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The 2023 Stanley Cup Playoffs Entrance Survey

Is anyone going to beat the Bruins? Can Connor McDavid get over the hump? Can the Toronto Maple Leafs win one (1) single series?
Getty Images/Ringer illustration

After the Boston Bruins broke the record for most wins in a regular season and Sidney Crosby and the Pittsburgh Penguins broke their streak of 16 straight playoff appearances, the NHL playoffs are here, with a considerable amount of intrigue. Will the domination continue, or will it once again be proved that no postseason is as unpredictable as the NHL’s? Ahead of Monday’s puck drop, The Ringer’s hockey heads got together to preview the players they’re most excited to watch, the teams they can’t wait to see get eliminated, and their picks to take home the Stanley Cup. 

1. What is your tweet-length preview of the Stanley Cup playoffs?

Andrew Gruttadaro: It’s 15 teams against the one in Boston, as far as I’m concerned.

Cory McConnell: Cocaine Bear vs. everybody.

Matt James: Will the Bruins choke? Will the Leafs choke? Will Rangers and Devils fans choke each other?

Katie Baker: No Ovi, no Sid, no problem! It’s the perfect year for the next generation of hockey talent to step right up—even if Patrice Bergeron (or Joe Pavelski) might have something to say about that.

Logan Rhoades: This season had tons of record-breaking achievements across the league, which means the heartbreak is going to be that much worse for so many people. Can’t wait!

2. Which player(s) are you most excited to watch?

James: I’m pretty excited to watch the best player in the world, Connor McDavid, play playoff hockey for a competitive team. He’s at a level where a Cup win feels like an inevitability. The Oilers might not be the favorite, but they have a decent enough shot, and they have the greatest hockey player alive. 

McConnell: Connor McDavid has been too good for too long not to have a breakout Stanley Cup run. I think it either happens now, or he goes Cup-hunting with whatever young, talented team makes the most sense in 2026. 

Rhoades: McDavid. He’s the most exciting hockey player on the planet. And it’s the most exciting time to watch hockey.

Baker: Leon Draisaitl, getting a chance at a postseason without a high ankle sprain this time. (Even with the injury in the first round last year, he went on to record 32 points in 16 playoff games for Edmonton.) Artemi Panarin, motivated to bring his regular-season touch to springtime at the Garden. Jack Eichel, finally appearing in his first Stanley Cup playoffs. Brad Marchand, forever and always.

Gruttadaro: Brad Marchand because he’s, you know, Brad Marchand; Connor McDavid because he’s, you know, Connor McDavid; and Jack Eichel, because after all the whinging he’s finally in the playoffs, so let’s see what he’s got. 

3. Which favorite will get bounced the earliest?

Gruttadaro: Am I absolutely rooting for a Bruins first-round exit? I’m from Western New York, of course I am. Do I think it’ll happen? I’m from Western New York, I’ve never been that lucky. So instead let me hitch my wagon to the Kraken—the Avs climbed the mountaintop last year, and maybe the expansion team in the Pacific Northwest will take them by surprise. 

Baker: Sadly, I can’t attempt to reverse-jinx the Rangers on this one, because they’re the series underdog against the Devils and thus don’t really count as a “favorite.” So instead, I’ll predict that the Hurricanes get bounced thanks to the lingering absence of Carolina’s Max Pacioretty following a season-ending injury in January, and the presence of Ilya Sorokin in net for the Islanders. Also, the only reason I’m not answering the Toronto Maple Leafs here is that the question denotes “earliest” and I think they’ll probably wait until Game 7, etc.

McConnell: For reasons I cannot fully explain, I don’t see the Hurricanes making a legitimate Stanley Cup run. Their series against the Islanders should tell us a lot. The Isles have no business beating a team like the Hurricanes on paper, but that’s a first-round upset I have my eye on. 

Rhoades: The Devils put together a really impressive season (as did Jack Hughes), but I think there’s a good chance they lose in the first round to the Rangers.

