Nick Kypreos Talks New Book, New Business, and the Ottawa Senators

Stanley Cup Champion and top Sports Analyst Nick Kypreos talks growing up in Ontario, making it to the big leagues, and putting it all on the table in his new book, Undrafted.

Photos: Nick Kypreos for Harry Rosen

Tell us about your childhood in Toronto. Was hockey a big part of your life growing up? Any special memories?

My family is Greek, so hockey wasn’t one of those things that we passed from generation to generation, from grandpa to grandson. My dad came to Canada when he was 17, and he’d never seen the game before. The only ice that he knew was in his drink [laughs]. I watched my dad discover the game almost at the same time as I did. My earliest memories were of him watching the game on our black and white TV. I remember how he marvelled at the grace and speed of the game, and at how big and strong and agile these athletes were. Naturally, I was drawn to that at a very early age.

Did you grow up a Leaf’s fan? Who were some of your favourite players?

My dad was a Leaf’s fan, so that’s where I got it from. I was very young and I don’t remember a lot about David Keon, but my dad always talked very highly of him. He always made it a point to mention how he thought he carried himself with class.

After a successful OHL career, how did it feel to be 18-19 and undrafted? Did you use it as extra motivation?

There’s no question that at the time, I was jealous of the first-rounders. I remember walking into our dressing room in North Bay and hearing of Kevin Hatcher who was a first-round draft choice of the Washington Capitals. He had something like an $80,000 signing bonus. This is in the mid-80s, so that’s a lot of money. I remember thinking “how do I get it in on the action?”. I felt like I was on the outside looking in. The saving grace in all of this was, and still is, that once you step on the ice with a Kevin Hatcher, or anyone else for that matter, and the Zamboni doors close, you’re all equals. At least for the next hour or so. There are no advantages if you’re fighting for a puck: it’s only about how hard you want to fight for it. So that’s how it basically started out for me. I knew that I had a bigger hill to climb, but I was willing to climb it.


Nick Kypreos for Harry Rosen

Tell me about the moment you were given a contract after training camp with Philadelphia. How did it feel?

I was surprised. I didn’t see it coming at all. To think that I went to Philadelphia’s training camp and left with a professional contract… I mean, I was thinking that I was just going for a great experience. Instead, I came home with a contract and a $10,000 signing bonus. I mean, it wasn’t $80,000, but it was $10,000 more than I had. It was an amazing feeling and it completely changed the way I felt about myself. To walk back into my Junior A city of North Bay as the property of the Philadelphia Flyers, was a game-changer.


Though you were a big scorer in the OHL, your role on the ice shifted to more of an enforcer in the NHL. Tell me about how this change took place, how you grew into a more physical role, and what that demanded from you as a player?

It was all me. I don’t think anyone really said “you have to do this or else you won’t make it”. As I say in my book, I was able to form a good friendship with Tim Kerr. Tim made a point to tell me that I was going to have to be patient when I didn’t score right away and that I was going to have to find different ways to contribute. I always enjoyed a little bit of the rough play. I fought in Junior… I didn’t fight often, but when I did, I knew I could handle myself and do fairly well without embarrassing myself or my team. So I always felt that if I wasn’t going to score, then there had to be other ways to help contribute and boost morale for my team. So when it didn’t click in the NHL, it was a little easier of a transition than for other scorers who never really could go to that place that I could go.


Tell me about being part of the 1994 Stanley Cup-winning New York Rangers. What was a highlight of that run for you?

Now you’re putting me on the spot here… why don’t you just ask me who my favourite child is? [laughs] To be honest with you, we had so many great moments, but throwing out the first pitch at the Yankee Stadium, the house that Ruth built, that was a very special day. It’s in great detail in the book.


You later played for the Toronto Maple Leafs. What was it like being able to play for your home team?

It was a fantastic experience, but I entered it cautiously. I grew up in Toronto and I knew the attention, the media, the circus at times, the scrutiny, the fan frustration of no championships since ‘67. The funny thing about it is that I always felt like I could handle anything, even booing or bad press. But what really stuck in my mind was that now my parents, my sisters, my family, my cousins, aunt and uncles, they were going to be right on top of me too. It was going to affect them as well. That’s just part of playing in your hometown, but it was also a tough time for the Toronto Maple Leafs because they came off the success of the Conference Final in the early 90s, and then it started to swing. I didn’t catch the Leafs at a great time, it was at the end of that Doug Gilmour era. He got traded to New Jersey, and a lot of those key guys that were instrumental in that success were either traded or let go.


