CBC Sports Oral Histories: The day Simon Whitfield came out of nowhere to make history in Sydney

CBC Sports Oral Histories: The day Simon Whitfield came out of nowhere to make history in Sydney

Behind the scenes of how a little-known Canadian triathlete captured gold in 2000

By Myles Dichter, CBC Sports
September 17, 2020

CBC Sports’ Oral Histories will take you behind the scenes of some of the biggest, most spectacular moments in Canadian sports history and into the minds of the athletes and people involved.

In this instalment, we take you back to the 2000 Sydney Olympic Games, where Canadian triathlete Simon Whitfield surprised everyone by becoming the first-ever men's triathlon Olympic champion.

Canadian Olympic triathletes Simon Whitfield and Sharon Donnelly stretch following Olympic training at Sydney Harbour on Sept. 13, 2000. (Tom Hanson/The Canadian Press) Canadian Olympic triathletes Simon Whitfield and Sharon Donnelly stretch following Olympic training at Sydney Harbour on Sept. 13, 2000. (Tom Hanson/The Canadian Press)

Simon Whitfield answers the phone from his stand-up paddleboard.

Across the water, he can see the United States. The ocean breeze occasionally muffles his voice. Twice, he pauses our interview to tend to visitors at the Paddleshack, a kayak and stand-up paddleboard rental service he runs near Victoria.

It’s been 20 years since Whitfield, now 45, won gold at the first-ever Olympic men’s triathlon at the 2000 Sydney Games. The result surprised almost everyone.

Australians had dominated the sport. It was introduced for their home Games. Both the men’s and women’s races were run on the first weekend in an attempt by organizers to ignite the home crowd.

Whitfield, meanwhile, was a 25-year-old from Kingston, Ont. At 16, Whitfield moved to Sydney to go to Knox Grammar School, the same boarding school his father Geoff, who was born in Australia and whose mother still lived there, had attended years earlier.

By the time the 2000 Olympics rolled around in Sydney, Whitfield had yet to win on the international circuit. He was no one’s favourite going into the race. He was everyone’s favourite after it.

For many, that one accomplishment from two decades ago defines their perception of Whitfield. He also won silver at the 2008 Beijing Games and enjoyed an illustrious career where he was known for his performance at big races.

“It's a funny thing, this thing that happened 20 years ago," he says. "And it's still, how do you walk that fine line of acknowledging it and celebrating it without living in it all the time? And sometimes we struggle with that.”


Whitfield ran his first triathlon when he was 11.

Whitfield: I did a Sharbot Lake trial just north of Kingston. It was just fun. It was adventurous, it was outdoors. It was just a great atmosphere. And that certainly sparked my love of this ridiculous sport called triathlon.

Barrie Shepley, Triathlon Canada coach: I think he might have had Mickey Mouse shorts, like these long shorts, and he did his first-ever triathlon. As an elite coach, even back then, you recognize certain kids move different than other kids.

Whitfield: I moved [to Australia] when I just turned 16 and I lived there ‘til I was 21. I went to [Knox Grammar School] for two years and then lived on my own for three and started racing on the international triathlon circuit when I got down there.

Greg Bennett, Australian Olympic triathlete (2004, 2008): I was still pretty rubbish but I'm starting to make a mark and went up from Sydney, there's a little town called Port Macquarie about four miles north and I did the race. I actually won the race and I met Simon I think just sitting around for the [medal] presentation. He didn't really know anybody and I think we -- when I say we I mean my parents and I -- we invited him to come stay a bit. And that relationship really grew from there and it was a little bit more like he was my younger brother and he's always felt like that to me.

Shepley: He got hardened in Australia. He lived on his own for two years. It's time to make a decision. He's got a dual passport. The Olympics have just been declared for Sydney. Like seven kilometres from his grammar house is where the Olympics are going to be in five years. He could be competing for Australia.

Whitfield: It's funny, I went to Australia and loving all things Aussie. You know you grow up with the [Aussie] dad, you think the grass is greener on the other side. But you get down there and I get to a boarding house where, frankly, what they considered multicultural is not what I consider multicultural. There were some things about Aus right away that I thought, ‘Wait a minute. I'm Canadian. I don't roll like this.’ And that happened quickly. I went there thinking, ‘Aussie, Aussie, Aussie.’ I came back thinking, ‘Ah there you go. Proud to be Canadian.’


