The Pittsburgh Penguins have arguably had more success than any other NHL franchise over the last decade and a half. With three Stanley Cups and numerous deep playoff runs since the beginning of the Sidney Crosby era, you can always count on the Penguins being a force in the Eastern Conference.
However, a decline seems to be nearing, as the Penguins haven't won a playoff series since 2018 and with an aging core, it's tough to say how long the group will remain competitive. Team leaders like Crosby, Kris Letang, and Evgeni Malkin are now all in their mid-30s and probably won't have too many more chances at another Stanley Cup with the team.
As of now, the Penguins sit seventh in the Eastern Conference in points percentage, which puts them in playoff contention but still raises the debate as to whether they're truly a contender at this point. With teams like the Tampa Bay Lightning, Carolina Hurricanes, and even Washington Capitals and Florida Panthers to compete with just to make it out of the conference, Pittsburgh's odds of a deep playoff run don't look great.
So as the trade deadline slowly nears, the Penguins will have decisions to make when it comes to their direction as an organization. If the team wants to have a legitimate shot at contending, adding pieces is much needed. That said, the Penguins have frequently been buyers for over decade and it's hurting their chances for success once the Crosby era comes to an end.
The reality is the Penguins have been depleted of draft picks for a very long time. The team has had just one first round pick over the last seven drafts and it's visible in the team's lack of young talent.
At this point, Jake Guentzel is the team's youngest star up front and he's 27 years old. With Crosby, Malkin, and Jeff Carter all aging and Bryan Rust now nearly 30 years old and on an expiring contract, the Penguins could be looking rough in a couple of years. Evan Rodrigues is having a breakout year but it could be unrealistic to expect him to keep a pace of 35 goals and 70 points per year going forward (he's already 28 years old as well). Kasperi Kapanen is off to a relatively slow start coming off a career year while Jason Zucker turns 30 years old this month and hasn't been an offensive threat in a couple of years.
On the back end, Brian Dumoulin is already 30 years old, while Letang will turn 35 years old this year. John Marino is certainly a bright spot at just 24 years old and signed to a long-term contract but he's an outlier. While Mike Matheson and Marcus Pettersson are both signed to long-term deals, neither is likely to play a huge role in keeping the team in contention in the coming years.
In net, Tristan Jarry's great play this season can't be overlooked and at 26 years old, he could certainly stick around. That said, his consistency has been an issue, and even now, it still remains to be seen if he's a realistic long-term option for the Penguins.
Buy or sell?
So the Penguins have a few options. First, they could sell. While there is merit to selling off players and building for the future right away if they don't feel they can contend, this seems very unlikely. Management has shown no motivation to move out key pieces and we can safely assume this isn't a route the Penguins are going to go.
Another option would be to stay where they're at, forego making any significant moves, and hope the current roster is good enough to make a deep run. The issue is that signs likely don't point to the team, as currently constructed, winning another Stanley Cup, or even necessarily getting that far into the postseason.
The last option, as previously mentioned, is to add weapons. The Penguins are certainly no strangers to adding pieces to strengthen their chances at a deep run. Again though, this is also a key reason Pittsburgh has a very shallow prospect pool and seems set for a long rebuild once the core players hit a more steep decline.
So the Penguins essentially face a choice: Do they feel confident enough in their current group to add pieces to win another Stanley Cup? If the answer is yes and they do decide to sell even more future assets to compete now, they must accept the fact that in a few years, they will almost surely be facing a long rebuild, given the lack of young talent within the organization.
It's a difficult position to be in. Without making moves, the Penguins must accept that there's a good chance they won't win another title in the Crosby era. If they do add pieces, they must accept that their future is looking worse and worse. Either way, the decisions the Penguins make leading up to the deadline and in the near future could heavily impact the direction of the organization.