A thousand boats had gathered on Long Island Sound to witness the spectacle, among them a US Navy destroyer. Helicopters buzzed overhead and the Goodyear blimp floated in the sky. It was the afternoon of 26 September 1983.

For more than four hours, two 12-metre class yachts had been fighting a gruelling series of duels as they tacked and manoeuvred through the choppy waters and gusting winds off Newport. At stake was an ornate silver jug that had been in the exclusive possession of the New York Yacht Club for 132 unbroken years. For most of those years, it was an object of indifference to all but a small number of enthusiasts and patricians. But it was a prize coveted by both sailors and millionaires.

Sir Thomas Lipton, the tea mogul, backed three unsuccessful attempts to win it. Before he married Jane Fonda, Ted Turner both owned and skippered a successful defender, Courageous. Nor were Australia’s rich men immune to the lure. In the ’60s, Frank Packer hazarded his hand with Gretel and Gretel II and the Royal Sydney Yacht Squadron took a shot with Dame Pattie, named for the prime minister’s wife. Australian cheque books and seamanship proved no match for the Americans, however, until Alan Bond arrived. Three times he financed attempts at the cup, failing in the effort. But by 1983, one step ahead of his bankers, he had a secret weapon.

Australia II was lighter than a conventional 12-metre and its winged keel gave it exceptional manoeuvrability. It also had another advantage. John Bertrand, the skipper, realised that its revolutionary upside-down design had the potential to psychologically unsettle his opposite number, Liberty’s hyper-competitive Dennis Conner. An air of secrecy and controversy was confected around the boat. When it was unloaded on the dock in Newport, it was hidden behind a shroud and guarded night and day.

By comparison, Liberty was a tub when she was racing downwind. But Dennis Conner was the best sailor in the world. He’d already won the cup twice. He told his crew to put winning it above everything else in their lives.

Things did not start well for Australia II. In the first race, its steering failed. In the second, a pin holding up the mainsail broke. But in the third, it won by the biggest margin of any challenger ever. In a cliffhanger ending to the deciding seventh race, Australia II pipped Liberty by a mere 41 seconds.

Four years later, the Americans won back the cup. No Australian challenge has been mounted since 1995, when One Australia broke apart and sank on television. In 2003, the America’s Cup was won by the Société Nautique de Genève, finally putting landlocked Switzerland on the map.

Shane Maloney and Chris Grosz

Shane Maloney is a writer and the author of the award-winning Murray Whelan series of crime novels. His 'Encounters', illustrated by Chris Grosz, have been published in a collection, Australian Encounters.

Chris Grosz is a book illustrator, painter and political cartoonist. He has illustrated newspapers and magazines such as the Age, the Bulletin and Time.