How sailing led Olympian John Bertrand to cross paths with the likes of Princess Diana, the Kennedys and Prime Ministers
From hiding in yacht club rafters to dining with Jackie Kennedy, Olympian John Bertrand’s extraordinary path started with six words from his grandmother.
A simple note from his grandmother set legendary America’s Cup winning skipper, businessman, Olympian, motivator, team builder and philanthropist, John Bertrand on a path to an extraordinary life.
Relentlessly curious and a believer in constant improvement, Bertrand, who famously led Australia II to victory in the 1983 America’s Cup, was born in Melbourne in 1946 and grew up in Chelsea with a love of the ocean.
“My mum and dad were renting a house and the first thing I can remember is climbing over the side fence onto the beach at Port Phillip Bay,” he said.
“Half a kilometre down the beach, this is at Chelsea, towards Frankston was the Chelsea Yacht Club and that was our kindergarten.
“We used to hide up in the rafters listening to the old guys tell jokes around the big 44-gallon drum with their VBs, and dreaming about getting out on one of those yachts.”
In 1959 American evangelist Billy Graham came to Australia and 100,000 filled the MCG to hear him speak.
“My grandma and brother went there,” Bertrand said.
“She used to write me notes as a result of that presentation and one of them was ‘Johnny, anything is possible, anything is possible’.”
Bertrand took that to heart and throughout his life has proven his grandmother correct.
Now 78, Bertrand is preparing to step down as the Chair of the Sport Australia Hall of Fame after 20 years in the role.
It is an incredible stint given the prestigous organisation marks its 40th anniversary this year.
“It’s a huge honour to be involved with such incredible people,” Bertrand said.
“Very rarely do you have an opportunity to be involved in this type of institution that is the best of the best. It is the legends of sport in this country all under one umbrella.
“It is unique globally. There is nothing else like it in the world where one Hall of Fame represents all the sports of one country. In the US, you have the NFL Hall of Fame and the NBA and so on, but nothing that encapsulates everything.
“It is an amazing organisation and it has been a real privilege. Twenty years has gone real fast.
“My plan is to retire at the next AGM (annual general meeting), which is September (2026).
“That is the plan and it is a matter of having the right people involved and we are working on this.”
Bertrand is a passionate believer in the power of sport and the importance of the Sport Australia Hall Of Fame and its impact and influence on the wider community.
The Hall of Fame was established in 1985 to preserve and celebrate the history of Australian sport and to excite the next generation of young Australians to achieve their potential both in sport and in life.
“We (Australians) pride ourselves on sport being an important part of the building blocks of this country and you’ve got the greatest sports people, men and women, that have ever been, inducted in his hall. It is a wonderful situation,” he said.
“It’s really the opportunity for young people looking at these people and what they have achieved to say, ‘maybe I can do that’.
“It is not necessarily about winning Olympic medals, but just to dream bigger.”
The Sport Australia Hall of Fame will this year introduce a new award, ‘Celebrating Sport’s Unsung Heroes’, which highlights grassroots sport and people creating opportunities and bringing communities together.
“It is the heart and soul of this country,” Bertrand said.
“I see that type of project as being of national importance to the country, particularly when, as in many countries around the world, community cohesion in many cases is under attack.
“Social cohesion via the power of sport is a wonderful opportunity, and it’s true and it’s real. We are wanting to celebrate that.”
While handy at footy, sailing was always Bertrand’s first and greatest sporting love.
Around the age of seven he started sailing and by 15 he was getting serious about competing.
And he dared to dream big.
Bertrand had his first America’s Cup experience in 1970 as part of the crew on Sir Frank Packer’s yacht, Gretel II, which was skippered by James Hardy.
“I was the youngest guy to ever sail on an America’s Cup boat,” he said.
At the Munich Olympics in 1972 he competed in the Finn Class.
“I finished fourth, worse than last,” he said.
“It’s called the leather medal. Terrible. Nobody cares except mum and the kids. It’s all about getting on that podium, I can tell you.”
Bertrand was back in the America’s Cup fold in 1974, this time on Alan Bond’s first America’s Cup challenger, Southern Cross.
“I was the assistant designer with Ben (Lexcen). I was in charge of everything from the deck up, all the aerodynamics and the masts. In 1974 we got hammered by the Americans, again.
“I said I’d never go back.
“In 1977 Alan (Bond) went back and got beaten again and I went to the 1976 Olympics in Montreal and won the bronze medal (for Australia in the Finn Class).
“I got on that podium, thank God.
“I concluded, maybe three or four months after that Olympics, that I could have won the gold just as easy as the bronze if I had been mentally tougher.
“That was the start of my road to the whole world of sports psychology, which was way ahead of its time, and which was key for our ‘83 America’s Cup win, looking back at it.”
While Bertrand had vowed never to return to America’s Cup competition a sliding doors moment changed the course of his life.
“It is very interesting, the twists and turns of fate,” he said.
“I won selection in the 1980 Olympic Games for Moscow and the Australian Sailing Federation concluded that they’d boycott, the whole team didn’t go.
“Then Alan Bond rang me up halfway through the America’s Cup in 1980, this is at the same time, and said you’ve got to come to Newport (Rhode Island in America) and be involved in the project, which I did.
“I could have gone to the Olympics and tried to win a gold medal, but the sliding door opened and I went to Newport.
“As it turns out, we got blown out of the water again.”
For Bond’s next crack at the America’s Cup in 1983 he asked Bertrand to be the team leader and skipper of the Australia II project, with the boat, including the famed and mysterious winged keel, designed by Bertrand’s great friend Lexcen.
“In the past I’d been on the crew, in tactical roles, but never actually in charge of the whole program,” he said.
