Hobart, Australia — It is often a predicament faced by many retired athletes after years of punishing both body and soul in the pursuit of success: becoming too comfortable.

During his debut in the Rolex Sydney Hobart Yacht Race, Australian swimming great Ian Thorpe was reminded of his capacity to dig deep.

“I realized that I can do things when I’m exhausted and tired that I wouldn’t normally think I was capable of,” Thorpe told The Athletic at the docks in the Tasmanian city of Hobart on Sunday.

“I’m kind of moving away from a sporting career, so I need to be reminded of that at times. This is a rough-and-tumble race.”

The five-time Olympic gold medalist twice retired from swimming — first in 2006, and again after failing to qualify for the 2012 Olympics. In this year’s Sydney Hobart Race, the 43-year-old was a member of the crew aboard Christian Beck’s 100-footer LawConnect, which won the John H. Illingworth Cup for line honors — given to the first boat across the line in Hobart — in both 2023 and 2024.

On Sunday, she finished second on line honors behind Master Lock Comanche in a 628-nautical-mile race that on Monday had yet to confirm the winner of the coveted Tattersall Cup, a trophy awarded to the overall race winner based on International Rating Certificate (IRC) corrected time (a mathematical formula that handicaps the bigger, faster boats against the smaller, slower boats).

Like the rest of the LawConnect crew, Thorpe’s drawn but tanned face lit up with a broad smile as they arrived in Hobart after two days at sea in conditions that tested them with wind, gusts, rain, seasickness and both boat and sail damage.

“I’m exhausted. I’m tired. But we had a great crew. I’m just really happy to be here,” were Thorpe’s first words to The Athletic as he stepped off LawConnect.

Asked what he found most challenging, Thorpe said communication.

“The hardest part is not being able to communicate easily with people,” he said. “You’re on a boat together, working in shifts, going up when it’s your allocated time, and making sure everyone’s safe. Being able to share that responsibility and build that bond together — that’s a big part of it.”

LawConnect leads at the start of the annual Sydney to Hobart race on December 26, 2025. (David Gray / AFP via Getty Images)

Beck was impressed by Thorpe, even though he noted that the prevailing conditions until Sunday afternoon had limited the duties Thorpe would normally have been asked to perform.

“In a race like this, especially when it’s predominantly upwind, you’re only using a few crew in that mode,” Beck said. “There’s not a lot of spinnaker work or sail changes like you get downwind. It was hard for any of us to do much more than our core roles.”

For Thorpe, the greater rewards of stepping out of his comfort zone and crewing in one of the world’s toughest ocean races may take time to sink in as fatigue wears off. There will, of course, be memories of a fast race start that saw defending champions LawConnect lead the fleet out through Sydney Heads on exiting Sydney Harbour.

There was also his role alongside Beck in a race tribute to the victims of the Bondi terror attack, when rose petals were released off Bondi Beach shortly after the start.

Sunday afternoon provided equally rich memories, even though LawConnect’s hopes of a third straight line honors victory had long since faded.

As the boat surged downwind under a glorious setting sun, Thorpe was given the honor of steering LawConnect for a spell toward the Hobart docks and a cheering crowd. For Thorpe, those final hours were just the tonic he needed.

“After a race where there wasn’t much opportunity to really enjoy the experience because the weather was so tough most of the time, it was nice to arrive,” he said. “It’s a beautiful day here in Hobart, in Tasmania. It was great to enjoy that part of it.”

For Thorpe, the Sydney Hobart — first raced in 1945 when just nine boats started — represented a major box to tick, one that many Australians place on their bucket list.

“I live in Sydney, so I do a bit of sailing, but I’d never done anything like this before,” he said. “It’s such an iconic race in Australia, and I wanted to be part of it.”

Thorpe made sure he prepared thoroughly. He impressed Beck with his inquisitiveness about the boat and tactics during final preparations in Sydney.

He crewed aboard LawConnect in training and in the SOLAS Big Boat Challenge on Sydney Harbour on Dec. 9, the final lead-up race to the Sydney Hobart Race. Thorpe even attended sailing school to improve skills previously limited to harbor sailing, training at the Pacific Sailing School in Sydney run by Terry Wise, a respected instructor whose former students have included musicians David Bowie and John Denver.

This is far from the first time Thorpe has embraced a challenge with limited experience — and under public scrutiny.

In 2021, he appeared on Season 2 of Celebrity MasterChef Australia, where he was the fourth contestant eliminated. In 2024, he competed on The Amazing Race Australia: Celebrity Edition, alongside childhood friend Christian Miranda. Their race ended in Namibia, where they were eliminated in fifth place, with Thorpe nursing a shin injury.

Thorpe has immersed himself in numerous pursuits, from public speaking and television commentary to authoring two cookbooks — Cook for Your Life (2011) and Eat Well Now (2016) — and advocacy for mental health, LGBTQ+ causes and Indigenous Australians.

It is hard to imagine him ever becoming too comfortable in life. But with his first Sydney Hobart Race behind him, he at least deserves a good night’s sleep.