Left off the Australian Olympic team, Bennett moves to Canada at the invitation of Whitfield.

Lance Watson, coach: Greg was just a huge catalyst for Simon as well because Simon, he sort of had that athleticism and that prowess and Greg was like your classic, put on your hardhat and go to work every day kind of athlete, just brought grit and determination and consistency day in and day out.

Bennett: About three weeks out [from the Olympics], we did a run workout where it was two loops and it must've been about an 8-kilometre run and he ran away from me for the first time. And my ego was hurt. I was meant to be one of the top in the biz, and here he is beating me. And I've watched his swim progress and I've watched his strength come across in the bike. But I knew at that point if it came down to a run race, if that bike came together, that no one would beat him in a sprint.

Whitfield: I think we thought, ‘OK, we can be in top-10 shape,’ and I kind of secretly thought, ‘Nah, magic happens, I'm going to make this happen.’ But we know, top 10 -- people would have just thought that was the greatest result ever.

The Olympic Games open in Sydney on Sept. 15. The men’s triathlon is scheduled two days later.

Watson: Being the first Olympics for triathlon there was a real silver lining to that because while there was a lot of hope and expectation, it was kind of a new environment as well.

Whitfield: Ignorance is bliss. I had no right to think I was going to win, but I've seen in my mind's eye over and over again and I just was like I've already watched this movie and I'm going to play the movie that I've already seen and that's how it played out.

Terry Leibel, CBC Olympics broadcaster: Simon was on our radar right from the get-go because triathlon was making its Olympic debut. And it happened very early in the Olympic Games in Sydney. So it was like, we were super excited about the introduction of the sport to the Olympic menu and it happened during my broadcast.

Canadian Simon Whitfield, left, battles for position with Sweden's Joachim Willen during the men's triathlon in Sydney, Australia on Sunday, Sept. 17, 2000. (Laura Rauch/The Associated Press) Canadian Simon Whitfield, left, battles for position with Sweden's Joachim Willen during the men's triathlon in Sydney, Australia on Sunday, Sept. 17, 2000. (Laura Rauch/The Associated Press)

Whitfield: We didn't march in the opening ceremonies because [our event was] so close to it, but I did march with the field hockey players. We tied a Canadian flag to a field hockey stick and wandered around the village doing our own little march. And again, you know like the world No.1 at the time, Simon Lessing, was sitting in his room stewing over all the pressure he was under and I was out there marching around the village with a flag.

Shepley: A month out I asked for our uniforms from Speedo -- no uniforms. Three weeks out? No uniforms. Two weeks out? We're leaving, we'll send it to you in Australia. Four days out, three days out, two days out, the night before I finally get the women's bathing suits and their names are spelled wrong on their suit. I'm like 'Oh my God, you can't go in front of two billion people and your grandma watching at home with your last name spelled wrong.'

Shepley: If you look at any of the women's bathing suits at the Sydney Olympic Games they’re these tattered, black, crap suits that we wore at the Pan Am Games 12 months before.

On Sept. 16, the women’s triathlon was the first medal event in Sydney. Canada’s Carol Montgomery is the favourite but she crashes and breaks her arm in the cycling leg. The men’s race is the next day.

Shepley: Everything that I had been dreaming about for six-to-10 years was on the most opposite side of the scale you could ever imagine. Tears, broken arms, no finishes. Disaster.

Whitfield: I had the advantage of seeing what Carol was going through and much like a younger sibling gets to see you know all the trips and stumbles that the older sibling does, I kind of had that advantage.

Shepley: It's now like eight o'clock at night, I'm rolling back into our room. I had to take the train back to the village and I finally [got] Simon's bathing suit.

Whitfield: Barrie's got a great story about how I insisted on wearing it. My version of the story was there was no other option and so I put on this jersey and the one thing we didn't get to do was, we didn't get to try it when it was wet.

Shepley: He's not run a step in it, swam a metre in it, biked a pedal stroke in it. And I'm nervously looking at it because of the spelling mistakes on the women's side. This thing is so tight. But he’s like, ‘Oh, it looks cool.’

Whitfield: I remember getting to the start line and saying to [contender] Hamish Carter like, ‘Hey man, I hope the surfs don't eat us’ and he says, 'Get away from me.’

