Tom Slingsby sits for the Archibald ahead of Sydney chapter of SailGP

When Tom Slingsby and Bruno Jean Grasswill met this week, it was the coming together of two supposedly separate worlds: sport and art.

But in a city home to the Archibald and SailGP, it makes perfect sense that Slingsby, a world champion skipper and Olympic gold medallist, might be asked to pose for the country’s top portraiture prize.

2015 People’s Choice winner Bruno Jean Grasswill is painting champion sailor Tom Slingsby for this year’s Archibald Prize.Credit: Dominic Lorrimer

“It’s simple,” Grasswill says of why he wanted to paint Slingsby. “Tom is the best sailor in the world. He’s a modern-day Ginger Meggs.”

The 39-year-old redhead, sometimes called the bad boy of sailing, will take to Sydney Harbour this weekend to lead Team Australia through its home SailGP race, chasing their first win of the series.

This is season four of the Formula One-style event, featuring the world’s 10 best sailing teams, of which Slingsby’s remains the one to beat. They have won the competition every year since its 2019 inception (2020 was skipped due to COVID-19) and remain atop this year’s leaderboard.

With its high-performance catamarans and fast action, the GP has changed the sport of sailing, Slingsby says. “Every year, we get bigger. The first time we came to Sydney, we had to convince Destination NSW and Maritime that we were deserving of shutting down the harbour over the weekend. Now they realise and see its potential.”

Tom Slingsby with fans at a 2021 SailGP event.Credit: Bob Martin

Slingsby says it is a huge honour to be selected by Grasswill for his Archibald entry. In 2015, the painter took the Packing Room Prize and the People’s Choice award for his portrait of actor Michael Caton. Grasswill has elected to paint the sailor full size, from head to toe.

“It’s something new for me,” Slingsby says. “I’ve had a lot of pictures taken, but no paintings.”

Slingsby’s sailing honours are near endless. He was named male World Sailor of the Year in 2010, a gold medallist at the London Olympics in 2012, won the America’s Cup as strategist for Oracle Team USA the following year, skippered Perpetual LOYAL to victory in the 2016 Sydney to Hobart, and has been crowned Australian Male Sailor of the Year five times.

This time last year, the Sydneysider married former Bachelor contestant Helena Sauzier in a ceremony that, naturally, took place on Sydney Harbour on a luxury yacht, just days after his home SailGP race.

Slingsby is also renowned for his ambition and his sometimes fiery mood. “It’s known as ‘red mist’ on board when I start losing my temper – but my passion is what gets us to the top,” he told Ocean magazine in 2022.

But he has been an excellent portrait subject so far, Grasswill says, and can even abide the Ginger Meggs comparison. “I’ll take it,” says Slingsby. “Gingers are usually the last to be painted.”