Stories About Partners Share Your Story Subscribe →
Stories People

A look back at iconic Spithill’s Offshore appearance

By Offshore Online Contributor
June 2026
9 min read

Jimmy Spithill is an icon of sailing the world over, having won more than his fair share of big trophies. Now the owner of SailGP’s Italian franchise and a commentator for the CYCA on Nine’s broadcast of the Rolex Sydney Hobart, Spithill has done a lot since this interview for Offshore’s April/May 2010 edition. But looking back, what a great read….

When he was just seven years old, James Spithill had already mastered a Hobie Turbo 14 catamaran sailing in his backyard of Pittwater, north of Sydney. Twenty-three years later, now aged 30, the guy the Americans call “Jesse James” after the legendary gun slinger of the Old West, has turned his extraordinary sailing ability to steering the giant trimaran USA to victory in the 33rd Challenge Match for the America’s Cup, sailed recently off Valencia, Spain.

Spithill and his BMW Oracle Racing crew combined the incredible boatspeed generated by the tri’s revolutionary 70-metre-high wingsail rig in combination with aggressive match racing tactics to outsail Alinghi 5, the Swiss defender’s equally huge catamaran, in two straight races. Syndicate head Larry Ellison, a Californian software mogul, sailed aboard USA in the second and final race to regain the world’s oldest sporting trophy for the Americans for the first time since 1992, when America3 defeated Il Moro de Venezie off San Francisco.

For syndicate CEO, Russell Coutts, this was his fourth America’s Cup win – twice with his native New Zealand, once at the helm of the Swiss Alinghi team and now masterminding the success of Larry Ellison’s BMW Oracle American team.

In steering USA to victory, James Spithill became the youngest winning skipper in the history of the America’s Cup, as well as joining John Bertrand as the only Australians to helm a yacht to victory in a Cup Match. Bertrand steered the 12-metre class yacht Australia II to beat the US defender Liberty, skippered by Dennis Conner, off Newport, Rhode Island, in 1983. Spithill has regained the Cup for the US.

“When they told me I was the youngest skipper ever to win the America’s Cup, I said, ‘But I’m 30… they must have been pretty old’,” Spithill said in an exclusive interview with this magazine.

He was also the youngest skipper of an America’s Cup challenger when he steered Syd Fischer’s Young Australia in Auckland back in 1999. Somewhat prophetically, Young Australia beat the Swiss yacht in several Louis Vuitton Cup races that year, but did not progress to the America’s Cup regatta itself.

Spithill is literally bubbling over with enthusiasm about his Valencia victory and was eager to tell his story of the 33rd Match to Australians. He began this at his home club, the Royal Prince Alfred Yacht Club – across the waters of Pittwater from his boyhood home in Elvina Bay – with a presentation to members, which was also a fundraiser for the club’s Youth Development Program, of which James was a teenage graduate.

Spithill described the 33rd America’s Cup Match as “awesome … sailing on the edge all the time,” because of the power-to-weight ratio of the trimaran with its revolutionary wing-mast. “It is an amazing and complex boat, with such speed and massive loads, and the remarkable thing is that the first race of the America’s Cup Match was actually the first time we had raced the boat,” he added.

“We won the America’s Cup on the water with a great design, but it was also won by the intensive preparation and ongoing maintenance by the shore team,” he stressed.

“We were on a steep learning curve as the goal posts were moving all the time, and we had to maintain total discipline in our approach to the Challenge. However, once we launched the trimaran we realised the sailing skills required were fundamentally the same.

“Nevertheless, once we went to the bigger rig we realised that a key factor was to get the boat back in one piece from sail training,” he said. “In fact, our sailing time in the big trimaran was limited because of maintenance factor.”

Spithill said that once he knew that the America’s Cup would be raced in multihulls he did some serious sailing in smaller racing catamarans, including contesting, and finishing sixth, in the A class world championships, and also sailing high-performance F18, wing-sail C-class and Extreme 40 catamarans.

Spithill was quick to point out that the Valencia victory was the result of a huge team effort, not just the crew but the designers, engineers, sailmakers and coaches. “New Zealander Russell Coutts, the syndicate CEO, and American tactician John Kosteki were key members of the crew, but also sailing was Australian Joey Newton as a trimmer. Joey and I have been sailing together around the world since the Young Australia challenge,” he said.

“In fact, there were quite a few Aussies involved in the syndicate team,” James said. “In addition to Joey and myself, Ian ‘Fresh’ Byrnes was the design co-ordinator, Craig Phillips was a sailmaker while world champion A class sailor Glenn Ashby, the ‘King of the Cats’ coached me and the crew.”

