More than two decades after a lowkey start to his America’s Cup career, two-time champion Jimmy Spithill is back in Auckland, New Zealand, hoping to help steer Italy to its first victory in the 170-year-old competition.

Spithill has come a long way since the 1999-2000 regatta, when he was the 19-year-old skipper of Young Australia. The syndicate was so underfunded it sailed an old boat, housed its sailors at a hostel and used a 164-foot crane barge as its base.

“It could do everything. It was called the Hikinui,” Spithill recalled. “Have no idea where it is, but it had a crane on it, had a container, a little bit of a workshop on there. We used to joke it was our hospitality lounge as well, which basically consisted of a couple of those plastic chairs and a cooler and I think some old umbrella someone found. It was quite the base.”

Although the Aussies were eliminated early, Spithill’s precocious talent launched him to a successful career racing some of the fastest boats in America’s Cup history.

Six America’s Cup campaigns and 21 years later, Spithill is now co-helmsman of Luna Rosa Prada Pirelli Team, which is backed by two iconic brands whose logos are plastered on a stylish, black 75-foot boat that rises on foils and speeds across the tops of the waves of the Hauraki Gulf.

Luna Rossa Prada Pirelli Team faces Sir Ben Ainslie’s INEOS Team UK in the best-of-13 Prada Cup final starting Saturday, New Zealand time. The winner of the first all-European challenger final will face defending champion Emirates Team New Zealand in the 36th America’s Cup match.

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“We’re going up against one of the best teams in the world and as an athlete, that’s what you live for,” said Spithill, who makes his permanent home in San Diego with his American wife and two sons. “That’s going to be a really tough series against these guys.”

In the last matchup between the heavyweight crews, there were nine lead changes and the race came down to the last maneuver on the last leg. The British team won to advance to the Prada Cup final. Luna Rossa then swept American Magic 4-0 in the semifinals.

Spithill and Ainslie — the most-decorated sailor in Olympic history — were teammates during Oracle Team USA’s thrilling comeback victory in 2013.

Joey Newton, a trimmer with INEOS Team UK, was on Spithill’s Young Australia crew and sailed with him when Oracle Team USA won the Auld Mug in 2010 and 2013.

Ainslie said he’s had a great relationship with Spithill, whether racing with or against him.

“I think it’s a pretty healthy respect there between us,” Ainslie said. “Whenever we race against each other it really ends up being pretty exciting. I’m looking forward to it.”

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Now 41, Spithill has packed a lot into his America’s Cup career. By his third campaign, with Luna Rossa in 2007, Italian fans and broadcasters smitten with his aggressive tactics gave him the nicknames “Jesse James Spithill” — after the legendary American gunslinger — and “James Pitbull.”

Three years later, at 30, he became the youngest skipper to win the America’s Cup when he helmed Oracle Team USA’s giant trimaran to victory over a Swiss-backed catamaran. In 2013, his confidence on and off the water helped lead one of the most remarkable comebacks in sports. After a ragged start on San Francisco Bay, Oracle Team USA promoted Ainslie from the backup boat to the race crew and eventually won eight straight races to beat Emirates Team New Zealand 9-8 in 72-foot catamarans.

Spithill and Oracle Team USA looked mortal in 2017, when they were routed by Emirates Team New Zealand in 50-foot catamarans in Bermuda.

After tech titan Larry Ellison decided not to continue on in the America’s Cup, Spithill reconnected with Max Sirena, Luna Rossa’s team director and skipper. The two had been teammates with Luna Rossa in 2007 and Sirena was the wing mast manager for Oracle Team USA in 2010.

Spithill was stoked when he learned the boat for this America’s Cup would be a foiling monohull capable of sailing faster than 50 knots (57.5 mph).

“The foiling is just so fun and it’s pushing the limits,” Spithill said. “I knew I wanted to be part of it because it’s such an amazing concept of boat. It seemed like a logical step given the last couple of campaigns.”

Sirena said it was “natural to get him on board. He’s one of the most talented sailors and is used to sailing fast boats.”

Sirena said Spithill is competitive “not just when he’s racing, but in the gym or even when we’re having a technical discussion with the designer. The guy is always pushing the limits.”

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Follow Bernie Wilson on Twitter at http://twitter.com/berniewilson