Shepley: I'm looking at Lessing who is the five-time world champion, the favourite to win this race. He looked green. He looks like he would rather be any place in the world than what's going to happen in the next 90 minutes. He just looked terrified and not fun. And I remember how vivid that was in my brain of the difference of this kid who felt no pressure.

Canada's Simon Whitfield, right, currently second place to an unseen runner, leads Simon Lessing of Great Britain in the run leg in the men's Olympic triathlon across from the Sydney Opera House, Sunday, Sept. 17, 2000. (Rick Rycroft/The Associated Press) Canada's Simon Whitfield, right, currently second place to an unseen runner, leads Simon Lessing of Great Britain in the run leg in the men's Olympic triathlon across from the Sydney Opera House, Sunday, Sept. 17, 2000. (Rick Rycroft/The Associated Press)

Whitfield: I grew up here. I [have] swum in this harbour. I graduated from the steps. My grandmother's on the other side... like this is just, this is just gonna happen. And that's what happened.

Leibel: I would say the Australians were favoured, followed by some of the Europeans, the Americans. There were other participants and Olympians that we thought stood a better chance than Simon Whitfield, but our excitement level wasn't specifically to the Canadians. It was to be the inaugural appearance of this sport.

Whitfield: My boarding school mates all showed up [with their] faces painted half green and gold and half red and white. I graduated from high school from the steps of the Opera House.

Bennett: I watched it with Lance and Barrie and the team up on the Opera House stairs. Four or five rows back you could see the big screen TV and I remember watching the race. There was a little bit of a sinking feeling. It was tough for me to watch -- I'm not going to lie, I wanted to be out there.

Whitfield: The gun goes off and everything clicks into ‘into-it’ mode. You're so intuitive, you're into it and you're no longer thinking about outcomes you're no longer thinking. You're just simply performing.

Shepley: So the race starts. Simon has a terrible swim. Thirty-third-, 34th-, 35th-place swim, terrible. And already he's out of it at this point.

Watson: He would have, I would say, not a great swim, and he was back, and if you're behind to start the bike it's actually pretty hard to catch up.

Whitfield: I think I had a decent swim.

Shepley: A spectacularly talented cyclist from Australia had an equally inept swim, Miles Stewart, and he and Simon start to rockstar with a couple other guys on the bike. And by the last lap, they pull up right to the leaders and I'm like 'Oh my God, this guy can run and now he's with like there's 20 of them in that lead pack.'

Whitfield: I had ridden with these guys before and they always thought of me being a weaker cyclist and yet there I was just like leading our group through and doing my turns and this is having two effects. They're thinking like, ‘Wait a minute, where'd he come from?’ And I'm thinking like 'Ha, I just arrived. I'm meant to be here.'

Shepley: They've got six kilometres to go on the bike and then it's the run and that's his forte. And I look up at the big screen, the announcer says there's been a crash.


Whitfield gets caught up in a crash involving 14 other riders towards the end of the bike. But despite the delay, he manages to catch up to the leaders.

Whitfield: I turned that moment to something I was able to ride back up to the main group and then go like, ‘Man I'm quick. I'm ready for this.’

Shepley: Maybe it's over just like the day before with the women's crash and it's like I'm literally feeling tears welling. So over a minute later, Simon comes in with about four other guys, their handlebars are all mashed and wheels are all banged up, gets off the bike and he's in 26th place.

Watson: It was in his mental game plan that he had to be at the front of the run. He just took off from transition. I remember he actually ran by one of the Japanese guys and he actually kind of pushed him out of the way and it wasn't like he was being aggressive or whatever, it was just like, 'I have to go there. Excuse me.'

Whitfield: I had athleticism that helped me through hitting the deck. I was able to keep my wits about me and chase back up to the group and caught the group. Everybody was in that cautious stage of not wanting to be the person that took any risks.

Watson: Imagine if you watched a 10,000-metre final on the track and one guy had to start 15 seconds behind everybody. You'd never catch up, right?

Shepley: At this point, I'm not thinking [about a] medal [finish]. So it's a 5km loop, really hard and this kid, because he had lived in Australia for those years, had probably run that Macquarie Loop 25 or 30 times in his life... because it's a cool place around the park by the Opera House and his grandmother lives 3km away. So he knew it intimately. He ran like a wild, crazy man.

