When Jimmy Spithill first came to Auckland as an America's Cup skipper, he was living in a student dormitory, sharing a room with two others.
The team base was on a crane barge and the 'hospitality area' was inside a shipping container. Their boat was seriously antiquated technology – likened to an "aircraft carrier" – and they lost 26 of 30 races.
But it was heady days for the kid from Broken Bay, who was only 19 years old when the campaign began.
It was the beginning of his Cup love affair, and in many ways, Auckland was the making of Spithill.
Two decades later the Australian is back duelling on the Hauraki Gulf, the key figure in the Luna Rossa team as they take on Ineos Team UK in the 2021 Prada Cup final.
The Italians are underdogs – after being swept by the British in the round robin series – but Spithill is no stranger to battling the odds.
"For the most part in a lot of these campaigns there are plenty of guys I find better than me," Spithill tells the Weekend Herald. "And I've got to work super hard to get up there and put in extra hours."
Back in 1999, Spithill was the surprise choice to helm Young Australia in the 2000 America's Cup regatta.
"That experience launched so many campaigns, so many careers…if it wasn't for Syd [Fischer], who knows?" says Spithill.
Fischer is a legendary Australian sailor, with victories in the One Ton Cup, Admiral's Cup, Fastnet Classic and Sydney to Hobart. He has also challenged for the Auld Mug on five occasions – a record shared with English tea baron Sir Thomas Lipton – and was one of the first to recognise Spithill's raw talent.
The two met at an Australian Sailing awards function in the mid-1990s, where Spithill won a youth gong.
"I went up and introduced myself – Syd was a legend – and said, 'I've heard a lot about ocean racing and if there is ever any opportunity, I'll do whatever it takes'," recalls Spithill.
Fischer enquired what plans the youngster had the next day – "nothing" was the swift reply – then told him to come to the dock at 8am.
"I got there at six", laughs Spithill. "My dad dropped me off and told me to keep my mouth shut and my ears open and learn what you can."
As Ragamuffin sailed out of the harbour that morning, Fischer turned to the teenager and said "you're driving".
"I was shocked," said Spithill. "But we got lucky, we won the race and that started a relationship with Syd. If it wasn't for that moment, I probably wouldn't be here now. There are some key moments when you look back and that was a huge one.
"Don't get me wrong – Syd cracked the door open and he makes it tough to walk through it, but nothing worthwhile is meant to come easy anyway."
Spithill has some subsequent success – a win in the Kenwood Cup and third place in the Sydney-Hobart race – but the America's Cup opportunity came out of nowhere.
Fischer had his boat (Sydney 95) from the previous Cup campaign in San Diego and had already paid the US$250,000 entry fee, so took a chance on the teenager.
"The only way to get the entry fee back was to turn up for the first race and he had free shipping," explains Spithill. "So, he told me to get a team together. We had to get Sydney 95 up and running, raise some money, and find the crew. Who else would take a punt on a 19-year-old?"
The Australians arrived late – many teams were already well established - and faced a battle to make their yacht ship shape.
"Not only was it a dinosaur, it was a dog," laughs Spithill. "Sydney 95 came dead last in 1995, so it was already behind. Five years later it was a quantum leap; our boat was twice the width of anyone else…we were on this aircraft carrier."
There was also a twist with their accommodation. Expecting to be staying somewhere in the Viaduct, there were collective groans when Fischer told them about a budget alternative.
"He said some 'Railway campus' and we were like 'what?'" said Spithill. "Rob Brown and I went there, and we thought 'actually this looks great, pretty much brand new'. We asked the lady about the other residents and she said they were all exchange students, 80 per cent female, 20 per cent male.
"You could not wipe the smile off our faces. We landed on our feet. We made lifelong friends and had the time of our lives."
The campaign on the water was a struggle, though early signs of Spithill's tenacity emerged.
"We had some great battles with the Spanish and the Swiss," says Spithill.
"We were good at starting and manoeuvring and we were in it for the first leg with some other teams, but she was no thoroughbred."
But the Ocker underdogs – who used a 50-metre crane barge as their base – became local favourites.
"Kiwis took us on as their team," recalls Spithill. "There were old ladies baking us cakes, people giving us bikes, amazing Kiwi hospitality. It was incredibly hard work – a lot of time we slept on the barge – but some of the best times I can remember."
If that regatta catapulted Spithill onto the world circuit, his first campaign with Luna Rossa in 2007 launched a legend.
Spithill had a fast-growing reputation, winning the world match racing championship in 2005, after finishing runner up two years before. He was part of the One World team in 2003 before being signed to helm Luna Rossa.
The Italians reached the Louis Vuitton Cup semifinals in Valencia, but were rank outsiders against BMW Oracle, who they couldn't beat in the round robin. Thanks mainly to Larry Ellison, the American syndicate had massive financial resources – more than any other team – and were helmed by Kiwi cup veteran Chris Dickson.
"We were lacking boat speed and Oracle were significantly faster, so we knew the only way we were going to have a shot was to go real aggressive, take a lot of risks," recalls Spithill.
A plan was hatched by sailing coach Philippe Presti and executed brilliantly by the crew. Spithill was imperious in the starting duels as he hunted and hounded Dickson, highlighted by an incredible performance in the fifth race, when he drew two pre-start penalties to all but end the contest.
"What an astonishing display, by the man who is the absolute hot shot at the moment," said an enraptured TVNZ commentator, while Italian media christened him 'Pitbull'.
Ellison had seen enough – removing Dickson as helmsman that night – but Spithill finished the job the next day. In the final Team New Zealand was a bridge too far – "they were another level" – but Spithill had made his mark, quickly recruited by Ellison and winning, then defending the Auld Mug for Oracle.
Despite his myriad accomplishments, which include being the youngest helmsman to take the Cup and the remarkable San Francisco comeback in 2013, Spithill isn't one to rest on his laurels.
"I've always had to work hard, because I just haven't had the talent of the other guys, most of the time," says Spithill. "I had to work pretty hard to get up to their level and for the most part a lot of these campaigns there are plenty of guys I find better than me. It's hard to shortcut, the harder you work the luckier you get."
Spithill brings a discernible hard edge to Luna Rossa in 2021. There might be a different persona to the gunslinger we saw in San Francisco and Bermuda, where he was encouraged to play a certain role by his American paymasters, but he remains a ruthless competitor.
Although the Italians emphasise their team approach – skipper Max Sirena told the Herald there are "no rock stars" – Spithill is a focal point.
"Jimmy came in from winning the Cup two times," says veteran Luna Rossa sailor Pierluigi de Felice. "He's the never give up story, the 'we are down now, we are going to come up'. With him, it's 'we want to win and nothing else', that determination that is pretty special."
"He has lots of experience and his mentality to always be cool on the boat, even when things go wrong," added grinder Nicholas Brezzi. "He's a great guy, very chilled. [But] he's like a wolf…. he knows what he wants and he is really going to go for it."
Heading into the Cup racing?
• Give yourself plenty of time and think about catching a ferry, train or bus to watch the Cup.
• Make sure your AT HOP card is in your pocket. It's the best way to ride.
• Don't forget to scan QR codes with the NZ COVID Tracer app when on public transport and entering the America's Cup Village.
• For more ways to enjoy race day, visit at.govt.nz/americascup.
After defending the America's Cup, teammates became SailGP rivals for Andy Maloney.