The Pittsburgh Penguins and Kyle Dubas believe they're doing the right thing by extending the team's contending window. Sidney Crosby, Evgeni Malkin, and Kris Letang have been some of the franchise's best all-time players, and they're avoiding a rebuild with them on the roster.
However, the front office could be doing irreversible damage to their future if they don't make some difficult decisions. If the Penguins aren't contenders by the Four Nations Faceoff break, it's time to accumulate assets by moving on from their veterans. It would be the only way for the Penguins to correct their fatal flaw in 2024-25.
Dubas tried to pretend that he was addressing this issue by acquiring Rutger McGroarty in the offseason. However, the trade was a lateral move for the franchise. The Penguins traded their 14th overall pick in the 2023 draft, Brayden Yager, to the Winnipeg Jets for McGroarty, the same selection in the 2022 draft. McGroarty could have a higher ceiling than Yager, but if anything the Penguins made their prospect pool older with this move.
Crosby signed a two-year extension during the offseason. It's a no-brainer for them to lock up their captain for the rest of his career, as he's been such a cornerstone for the franchise. Crosby is also still a valuable contributor, recording 94 points in 82 games last season. If Dubas can turn the Penguins into a contender one more time before Crosby retires, No. 87 will be an integral piece.
Penguins roster isn't competitive

The Penguins showed in their season opener that they're far from contending in the Metropolitan Division. The New York Rangers dominated them for a 6-0 victory, a good indication of how the season will go. Pittsburgh bounced back the following night with a 6-3 win over the Detroit Red Wings, but results like that will do more harm than good. The Penguins have enough pieces to win some games, but they'll be a middle-of-the-pack team at best.
Middle-of-the-pack rosters are what can get franchises into trouble. They'll win enough games to give the fans hope but fall short of the postseason. The finish lands a mid-first-round draft pick and no substantial prospect to add to the pool. If the team has too many seasons like that, they'll end up with an aging roster and a weak prospect pool. This is now the position the Penguins find themselves in.
Paying Erik Karlsson $10 million annually for the next three seasons doesn't help. Karlsson was a top defenseman at the deal's signing, but injuries have hindered his abilities. Karlsson joined the Penguins after a resurgence in 2022-23 when he recorded 101 points and won the Norris Trophy. Many questioned whether it was a stretch to believe he could maintain that pace, and they were correct. He had just 56 points in 82 games last season.
Article Continues BelowThe Penguins will also only go as far as their goaltending carries them. It feels like a mistake to extend a competitive window but do it with Tristan Jarry as your starting goaltender. Jarry maintains average numbers during the regular season but can occasionally fall apart. He also has horrendous career playoff numbers, which will be a concern until they make the postseason and he proves otherwise. He hasn't played a playoff game since the 2021-22 season.
Who could get the greatest return at trade deadline?
The Kris Letang contract is the best of the tradeable assets. He has four years remaining at $6.1 million, which is a steal if he can stay healthy. The contract creates a catch-22 for Dubas and the front office. It'd be a valuable piece to keep if contending but would fetch a massive return if traded at the deadline. Right-handed defensemen are a hot commodity in the NHL, and there will undoubtedly be a team looking for a player like Letang.
Malkin is another player whose name still has some value. He recorded 67 points in 82 games last season, a dropoff from his career averages. An encouraging sign for the player and team is that he played 82 games in back-to-back seasons. Malkin battled some short seasons in the past, which also hurt the Penguins' contending chances.
Crosby and Malkin were able to carry the Penguins through the mid-2010s. They won two Stanley Cups in 2016 and 2017, but haven't been past the conference semi-finals since the last championship. Malkin and Letang's inability to stay healthy played a major part in their struggles. It'd be tough for the team and their fanbase, but trading one of Malkin or Letang would set them up better for the future.
Dubas has not indicated that he is willing to make that deal. However, everyone except him knows it's the best move for their future. It's commendable that Dubas is doing his best to win Crosby and co. another Stanley Cup, but it just doesn't seem attainable with the current roster construction.