Early Life and Career

Despite his outstanding career in sailing, notably in match racing, James Spithill remains a modest bloke, giving great credit to those who have helped develop his sailing career over the past 25 years. His first sailing boat was a mini windsurfer he was given as a Christmas present as a five-year-old so he could get on the water with his dad, Arthur Spithill. The proud parents were at Valencia to watch their son’s greatest sailing achievement, winning the America’s Cup.

James’ first race as a skipper was in an old timber Manly Junior at Avalon Sailing Club as a nine-year-old with his six-year-old sister Katie as crew – a race they won, prompting the club’s then hon. secretary Ian Craig to write a letter of congratulations: “A win in your first race must be like scoring a century in your first Test Match…the club can expect great things of you in the future.”

James and Katie would sail across from Elvina Bay to Avalon and, if the racing was cancelled because of strong winds, they would sail back home.

Although a big lad for his age in junior and intermediate classes, James notched up a fifth in the Manly Junior nationals and a third in the Flying Eleven nationals. At Pittwater High, he was among other talented young sailors and the school dominated the Australian schools team racing scene for a number of years.

A significant step forward in James’ sailing career was when he completed the “Alfreds” Youth Development Program (then a six months, every weekend match and fleet racing program) in 1995. The following year he began dominating youth match racing in Australia and New Zealand, twice winning the Cruising Yacht Club of Australia’s youth match racing, the Royal New Zealand Yacht Squadron Coke Cup and the Royal Prince Alfred Yacht Clubs’ Harken Youth International.

“The training and support of the RPAYC was instrumental in raising his skills to the point where he was chosen as NSW Youth Yachtsman of the Year while still at school,” his father recalled. “At the presentation he was introduced to noted ocean racing yachtsman Syd Fischer who invited him to sail on Ragamuffin in a short offshore race the following Saturday.”

The storm-battered 1998 Sydney Hobart Race was a baptism of fire for the 19-year-old, sailing as a helmsman on Ragamuffin which finished fourth across the line and third overall. He was also aboard Ragamuffin in winning the Kenwood Cup in Hawaii.

That led to James’ involvement in Syd Fischer’s Young Australia America’s Cup campaign and, although they only won a few races in Auckland, he was among the big boys of international yacht racing, albeit the youngest skipper in the regatta. Rob Brown was the team coach and he had a big influence on James’ development. At the end, famous French yachtsman Bruno Troublé introduced him to the media as, “This is James Spithill, he will one day win the America’s Cup!” Bruno recalled his prophesy when he and Arthur Spithill met again in Valencia.

Since then he has concentrated on honing his match racing skills, ranking second in the 2002–2003 Swedish Match Tour and winning the Nations’ Cup in 2003, 2004 and 2005. In 2005 he won the World Match Racing Championships, the Melges 24 World Championship and the Bermuda Gold Cup, both fleet racing events.

His next America’s Cup involvement was with fellow Australian Peter Gilmour in the OneWorld syndicate, reaching the semi-final of the Louis Vuitton Cup, where he was beaten by BMW Oracle Racing. Italian Francesco De Angelis, whom he had beaten in the 2003 Louis Vuitton quarter-finals, then chose him as his heir as helmsman of the Luna Rossa Challenge in the 2007 America’s Cup.

Spithill was a mainstay of the Italian team in reaching the finals of the Louis Vuitton Cup 2007 after beating one of the favourites, BMW Oracle Racing, 5–1 in the semi-finals.

James admits that during his time with the Italian syndicate he earned the nickname of “James Pitbull” among Italian fans because of his aggressive tactics in the pre-start manoeuvres of the match races. His more recent, US-based nickname has been “Jesse James”. James laughs at both, but concedes that his reputation as a fearsome competitor is close to the mark.

James says that three yachtsmen in particular have moulded and developed his international match racing career: Australians Syd Fischer and Peter Gilmour and New Zealander Russell Coutts.

“Syd gave me the opportunity to become an America’s Cup helmsman, Peter guided my development as an aggressive and tactical match racing helmsman, and Russell has been a great mentor leading up to and throughout the 2010 America’s Cup campaign. He told me to forget about all the legal arguments and just concentrate on sailing – which we did!”

Of the next America’s Cup, James Spithill is unsure as to where it will be sailed, or in what type of yachts. “Originally, I thought we must get back to some sort of monohull boats, but right now I’m not so sure,” he said.

“Two things are certain – it must be a demanding boat to sail to give it the status of an America’s Cup boat and it must have that ‘wow’ factor to command international interest,” he added.

Of a future Australian challenge, he says: “We have the right people for a challenge: the designers, the engineers, the sail designers and the sailors, but we would need positive and large-scale resources before a challenge is feasible.”

One thing’s for sure, Australia can tick helmsman off the crew sheet.

Originally published in Offshore Yachting, April/May 2010

By Peter Campbell

Featured image: BMW ORACLE/Giles Martin-Raget pic

Offshore Online Contributor

Leave a Comment

Your email address will not be published. Required fields are marked *