The 1899 America’s Cup racing yacht, Columbia, a Nat Herreshoff-designed vessel with a hollow steel spar, crewed by the “Deer Isle boys.” PHOTO COURTESY OF TOM DUYM

From then to now: Deer Isle’s ties to America’s Cup

The Deer Isle boys who made up the Defender crew in 1895.

DEER ISLE — More than 125 years ago, when men were men and fishermen had little use for yacht racing, sailing captains connected to the New York Yacht Club showed up at the Deer Isle Town Hall to recruit sailors for the most famous yachting race ever, the America’s Cup. 

“Who were these guys? Am I related? What’s the big deal about a sailboat race?” Tom Duym, a former marine trades teacher at Deer Ise-Stonington schools who grew up in a family boatyard in Blue Hill, recalled the questions a handful of young Deer Isle teenagers asked him in 2007. 

“The kids didn’t know the America’s Cup,” he said during an Acadia Senior College online talk on March 25. “Almost to a person, they hated sailboats, the reason being they were all lobster fishermen.” 

The students not only discovered that sailors from Deer Isle and Stonington crewed the Nat Herreshoff-designed Defender and the Columbia in the 1895 and 1899 America’s Cup, respectively. They also flew to Valencia, Spain, to watch the 2007 race, after Duym contacted the Oracle/BMW team. 

His students had wanted to compare what the 19th century Deer Isle crew endured compared to being a crew member today, so Duym thought, “What the heck. Why don’t we call them?” 

He shot off an email and three days later heard back. The gist of the reply? “We love your story, we know your Deer Isle boys, they’re a huge part of the America’s Cup. We’d love to host you in Spain, if you can find your way over here.” 

Some fast fundraising and generous local donations later, five students and five teachers flew to attend – and be celebrated by – the America’s Cup race. 

The Deer Isle boys who made up the Columbia crew in 1899.

Duym said he had students keep a few questions in the back of their minds to help learn about the 1890s culture of Deer Isle. 

“Why did the richest men in the country from New York Yacht Club fund these traveling vessels? How did our ancestors get to be the guys who sailed these boats?” Duym posed. “They really started to look into that.” 

Research led them to an age-old truth: It’s all in who you know. 

“It wasn’t just because they were tough, rough and ready, though that was true,” Duym said. “It really boils down to who you know and being in the right place at the right time.” 

Captain Henry Haff, from Montauk, N.Y., was captain of the 1895 Defender. Deer Isle native George Conant was a sailor for hire in yachting circles who had worked for Haff. And Deer Isle captain Fred Weed, who held the world’s trans-Atlantic speed record for a merchant ship, was now ashore running a shipping company out of Stonington. 

Charles Iselin, of the New York Yacht Club, was the fourth player. He sailed up every summer to Northeast Harbor and had “seen these guys in Friendship-style sloops groundfishing,” Duym said. “Basically these four men and their relationship formed the history of the America’s Cup and Deer Isle.” 

However, part of the story also was that the New York Yacht Club had been winning the cup since the 1850s using European crews, Duym said. “There was criticism of hiring professional sailors, especially from Scandinavia … The Europeans, especially the English, were especially critical that these boats were winning but were sailed by European sailors.” 

So the men behind America’s stake in the race took a chance and went with an all-American crew, leaving Haff in charge of finding the men. 

“That could be a daunting task, knowing the coast was full of good sailors,” Duym said. “This is where the connection came in.” 

Tom Duym taught marine trades at Deer Isle schools for 40 years. His students dug into the history of the local sailors who crewed the 1895 and 1899 America’s Cup races.

Conant had a reputation among people with shipping interests, and Duym’s students discovered that Conant and Captain Weed’s properties abutted, something not evident in today’s changed landscape. 

“We believe that Conant convinced Iselin to contact Weed,” Duym said. 

This eventually led to the meeting at Town Hall, where Captain Weed, Haff and Conant supervised interviews of the local sailors and selected the Defender’s America’s Cup crew. Many of those 1895 crew members would return in 1899 to crew the Columbia.  

The Columbia was captained by Scotsman Charlie Barr. According to research, his assessment of his crew? “When given a command from one of the officers, they take it as more of a suggestion than an order,” Duym related. 

In all, over 80 men from Deer Isle sailed as crew on one or both of the Defender and Columbia. 

An interesting postscript to this story is the Retired Skipper’s Race, held every summer in Castine. 

“[It] actually started out as a grudge match between the surviving “Deer Isle Boys” and some of the offshore cod bank sailors,” Duym said. 

The Bucksport captains challenged the Deer Isle boys to race identical sloops down Eggemoggin Reach. “The Deer Isle boys beat them quite handily,” Duym said. And when the Bucksport boat reached the Bucksport harbor, Deer Isle supporters threw clams at them. 

This led to the Clam Hod Award, given each year at the Retired Skipper’s Race to the boat that finishes last. 

And those students of Duym’s, from 2007 until he stopped using the America’s Cup story in his curriculum, now looked at sailboats through a different lens. 

“The only image of sailboats [they’d had] is they drag people’s gear up and cut it up and lose it,” Duym said. “That attitude had definitely changed. They also saw a real connection between these men of 1895 and 1899 and people that are revered as good fishermen, good seamen, in the community today.” 

He added, “If you took the diesel engines out of lobster boats, you’d be looking at the same guys today. The same kind of competitive spirit, working hard, doing your job even if it meant risking your life – those kinds of attributes they really recognized both in the men of those times they researched and in their own families today.” 


Anne Berleant

Anne Berleant

Reporter at The Ellsworth American
News Reporter Anne Berleant covers news and features in Ellsworth, Mariaville, Otis, Amherst, Aurora, Great Pond and Osborn. When not reporting, find her hiking local trails, reading or watching professional tennis. Email her at [email protected]

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