He's your quintessential Aussie larrikin from Perth — a world-traveling, working-class jack of all trades.
Now he's been elected Mayor of one of America's oldest cities.
Gavin Buckley landed in Maryland's capital Annapolis when he fell in love with his wife in the 1990s.
Last week he toppled the Republican incumbent to be elected Mayor.
"What I love about doing this stuff in America is they never knock you for trying, so it is that kind of country of dreams where you can give a go to anything," he tells me over coffee.
Mr Buckley was born in South Africa for no reason other than the fact his father was a travelling mine explosives expert.
He then grew up in a blue-collar family in the Perth suburb of Belmont.
He describes himself as a Westie, a bogan, a battler, and a mongrel, who had some tough times during childhood.
He lost his dad young and his twin brother died when they were in their teens, but there was a lot of love.
"You never think you grow up tough in Australia. The sky is blue," he says.
"Life's good even if you're sort of poor. Not that I was really poor but definitely working class.
"I didn't long for anything. I was lucky because your parents gave you everything they could, you know."
'He's got a couple of kangaroos loose in the top paddock'
Now a naturalised American, he and his wife own several restaurants in Annapolis, where he ran as a Democrat on a platform of supporting local business and revitalising the town centre.
He was endorsed by the local paper ahead of the election despite some local misgivings about some of his ideas for the town.
A mural painted on the front of one of his restaurants, for example, was judged by some to be out of keeping with the old city.
Opponents also dredged up past immigration and financial indiscretions, and a print mailout used some choice Australian insults.
"They would say, 'Crocodile Dundee, Gavin Buckley, says he's not going to raise taxes and that's a pig's arse' and then they would say, 'He's got a couple of kangaroos loose in the top paddock'," he said.
"They must have gone to some really bad Australian dictionary to find all these terms."
However, he bears no rancour towards his opponent after a decisive victory on a day when Democrats swept state and local elections amid national anti-Trump sentiment.
"I think people in America are sick of politicians. I'm the anti-Trump because our campaign has been about togetherness, bringing people together," he says.
"Donald Trump was about dividing people and scaring people."
On the streets of Annapolis, the new Mayor is stopped repeatedly by well-wishers congratulating him on his victory.
"Being Australian, this must be a matter of great pride," one says.
"This is the American dream, and we are proud of him."