The 38-year-old native of Kingston, Ont., said Tuesday that he considers himself "semi-retired,'' and there's just a "10 per cent" chance he'll return to full-time racing.
"I'm leaving the door open simply because I don't want to pull a Brett Favre and say I'm done and then come back," Whitfield said at a Toronto Triathlon Festival news conference. "Maybe I just haven't come to terms with saying 'Fully retired,' so I'm putting semi in front of it to give myself an out.''
Whitfield said although he's currently training at less than 50 per cent, he could still decide to race if he so desired. But where it would normally take him 12 weeks to prepare for a competition, Whitfield said he'd likely need between 16 and 20 weeks to ensure he's able to cover a triathlon's 1.5-kilometre swim, 40-kilometre bike ride and 10-kilometre run at a high level.
Trouble is, that would also mean being away for his wife, Jennie, and their two daughters, Pippa and Evelyn.
"My family is my priority now and spending more time with them," Whitfield said. "I know what it takes to be at that top level and I really didn't like when people downplayed how much it took so now for me to do both is very difficult.
"If I can find a place where I can balance it then I'll do that. Right now I can't so I'm not going to.''
And time is no ally. The longer Whitfield doesn't compete, the harder it will be to close the gap between himself and the younger members of the national squad, headed up by Kyle Jones, 28, of Oakville, Ont.
"I know Kyle has taken his racing to a level now that would be very hard to get back to," Whitfield said. "I think the rest of that team is stepping up so I think they'll close that door pretty quickly if I didn't get back into it very soon.''
Whitfield plans to compete in the Toronto Triathlon Festival on July 21. He took part in the inaugural event last year, which was his final tuneup for the 2012 London Summer Games.
"As of right now I have no races on the calendar other than trying to beat my record from last year," he said. "I will be competing to be in it and not be embarrassed by some young guy.''
Whitfield opened his fourth career Olympic competition as Canada's flag-bearer in London. But he suffered a broken collarbone in a bike crash during the triathlon.
It was a tough way to go out for the 2000 Olympic gold medallist, who also won silver at the 2008 Games in Beijing. But if Whitfield's full-time racing career is over, he's more than at peace with it.
"That's the beauty of it ... I could never have asked for more," he said. "I went to four Olympic Games, I got to carry the flag and, oh, I won two medals.
"It's beyond anything I ever imagined. I mean, I ran around in a Speedo, it's kind of ridiculous when you think about it. But I got to do that for a living, see the world and do something I loved doing. If that's it, that's it.''
Alan Trivett, Triathlon Canada's executive director, said Whitfield will forever be an ambassador for the sport in this country.
"I don't necessarily look for Simon to come back and be on our national team and our Olympic team as necessarily the ultimate goal," he said. "There are other disciplines and other distances that Simon could race on.
"But Simon is bigger than the sport here in Canada and the more exposure he has, the more exposure the sport has so for me it's not necessarily about him coming back. Simon Whitfield is the greatest ambassador we could ever have.''
However, Trivett admits the sport will have a huge hole to fill when Whitfield retires as an active triathlete.
"Obviously, there will be a void because so many kids coming through look at it as, 'If Simon can do it, maybe I can do it too,''' he said. "The longer that goes, the next generation will know less and less about what Simon has done and it's important we capitalize on that legacy over the next few years.''
When Whitfield does step away from racing triathlons, don't expect him to become inactive. The idea of competing in Iroman events — 3.8-kilometre swim, 180-kilometre bike and marathon — has its appeal.
So, too, does playing recreational soccer, which Whitfield does back in Victoria in a league that also features the father of NBA star Steve Nash.
"It (retirement from triathlons) will probably happen on the soccer field when I will blow an Achilles or something," Whitfield said with a chuckle. "But I still want to be able to run around at 68 like Steve Nash's dad and be able to dominate the young guys.''