Predicting Round 1 of the 2021 Stanley Cup Playoffs


Winnipeg Jets goaltender Connor Hellebuyck (37) saves the shot from Edmonton Oilers' Connor McDavid (97) as Jets' Josh Morrissey (44) defends during first period NHL action in Winnipeg on Wednesday, April 28, 2021. (John Woods / CP)

With a dozen or so years behind me now as a member of hockey’s media, I’ve come to grips with something about writing Round 1 prediction articles. You can either go for being as close as possible to correct, which logically seems like it would be the goal. Or you can use your predictions to actually say something, which is far more interesting.

What I mean is, there are favourites in almost every series, and so the safe thing to do with the way hockey goes is to pick them to win in six, and you’re probably going to be either exactly right or off by a game. Then you call the closer series to go seven, and when it’s all said and done, you’re well insulated against being a punchline.

I’m gonna get a little friskier this year. To hell with insulation. Below are the eight series we’ve been handed to start the playoffs with my aggressive picks and rationale.

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As far as I’m concerned, the first round is the absolute PINNACLE of the hockey season. There’s nothing better, not even the Cup Final. I’m excited.

Below is a look at the bracket for Sportsnet’s contest that pays the winner a cool $25,000. You could probably use 25K, yeah? You pick the winners and the number of games (with some tiebreaker questions). You can enter here, we’ll start top left and work our way around.

Toronto Maple Leafs vs. Montreal Canadiens

The Leafs and Habs are playing in and honest-to-goodness, best-of-seven Round 1 Stanley Cup Playoff series, and the stress on both fanbases right now has to have the most diehard fans pretty close to spontaneously combusting.

I’m taking the Leafs in five.

The Leafs could finish the 56-game regular season 20 points ahead of the Canadiens, who head into post-season with a playoff-team worst goal differential of minus-nine. That differential is exactly 50 worse than the Leafs (plus-41), who have one game left on their docket.

Montreal hasn’t been healthy, and it looks like it should be able to field a full team in Game 1. The thing that was supposed to make the Habs so good this year – depth throughout the lineup – will finally be available to them as a strength.

But barring catastrophe tonight, the Leafs will have their full complement of players available to them as well, and a healthy Toronto offence is a force to be reckoned with. I think the games will be close given Montreal’s playing style and newfound health, but in tight games, give me the team with the game-breakers. There’s not much doubt which team here has more of those.

Edmonton Oilers vs. Winnipeg Jets

If you toggle to the “last 10” games on’s standings, you’ll note the Jets are 2-8-0, while the Oilers are 8-2-0. The Oilers have two of the five best players in the world (including the best in Connor McDavid), and even in hockey, the best tend to find ways to pull their team through.

With that, I hate, hate, hate betting against McDavid here, but I’m taking the Jets. Were it not for McDavid, maybe I’d be making a more bold selection than “in seven games,” but I can’t bring myself to do it against a guy who surpassed 100 points in a 56-game season.

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Mike Smith was the best goalie in the division this season, but if you’re asking me who I like to play better over the next seven games, give me the younger recent Vezina winner in Connor Hellebuyck. He’s a massive difference-maker who’s played well after returning from injury. The Jets may not be able to hang with those two elite names in Edmonton, but with Nikolaj Ehlers coming back, there’s no shortage of offence in their top-six, and I love their botton-six. The Oilers have improved there, but the Jets group is simply better in forwards spots seven through 12.

Neither team looks great on the back-end, so it’s going to come down to scoring and goalies. Give me quantity of talent on offence and Hellebuyck vs. McDavid, Leon Draisaitl and Smith.

Colorado Avalanche vs. St. Louis Blues

By the vast majority of measures, the Colorado Avalanche were the best team in the NHL this year. The Vegas Golden Knights edged them out in goal differential (plus-67 to their meagre plus-64), but in most shot and chance metrics they were worlds beyond the rest of the league.

It doesn’t feel good picking a short series victory over a St. Louis Blues team that’s not far removed from a Stanley Cup, that can get hot goaltending and that has a D-corps that, on paper, looks pretty good.

But fun fact: Of the 16 teams that qualified for the playoffs this year, no team allowed more goals against St. Louis. So, the best offence in hockey (averaging over 3.5 goals per game) is up against the team with the worst goals against.

Colorado in five.

Vegas Golden Knights vs. Minnesota Wild

It was an awesome, surprising season for the Wild, who represented themselves as a team that’s going to be formidable in the years to come. I mean hey, they can score! They have an interesting player in Kirill Kaprizov! Everything is upside down.