Bennett: Once the run got to about halfway and I saw where Simon was I started to get this feeling like, ‘Hang on, if they haven't got rid of this guy they're in trouble.’

Whitfield: I remember catching up to the lead runners and then just thinking like, ‘Holy smokes, I'm in this.’


Shepley: He's essentially run probably his fastest 5km of his life and he's in fourth place and instead of getting excited, I got more nervous because usually after a crash you get a bit of adrenaline for a time and then the scrapes and the pain and the hip and the soreness start kicking in and you fail miserably in the second part of a run.

Watson: I watched him work his way up through the field and then yo-yo back a bit because he had to exert so much to catch up and then when he ran past the grandstand after lap 1, I was smiling and I thought, ‘OK, he's in a good space.’

Bennett: Simon fell off the back and I thought, ‘Ahhh’ but I'm like, ‘You know what, we have trained Macquarie Street, he knows how to run this final kilometre and [Germany’s Stephan] Vuckovic, he was only 20 [or]… 30 meters in front.

Whitfield: Vucko and I were friends, we'd grown up, we'd started our first races together, we'd been friends at the other races, we had a camaraderie and I remember just saying to him like, 'Dude, look at that. We're here. Like we've arrived.’ And then we got back down to battle.

Shepley: He's in fourth, then he's in third, then he's in second and this German kid — who had been the kid [Whitfield] was poking each other early in the morning side-by-side [is first]. Next thing you know, they are coming down Macquarie Street with about 300 metres to go.

Leibel: As I recall there was an image of [Vuckovic] and Whitfield is not in the picture. And then the next thing you know, and remember it's an Australian commentating team for the audience, so I'm listening to the Aussies’ call and all of a sudden I hear Simon Whitfield. Out of the blue his name comes up. Now I'm like, 'Oh my God.’


Bennett: I think I was yelling at Lance, ‘I think he's going to win this. He's gonna do it.' And we're all getting really excited by now. We have tears coming down our faces and everything like it was a very, very emotional moment. And then he came, hit the bottom and then I was like nobody in the world's out running Simon with 200 metres to go. Nobody.

Shepley: Simon, in this incredible acceleration, and he tells a story that he just pictured himself as a nine-year-old kid on a soccer field racing after the ball at the end of the field. It was just pure, little kid, crazy, wild adrenaline and he blows by the German kid. The German kid didn't even put up one ounce of try.

Whitfield: I saw the third-place guy was catching me and I thought, ‘Oh man, bronze would be fine too.’ And then I start looking back and I started realizing fourth was catching me and I was like, ‘Oh s--t, I don't wanna come fourth.’ So I was sprinting away from fourth and all of a sudden I caught Vuckovic and then I just went right by him. The next thing I knew I was standing on top of a podium singing ‘O Canada.’

Simon Whitfield is shown during the medal ceremony at the Sydney Games. (Bongarts/Getty Images)
Simon Whitfield is shown during the medal ceremony at the Sydney Games. (Bongarts/Getty Images)

Bennett: After he wins, he ran over and put the medal around my neck and said, ‘This is yours.’ It was a really special moment that we had that for me still gives me goosebumps. It's almost like a career highlight in my own career.

Watson: There was the moment I almost killed the Olympic champion because he just had finished and of course he was absolutely anaerobic and I yelled at him and he came over to the edge of the grandstand and I picked him up and was hugging him and basically lifting him off the ground and then suddenly he kind of went limp in my arms and like, ‘Whoops, did I just knock the wind out of him?’

Shepley: Even right now I can feel tears. It was, I can't describe, but this surreal, ‘my God, did this thing that we had dreamed just happen?’

Leibel: I'm freaking out now. I have a cell phone and a production assistant and the control room has got us in their ear and they're saying go to number seven. So I'm looking for seven -- it's not the seventh cubicle, it's Australia's Seven Network. They loaned us their camera and their microphone and patched CBC live to their broadcast. That's how we got the interview at the end.

Whitfield: I threw on the yellow banner and I yelled, ‘How's that!’ because I'd always been visualizing that that's what I was gonna do.