After the NHL, you went on to have a successful career in broadcasting. Do you remember what you thought of sports reporters before you got into the profession?

I always valued them. I knew they were a conduit for the fans, so I valued them because I knew they played an important part in your image and how you were perceived. I always had a lot of time for all of them, and I always thought I had a good report for every beat reporter in my respective cities. I was proud of the fact that people genuinely thought that hockey players were the most down-to-earth athletes of them all.


You’ve recently released your book Undrafted. What was the writing process like for you? Why was it important for you to write this funny but honest memoir?

It needed to come out in my voice, and I tend not to take myself too seriously [laughs]. I wanted to take people inside the story of someone who wasn’t a first-round draft choice, someone who wasn’t destined to be a superstar, or to be in the Hockey Hall of Fame. This is for the 99 percent of us who had to find a different way to get there.


Did you enjoy the process?

It was meticulous and time-consuming, yes, and I needed every bit of one full year to do that. Perry Lefko did a great job. My wife graduated with a journal-ism degree and does a lot of writing, and she helped me find my voice in the book which I’m forever grateful to her for. There are times when I’d wake up and think “this is a great story” and then a week later I’d say “take it out” [laughs]. So it’s hard, it’s not easy and it’s time-consuming, but coming off of broadcasting after 21 years and finding yourself in new and unfamiliar surroundings, I found working on the book almost therapeutic at times. It’s a great chance to reflect. They say that you won’t appreciate a lot of these things that have happened in your life until your career is over. Then, when your career is over you’re caught thinking about the present or the future and you never really go back. There’s really never a great opportunity to go back and reflect. I think when you put pen to paper about your life and truly reflect, you find in hindsight that some things wouldn’t have happened unless other things had happened, things that at the time looked really bad, but ended up being really good be-cause it led to something else.


Nick Kypreos for Harry Rosen

Doing all of that reflecting and putting so much detail into the book, were you nervous for the release? What did that feel like for you to put it all out there?

It’s kind of surreal to hold a book with your face on the cover and your life on 300 pages. Fifty years of your life. It was a strange but good feeling. It was no different than reflecting on a championship or crossing the finish line in the New York Marathon. I felt a tremendous sense of accomplishment when I held it in my hands for the first time.


If you could go back in time and speak to the 19-year-old Nick, just before he entered the NHL, who was currently undrafted, what would be your one piece of advice to him?

Breath. Take a deep breath, and just truly believe that you’re in it for the long haul. You want to be there standing at the end, which means you’re going to have to be patient, and you’re going to have to get up a lot when you fall.


Looking at this upcoming season, what are your thoughts about the rumoured Canadian division?

I think the Canadian division is going to be fantastic. I wonder if there will be such a demand for it that fans will refuse to go back to the old divisions. All the teams have really improved in many ways. Expectations have never been higher across the country, and I include Ottawa, who I think has spent some money wisely. I’m really looking forward to it. Hopefully everybody can stay healthy and we can put the worst of this pandemic behind us.


Tell us about Little Buddha Cocktail Company.

This idea was formed at a dinner party at our at our friend’s farmhouse in Creemore, and I was talking about needing a different challenge away from hockey. So we started discussing these RTD’s, ready-to-drinks. We discussed which ones that we liked and ones that we didn’t like, that we found too sweet or gave us a headache after having two. We made a wish list, and that wish list came to fruition because of my wife and our business partner Kimberley who handles the day-to-day operations. We’ve built the company in the last 14 months. Our drinks are certified organic, zero sugar, gluten-free, and keto-friendly premium distilled vodka cocktails. We’ve sold close to 25,000 cases in the LCBO and the plan is to go national. We’ve already been able to go to Alberta and Saskatchewan, and we’re hoping by this time next year we will be across the country. I think what’s even better about it is that it’s run and driven by two amazing women.




Nick Kypreos for Harry Rosen


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