Skip to main content
weekends with
Open this photo in gallery:

Jon MontgomeryPhoto illustration The Globe and Mail. Source photo Christopher Katsarov/The Canadian Press/The Canadian Press

Has any athlete made more out of a single nonathletic moment than Jon Montgomery? Sure, his victory in skeleton at the 2010 Vancouver Games was thrilling, but Canada won 14 golds that year. It was his impromptu beer walk through the streets of the Whistler Olympic Village, broadcast coast-to-coast in prime time, that catapulted him into celebrity. Trained as an auctioneer, Montgomery still talks for a living, as a paid speaker and host of The Amazing Race Canada. And the skeleton and beer? That’s behind him. Mostly.

Have you made peace with the fact that the first line of your obituary will almost certainly mention beer?

I don’t know that I would have to make peace with that. It’s something that I am eternally proud of. Even though I don’t drink a ton of beer any more – I have realized certain physiological limitations that would prevent me from continuing to imbibe the way that I used to. But I love it. And that beer, presented to me from my beer angel, shapes my immediate life and the foreseeable future.

One thing it gave you was a spot on the paid speaking circuit.

That’s the core business.

What do people usually want you to talk about?

I think the reason why I get invited out to events is for the fluff. I can’t take why I’m being asked out too seriously. I’m not an expert on what these corporate folks do. But I guess the goal that I set for myself is to deliver a series of stories in an authentic way, using humour and self-deprecation as a means by which to connect and to illustrate who I am, how I perceive myself, and in doing so leave them with some sort of a key take-away. Something that might be – and I would be going way overboard to suggest that it is inspirational or motivational – but the overarching key message that I leave audiences with is building confidence, building something that I refer to as self-efficacy. It’s the unwavering belief that I will accomplish that which I seek.


When were you happiest?

I hope it’s today. Trying to achieve that sense of yesteryears – yesterday, what you had – is an exercise in futility. Focusing on what you’ve got now, where you are now, that’s the reality. That’s what I think the goal is, to be happiest in the moment, to find something to be grateful for.

What is your favourite trait of yourself?

Curiosity. I think that it’s a difficult trait to cultivate. I don’t know how one would go about becoming more curious. I know a lot more ways to get healthy, to build muscle, to find positivity in life. I come by that innately, I’ve always asked questions. I’ve been told a lot of times to ‘Shut up with the questions, man’ – maybe not in those words, but that was the general take-away. But I love it, because it keeps me pursuing – not truths but information, and I’ll determine, hopefully through some semblance of the capacity to critically think, what the truths are for me.

What is your least-favourite trait of yourself?

Reaction. Especially my reaction to being maybe embarrassed or feeling less than. I take it personally and I probably move toward the desire for retribution, to perhaps make somebody feel as small as they made me feel through, really, when I was a kid, almost cruelty. I think that is innate with me. Being aware of it definitely helps mitigate it and keep it in check. But I think that’s a really undesirable quality to possess, and something that I contend with.

Do you have a favourite author?

I don’t read books prolifically. I would like to. I have a whole stack of them on the side of my bed. And I just told my wife, I said my goal in 2024 is to read all of these, I’m not buying another one until these ones are complete. But that being said, there’s books that have left impressions on me. One was Jonathan Livingston Seagull.

Oh sure, the Richard Bach story from the seventies.

That’s right. I was given that book by my grandmother, maybe while I was in high school or early years of college and I didn’t read it for maybe close to a decade. And when I did, she had just passed, and this book about trial and error and being authentic and not necessarily following the herd and trying again and again and again was resonant for where I was in my life, doing this tobogganing. And then we were in Italy and we were playing a game of charades and one guy, he was Italian, wrote that down as something to act out, and I wouldn’t have known what the hell that was, but I had just read it, and it was like she was talking to me in that moment.

Who are your heroes in real life?

My father was inextricably intertwined with my athletic career, and using physicality as a means by which to expel energy, to develop confidence. And that paved the way for me to be able to represent my country on the world stage. And what he did in terms of community building, volunteerism and the rhetoric that was preached by my mom and my dad about giving back, about being modest, about working hard. All these things are inextricably intertwined with my perception of myself, what’s important in life and what I want to continue to work on and make unique for my delivery to my children, and how I hope to be able to pass on a lot of those great lessons.

Do you have a favourite possession?

I haven’t held anything so near and dear to my heart that I would be mortally wounded should it disappear from my life.

Is there a talent you wish you had?

Oh, lots. I wish I could dance real well. I think that being a fantastic singer would be incredible. I don’t mind being on stage, but to have an entire stadium full of people that are absolutely connecting with you energetically for what it is that you’re producing with your vocal cords – ahhh, I think that would be tremendous. I wish I was a talented hockey player, because I think playing in the NHL would have been awesome.

Do you have a favourite sport to watch?

I watch hockey. I watch a little bit of skeleton racing, which is odd.

Why is it odd?

Nobody knows what it is.

Is that true?

Well, back in the day, nobody knew what it was. People would think that I was talking about sculling when I would say skeleton. I think there’s a little bit of recognition now with the way that sports have been covered, and especially the Olympics and skeleton’s reintroduction in 2002. But folks don’t tune into it outside of the Olympic cycle.

So even though you’re no longer racing, it’s a pleasure for you to watch?

It is. It helps me connect with a time that was really fulfilling in my life. I was so proud to tell people that I was an athlete. Sitting on a plane, you’re like, ‘I wonder if they’ll ask me what I do, so I can tell them I’m an athlete who does skeleton racing’ – that sort of thing. For a while there, we wondered what we would do in our lives that would replace skeleton racing. And my wife [Darla Deschamps] and I came to the conclusion – she’s a former skeleton athlete as well, she won World Cup medals and represented Canada – that we can’t replace it. It is irreplaceable, and I think if we revere it as such, it’ll maybe have better resonance in our life today than to long for it and to think, What can we do to replace that feeling?

I think we need to be happy with the fact that we had it. And that knowing that we had this sense of fulfilment and pride in what we do, that we can create it through other means, whether it is raising children, developing a business, whatever it is – you don’t have to replace it. And I think to try and do so would be foolhardy.

Follow related authors and topics

Authors and topics you follow will be added to your personal news feed in Following.

Interact with The Globe