James: The Leafs are about to face the same opponent that bounced them from the first round in seven games last year: Tampa Bay. I truly believe that the Leafs are a better team right now than Tampa. But I also believe that no team is more consistently haunted by their past than the Leafs. And should the Leafs beat Tampa, they’ll still likely have to face the regular-season buzzsaw that is the Boston Bruins. It’s a rough road out of the East for the Leafs.

4. Can the Bruins keep up their ridiculous pace?

McConnell: What the Bruins have done in the regular season is incredibly impressive, and no team is going to look forward to playing them. That said, trying too hard too early is an age-old NHL no-no. I’m betting on another, less tired team taking the reins at some point in these playoffs, and Boston will have another ‘07 Patriots team to think about what could have been. 

Rhoades: Nope. Anything less than hoisting the Stanley Cup will be a letdown for this team, and I, for one, cannot wait for them to get eliminated as extreme disappointment washes over their entire fan base.

Baker: OK, I was trying really hard not to answer “the Bruins” to the previous question because I knew it would come back to bite me, and also because I don’t actually think they’ll fall to the Panthers after setting a new NHL record for wins. All that said, this question is forcing my hand, so I’ll just note that when Jack Han tweets, I listen, and he makes the case that Florida could be a particularly tough first-round matchup for the Bruins.

James: Boston will likely beat the Panthers but I doubt the Bruins will get out of this series in four or five games. The Panthers and Bruins split their season series 2-2 and they’re very familiar with each other. The Bruins had an all-timer of a regular season, but we all know that those regular-season points don’t count for anything in the playoffs. As you probably remember, the 2019 Lightning, who finished the regular season with just seven fewer points than this year’s Bruins team, were swept in the first round. Nothing is a given come playoff time. Boston is probably on the way to a Stanley Cup, but things might not look so effortless from this point on.

Gruttadaro: Every hockey fan outside of Massachusetts should have a vested interest in the Bruins falling flat after a record-breaking regular season. Always root for content, and a Bruins loss would easily be the funniest outcome. 

5. Which first-round series will be the feistiest? (I’m talking coach-fight levels of feisty.)

McConnell: [Googles which team Ryan Reaves is on.]

[Watches the Dean Evason video again.]

Yeah, it’s gonna be Wild-Stars.

Rhoades: The Devils-Rangers matchup seems ripe for a few fights (and possibly an upset), but I’m going with the Stars and Wild here. We obviously know Evason isn’t afraid of a little scuffle, but these two teams are also evenly matched and I wouldn’t be surprised if this series goes to seven games.

Gruttadaro: I need Rangers-Devils to go seven. 

James: Rangers-Devils is a deeply bitter division rivalry and with Madison Square Garden and Prudential Center being less than 15 miles apart, no game in this series will truly feel like a home game. A flood of opposing fans in each arena should bring the feistiness on the ice into the stands. With just five points separating the two teams at the end of the regular season, this heated rivalry should be one of the more competitive first-round series. 

Baker: I say we get Dean Evason out there for his next challenger! You know he wouldn’t mind. (Sorry, Pete DeBoer, but at least you have experience in this realm.)

6. Which first-round series will be the best?

Gruttadaro: I keep gravitating toward Toronto-Tampa. There’s history there, there’s playoff experience there, and there is the weight of an entire city sitting on one of these team’s shoulders. It ought to be highly competitive, as Tampa clings to the last vestiges of its mini-dynasty and Toronto grasps at its first series win in 19 years. Either outcome will be incredibly entertaining. 

Rhoades: Leafs vs. Lightning. With Boston immediately running away with the division, we knew this was going to be the first-round matchup for basically the entire season. Toronto is the better team, but Tampa has the best goalie in the world. And everyone knows how long it’s been since the Leafs won a playoff series. They have to get this monkey off their back.

McConnell: In terms of on-ice action, it’s tough to beat the promise of Maple Leafs vs. Lighting, but I think Rangers vs. Devils might be an extremely fun series that could go seven, and provide some great tri-state rivalry fodder. 