Bad news though: It’s easy for your offence to eat when they’re fed a diet of the Anaheim Ducks, San Jose Sharks, Arizona Coyotes and Los Angeles Kings. Vegas was the stingiest defensive team in the entire NHL this season, giving up just 2.18 goals per game, a number even the notoriously stingy New York Islanders couldn’t beat.

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Given that Vegas is a top-three offensive team too, and the Wild aren’t exactly the trap-era New Jersey Devils, we should be pretty confident in the series outcome here. I’m confident enough to take another short one.

I’ve got Vegas over Minny in five.

Pittsburgh Penguins vs. New York Islanders

The Islanders join the Jets as a team with lots to like on their roster that unfortunately hit the final hurdle of the race and found itself stumbling toward the merciful game-56 finish line.

What you’re going to see here is a stark difference in who’s controlling the play, and the scoreboard. Because the Penguins are middling defensively, and the Isles are middling offensively, ho-hum, nothing to see there. But Pittsburgh is one spot removed from being the best offence in the NHL, and the Isles are one off being the best league-wide defence.

I expect the game to look like the ice rink has been tipped a few degrees downhill toward the Isles’ net, as the Pens repeatedly jam the fortress door and try to break through. I expect black-and-blue Islanders players as they try to keep Crosby and crew at bay.

One of two things will happen: Pittsburgh will get through early and the Isles strength will be nullified as they have to open it up. Or they Isles will get shot blocks and saves, the Penguins will get frustrated and start obsessing over breaking through, leaving surprise openings for the Isles to find their offence, at which point things could get weird.

In the end, you can’t bet on the team that’s likely to be skating uphill. And while I love my Isles, something about the Pens this year feels dangerous.

I’m taking Pittsburgh in six over NYI.

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Washington Capitals vs. Boston Bruins

This is easily the series that’s giving me the hardest time, which is instantly cause for me to declare it’s going seven. My thinking for a while was that this series was shaping up a bit like Penguins/Islanders. The Caps have a ton of offence (fourth best in NHL), the Bruins thrive by defending (fourth best in the NHL), so we could expect a lot of Washington pushing and Boston holding. (Boston was mid-table offensively and Washington mid-table defensively.) And as I said, I don’t like betting on the team doing the holding in those scenarios.

But the addition of Taylor Hall makes me think the Bruins’ offence could be better than it was over the season as a whole, which combined with the team’s ability to defend would give them a leg up. They’ve also got somewhat dormant talent throughout their roster that make me go “you just never know” about what they could do. DeBrusk on the fourth line isn’t your typical fourth liner. Rask can slam the door in the post-season. Charlie Coyle, David Krejci, Brandon Carlo, every time I look at their roster I find players that can make a positive difference beyond David Pastrnak-Patrice Bergeron-Brad Marchand.

I know the Caps have a lot to like too, but picking them feels like forcing it. So I won’t.

Give me the Bruins in seven.

Carolina Hurricanes vs. Nashville Predators

When you think of the Canes you might think of young offensive skill, but their success comes on the back of one of the league’s sneaky best D-corps. They’re inside the top-five in goals against this year thanks to that talent combined with the player buy-in earned by head coach Rod Brind’Amour.

So when you take one of the league’s best defensive teams and match them up against an offence that finds itself in this pocket league-wide:

And I think we’ve found a clear favourite.

The only way I see this series getting interesting is if the Canes badly lose the goaltending duel (it is hockey, after all), but given their options there right now – by the way, Alex Nedeljkovic posted a .932 save percentage and 1.90 goals against this season – I think they’re going to be OK in the crease.

I’ve got Carolina in a sweep.

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Tampa Bay Lightning vs. Florida Panthers

I’ll say this about the Panthers – they’re not a flash in the pan this season, they’re legit. At no point did they fade away, seeming to add depth of play to their already dangerous offence. Coach Joel Quenneville has them bought into their system, general manager Bill Zito added some guys who were a little more difficult to play, and it’s panned out.

Now, that out of the way, the Lightning have … um, taken advantage of the salary-cap system, we’ll say. In Game 1 of the playoffs, their 18 skaters plus starter come to around 85 million, $88 million considering that only a fraction of David Savard’s salary is on the Bolts’ books. With the loss of Aaron Ekblad, the Panthers group will total closer to $60 million.

Now, this doesn’t mean the cheaper team can’t beat the more expensive team. Steven Stamkos and Nikita Kucherov, in particular, may be rusty after all. But it’s hard to see the defending Cup champs, now healthy, with the best goalie in the world in their crease, and think, “I’m gonna pick the other team.” I like this Panthers team more than I thought I could when the season first started.

But I’m still taking Tampa in six.

And so here you have it, here’s how I see the first round playing out:

Round 1 baby, let’s drop the puck.


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