Nick Kypreos Q&A: Trade scoops, Leafs chances & his career highlights

I figured my first company iPhone deserved a special case. Something protective but also fun. Something that spoke to my personality. I landed on rubber covering that made my refurbished iPhone 4 look like a 1980s cassette tape. Probably not the most professional choice for a new job, but hey.

As a newcomer to Sportsnet in the early 2010s, I’d been invited to sit in on weekly Hockey Central meetings. Mostly I’d sit quietly in a boardroom dominated by the booming voices of Nick Kypreos and Doug MacLean, occasionally offering up ways for the website and TV to work together on a developing story.

Truth was, I felt like a journalism nerd in a space dominated by supersized personalities and impressive NHL resumes.

The meeting where Kypreos spotted what he thought was an actual cassette tape beside my notebook broke the ice. He ripped into a series of chirps straight out of a dressing room, asking where my boom box was and did my car come with an 8-track player too. Delivered in good fun, of course.

They say you don’t tease people you don’t like.

I doubt Kyper thought twice about it at the time, as he laughed and reminisced about his own cassettes of years past, but it was an inclusionary act. And the guy has always been team-first.

Kypreos and Sportsnet parted ways a year ago, but he didn’t stop working long.

He linked up with a betting site and launched his own hockey podcast. He has backed Little Buddha Co., a new organic cocktail brand run by wife Ann-Marie and family friend Kim Taylor, and watched cans fly off the shelves.

“It’s exciting to watch it grow,” Kypreos says, “and watch my wife thrive in what’s historically been a male-dominated industry.”

He also penned his first book, Undrafted: Hockey, Family, and What It Takes to Be a Pro, a page-turning autobiography with Perry Lefko.

I called Kypreos from my iPhone (new era, new case) this week to chat about life after Sportsnet, some inspiring moments in his career, and his predictions for the all-Canadian North Division.

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This interview has been edited for length and clarity.

SPORTSNET.CA: Let’s start by addressing the elephant in the room. Why are you not quarantining in Florida with Doug MacLean right now? You guys should be on the Auston Matthews–Freddie Andersen program, playing basketball in the swimming pool.

NICK KYPREOS: [Laughs.] Pandemic aside, you can only take so much Doug, right? I didn’t want to overstep my dosage. All kidding aside, it’s always nice to know that you have a good friend there. If you want to get together and talk hockey, he’d be on the top of my list. The beauty of it is, we don’t have to be physically together — that’s the new world of digital. And we’re able to get together on occasion on my show, Real Kyper at Noon, which has been a blast.

I happened to be with a bunch of other hockey reporters that morning in August 2019 when you tweeted that you were leaving Sportsnet after 21 years. We were all shocked. In your book, you write: “If you don’t feel inspired by what you do anymore, it’s time to move on.” Those first few days after leaving the network, how did you process the change and decide what to do next?

It’s a common theme in my book. You’re gonna have these challenges where it feels a little bit empty, a little bit lonely. But you have to have faith in your abilities to create. I took it upon myself as a challenge, no different than I did when I played minor hockey, junior hockey, or in the American Hockey League. You gotta stick with the process of believing in yourself. Nothing really happens overnight, but there’s a building to it. And although I’m a little older and more experienced and have more financial security, you still have those feelings of, OK, now I’ve got the juices flowing to reinvent myself again. That’s the way I went about it: OK, here’s my next challenge. I had a great challenge in hockey, I had a great challenge in broadcasting, and now I have a great challenge again, at 53 years of age.

Were job offers sent your way immediately? At the time, people wondered if you’d end up doing analysis for NBC or another outlet.

The great part is, you still have many great friends and many great contacts, and those follow you no matter where you work. So, I had a wide range of conversations from the broadcasting world to getting involved in teams. I got offers to go into agencies. There were also outside-of-hockey business conversations. But the one thing, Luke, I wanted to do more than anything else is just take a deep breath. Since the age of seven, I had a hockey season to get ready for, as a minor leaguer, as a pro, or as a broadcaster. This was the first time since I was seven that I would have no hockey season to prep for. I wanted to know what that felt like. I wanted to know how I would respond to it. Knowing so many hockey players, I know there’s a struggle for many of them once they retire. I was fortunate because Sportsnet came along right away [in 1998] and didn’t give me time to miss playing, because I was so in the here and now and trying to build something with Sportsnet. But I’d never experienced that lull, and I wanted to know how I’d respond to it. I was lucky. Much like when Sportsnet came along, I was lucky that a book deal came along. And I was lucky that my wife and family friends collectively came up with the idea to launch a cocktail beverage. So those things, in many ways, were my Sportsnet in 2000. So far, so good. Don’t get me wrong: I could still end up curled up, sucking my thumb on the bathroom floor, but it hasn’t happened yet.

