TORONTO — Asked for his take on the Maple Leafs' recent free-agent shopping spree, Nick Kypreos pauses.
"If I knew they were signing 40-year-olds, I certainly would have tried a comeback a few years ago," joked the 54-year-old Kypreos, referencing the addition of 41-year-old Joe Thornton.
The former Capital, Whaler, Ranger and Leaf winger has not lost his sense of timing. Although after 21 years as a hockey analyst with Sportsnet, he is now forging a new path. Kypreos details both careers in his autobiography "Undrafted. Hockey, Family, and What It Takes to be a Pro," which is released Tuesday.
In looking inward trying to understand why his broadcasting career at Sportsnet had become stale, Kypreos came to a realization.
"I discovered that I liked the climb," he writes. "Tell me I can't do something and it gives me a mark to reach. I like being the underdog. Helping to build something from nothing gave my work more meaning."
These days, Kypreos is attempting new heights with his YouTube podcast "Real Kyper at Noon" and his role as director of hockey operations with i3 Interactive, a Canadian-based online gaming company. His podcast provides it with online hockey content while allowing Kypreos a foot into what he sees as a "one of those trending sectors that is moving towards mainstream."
He and wife Anne-Marie have also helped launched the Little Buddha Cocktail Co.
And like everyone else, they are negotiating the global pandemic with their kids aged 16, 20 and 21.
For Kypreos, the journey usually trumps the destination.
"I've learned enough from my past life lessons that the end result's the furthest thing from my mind. It's all about the process, it's all about the here and now," he said in an interview. "And every day I wake up, I do feel the same challenges I had from minor hockey to junior hockey. From junior hockey to the American (Hockey) League. From the American League to the NHL. And then the same thing all over again in broadcasting.
"Remembering the people that said why you probably can't be successful to the little voice in me that said 'Find a way to be successful.' I've gone through that process now starting at age 53 (when he left his broadcasting job in August 2019) and my juices are flowing again, like they have in the past. Unfortunately my last few years at Sportsnet, that feeling dissipated."
Reading "Undrafted," one can't help but think that Kypreos made the most of his opportunities even if a fight-caused concussion cruelly ended his NHL career. He retired in 1998 at age 32.
Smart enough to see his best route to the pros, Kypreos went from a high-scoring junior (152 goals and 112 assists over his last three seasons with the North Bay Centennials) to a role player who was willing to put his body on the line and fight for his team as needed.
A middleweight willing to take on heavyweights, Kypreos came close to joining a select club of tough guys with 20 goals and 300 penalty minutes in a season in 1992-93 with Hartford only to miss out when injury cut his campaign short (with 17 goals and 325 PIM).
Kypreos won a Stanley Cup with Mark Messier and got to play for his hometown Leafs. He has suffered broken bones and served as the bone-breaker.
"Although I don't regret the way I played, I regret the way some things turned out," he writes.
At first, Kypreos was resistant to the idea of a book. "I said I'm not sure its sellable," he recalled.
But he came round.
The final product is an entertaining read that details how he made the best of his skills in both hockey and broadcasting. And it gives him a chance to pay homage to family and friends who helped make him who is today.
While his book is by no means a tell-all, tyrannical coach Mike Keenan will win few fans among readers. And Kypreos has no issue with dishing on how his producer would call him on air to provide some drama if trades were lagging on deadline day.
But by the end of his time with Sportsnet, Kypreos tired of talking hockey from a desk. He's not sure if he will return to broadcasting, at least in its traditional form.
"Because I don't know really where my old job is heading. At times it looks like a bit of a dinosaur. I don't know what broadcasting sports will look like in five or 10 years. But it could be much different than turning on the TV, especially with Amazon and Apple and Netflix out there.
"Could I reinvest myself somewhere else and consider it a challenge? Yes. Could I go back to the way I did it before, where it felt like a wash, rinse and repeat? God I hope not."
He notes this year was really the first since he was seven years old that he didn't have a hockey season to get ready for, although eventually his podcast drew him back.
"I kind of welcomed that first break to really find out a little bit more about myself away from the game," he said.
As for the recent NHL season in the bubble, he said he liked it better than the alternative -- "and that's watching cable news."
"I truly believe that they made the best out of a very very difficult situation. And I enjoyed it enough to watch it and for a few hours forget that we're going through the toughest phase of our lives."
"Undrafted. Hockey, Family, and What It Takes to be a Pro." Nick Kypreos with Perry Lefko. Simon and Schuster, 278 pages, $34.99.
This report by The Canadian Press was first published Oct. 19, 2020