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From An Olympic Medal To Worlds To America’s Cup, Sailor Caleb Paine Has Big Plans

By Scott McDonald | Aug. 07, 2018, 2:56 p.m. (ET)

Caleb Paine competes in the men's finn at the 2018 Hempel Sailing World Championships on Aug. 2, 2018 in Aarhus, Denmark. 


The view from Caleb Paine’s home is worth a million bucks, yet he affords it on a shoestring budget. Sitting on his 33-foot sailboat docked in San Francisco Bay, the Olympic sailor enjoys views that can take your breath away.

Paine has spent most of his life on the water, from sailing his first boat at age 7 in San Diego to wining a bronze medal at the Olympic Games Rio 2016. Now he hopes to finish among the leaders at the world championships this week in Aarhus, Denmark. After worlds, he has aspirations for the 2020 Tokyo Games, all while training for the 2021 America’s Cup, where he’ll work as a grinder.

“There are three pinnacles in sailboat racing — the Olympics, America’s Cup and the Volvo Ocean Race,” Paine said Monday from Denmark after one of his races. “Any one of those is fantastic, and I’m just honored to be a part of two of them now.”

Paine races in the Finn class — the heavyweight dinghy — and was Team USA’s only sailing medalist in Rio and first since 2008. He only resumed training in December 2017.

During his time away, Paine relaxed and partied it up. When it was time for him to find a job and resume training, Bill Kreysler, a longtime sponsor and donor, had some businesses in the San Francisco Bay Area. So Paine left his native San Diego and traveled up the coast for work. Meanwhile, he bought a boat and joined a yacht club, where he lives and trains still today.

“Rent is so expensive in the Bay Area, and being around the boat industry all my life, I bought a boat and joined the Richmond Yacht Club,” Paine said. “I have a million-dollar view for only $400."

“They let me keep my sailing gear there, and I love it.”

His new training base has mostly been a success, he said, though the 2018 season has at times been as choppy as a tropical storm.

“We had a great Miami (world cup) and did pretty good in European events,” Paine said.

But the world championships have been up and down. Following six rounds of racing and sitting in 27th place, Paine described his performance as “kind of a struggle.”

However, following two races on Tuesday he jumped up to 15th with one remaining until the medal race, for which the top 10 sailors qualify.

“Our goal is to be in the top eight,” he said, "and it’s totally achievable.”

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Over the next two years Paine will dual-train for the 2020 Olympics and the 2021 America’s Cup. Paine said he plans on parlaying his stellar Rio finish and combining it with America’s Cup training to become an all-around better sailor.

“I’m looking forward to having awesome training partners with America’s Cup training,” he said. “The America’s Cup style of racing brings more versatility to an Olympic sailor. The amount of tact and innovation in those environments is awesome, and it trickles down.”

The initial roster of 17 sailors for the New York Yacht Club American Magic team, which competes at the America’s Cup. was released in early July. Paine is one of five grinders for Terry Hutchinson, skipper and executive director of American Magic.

Paine said his trek to become a more well-rounded sailor will start with his fitness.

“There’s also understanding refinement of the game with equipment, and the different pieces of equipment that are introduced,” he said. “Overall we want to create greater boat speed and better understand the courses we’re sailing.”

Paine often uses the word “we” when talking about his one-person competition.

“It takes a village to support an Olympic sailor,” Paine said. “Though it’s one person who’s representing all of the family, friends, sponsors and donors, it’s really a group effort. I couldn’t do it without a great support group. The sailing community really comes together for each other.”

In the short term, though, Paine’s goals are simpler.

After Denmark it’ll be back to the 33-foot Nauticat with a pilothouse, watching the sun set on the entire San Francisco Bay while getting ready for another day of training.

“The boat I live on isn’t fast by any means, but it’s comfortable and I love the lifestyle,” Paine said. “It’s got everything I need.”

Which is fitting, since his life revolves around sailing, and wherever the wind takes him next.

Scott McDonald is a writer from Houston, Texas, who has covered sports for various outlets since 1998. He is a freelance contributor to TeamUSA.org on behalf of Red Line Editorial, Inc.

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Caleb Paine