Simon Whitfield is in a good place. It’s a Tuesday night, and the four-time Olympian has finished his weekly soccer outing in Victoria, British Columbia — a men’s league where the competition is a far cry from the rigours of racing against the world’s best triathletes.

“I can’t just run the entire time; I get sore now,” Whitfield jokes. “I’m out there making truces [with the opposing team].”

At the end of the night, he unwinds with a beer at a host’s apartment and reflects on what has led him to this point: a spot in the Canada Sports Hall of Fame, a pair of Olympic medals, a budding rivalry with the Gorge boys of the Vancouver Island Soccer League.

Dearest Mother-

As tired as I am I feel very alive. The Gorge boys pelted us with shots and although Matty held his own and kept us in the game for a time, the barrage was too much and we evenly succumbed to the onslaught. We live to play another day-S p.s. I am now limping — Simon Whitfield (@simonwhitfield) November 22, 2018

Make no mistake: at 43, the Kingston, Ontario native is still an athlete. 19 years after winning the first-ever Olympic gold in the triathlon at the Sydney Games, and seven years after his last hurrah at the London Olympics, Whitfield still swims, still cycles, still runs. Add paddleboarding into the mix, and one gets the impression he could still outperform athletes twenty years his junior. But these days, the drive is different.

For as long as Whitfield has lived, there has been sport. Growing up down the road from Queen’s University, he’d head to nearby Tindall Field, or — more often the case — around the corner to Couper Street for makeshift games of road hockey, where centre ice was marked by a pothole and he and his friends took turns pretending to be Wayne Gretzky.

“It was one block long,” Whitfield jokes. “C-o-p-p-e-r at one end, and C-o-u-p-e-r at the other end. It’s like the French Canadians and English Canadians couldn’t decide.”

At twelve, he competed in his first triathlon, a Kids of Steel event organized at Sharbot Lake. (“I did it in a pair of boxer shorts,” Whitfield recalls.) By the race’s end, he was hooked.

“I just loved the outdoor atmosphere of it,” he says. “It was a festival of sport where you did this thing, this excursion.”

“I was itching to push ahead with this thing I loved to do, and there was no containing me then.” – Simon Whitfield

Before long, Whitfield was in the pool at 5:15 a.m. on training days. At 16, he moved across the world to attend Knox Grammar School in Australia and continue his training.

“I was itching to push ahead with this thing I loved to do, and there was no containing me then,” he says.

A year after his arrival in Wahroonga, on the northern fringes of Sydney, Whitfield learned that Australia would be hosting the 2000 Summer Olympics, and the triathlon would make its debut as an Olympic sport. The stars had begun to align. Flash forward to 2000, and the triathlon would begin and end at the Sydney Opera House, the very same place he had once graduated from boarding school. Was there any doubt of what would happen?

“It was magic. A fairytale,” says Whitfield.

At 25 years old, he won the race and became a Canadian hero. When the Games ended, he carried the country’s flag into the closing ceremonies.

“I will say, the only thing I wondered at the time was, ‘will I get goosebumps again?’ Because I had this pinnacle experience … like, ‘wow, that just happened.’ And then I wondered, like, ‘how do you recreate all that circumstance?’”

“I had this pinnacle experience … like, ‘wow, that just happened.’ And then I wondered, like, ‘how do you recreate all that circumstance?’” – Simon Whitfield

It would take eight years to reach the Olympic podium again, this time earning a silver medal in Beijing. Finally, he was asked to carry the flag once more, this time at the opening ceremonies in London. After his fourth Olympics, Whitfield retired from competition.

“I just wasn’t willing to make the sacrifices required. Plain as that,” he says. “There was a time in my life when I thrived on sacrifice. Truly. I thought everything I did was based around … was I sacrificing and giving more than other people were, to fortify myself for the next moment I had to compete.”

“I paid for it with relationships,” says Whitfield. “When I look back, in the end, it’s the people.”

Nowadays, the father of two has a different focus: namely, those closest to him. There’s still the love for sport, but the temptation to relive past glory? Not in the slightest.

“I work towards contentment,” he says. “I accept the struggle as part of it. And it’s actually where the good stuff is.”