Could have been when he stomped up onto the medal podium late Friday night and let out one of those full-body roars that may have been heard down the mountain in the village.
But, for me, the true impact of his gold-medal win in the Olympic skeleton event started to crystallize the very minute the Russell, Man., product stepped off the gondola into Whistler and then started chugging straight from a pitcher of beer thrust into his mug by a fan.
It was then -- watching this genuine, energetic, infectious, working-class hero wipe the beer from his beard -- when it was impossible not to think about what's next for Montgomery.
And we came to this conclusion:
Dude, you need an agent. And you need one ASAP.
"What? Do you think that if I had already had an agent, then I wouldn't have been allowed to chug that beer?" Montgomery said with a laugh Sunday night before taking in the Canada-United States hockey game. "I don't know what might transpire from here on out, but maybe that's something I should look into.
"If I could handle all that on my own, I'd love to. But then again, I don't know the nuances of the sports-business world. That's something I may have to learn and discover as we go along.
"It's something, believe me, I'll love to embrace and learn."
Funny, isn't it, how .07 of a second -- seven one-hundredths of a tick -- could potentially change a man's life forever.
Now, it's not like had Montgomery finished second to Latvian Martins Dukurs that he would have been disowned by his family, friends or his hometown. No chance. He's too loved, too popular, too connected with folks that if he had finished first or 21st, their bond with him would remain as tight as ever.
But that .07, the teeny-tiny difference between gold and silver, will have a direct impact on his bank account.
First and foremost, Montgomery will earn a $20,000 bonus from the Canadian Olympic Committee for winning gold (silver would have meant $15,000). But it's Montgomery's 100-kilowatt smile, his ability to instantly connect with people that mean his marketability is through the stratosphere. Consider that while one gold may pale in comparison to the five medals Cindy Klassen won in Turin -- which helped land her a $1-million endorsement deal with MTS Allstream -- Montgomery's gift of the gab almost certainly means he should soon be able to parlay his success into some cold, hard cash.
"We were talking about that this morning," said his father, Eldon. "I think he's worked very, very hard and maybe it's time... Look, he didn't work this past summer at all and money's not that plentiful. He has funding and some sponsors, but maybe it's time for a little payback for him.
"We know the time and energy he's put into this. I think his mother gave him a book called Tenacity one year at Christmas when he was just a little kid and read it and read it to him. He HAS been very tenacious. He's earned this."
That's just it with Montgomery: He insists he doesn't believe in destiny, that fate is nothing but hooey. His mantra: You get out of life what you put into it.
After all, he didn't cash in a winning lottery ticket here. This gold, and what it will bring, is the result of hours in the gym and on the track.
The rest -- the way people are drawn to him -- is just pure Jon Montgomery.
"Look, I could have given up easily on this sport in Year 2 when I had my ass handed to me (at a World Cup event) in Lake Placid," he said. "But I didn't believe that was all I could do, and with some perseverance and some tenacity I pushed through, continued to develop and... I am the turtle in the Canadian skeleton program. Bit by bit, year by year I progressed, I developed.
"Some people have become doctors in the amount of time that I spent chasing down this dream, and they're saving lives. And although I'll never do that with skeleton, hopefully with competing with some honour and some dignity I can inspire a few lives."
Now what company wouldn't want a pitchman like that?
VANCOUVER -- The prime minister called. So did Manitoba Premier Greg Selinger. Then came the call from his boyhood idol, a guy who also called Russell home, Theoren Fleury. And, oh yeah, Jon Montgomery's got an Olympic gold medal hanging around his neck.
Does it get any better than this?
"It was definitely pretty cool to hear from (the prime minister)," Montgomery said. "It's been all kinds of friends and family... all kinds of folk.
"It's been goofy crazy, that's for sure. It's been absolutely surreal, but it's all good. It's not anything I think I could grow accustomed to, but I'll plow through with a smile on my face."
Interestingly, Montgomery said that other than the few hours of sleep he's had since winning gold Friday night, he hasn't had a whole lot of time to himself. Not that he's complaining. He plans to soak up as much of the Olympic atmosphere as he can in the final week of the Games while working around his other commitments.
"I'm going to enjoy the hockey game (Canada-USA, Sunday night)." he said. "And then (today) I've got some commitments with sponsors,
"Plus, I'm going to meet Phil Gray, the gentleman who designed my helmet at the Black Tusk Gallery in Whistler on Tuesday. I'd also like to help out with Right to Play.
"After that, I do want to take in some other events, cheer on my Canadian teammates and enjoy as much of this as I can."