The Americans had held the Auld Mug from 1851, when the yacht, America, led home the best Britain could muster in a race around the Isle of Wight. Then came the fateful day, 26 September 1983, off Newport Rhode Island, when an upstart Australian, Alan Bond, with an upstart designer, Ben Lexcen, and an upstart little boat, Australia II, upset that bastion of US yachting, the New York Yacht Club.
Bertrand, the man at the helm, was just a spectator for the Australian defence in January 1987. Bond failed to win the job as his yacht was beaten by an equally upstart local businessman, Kevin Parry, and his gold-painted Kookaburra.
It was to wreck Parry financially, while Bond was scheming his way into even greater financial strife. But first Parry was broken in two by the man Bertrand had beaten 4-3, Dennis Conner. The 4-0 annihilation of Australia was almost as painful for the Strines as had been Conner's isolation when he became the first man ever to lose the cup.
Bertrand's absence was the right thing, politically. Why, having made yourself a national hero, should you immediately risk it all on a defence that might, and did, fail? But Bertrand is back, 12 years older at 48, wiser from some rough cut and thrust inthe world of Australian business, and this time managing his own campaign from start to finish.
Not only that, his oneAustralia campaign has consistently been picked out by Conner as the one to be watched most carefully of the seven challengers who, on Saturday, will start battling for the sole right to square up to the Americans in a best-of-nine on 6 May.
Bertrand is an MIT man and, like Bill Koch who successfully defended in 1992, he has put the accent on science and technology to produce what the America's Cup has always been about, a boat with a speed advantage.
"We have brought in people from all around the world and made our benchmark the McLaren motor racing team," said Bertrand yesterday after a day out testing his first new yacht, and then taking delivery of the second and latest 75ft machine, which will not race until February. "We looked at them very closely and then thought about what we would have to do to beat them in Formula One. Then we applied the same approach to the America's Cup."
But more important is the underlying attitude which that explanation conceals. Bertrand is an affable man with a soft exterior. He talks easily and willingly, but this image can be deceptive as he has a very tough seam underneath.
Most people do not reach the top by accident and Bertrand is no accident. He has an ego about which he is not self-conscious; the affability can also be used to good public relations effect. This is his fifth America's Cup, not as many as Conner nor evenhis co-skipper and the upwind helmsman, Rod Davis. But they go back to 1970, four years before Conner made his debut.
Asked whether he still has the hunger, he said: "It's not just hunger. You have to have a passion to get involved in something like this." Part of that passion comes from his wife, Rasa, a forthright mother of two sons, Lucas and Andre, and a 15-year-olddaughter, Sunshine, who is tall, pretty and athletic, altogether the healthy outdoor Australian.
Part comes from a confidence that his perspective on the America's Cup is right: that he understands the preparations are for a marathon, not a sprint, something Conner also emphasises. The team Bertrand will have around him will have a higher average age than in 1983.
"We didn't want to go into the business of teaching people to sail," he says. "We have the experience and this first round-robin is just a preliminary skirmish. Important, because we will see where the others stand, but the Louis Vuitton Cup will heat upas it progresses."
He acknowledges that someone could "come out from left field and produce a solution that is radically different and better in most conditions", but feels it is unlikely. About the beating of the Americans, he has no doubt.
"It's not a question of whether it can be done or not. We did it in 1983. We just want to do it again. We have a great sense of anticipation," are not the words of a man riddled with doubt. And if the media get their wish for a needle re-match with Conner? "That is something I would look forward to very much." On that, at least, both men are agreed.