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The former Dunedin student took a less than conventional path to America’s Cup glory with Team New Zealand last week.
Two years ago, the 27-year-old was sweeping floors and doing all the little jobs for the Team New Zealand shore crew.
It led him to becoming a grinder on the crew which beat Luna Rossa to retain the America’s Cup on the Hauraki Gulf in Auckland.
Having grown up in Kaikoura, Henry moved to Mount Aspiring College for his final year of school. He had wanted to get more involved in outdoor education and, after doing that in Wanaka, moved to Dunedin to study the subject at Otago Polytechnic.
Three years in Dunedin followed, during two of which he played for the Alhambra-Union colts before the last in the club’s premier team.
The second of those years was his highlight, captaining a colts team which included his brother, and moving from second five-eighth into No8.
They were years he enjoyed and he retains many great memories of playing there.
"It turned out to be the best family club," he said.
"It was 100% the best club for me; we got looked after really well.
"I don’t think we were ever in the top four, we were more in the bottom four.
"We were capable of putting together really good rugby games, but most of the time it was about the family atmosphere and how much we enjoyed each other’s company."
In 2016, he made the left-field decision to join a United Kingdom boat called the Leopard 3, working as a deckhand.
After initially being given a one-month trial, he ended up staying for two years.
It was a busy time though and following that he took a long break, travelling down the Pacific Coast of Central America.
On his return home, he again opportunistically landed an interview to join the shore crew at Team New Zealand.
They took him on and he spent six months working hard, doing all the little jobs such as sweeping floors.
He began tagging on to the group using the grinders in the gym after work, just for a bit of fun.
As it turned out, he was pretty good at it.
A competition began among the shore crew to see who could post the best numbers and that sparked his next step.
"I was hiding behind that for a while, then eventually even some of the sailors were like ‘You should do the things we’re doing’.
"I started doing that and writing my numbers up on the board and after a long period of time enough people noticed and they let me trial for the team."
His brother, Rufus, who has Down syndrome, followed him into the crew and became its "everywhere man" — providing plenty of support for the team.
While it was different grinding on a boat, it was something he enjoyed.
He was still buzzing from the win and while it had not sunk in yet, he said it had been "nuts" to be at the centre of the event.
Henry hoped to continue to the next America’s Cup, possibly spending time in Europe before then to get more experience match racing.