“I thought if we could just get equal equipment, we could get the job done.”
He was right and the world stopped to watch in awe as the raiders from Down Under, with a secret keel and a belief in visualisation, did the impossible by winning the America’s Cup – marking the first time in 132 years that America had been defeated in the iconic sailing competition.
Then Prime Minister Bob Hawke declared, “Any boss who sacks anyone for not turning up today is a bum,” following the historic win.
“You look back and it’s kind of interesting, Australia was going through a tough recession around 1983, as the world was, but in addition, we were going through tough bush fires and floods; the backs were to the wall,” Bertrand said.
“And here we (Australia II) were, with our backs to the wall. We got 3-1 down against the Americans (in the best of seven races) and came back from 3-1 to 3-2 to 3-3 and eventually won that final race.
“Also television coverage (of sport) was coming on stream.
“This is the power of sport and thank goodness that’s part of who we are as a nation.”
Sailing opened endless doors, with Bertrand crossing paths with extraordinary people including Jackie Kennedy.
“It’s been fascinating, all these different characters,” he said.
“The Kennedys, as it turns out, were mad keen America’s Cup followers and dreamers and one of the dreamers was actually President Kennedy, John F. Kennedy.
“His dream as a kid was to defend the America’s Cup. Rasa (Bertrand’s wife) and I, we met the whole Kennedy clan. I stayed with Ted Kennedy over in Washington, we spent time with Jackie on the beach at her house, we had dinner with Jackie in downtown New York.
“When she entered the restaurant, everyone stood up. Royalty had entered.
“Bob Hawke, he was a remarkable individual, talk about ability to seize the moment.”
He and Rasa dined with Prince Charles, now King Charles, and Princess Diana on one of their visits to Australia.
“I said to Diana, ‘What’s freedom to you?’ and she said, ‘Freedom with all the security is to break out at midnight with no guards following me and drive in my sports car by myself’.”
In 2004, Bertrand was invited to skipper a boat for the then Mary Donaldson in a royal match race in Denmark just days before she wed Danish Crown Prince, now King, Frederik.
“Mary was on my boat as tactician. Frederik was the skipper of the other boat, so I asked her, ‘is there any protocol here?’,” he said.
“And she said, ‘yes, it’s to win.’
“We had three races and we won two out of three.”
That night during a dinner at the Danish Palace Bertrand, then Chair of the Alannah & Madeline Foundation, a charity established in Australia to prevent violence against children, asked Mary to be patron of the Foundation.
She agreed and held the role for 19 years before stepping down in 2024.
Bertrand was Chair of the Alannah & Madeline Foundation for 13 years from 2001 – 2014 and was Chair and president of Swimming Australia from 2013 until October 2020, during which the Australian team was completely revitalised.
“I am just as proud of the turnaround with Swimming Australia as I was in skippering Australia II to win the America’s Cup,” he said.
The Sport Australia Hall of Fame has proudly been a constant in his life for two decades.
Currently he is working with companies, building high performance teams in the world of defence.
And a passionate Magpies supporter, he has a small involvement with the Collingwood Football Club.
Bertrand said the key to life was being curious, asking questions and listening.
“One of the key pieces of advice I give when I mentor young people is to walk and talk, to get out of your comfort zone,” he said.
“The walking and talking scenario, particularly when you’re moving from one transition to another or are in a transition stage, is about finding your next passion in life because if you find a passion that really excites you, then anything is possible.
“As my grandmother would say, ‘Johnny, anything is possible’.”
The 2025 Sport Australia Hall of Fame Inductions and Awards Gala will be held at Crown, Melbourne on Monday, November 17.
sahof.org.au
FAST FACT QUESTIONS WITH JOHN BERTRAND
What was your first job?
Washing boats when I was about 12 at my uncle’s marina, which was on Patterson River, for a dollar an hour.
If you had not found your passion in sailing what would you have done?
Football. I got to under 19’s with South Melbourne. Then I had to make the choice between football or the Olympics.
Name five people dead or alive who you would invite to a dinner party.
John F. Kennedy, Bob Hawke, Winston Churchill, Elon Musk, Margaret Thatcher.
What book should everybody read?
Ernest Hemingway’s The Old Man And The Sea. It is about life. It is beautifully written.
If you could live anywhere in the world besides Melbourne, where would that be?
I think London. It is where our two of our grandchildren and our son eldest son live.
What was your first concert?
The one that was most impactful for me was Swan Lake, here in Melbourne.
Who inspires you?
Rasa (his wife).
What advice would you give your 18-year-old self?
Be really, really curious and learn as a result.
What was your first car?
An old FJ Holden where you had to fill it up with oil and check the petrol.
Current car?
A Porsche Boxer.
Dream car?
Probably a McLaren.
What is your biggest career regret?
I don’t have regrets.
What’s the best piece of advice you’ve received?
When I was making the transition from international competition yacht racing to the real world, (it was) to walk and talk; to knock on doors to find out how other people are making a dollar.
This year I’m most looking forward to ….
All the kids are coming out from Europe and around the world. We will have our three kids and seven grandchildren all together. It will be fantastic.
The one thing I’d love to change about Victoria is …
It would appear we’re still going through this incredible lockdown world of Covid. We just have got to get off our ass in so many ways. Working from home is a killer. It lacks interaction with real people. Online, in terms of Zoom, is terrific, it’s great, but nothing like being around people and talking and integrating. We need to have a can do attitude.
What is the one thing you love about Victoria?
The hospitality of people. We’ve lived in London, we’ve lived in the US. If you come to Sydney you entertain people by meeting them at a restaurant, which is great. But when you come to Melbourne, they come to your home for a family dinner. I think that’s beautiful.
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