The Pittsburgh Penguins are one of the only National Hockey League teams that have won a Stanley Cup in the 1990s, 2000s and 2010s. They've been a Stanley Cup contender for the better part of 30 years, led by past superstars Mario Lemieux and Jaromir Jagr, and a few of the game's most marketable current players in Sidney Crosby, Evgeni Malkin and Kris Letang. Each of those three skaters have three Stanley Cup titles to their name, and as they continue to age, the goal within the organization is to bring one more to Pennsylvania.

But after making the playoffs every season since Crosby was drafted No. 1 overall ahead of the 2005-06 campaign, the Penguins failed to keep the streak alive in 2022-23. Pittsburgh won a respectable 40 games, but were unable to sneak into the final wildcard slot in the Eastern Conference.

It was clear this offseason that a Penguins team missing the playoffs while Crosby is around is simply unacceptable. A new front office led by Kyle Dubas got to work this summer, making multiple moves that should put this team back in contention not only for a playoff berth, but also for a potential fourth Stanley Cup in the remarkable careers of Crosby, Malkin and Letang.

Erik Karlsson is a Pittsburgh Penguin

The first step to transforming the Penguins back into the caliber of team that won back-to-back Cups in 2016 and 2017 was making the blockbuster trade of the summer. Dubas brought superstar D-man Erik Karlsson into the fold. Yes, the same Erik Karlsson who just put up an absolutely stunning 101 points over a full 82-game slate for the lowly San Jose Sharks.

With one of Letang and Karlsson manning each of the first two pairs, along with excellent defensive defensemen in Ryan Graves and Marcus Pettersson, the Pens have built one of the more formidable defensive groups in hockey. That isn't even including Ty Smith, who will be back on the third pairing barring an unforeseen circumstance before opening night.

Expecting Karlsson to score 100 points again is lofty, but on PP1 with Crosby and Malkin, there's certainly a chance. The Swedish superstar absolutely transforms the Pens, and his presence alone could be enough to get this team back into the postseason next April. He is motivated to win a Stanley Cup; the furthest he's made it is Game 7 of the Eastern Conference Final in 2017, a series that was lost on a double overtime goal against these same Penguins.

Kyle Dubas went to work

But Kyle Dubas wasn't done after the most notable trade of the offseason. After an odd few weeks for him, between being fired by the Toronto Maple Leafs and subsequently taking a job in the Penguins front office shortly after, he got right to work. That included the shrewd signing of Graves, bringing back starting goalie Tristan Jarry for the next five years, and shoring up the forward group by acquiring Reilly Smith just days after he won the Cup with the Vegas Golden Knights, as well as signing Lars Eller, Noel Acciari and Matt Nieto.

The Penguins were one of the busiest offseason teams after missing the playoffs, and Dubas should be commended for some very tidy business with his new team this summer.

Good enough to win a Stanley Cup?

The Pittsburgh Penguins are good enough to win the Stanley Cup, and any team that has to face them in the postseason will know they are one of the toughest outs in the Eastern Conference. But there a ton of great squads who will be fighting for a berth in the top-eight next April, and there's no guarantee this team will get in.

Health will obviously be a huge factor. Karlsson was healthy last year, but hasn't played a full season aside from 2022-23 since 2015. Crosby is 36, Malkin is 37, and Letang is 36 and returned from multiple strokes last season. Malkin also missed a large part of the year. A lot of things need to go right for this team to be one of the top squads in the East.

But Kyle Dubas did what he needed to. He took an aging core that is laser-focused on winning another Stanley Cup, and provided it with the tools. Karlsson is obviously the biggest addition, but the signing of Ryan Graves and acquisition of Reilly Smith should also help this team return to elite status.

Similar to the Washington Capitals, it's only a matter of time before the Penguins are forced to undergo a full-scale rebuild once Crosby, Letang and Malkin retire. But the big three has now become the big four, and this 2023-24 Pittsburgh team knows how to win hockey's ultimate prize. Anything less than that will be a failure.

Final roster projection

Forwards: Sidney Crosby, Evgeni Malkin, Bryan Rust, Jake Guentzel, Rickard Rakell, Reilly Smith, Alex Nylander, Lars Eller, Jeff Carter, Drew O'Connor, Noel Acciari, Matthew Nieto

Defensemen: Kris Letang, Erik Karlsson, Ryan Graves, Marcus Pettersson, Chad Ruhwedel, Pierre-Olivier Joseph (Ty Smith)

Goalies: Tristan Jarry, Alex Nedeljkovic