Within seconds of getting onto his bike, the 37-year-old crashed spectacularly in a freak accident Tuesday at the London Games and couldn't continue.
Whitfield watched Britain's Alistair Brownlee win gold from the medical tent while he received stitches in his toe and treatment for other assorted hurts.
The Olympic champion of 2000 and silver medallist of 2008 may have been a medal longshot in London, but he'd invested heavily in one last go at the podium.
Whitfield's chin dropped to his chest while speaking of the time away from wife Jennie and their two young daughters Pippa Katherine and Evelyn.
When he met with his family under the grandstand, he said five-year-old Pippa Katherine had a bouquet of maple leaves for him.
"My breakdown moment was seeing my wife because I know how much Jennie puts into this and we're a team and she's put in so much sacrifice being at home a lot alone," Whitfield said.
"It was hard to see my daughter upset, my wife upset and I was pretty upset. That means it means something doesn't it?"
Only one other triathlete in the field — Hunter Kemper of the U.S. — has competed in all four Olympic triathlons to date.
Brownlee was so dominant that he walked the last few steps draped in the British flag before breaking the tape.
Announcers said prior to the race they expected 200,000 people to line the scenic Hyde Park course and spectators were 50 deep in some areas.
Spaniard Javier Gomez earned silver and Brownlee's young brother Jonathan took bronze. It wasn't a banner day for the Canadian team. Kyle Jones of Oakville, Ont., was disappointed in his 25th-place finish. Victoria's Brent McMahon was 27th.
Whitfield came out of the 1.5-kilometre swim in the Serpentine in 15th. He was in contact with the lead group and left the transition area 31 seconds off the lead. Whitfield hadn't even got his bare feet into his shoes when he lost control of his bike coming off a speed bump.
His bike wheels skidding sideways, the front wheel of competitor Leonardo Chacun made contact with the back of Whitfield's bike. The Costa Rican was dashed against the pavement while Whitfield careened towards the metal crowd barrier to his left.
When Whitfield's bike wheels connected with the struts supporting the barrier, he too went down with his bike cartwheeling in front of him.
"I hit the speed bump just as I went to put my shoe on, I think," Whitfield said. "I'm not quite sure what happened. I hit the speed bump on a funny angle and ended up crowd surfing, which is good for concerts and not so good for sport events.
"My bike went out from underneath me. I have some pretty serious gashes. My big toe is stitched up. Both knees have seen better days. My shins have seen better days. I've got a good goose egg on my head."
Whitfield was digging deep for that trademark sense of humour to deal with his disappointing result. While he conceded Alistair Brownlee is currently in a class by himself, Whitfield wanted the chance to show the work he's done with coach Jon Brown and see where it put him in the field.
"Bitterly, bitterly disappointing," said Brown, a former Olympic marathoner for Britain. "He was in a position we wanted him to be in and then to be taken out (because) of something kind of stupid really, it was just a bad accident. He just got caught out by something small."
Whitfield grew up in Kingston, Ont., but lives in Victoria. He is one of the top figures in triathlon, having won gold at the Sydney Games in 2000 and silver in Beijing four years ago. He was 11th in Athens in 2004.
Whitfield bore the Maple Leaf as Canada's flag-bearer into the opening ceremony in London.
"I've had two incredible races at Olympics, I've had a pretty good race and I've had now that race," Whitfield said. "Stupid speed bump.
"It's racing. If it was easy, everybody would do it."
As for his future, Whitfield wasn't thinking beyond making up a time deficit with his wife and daughters and cheering on Canada's canoe and kayak team.
"As I said all along, if I had shiny object or not I was going to be at the park tomorrow after I cheer on Adam van Koeverden as he chases down medal No. 4," he said.
Whitfield has long touted Jones as his heir apparent, but Canada's No. 2 came out of the water in 46th.
"The swim was just brutal," the 27-year-old said. "I probably had my worst swim of the year and maybe in the last couple of years. Today wasn't reflective of where I'm at. I should have been in the mix today. Today, I had a rough swim and it took me out of the game."
McMahon gave a glimpse of how punishing and dog-eat-dog the swim is.
"It's desperation out there and guys want to move forward and they do that by grabbing you and pulling you under," he explained. "I saw a little bit of a gap and I went to jump into that front group.
"Just as I did so, someone grabbed me and under I went. That happens and sometimes you can shoot that gap and get on. Simon and I were right beside each other and he got to that gap."
After 16 years of racing for Canada, two Olympic medals and multiple World Cup titles, Whitfield has considerable clout in Canada's high-performance sport community.
He'd wielded that influence over the weekend when he called out the coach and support team of teammate Paula Findlay, who finished last in the women's triathlon. He accused them of mismanaging her training and an injury that had lingered for a year.
Whitfield routinely talks about other Canadian athletes competing at the Olympics and the relationships he's built with them. He's been an effective advocate for the Canadian team here and is a possible candidate for chef de mission in the future if he's interested.
It's difficult for an athlete in the moment of competition to put a career in perspective, but Whitfield has always been a big-picture thinker.
"I don't know that I ever dreamed of four Olympics, two medals and flag-bearer," he said. "I'm absolutely blown away by the whole thing."