
The Pittsburgh Penguins face the Philadelphia Flyers in an unexpected first-round matchup in the 2026 Stanley Cup Playoffs. Key players like Sidney Crosby, Evgeni Malkin, and Erik Karlsson will be crucial, but the performance of secondary players may also determine the outcome.
PITTSBURGH, PA - DECEMBER 30: Ben Kindel #81 of the Pittsburgh Penguins skates against the Carolina Hurricanes at PPG PAINTS Arena on December 30, 2025 in Pittsburgh, Pennsylvania. (Photo by Joe Sargent/NHLI via Getty Images) | NHLI via Getty Images
Based on preseason expectations there might not be a more improbable first-round matchup in the 2026 Stanley Cup Playoffs than the Pittsburgh Penguins and Philadelphia Flyers. Neither of these teams were expected to be here. Up until about three weeks ago, I am not sure the Flyers were expected to be here. But none of that matters now, and starting this weekend the battle of Pennsylvania gets renewed, with Sidney Crosby having a chance to deliver another punch to the Penguins’ cross-state rivals.
We know who the main players in this series and playoff run are going to be for the Penguins.
Sidney Crosby, Evgeni Malkin and Erik Karlsson are going to be at the top of the list, and their play will obviously have a major role in what the Penguins do and how far they can go. But no matter how well they play, they can not do it all for the Penguins. The team’s success or failure will also come down to the secondary and support players on the team and a few potential X-factors.
Let’s talk about some of them.
Every Penguins team that won the Stanley Cup or reached the Stanley Cup Final in the Sidney Crosby era has done so with a third-line that can carry play and swing games. A lot of times in the playoffs each team’s top players can cancel each other out due to the aggressive line-matching that tends to take place, and it can then come down to which team has the better support players.
In 2008 and 2009 it was the Jordan Staal line.
In 2016 and 2017 it was the HBK line.
Can the Penguins get something similar from the Kindel line?
It is going to be fascinating to see how his first playoff experiences goes. He is, after all, only 18 years old and will be getting his first taste of playoff hockey. He also seems to have hit another rookie wall over the past month with his offense going cold and some of his underlying metrics regressing a bit. From a big picture perspective, it is nothing to be overly concerned about. There is a reason most 18-year-olds do not get a full-season in the NHL. It is a huge adjustment and there are going to be some growing pains.
But everything resets now going into the playoffs, and regardless of who the Penguins put around him on a line they are going to need a big showing from his trio if they are going to advance and go on a potential run.
He has exceeded expectations and rose to the occasion all season. This is going to be his biggest test yet.
You can include Kris Letang in this category as well, because their defense pairing is going to be significant.
When they were first put together following the trade with Colorado, they looked like an absolute disaster, with Girard especially struggling in his new environment. He seemed to lack confidence, was indecisive and just not playing well.
And then, about 10-12 games ago, something clicked.
It clicked for him.
It clicked for Letang.
It clicked for both of them together.
In their total time together, including the initial rocky games, the Girard-Letang pairing has outscored teams by a 13-9 margin with a 52.5 percent expected goals share during 5-on-5 play. Very solid numbers.
Over their past 10 games, however, those numbers go to an 11-5 goal advantage and a 57.8 percent expected goal share.
They are now carrying play.
Girard especially looks completely different and like a player that is oozing with confidence. Everything is being done with a purpose, there is no hesitation, he is joining the rush smartly and moving the puck well.
You know the Karlsson-Parker Wotherspoon pairing is going to give you a chance.
Having reliable pairings beyond them was always going to be the concern. If Letang and Girard can continue playing the way they have over the past month the Penguins are going to have a second pairing they can lean on. That is a game-changer, both in terms of their chances in this series, and their potential ceiling in the playoffs.
Sticking with the defense, the third-pairing is also going to be significant because at some point they are going to have to play. Even if you lean on the top-two pairings for more than 40 minutes, that still leads nearly a full period’s worth of hockey that the third-pairing has to log.
Sometimes playoff success or failure is not necessarily about what you do well or your strengths, but what you don’t do well and your flaws. The things that can be exploited in a best-of-seven series when opposing coaches are doing more in-depth game-planning and can drill down to weaknesses.
Clifton is one of those players that I fear being exploited.
I will say this: I think he’s played a lot better down the stretch, and a lot of his underlying numbers over the past month have, at times, been REALLY good. But over the course of a season his pairing has at times been the one that gets pinned in the defensive zone and has a tendency to lose the territorial and possession battle. That could be a problem. They do not need Clifton and Ryan Shea to be game-changers. They just need them to play to a 0-0 tie.
Then we have the biggest X-factor on the entire team.
It is the goaltending. It is always the goaltending. It can lift a struggling team or sink a good team, and there might not be a more important player for the Penguins this postseason than Skinner.
It is just a matter of which version of him they are going to get.
He has big-game experience and backstopped the Edmonton Oilers to consecutive Stanley Cup Finals in each of the past two seasons. He is capable of putting together a good stretch of play, and we have seen signs of it down the stretch. He has clearly taken the No. 1 spot and at least earned the right to go into the playoffs as the Penguins’ starting goalie.
But can he do enough to give the Penguins a chance?
Over the past 20 games he has saved four goals above expected for the Penguins, which is good enough to give them a chance. The Penguins have the potential to score enough goals to win, and in at least the first round the Flyers do not have an overly potent offense. They are probably not going to need Skinner to steal many games. They just need him to not lose any.
The Pittsburgh Penguins are set to face the Philadelphia Flyers in the first round of the 2026 Stanley Cup Playoffs.
Sidney Crosby, Evgeni Malkin, and Erik Karlsson are the key players for the Pittsburgh Penguins in the 2026 playoffs.
The Penguins' success will depend not only on their star players but also on the performance of secondary and support players.
The Penguins vs. Flyers playoff series is set to begin this weekend.

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