I love the image of your Sportsnet career starting with you wearing flip-flops to a job interview with then-president Scott Moore. How did you land a job in that outfit?

It could’ve got me thrown out the door a minute later. Or it could’ve worked in my favour, for Scott to think, “Hey, there’s something different about this guy. Let me find out more.” Thank goodness it was the latter. He stuck with the process of learning more about me. I would hope it would be the commitment and the work ethic of getting into the broadcasting world that he’ll remember most. Not the flip-flops.

It’s one thing for hockey writers who never made the NHL to criticize a player’s game. It must have been another thing for you, analyzing your peers. How do you ride that line of giving credible analysis but not ticking off people you know personally?

It’s really hard. I didn’t go in blind. Scott Moore and many others at the time warned me about that. You’re just gonna have to find a way to manage through it. But it was hard. One of the best examples I have in the book is when Tie Domi called me during a hockey game and gave me crap on what I was saying about Wade Belak.

What did you say about Belak?

I said he was taking bad penalties — and he can’t be doing that playing in his role. I know better than anybody that if you take a couple bad penalties when you’re on the fourth line, you’ll soon be on the fifth line. Tie, true to every fibre in his body, he’s going to defend his teammate. This wasn’t on the ice; this was on TV, that’s all. So in between periods, he caught what I was saying on TV, and he called my cellphone right away: “Start saying nice things about Wade Belak, or else you’ll have to deal with me.” [Laughs.]

Did that influence you?

One thing you learn real quick in a hockey dressing room is that if you take it once, you’ll take it all year. I did not want to disrespect what Tie was saying, but I said, “Listen, I’d be happy to discuss my comments with you. I don’t think right now, with you preparing for the third period, is really a good time.” I didn’t rip Wade. I wasn’t harsh on him. I didn’t say it with venom. I just said it objectively. But, you know, Tie didn’t take it that way. And that’s fine. But I was in no situation to back down.

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Trade deadline day is this high-anticipation, high-energy day at the studio. Does one stick out as your most competitive?

Around 2007 or 2008, I went on a tear where I broke a dozen trades in one show. They’re just coming at me fast and furious. You just don’t know how the day’s gonna go. You don’t know how certain people are going to respond. But for whatever reason, I had a lot of people in my corner that day in breaking trades, and that day really established that whole Sportsnet versus TSN. I loved being a part of that rivalry. Of course, we were the underdogs coming in. TSN had started 15 years earlier. So, we had everything to prove and nothing to lose, because a lot of people said we wouldn’t have lasted five years in the industry. They said Canada’s not big enough to support two sports stations. And look at us today in 2020.

Diehard fans are fascinated by the role of the insider. How often do you get scoops as a result of your own digging versus sources reaching out and handing you info on a platter?

It starts with trust. Understand that this is very sensitive information. A lot of people within a hockey club don’t like that information getting out until they’re ready to release that information. So, while you can say you’re digging, you’re digging, you’re digging, you can only dig so much and then you hit bottom. It’s gonna take someone to call you back or trust that the information they’re going to give you isn’t going to come back to haunt them. That’s a really touchy subject. Sometimes you put livelihoods on the line here, which is not a great feeling. It’s not a very glamorous job to call people up and say, “Hey, tell me something you’re not supposed to tell me.” It comes down to having good relationships and a trust that you’re not going to burn people.

Gimme a trade you broke that felt like scoring a playoff goal.

I had a lot of those feelings in the early 2000s. Eric Lindros to New York in 2001 was a big one, for sure. That same year, I had Dave Manson being traded from the Leafs to Dallas for Jyrki Lumme. I spent the whole day telling Sportsnet that for the six o’clock show. We’re actually broadcasting the Leafs game that night — and Dave Manson’s taking warm up. People are saying, “If the Leafs are trading him, why is he on the ice?!” At this point, I’m like, “Guys, I’m telling ya! I really believe it. I’ve gotten it from a couple of good places that he’s been traded.” I found out later the Leafs and [then assistant GM] Bill Watters put Manson on the ice to throw off the scent. Because I broke the trade way too early. The trade was announced after the game, and that was a wow moment. That was probably my biggest-man-on-Earth feel I had in 21 years at Sportsnet.