James: Oilers-Kings and Leafs-Lightning are both rematches of first-round matchups from last year that went to seven games. Both matchups should be close, bitterly fought affairs between teams that are very familiar with each other. But I have to pick Rangers-Devils. This series is a coin toss and the disdain that the two fan bases have for each other should amplify the intensity of every on-ice transgression to ridiculous levels. I would not want to be a ref in this series trying to identify a distinct kicking motion inside an arena of incensed Rangers and Devils fans.

Baker: We can only hope that Rangers-Devils lives up to even a fraction of its hype. New Jersey has one of the league’s youngest and most exciting teams, featuring Jack Hughes and Nico Hischier, while the Rangers’ moves near the trade deadline to add Patrick Kane and Vladimir Tarasenko clearly indicate that the team fancies itself just a few pieces (and goals) away from having a real shot. The speedy Devils will hope to force the Rangers into a high-speed transition game that plays into their whippersnapper strengths; the Rangers will try to bank on the supremacy of Igor Shesterkin, the spread-the-wealth scoring distribution of the team’s skaters, and, more broadly, last season’s Eastern Conference final experience for the majority of the roster. The New York Post will be loving it; so will fans of the PATH train and old clips of David Puddy

7. Who is your pick to take home the Conn Smythe?

Gruttadaro: Picking David Pastrnak, as a jinx!

James: I would pick a Bruins goalie if I felt confident which one to pick. Linus Ullmark seems to have gotten the nod to be the starter heading into the playoffs and I expect the Bruins to make a deep run, but having Jeremy Swayman available complicates the pick. If Ullmark struggles, Swayman could come in, get hot, and never come out again. So I’ll pick Patrice Bergeron, the captain, in his quest for one last Cup, to come up huge and ride off into the sunset.

McConnell: Connor McDavid.

Baker: Connor McDavid.

Rhoades: My gut says McDavid, but I’m going to go with Mitch Marner. (That’s right.)

8. And which team will win the Cup? 

Gruttadaro: Picking the Boston Bruins, as a jinx!

Rhoades: The Leafs! They were my preseason pick and I’m sticking with it. All they have to do is beat the team that knocked them out last year and then immediately go up against a team that put together a historically great regular season (assuming Boston doesn’t choke in the first round) before facing whichever team advances to the conference championship. And then it’s just four more wins after that. It’s pretty simple, TBH.

McConnell: Before the season I predicted the Oilers and Connor McDavid would win the Cup, and though their regular season was less than convincing, I’m going to stick with it. Coming out of the East is going to take a toll on the Bruins (or whatever would-be Eastern Conference challenger), and the West is open enough that I think the Oilers could make a run.

James: The Boston Bruins. Regular-season stats aside, if you’ve been watching hockey this year, you’ve seen how special this Bruins team is. They’ve got two incredible goalies and they’ll be motivated to win one more for Bergeron. My dark horse pick, though, is the New York Rangers. If they survive their bloodbath against New Jersey it’ll be because the team is firing on all cylinders. And if the Rangers’ skill players are clicking and Shesterkin looks like he did last postseason, the Rangers will not be an appealing matchup for any team.

Baker: Last year, the young(ish) guns on the Edmonton Oilers finally got a sweet, sweet taste of how fun it is to play deep into the spring. Three different players hit 100-point campaigns, including McDavid, who finished terrifyingly close to a pace of two points per game. “We understand how hard it is,” said one of them, Ryan Nugent-Hopkins, this weekend. “Every single game in the playoffs is a battle and I think the more experience you have, the more you learn that.” 

Yeah, yeah, there are questions in net—their goalie is a rookie, after all, but he’s also a rookie with a killer stache who will likely win the Calder Trophy. And this season, the team in front of him has shown an impressive amount of patience, resilience, and maturity, refusing to let bad losses spiral into bad months and finishing the regular season with a nine-game winning streak. It is time.

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