacity for a long time. Now we’re going to continue to build upon that in our training. He’s highly coachable and just a good person. He’s consistently hardworking and not afraid to take on the work.”

West has worked three Cup campaigns as an athletic trainer and has an intimate knowledge of the evolution of the athlete’s build in the foiling catamarans.

“Athletic performance in the America’s Cup is absolute, not relative,” he says. “In cycling for example, the amount of power you have to output is relative to your body weight. In the America’s Cup, the loads are the same regardless of the weight of the sailor. We don’t look for any particular height as long as they can output enough power, but there is a weight limit on the boat. The maximum total body weight for the 11 crew is 990 kilos [2,182 lbs.] and the minimum is 960 [2,116 lbs.], so the strength-to-weight ratio of each athlete has to fit with the rest of the team.”

As the team awaits the launch of its 75-footer, O’Halloran’s day-to-day work hadn’t changed much, yet. He is still driving a chase boat and doing maintenance on the deck hardware of the test boat, but now that he works out with the team, the days of waking up at 5:15 a.m. are over. He will begin sailing with the team on the full-size AC75 when it launches later this year and will continue his work maintaining the deck hardware.

“I guess it hasn’t really sunk in because I haven’t sailed on the boat yet,” he says, “but I’m just focusing on what I have been from the beginning: being the best asset to the team that I can be.”