For the first time in superstar captain and franchise icon Sidney Crosby's career, the Pittsburgh Penguins missed the postseason two years straight after falling just short of qualifying this past spring. The Penguins were locked into a three-team battle with the rival Washington Capitals and Detroit Red Wings for the final Wild Card spot in the Eastern Conference, which ultimately went to the Capitals.

The 2023-24 campaign was the first with Kyle Dubas at the helm as general manager following a major front-office haul in the summer of 2023, and his goal of getting the most out of the remaining careers of Crosby, Evgeni Malkin, and Kris Letang hasn't quite worked out yet. All three players are on the wrong side of 35 years of age and aren't getting any younger, leading to rampant speculation that the Penguins could soon be entering a period of darkness that includes a painful, lengthy rebuilding process.

As they continue preparations to enter the 2024-25 campaign, which players on the current Penguins roster are primed to experience a performance regression?

How much longer can Kris Letang play? 

Pittsburgh Penguins defenseman Kris Letang (58) moves the puck against the Boston Bruins at PPG Paints Aren
Philip G. Pavely-USA TODAY Sports

A mainstay on the Penguins blue line since 2007, Letang has been a key member in Pittsburgh's recent championship success by playing a prominent role in each of their 2009, 2016, and 2017 Stanley Cup victories.

However, multiple health issues have plagued him throughout his career. He's experienced not one but two separate strokes and also played through what Penguins head coach Mike Sullivan described as “significant” health challenges this past season via PensBurgh.

“What I will tell you is that he was dealing with a myriad of injuries for a long time,” Sullivan said shortly after Pittsburgh's season ended. “He’s a warrior — there’s no other way to put it — with some of the things he was dealing with down the stretch and continuing to play through to try to help us get to where we wanted to go. That was a big reason why he wasn’t practicing, that I will offer you.”

Additionally, Letang reportedly requested to be traded to his hometown Montreal Canadiens recently, though no deal ultimately materialized.

The Penguins' “Big 3” era of Crosby, Malkin, and Letang is nearing its end, and it won’t be long before Letang is no longer able to maintain the high level of play fans have enjoyed for nearly two decades.

Was Alex Nedeljkovic's resurgence just a flash in the pan? 

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Goaltender Alex Nedeljkovic experienced a career resurgence upon him being signed by the Penguins following two inconsistent seasons with the Detroit Red Wings. Signed to be the backup to Tristan Jarry, the Penguins turned to Nedeljkovic who ultimately took the starter's role down the stretch as the Pittsburgh came within striking distance of a playoff spot.

Despite falling just short, Penguins GM Kyle Dubas saw fit to retain Nedeljkovic with a two-year contract that will pay him $2.5 million per year, a healthy $1 million raise. He'll be looking to build on last season's record of 18-7-7 with a 2.97 goals-against average, a .902 save percentage, and one shutout.

But suppose Jarry once again begins to struggle and forces the Penguins to turn to Nedeljkovic – will he be capable of shouldering the load again, or will his numbers dip back to more closely resemble his stats in the Motor City?

Will Tristan Jarry continue to falter? 

Viewed as the Penguins goaltender of the future, Jarry was able to lead the Penguins to the postseason in 2021 and 2022 before falling short in 2023 and this most recent season. What's worse, his numbers have taken a considerable dip in each of the last three seasons, falling from 34 wins to 24 and then just 19 while his goals-against average has climbed.

Still under contract for several more seasons with a $5.375 million cap hit, it's up to Jarry to reclaim the starter's role that he lost to Nedeljkovic down the stretch last season. According to Dubas via Trib Live, he still believes that Jarry possesses “massive potential”:

“Tristan has massive potential,” Dubas said. “What I’m most excited about for Tristan is every player that gets in these spots at these points in their career can be a real inflection point. He has to make the decision of how he wants to respond. There is obviously doubt. There are questions. I don’t think that’s necessarily just because of his play, it’s because of the fact that when he got sick, Ned went in and ran with it.”

Critics are viewing the tandem of Jarry and Nedeljkovic as anything but a shoo-in to lead the Penguins back to the postseason, something that has fans rightfully concerned.