The first time Simon Whitfield participated in a triathlon, he ran, rode his bike and swam in a pair of boxer shorts with cows on them.
It was in Ontario in 1986 when Whitfield participated in the Kids of Steel Triathlon at a lake just north of Kingston. Whitfield was the type of kid that needed to be outside. When he was young, he would make up adventure games with his friends, play soccer and run races.
That's when his parents decided it was time for the 11-year-old to compete in his first triathlon.
“I don't think I did particularly well, apparently boxer shorts with cows on them aren't fast,” he joked. “I liked the festival atmosphere that comes with the triathlon. My parents instilled my sister and I with a real appreciation that the applause was given for the effort that was put in, and my sister and I were captivated by that.”
After that, he was hooked on the sport. By the age of 15, Whitfield was pursuing triathlons on a competitive level and moved to Victoria in 1997 under the advice of three-time Ironman Hawaii champion Peter Reid, whom he raced with in Ontario, to further pursue training.
Years of hard work and dedication to the sport paid off when Whitfield made his first appearance at the 2000 Summer Olympics in Sydney, Australia, and captured gold in the triathlon. But he didn't stop there.
Whitfield also claimed gold during the 2002 Commonwealth Games in England and went on to win seven World Cups and 20 national titles. While participating in his third consecutive games during the 2008 Summer Olympics in Bejing, he captured a silver medal as well — earning him the title of the most decorated triathlete in Canadian history.
He also competed in the 2012 London Games, but crashed out on his bike.
Looking back over his roughly 12-year-long career, Whitfield's proudest accomplishment came in his final year of competition, during the 2012 London Summer Olympics, when he was selected to represent Canada as the flag bearer during the opening ceremonies.
“When you're named flag bearer, you think it's about representing the athletes. But when you get there, you realize you're representing Canadians and it was a huge moment for me,” said the now 41-year-old Victoria resident.
“It was more about we as Canadians. When you win an individual race like that, you're representing your country, but you're also representing yourself.”
But his career hasn't been without its ups and downs. Whitfield said achieving Canadian fame, at times, made him feel like a bit of a novelty, noting being a part of the public domain is “not all it's cracked up to be.”
Since his retirement in 2013, Whitfield has kept busy, running a guide company that takes people to explore Victoria on a paddle board, and coaching his three kids' sports teams.
Whitfield is one of nine athletes who will be inducted into the Greater Victoria Sports Hall of Fame this week, a recognition he said was an absolute thrill.
“(Being inducted in the hall of fame) is more about the community that you're a part of and saying thank you,” Whitfield said.
“It's important for kids a generation from now to be able to look back and recognize that people who were young once too, went off and aspired to be athletes and represented this country and I'm proud to be a part of that heritage."
Simon Keith (soccer), Bob Moffatt (builder), Gerald Kazanowski (basketball), Kent Manderville (ice hockey), Nancy Mollenhauer (field hockey), Mike Spracklen (rowing coach), Randy Bennett (swimming coach who passed away), and John and Marilyn Bate (builders) will also be inducted into the hall of fame during a sold-out ceremony at the Westin Bear Mountain on Saturday, Oct. 29.