Leibel: You'll remember his chest was bare because the uniform didn't fit. And his chest, I mean it was heaving, right. I mean he was literally heaving because he was breathless. And I just, I don't remember the interview, I'd lie if I said I did. I just remember being there at the moment of triumph.


Shepley: So this is like Canada's first medal of the Olympics, spectacular debut of the sport, unbelievable way he did it. And it's live, because of the time of day in Australia versus Canada it's now it's 8 o'clock at night. People are watching this race live on a Saturday in September.

Leibel: He was a superstar. He was the face of the Sydney Olympics. There's no question for Canada.

Whitfield: And then everything changed. You went from anonymity to 15 minutes of fame and all the s—t that comes with it.

Shepley: So now it's like 7:30 at night. He's still in his bathing suit. We go back to the village to drop off his bike. We grab a bit of food and literally walk out with McDonald's from the athletes village and as we're walking out a moment I will never ever, ever forget. Carol Montgomery is walking in, her arm’s in a sling. She's got a cast, should've been the gold medallist the day before. Simon Whitfield is walking out with his gold medal.

Watson: I remember going [to Canada House] with Simon and sort of basking in the glory and celebrating a little bit and then him getting up on stage and singing with Blue Rodeo. I was like, ‘Well that's pretty cool.’ That's one of the perks of winning a gold medal.

Whitfield: I was hanging out with my high school friends with the tickets anywhere they wanted to go. I didn't pay for a drink. It was ridiculous.

Simon Whitfield  celebrates his gold medal victory. (Adam Pretty/Allsport) Simon Whitfield celebrates his gold medal victory. (Adam Pretty/Allsport)

Shepley: I got a phone call. I answer. It's Lance Armstrong. And he's like, ‘Is Simon there? I said he's in the shower. He said, 'Well can you call him? I want to talk to you about having my agent Bill Stapleton be his agent.' So long story short he became Simon's agent 24 hours later. As it turned out, it was a horrifically bad idea because within days he was so busy putting out fires for Lance's theoretical drug problems, which became real.

Whitfield: I had the golden ticket and I was able to go to any event I wanted. The next day I was standing there with Carl Lewis and meeting prime ministers and doing all that stuff. In many ways it was absolutely magical. And then in other ways actually it was absolutely awful. You become a meme. People have all these preconceived notions of you because they've seen snippets of you and then they assign the way you are.

Leibel: He was a quiet young man. I think the limelight, he handled it really well in the midst of it. He handled it graciously and with excitement, had a great smile, had a good twinkle in his eye. I mean he was a very attractive guy to portray and for sponsors to line up for. And he ticked off all the boxes, I thought.

Shepley: And then of all bizarreness he gets selected to carry the flag into the closing ceremony after nobody knew us and Carol was supposed to win.

Whitfield: Maybe you just start to expect that. I don't mean that from an arrogant standpoint, I think you just start to get a little wired like that when things start to be put on your lap, the next thing you know you're like ‘Yeah.’ You become infatuated with your own story because everybody else is infatuated with it.


Bennett: Post Olympics I, to some degree, lost a friend for a few years. Simon became pretty consumed in what that gold medal was to Canadians and I had my own career to get going.

Whitfield: You become a success. You think that all these trappings come with it, you start to love it, you start to think, ‘Oh my God, this is awesome. I make very good money doing it. I get to sit courtside at Raptors games.’ Like who doesn't want that? And then you start to figure out, ‘Oh, I see why people don't want that.’

Leibel: He was a very laid-back guy. Humble. And really a friendly, friendly person and very agreeable.

Whitfield: You bump into someone who’s like, ‘Oh hey, could you –', and you go, 'Oh yeah sure I can take a photo with you' and they go, ‘Oh sorry I meant, can you take this photo of me and my friend?'

Bennett: I think for Simon it really impacted his life massively. I don't think [it was] all positive. I think he described it: 'the opposite of adulation is isolation.' By the end of 2004 he was a groomsman at my wedding and ever since, I love nothing more than when I see my phone flash up and it's Simon calling for a FaceTime.

Whitfield: At the end of the day, it's such a privilege and such a joy to be so preoccupied with something individually and to be a master of it. When you're Olympic champion you're a grand master of whatever that thing that you're doing. And the journey and joy in that is something I feel very fortunate to have been able to do.

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