Can the Penguins extend their Stanley Cup window again?

When the Pittsburgh Penguins stumbled at the start of the 2018-19 season there was some concern that they were headed in the same direction as the Chicago Blackhawks and Los Angeles Kings. Recently dominant, championship teams that suddenly fell off of a cliff due to declining talent, a salary cap crunch, and no way to replenish the cupboard.

The concern as it relates to the Penguins was probably a bit overstated and a knee-jerk reaction to a slow start.

For one, the Penguins’ core talent is significantly better than what the Blackhawks and Kings have had, and they are still playing at a significantly higher level. Even though Sidney Crosby, Evgeni Malkin, Kris Letang, and Phil Kessel are all now on the other side of 30, they are still among the best players in the world at their positions.

That helps. A lot.

But as we saw during the end of the Dan Bylsma era, a handful of superstar players — no matter how good they are — is not enough. Given the cost of superstar players, those other complementary pieces usually have to come in the form of young, cheap talent that can represent a next wave of players to not only help the team win in the short-term, but to also extend the championship window.

What’s funny about the whole “championship window” thing is the past three Stanley Cups were won by teams whose windows had supposedly already closed.

With Crosby and Malkin getting older and the depth around them looking grim in most years, every postseason series loss by the Penguins seemed to be the window getting smaller, and smaller, and smaller. If you took a poll of Penguins fans and hockey media after the 2014-15 season and asked them how many more Stanley Cups the team would win in the Crosby-Malkin era I’m not sure anyone would have picked two. Or even one. Certainly not two in the next two years. One of those came against another team — the San Jose Sharks — whose window was supposed to have already been closed. The same thing was said about the Washington Capitals heading into the 2017-18 season, especially after another second-round disappointment and an offseason that saw them lose a lot from their roster.

But there they were at the end, winning it all.

The common denominator between the Sharks, Capitals, and Penguins is they all had Hall of Fame players (Crosby, Malkin, Alex Ovechkin, Nicklas Backstrom, Joe Thornton, Patrick Marleau, etc.) and also had some fresh blood make their way into the lineup. The Sharks had a young Tomas Hertl, who was one of the best players throughout the playoffs and early part of the Stanley Cup Final (until he got hurt). The Capitals got some production and big goals Jakub Vrana and Andre Burakovsky.

But the Penguins were the team that benefitted from fresh blood the most starting in 2015-16 with the arrivals of Matt Murray, Conor Sheary, Bryan Rust, and Jake Guentzel. For as much credit as Mike Sullivan gets, and for all of the trades that Jim Rutherford made to strengthen those teams, it was the arrival of that group of players that really helped turn things around for the Penguins. They helped bring speed, they helped change the way the team played, they scored huge goals in big games, and in the case of Murray, made huge saves in big games.

Eventually, though, that production and play means they too will get more expensive.

It’s already cost the Penguins Sheary, while Rust got his new contract over the summer and Guentzel will be due for one this summer. Even with the increase in the salary cap that creates a crunch on the roster which could mean somebody else has to go, and you’re still dealing with the whole father time aspect for your core players.

Once Sidney Crosby and Evgeni Malkin retire it’s really not going to matter what else the Penguins have coming through their farm system or the pipeline because there is not going to be anyway to make up for those losses. You don’t just replace those guys.

Even though they’re not going to put up the type of points they did when they were 22 or 23, they are still among the best players in the world and are going to give the Penguins a shot to compete. And they do. This isn’t a situation here where your best player is a 55 point, shutdown center (Chicago) or your captain and a top-line winger is a 50-point grinder (Los Angeles). This team is built around superstars and future Hall of Famers. That immediately makes it more likely that they are not going to just suddenly turn into the Blackhawks or Kings.

But even with that the best way of ensuring they can continue on at a Stanley Cup level, as opposed to just a team that ends up making the playoffs every year and bows out in the first round (let’s call this — the Ken Holland model) it would help to have another wave of young talent come through.

And that is what could be a little bit concerning. The Penguins don’t seem to have another Bryan Rust, or Jake Guentzel, or Conor Sheary (or all three of them at the same time) waiting in the wings in Wilkes-Barre/Scranton.

Their best young players to come through the system the past two years have been Daniel Sprong (who’s already playing for somebody else), Dominik Simon (who gets used like he’s Jake Guentzel or Bryan Rust but hasn’t yet produced like it), and Zach Aston-Reese.

The counter point to that would be “no one would have possibly expected for Matt Murray, Conor Sheary, Bryan Rust, or Jake Guentzel to become the players they did,” and that is entirely fair. That is why a player like Teddy Blueger becomes intriguing, or even an Aston-Reese.

That is going to be one of big the keys for the Penguins when it comes to extending their window in the Crosby-Malkin era (Matt Murray is the other important factor in this discussion, but that is a different post for a different day). They might need someone like Blueger, or Aston-Reese, or even Simon to take a big step forward and be someone they can count on to make an impact.

The Kings and Blackhawks never really had anyone else to to step forward when their core players lost a step.

The Penguins got that in 2015.

They need to find some more to maybe get one more championship out of this era.