Rolex Yachtsman & Yachtswoman of the Year Awards Ceremony

Terry Hutchinson and Stephanie Roble were honored at the New York Yacht Club on Feb. 26th.

Gathered between half hulls and America’s Cup models in the Model Room of the New York Yacht Club 44th Street clubhouse, guests of US Sailing and Rolex gathered to honor the 2014 Rolex Yachtsman and Yachtswoman of the year.

At first glance, Terry Hutchinson and Stephanie Roble appear to be the archetypal bookends of professional sailing. Hutchinson, though far from finished, has been at the pinnacle the sport—including earning his first Rolex Yachtsman of the Year accolade in 2008—which has brought him to where he is today. On the other side, sailing’s new golden girl, Roble, is just getting started.

When I arrive, Roble is holding a stuffed koala bear and hand drawn card from the Kilroy family, delivered in person by Liam Kilroy, the 11-year-old helmsman on the Melges 20 Team “WildMan,” with herself, Steve Hunt, and Erik Shampain. As Roble makes her way across the room, she is waylaid nearly every step she takes by a well-wishing friend or admiring peer. Dawn Riley envelops her in a hug, Gary Jobson eagerly shakes her hand, and even more guests approach to introduce themselves.


Meanwhile, Hutchinson patiently waits in the lobby for his wife and children to arrive with his suit, chatting with old friends. Only hours before, Hutchinson was crossing the finish line of—and winning—the Caribbean 600 aboard Hap Fauth’s Bella Mente, followed immediately by boarding Fauth’s plane to Teterboro Airport to arrive just in time for the luncheon. Even on his day, without his jacket, Hutchinson is barred from entering the model room. Despite the delay, he’s in good spirits and eagerly awaits the arrival of his loved ones, who appear just in time for lunch to be served.

Jobson takes the stage following the meal, proudly pointing out each of the returning award recipients and panelists who are scattered around the dining tables. Riley, introduces Roble first, and congratulates Rolex on an excellent choice of Yachtswoman of the Year.

Rolex USA President & CEO, Stewart Wicht, then presents Roble with her award, and pauses for a moment to let the room in on their most recent conversation over lunch. “Steph is currently ranked number three in the world, but soon to be number one,” he says. Roble nods in agreement. “We all agree on that,” he says, “So, well done.”


In their awards speeches, the two reveal that they are similar in the most fundamental ways. As Jobson is quick to point out, he is thrilled that Rolex is honoring two successful tacticians. Both are alumni of Old Dominion University, and Hutchinson and Roble credit ODU coach Mitch Brindley for their collegiate success—though Hutchinson argues that the harsher side of Brindley he experienced was different than Roble’s.

But perhaps the most important takeaway is that both winners focused on one central theme to which they attribute their success—the strength of their support team. These groups, which include their families, mentors, coaches, and teammates on the water, are what both Roble and Hutchinson identify as the keystones of their careers.

“When I think about the most successful times in my life,” says Roble, “It has been when a strong team has been backing me up. This year has been a prime example of that.”


In a more reflective mood, Hutchinson speaks about his father’s influence on his determined personality, his appreciation for Hap Fauth’s mentorship, and his constant support from coach James Lyne. In a difficult moment in his speech, Hutchinson gestures to a back corner of the model room to point out the empty space where the America’s Cup once lived.

“I had so many people who stayed with me through the toughest times,” he says, “I hope that someday that trophy can be brought back here, and return to where it belongs.”

To which the room erupts into applause.

Rolex Sailing Awards Ceremony

2014 Rolex Yachtsman & Yachtswomen

US Sailing President Tom Hubbell, Rolex Yachtswoman of the Year Stephanie Roble, Rolex Yachtsman of the Year Terry Hutchinson and Stewart Wicht, President & CEO of Rolex Watch U.S.A. Rolex/Daniel Forster