Rolex Yachtsman and Yachtswomen of the Year

The Rolex Yachtsman of the Year is a sailmaker and the Rolex Yachtswomen of the Year use his sails.

Rolex Yachtsman and Yachtswomen of the Year
Twins Carmen and Emma Cowles, 18, are the second-youngest winners in the Rolex award’s history. Jud Smith, 62, is the oldest.Christine Robin Photography

When Jud Smith was around 10 years old, growing up in Marblehead, Massachusetts, he and his pals would go into Ted Hood’s lofts and play in the sailmaker’s scraps.

“I would climb on those piles of cloth like it was a hayloft,” he says. “I don’t know if they wanted us there, but it was an open shed, and we were playing. It was about as much fun as anybody could have.”

Smith and his friends would use the scraps to make sails for small boats, or for canoes, so they could race. “I remember breaking our neighbor’s sewing machine and everything,” he says with a chuckle.

Fast forward a half-century, and Smith, now of Gloucester, has spent 20 years as a sailmaker with Doyle Sails. He also just earned the title of Rolex Yachtsman of the Year for the second time—becoming the oldest winner ever—following his team’s win at the 2018 J/70 World Championships.

As if to put a fine point on the matter of age, the Rolex Yachtswomen of the Year are Carmen and Emma Cowles, who are 18-year-old twins from Larchmont, New York, and the second-youngest winners ever.

For what it’s worth, none of them are surprised about the others.

“There’s a lot of people my age still doing it,” Smith says. “I was just coaching this weekend. I’d say most of the people steering and driving are around 50 to 60, even into their 70s, and then most of the crews are pretty young.”

The Cowles twins started messing about with sails at the same age Smith did. They were 9 when their mother sent them for lessons at the Larchmont Yacht Club and made them try one regatta a year. By year three, the sailing lessons clicked. The girls missed their middle school graduation so they could compete, and they’re about to miss their high school graduation, as well as defer their first year at Yale University, as they mount a campaign for the Tokyo Olympics in 2020 in the Women’s 470.

“We’re competing against people in their 20s, 30s, 40s,” Carmen says. “It’s their full-time job. It wouldn’t be a true effort if we didn’t focus just on the sailing for now.”

Guess who makes their sails? That’s right: Jud Smith at Doyle Sails, when he’s not out coaching other competitors.

“I want to help people use our product and get the most out of it,” he says. “It’s a good problem to have. If somebody beats me with my own sails, I’m happy for them. It’s a lot of fun.”