Were you second-guessing yourself as Manson is taking line rushes?

I wasn’t second-guessing my information. My second-guessing was: Was the trade called off? Did someone cancel? Did they go back and say, “No, I’m not doing the deal anymore”? And then I would’ve probably had to explain that the deal was done but it got cancelled. Would I have looked bad? You gotta understand, trades get broken all the time on deadline day, but it’s pending the trade call. If, in fact, the trade call goes sour, that doesn’t mean your information was wrong. It just means it didn’t get to the final stage.

We’re familiar with your playing career, but the story of childhood and your family is eye-opening. Your grandfather, Nicholas Kypreos, died in a farm field from heart failure — in your father’s arms in Sparta. Your dad, George, is only 15 at the time, and he’s in this field, trying to save his own father by pressing on his chest for two hours until the villagers finally make him stop. Did your dad tell you that story directly?

Yeah. My grandfather was long gone when I was born, but having that story told to me on a couple occasions… That story, I know for sure brought me closer to my dad and his experiences of survival in Greece and survival in those early years in Canada. What he had to endure to get to a place to even put me on the ice for the first time so I could start dreaming big, that was never lost on me. The one thing that’s been consistent from generation to generation is all hockey kids have this tremendous bond with their families and their parents and the sacrifices they made to get them to a place where they could one day fulfill their dream of playing in the NHL. When I say family, it’s also extended family — the aunts, the uncles, the cousins. It takes a village, man, to get somebody to the NHL. But it started with my dad and my mom.

Your coworkers at Sportsnet describe you as this incredible teammate, like a captain or glue guy. Reading the early chapters of the book, I sense this comes from your dad and the Greek community.

One hundred per cent. My dad being in the restaurant business, every night it’s like you’re inviting your friends to your house for dinner. You just want them to have a great time. My dad’s the type of guy that he’s not feeling great until everybody’s feeling great. And I understand, especially winning a championship in New York, those glue guys are important. They’re the ones that ultimately enable you to win a championship. Unlike a star pitcher carrying the momentum of a baseball game, even your Brian Leetches and Mark Messiers can only play 20-25 minutes a night. There’s a lot of minutes for other people to fill. I felt the same way at Sportsnet. I wanted to create a team feel, have great morale, great spirit to come in and feel every day that we can be as good or better than TSN. That’s a great competitive feeling. Ultimately, the fans and viewers are the winners because bars continue to be raised with that competition.

Mark Messier. You tell this cool anecdote from ’94 where you ask Messier why he never wore any of his Cup rings from his Oilers wins.

It reiterated that the things we can control are the here and now. And it’s OK to dream. It’s OK to have a wish list. But you don’t get to the dream or the wish without taking care of the here and now. Mark was really methodical in that process. Not to be disrespectful to Edmonton Oilers fans, but he couldn’t give a [expletive] about his five Stanley Cups in Edmonton when we were in New York. It was just about the next one. Kevin Lowe was the same way. They all have their proper place. They’ll look upon all those championships probably equally, but the only one that matters is the next one. And that’s why I’ve been able to, in the year 2020, focus on the here and now. I feel great about my playing career and my broadcasting career. That’s great. But I have to start working on the process all over again. So, get to work.

Whom were you most starstruck by in New York City during those glory days and nights, where you’re out on the town and running into celebrities?

The New York acting scene, whether it’s Robert De Niro or you’re at the China Club seeing Mel Gibson in his Lethal Weapon heyday. It’s all in the eye of the beholder. I’ve been in restaurants with Mark Messier and De Niro, and Mark’s getting a ton more respect because the crowd happens to be more sports fans than movie fans.

There was a time as a teenager when you were taking your talent in hockey for granted. Ironically, it was trying out for the Grade 9 basketball team that ramped up your work ethic.

