A lot of my year is spent with my co-host Nick Kypreos and our producer Sam McKee on Real Kyper and Bourne. We’re on air for 10 hours each week talking hockey, and over the course of that time, you get used to one another’s rhythms.
One of those rhythms from Kyper is the very real and important idea of zooming out and asking the big picture question: OK, but can you win with that guy?
I love that question and the ensuing conversations, but it’s clear the answer is more complicated than most want it to be.
The problem with the question is that it's almost always devoid of context. Some Leafs fans thought you couldn’t win with Phil Kessel, but then he was in Conn Smythe consideration for multiple Stanley Cup wins in Pittsburgh not long after he left Toronto. Nazem Kadri won in a different environment, and Mitch Marner is having success now. But it goes beyond just those guys, and the point isn’t only about the Leafs. (I will continue to use them as our example, however.)

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At one point on our show the question was skeptically asked “But can you win with Nicolas Roy as your third line centre?” The guy had just done it a few years ago in Vegas, so the answer was obviously yes. Yet it wasn’t happening this past season, so if you wanted to be cynical, you could answer “no” and be right about it.
Maybe you’ll look at his playoff contributions in Colorado this season and conclude he's “not good enough,” and that’s fine. But under different circumstances, versus different opponents, with different linemates, we know there was a different outcome. This applies all over.
If you accept the premise that under the right circumstances you can win with Roy as your third-line centre -- which you should, given that it’s self-evident -- you're armed enough to push back on the very idea that there’s a “right” way to build a Cup contender.
This is why the thought the NHL is a copycat league has offended me so much for so long. What worked last year may have been because of a team’s style, but it may have also worked because "rock beats scissors", and a rock-style team happened to draw three scissors-style opponents prior to the Cup Final. That same team could’ve been smothered by a paper-style team, but there’s a lot of luck in NHL playoff draw, isn’t there?
Vegas looked like a major disappointment all year and kept tripping on their own shoelaces in the league’s softest division, yet they limped their way into the playoffs.
But they also happen to have some experienced playoff performers, and drew happy-to-be-there Utah, and the young "this-has-already-been-a-successful-season" Anaheim Ducks in the first two rounds. By the time Vegas faced a badly-injured Colorado team they had some mojo going, and now they’re off to the final.
So what would you copy about these Golden Knights to replicate their playoff results? Maybe you’d have prime-aged elite superstars and should unload your assets to trade for a Jack Eichel, or a Marner, or a Mark Stone?
But then again, the Carolina Hurricanes are a win from the Cup Final too, and they don’t have a single forward you’d put in the league’s top-30 players. They’re built with depth and hustle and forechecking and the concept of “team.” And while Vegas is a “get hot at the right time” team, the Canes have been good since the puck dropped on the season, so that’s a bit of a fallacy too.
Additionally, there’s still time for Frederik Andersen to turn into a pumpkin, but he’s currently sporting a .928 save percentage in the post-season and wouldn’t be the first goalie with question marks around his name to have success in the playoffs. Adin Hill, who was deemed not good enough to start in the playoffs this year just won a Cup in 2023. Darcy Kuemper won it the year before, and he’s hardly some lock for the Hall of Fame.
It’s almost like there’s no one way, no right way to do it. It’s almost like trying to be a “copycat” team is a fool’s errand that leaves you like the Toronto Maple Leafs, who chased the shape of the Florida Panthers by getting bigger and older and slower, but against a young and talented team (which the Leafs once were) it’s tough to tell if they’re in the same league.
To bring it back to the original point, when we look at players and say “can you win with this guy,” it almost always depends on the greater build, the team, the system, the coaching, and everything that surrounds them.
All you can do as a general manager when building a team is to treat it like the NHL Draft, and get the best players available at whatever position they may play, until you’re so close to being Cup ready that you have one clear need. Maybe you’re a right-shot defenceman away, or a goalie, or a centre. But until you’re in that class of teams with very few needs -- which there are maybe three to five of in total -- everyone else should just be worrying about getting the best individual hockey players they can instead of focusing too much on how they fit.
Compile talent, keep talent, and work with what you’ve got. Lean into your strengths, and pray for luck.
It was a weird year in the NHL, with no clear super-power team save for the Avs, whose best players all got injured at the exact wrong time. That’s part of what makes winning the Stanley Cup such an impressive feat (and even more so to repeat). You need to build a team that's good enough to beat a variety of opponents, in a variety of ways, because you can’t plan on drawing anyone in particular. Beyond having very good players in the important positions, and a few loose guidelines we’d all agree upon, there’s no defined road to how a team should become great.
From there, you just have to cross your fingers and hope it’s a year you get a favourable draw, some injury luck, and a hot goalie.
You have to get yourself in among the group of teams that can take advantage of the rare year everything breaks right, and hang on in that pocket as long as possible.
Don’t chase how others do things, and eventually, others will be chasing you.






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