A soft-spoken master sailor who exemplified his motto of “sportsmanship before winning” has been hailed as a “backbone“ of the island’s sailing community.

Eugene “Penny” Simmons, inducted into the Bermuda Sports Hall of Fame in 2009, came with a formidable record of success on the water, spanning decades.

He advocated for sailing to be adopted as Bermuda’s national sport.

One of the island’s elder statesmen of sailing, Mr Simmons’s highlights included competing in the 1964, 1968, 1972 and 1976 Olympics, and finishing third in the 1967 Pan American Games competing in the Snipe class dinghies in Winnipeg, Canada.

Mr Simmons also won the International One Design World Championship six times between 1985 and 2005.

Raised in Spanish Point, Mr Simmons started out on the water in the home-made boats of a close-knit neighbourhood that he recalled as “like a community of probably about six to eight families” in a 2013 interview with the Bermuda Sun.

“It was like one big family and everyone looked after everybody else,” he said.

“We made little flat-bottom punts and used to sail them in the bay out there and things just went on from there.”

Mr Simmons began racing as a youngster from the Spanish Point Boat Club, joining the Snipe class of dinghies.

He said: “We didn’t have any coaches back then and so you learnt by watching others sail. It was a trial and error thing, quite honestly.”

Jim Amos, who represented Bermuda at the 1972 Olympic Games in Munich with Mr Simmons, said his friend was “extremely thoughtful and always studied people, listened to people — his nature was one of listening and learning”.

Mr Amos added: “He was a calm stoic and exhibited that in his sailing.

“There is very little conversation in sailing because it is all about concentration — and his powers of concentration were remarkable.”

He described Mr Simmons as unflappable once a race got under way.

“His feeling was we are here for one purpose and that’s to sail the race and make the boat go as fast as we can. You don’t think about anything else.”

Mr Amos said that “races are won on the water, not in the protest room” — and that Mr Simmons preferred not to file a complaint if another boat cut in front, opting to let infractions pass.

“Eventually, he was going to catch you anyway,” he said. “Penny’s competitive spirit was endless. He never gave up and his life was life that.”

Mr Simmons was introduced to sailing by his father, Frank, along with Geoffrey Wilson, a neighbour in Spanish Point.

For his first official race, aged 13, he sailed in the Cup Match Regatta and came first.

Mr Simmons went on to win 20 of 22 national Snipe Championships in the 1950s.

In 1954, he came sixth when he crewed for his cousin, Clifford Simmons, at the Western Hemisphere Snipe Championships.

He was named Bermuda Athlete of the Year in 1956.

In 1958, Mr Simmons was invited by fellow sailor Roddy Williams to join in the Newport to Bermuda Race but decided that “ocean racing wasn’t the type of racing I wanted to do”.

Mr Amos said: “I would judge him to be Bermuda’s most successful sailor, with due respect to Captain Bert Darrell, who is also in the Bermuda Sports Hall of Fame. Penny is certainly in that same category in history.”

Mr Simmons was selected by Kirk Cooper for the 1964 Olympics, where the crew came fifth.

“Halfway through the regatta, we couldn’t believe how well we were doing,” Mr Simmons recalled for his induction into the Sports Hall of Fame.

He crewed for Mr Cooper again in the 1968 Olympics. In 1976, he skippered a 470 dinghy at the Olympics with Larry Lindo as crew.

Mr Simmons brought in the International One Design boat in 1979 with a vessel, Ariel, that he raced ever since. In 1985, aged 46, he won the first IOD World Championship in San Francisco.

That same year, he claimed his second Athlete of the Year award.

Mr Simmons enjoyed sailing with his wife, Sacha, and the couple passed on sailing to their three sons, Scott, Blair and Lars.

The Royal Bermuda Yacht Club announced to its members that the island had lost “one of the backbones” of its sailing community with his passing.

“No matter how well he did, Penny always remained humble on and off the water. A quiet man, who observed everything. You did not want to meet him in the protest room, which was a rare occurrence.”

The club highlighted the “Sportsmanship before Winning” plaque on the Ariel that it said “sums up everything that was Penny Simmons”.

“That is the legacy of E. ”Penny“ Simmons that needs to be remembered — he was all about fair sailing.

“He just happened to be very good at winning races.”

A celebration of his life will be held today at St John's Church in Pembroke at 4pm.

Eugene Scott “Penny” Simmons, a Bermudian sailing legend who competed internationally, was born on November 15, 1938. He died in September 2024, aged 85