[Laughs.] The game of basketball saved my hockey career! I try to tell my kids that it really comes down to how badly you want something. That’s the greatest factor in trying to succeed in anything you do. If you can answer that question honestly, you’ll have a much greater chance of knowing whether you’re going to succeed. Because I was so insecure about my abilities in basketball, it just drove my work ethic tenfold. I could never do it in the game of hockey, but I could do it very quickly in the game of basketball. And then I just asked myself the same question: Why can’t you do it in hockey?

Any tales left out of the book that you wished you’d included afterwards?

Here we are months after the book is published, and you’re like, “Maybe I should’ve told the story of the time I cohosted a Sportsnet golf event with John Daly, and he ended up taking the limo to Niagara Falls for a day and a half with the Baldwin brothers.” Stuff like that. I’m not sure if there would’ve been any point other than it was a funny story.

Wait. Are you with John Daly in this party limo?

No. John and a small group decided to just take the limo on their own. [Laughs.] I think he wrote a new country western song on the bottom of a pizza box as well.

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Let’s switch gears. With the Maple Leafs, your former team and the team I cover most, Kyle Dubas has been preaching urgency over the break, finding a greater level of compete. Can heightened competitiveness be learned, or is it in some guys’ DNA more than others?

It can be learned, for sure. I asked you a while ago: How badly do you want it? I think we’re going to see a maturity out of Auston Matthews and Mitch Marner. It’s a natural progression for these kids to take their game to the next level, even physically. Forget the mental part of it. Physically, these guys will be stronger than they’ve been their whole life. They’re still developing, that’s how young they are. So, there is another level for sure. They are bona fide superstars in our game. That’s where you hope the Wayne Simmonds and Joe Thorntons can have a lasting effect on them. How much they can contribute on the ice remains to be seen. There’s a lot of people who think Wayne Simmonds is too young to believe his best days are completely behind him. And then Joe is going to be the most important guy to bring it all together and give these guys a confidence and a little bit of a strut. I mean, they have a strut when it comes to putting the puck in the net, but they lack strut in other aspects of their game.

You don’t add Joe Thornton unless you view yourself as a contender. Can this team go all the way, even though they haven’t won a single round?

No. They haven’t proven to me, from last year to these changes, that this is going to be enough to win a Stanley Cup. If we’re talking about true grit and finding ways to battle through adversity, we saw Tampa Bay do it. Tampa Bay can beat you playing a lot of different ways, including playing a heavy game. Look at the past champions, whether it’s Washington or St. Louis — heavy games. The Leafs aren’t a heavy team from top to bottom, and that’s still something that needs to be addressed. But can they get better from last year? Can they win a round or two, especially in a Canadian Division? The answer is absolutely yes. Could they get to a final four out of the Canadian division? Yes, this is their best chance. There is no Boston or Tampa to worry about now.

Who are your top three in the Canadian Division?

Toronto, Calgary and Winnipeg. I got Winnipeg as a dark horse. Edmonton, they’ve got two of the best in McDavid and Draisaitl, but they’re thin on the outside. Montreal is better, but game-breakers they don’t have. Ottawa is not ready. And Vancouver will be in a bit of a transition in the aftershock of losing Jacob Markstrom.

Having played alongside Hall of Famers, can you imagine what McDavid must be thinking, having only won one round in his career so far?

There’s got to be a level of frustration out of him. But, you know, he signed an eight-year contract and became the highest-paid player. Edmonton made that commitment to him, so it’s up to him to have that commitment back. To say, “I’m with you. We’re in this together.” I expect Ken Holland to continue to build around him. Ultimately, it is around him and Draisaitl. So, Ken Holland’s gotta continue to get to work.

Do you have another book in you?

Yeah, I like the process. Simon & Schuster were awesome. Perry Lefko was awesome. My wife also edited the book, to make sure my voice was heard, which was awesome. It was a great experience for all of us. I’d certainly look into that.

Interesting that your wife helped edit, because your sense of humour comes through on the page. Some hockey biographies are dry, but the reader can sense your personality in here.

I laugh at myself as much as anybody. That’s not hard for me. I wanted people to get that sense from the book. I put in the story where I accidentally tweeted, “Those [expletive] at TSN [try to discredit me all the time]” during the 2011 trade deadline. I was in a full panic. And it was my wife who just said, “Make a joke about it on your next tweet, that you passed the phone over to Charlie Sheen and look what happened.” That Sheen tweet had a really good response, to take the air out of the balloon. I’ve been lucky over the years that my wife has kept things on an even keel for me.