Penguins: Sidney Crosby, Kris Letang, or Evgeni Malkin? Who could the Penguins trade first to spark a looming rebuilding?

The Pittsburgh Penguins did not qualify for the playoffs last season, ending a 16-year run with three Stanley Cup championships. Ultimately, this generation of Penguins hockey has been led by Sidney Crosby, Evgeni Malkin, and Kris Letang.

Interestingly, the trio has skated together for 18 seasons, making them the longest teammates in NHL history while ranking among the top in professional sports history.

Evgeni Malkin, Sidney Crosby, and Kris Letang of the Pittsburgh Penguins

After watching their lengthy streak end by a single point, ownership fired the team president and general manager, hiring Kyle Dubas (formerly of the Toronto Maple Leafs) to take the reigns. Shockingly, in one of his first moves, he acquired Erik Karlsson, fresh off a 101-point season, winner of the Norris Trophy.

With four future Hall of Famers in the lineup now, the Penguins hope to win one more Stanley Cup championship before the trio eventually retire. However, after 29 games, the team is just 13-13-3 and struggling to stay in the wild card race, sitting back five points.

The Penguins are the NHL's oldest team in 2023-24

Unsurprisingly, the Penguins are the oldest team in the NHL based on average age, at 29.32, just .16 points ahead of their divisional rival, the Washington Capitals (29.15). For comparison, the Buffalo Sabres are the youngest at 25.37, while the league average is 27.58.

Besides Jeff Carter, who is the second oldest player in the NHL, the next three oldest Penguins are Malkin (37), Crosby (36), and Letang (36). Meanwhile, Malkin has three years left on his current deal, with Crosby's contract expiring in two seasons and Letang in five.

Realistically, for everything Crosby has accomplished in his career, he's earned the right to decide his future; whether he chooses to remain with the Penguins for his entire career or pursue opportunities elsewhere, he's the team's most untouchable skater.

Evgeni Malkin and Sidney Crosby celebrate their 2017 Stanley Cup win.

Meanwhile, Malkin is a former scoring champion who won a regular season and a playoff MVP award in his career. Although there have been rumblings online in the past that he'd be the player most likely moved in a deal to help the team, he's also earned the chance to determine his future.

However, Letang now seems like the odd man out regarding his future in Pittsburgh. As the franchise's most accomplished defenseman, he's got the second-longest contract on the books and most likely won't be in a Penguins sweater at 41 when the deal ends.

Considering the team pursued and acquired Karlsson in the summer, based on salary alone, the Penguins are more committed to the Swedish defender for the long haul, opening up a possible opportunity to move Letang to get some cap space, draft picks, or prospects.

Should the struggling Penguins move a core player like Crosby, Malkin, or Letang to salvage the season?

Statistically, Karlsson accounts for 12% of the Penguins cap this season, earning more than anyone else on the team, including Crosby, by $1.3 million. Even though he's got four seasons left on his current deal, expiring when he's 37, Pittsburgh just acquired him, making him one of the least unlikely players available.

Realistically, at 36, Letang is the oldest defender in the lineup, edging out Karlsson and Chad Ruhwedel by three years. Furthermore, when digging deeper into Letang's career, he's only played 82 games once (2010-11) with a long history of injuries, including multiple strokes because of a small hole in his heart.

As mentioned, Crosby, Malkin, and Letang have near-untouchable legacies in Pittsburgh, with the first two in the same conversation as Mario Lemieux, the greatest player to skate in black and gold.

Even though the Penguins have never had a defender like Letang in their history, given his age and health, he could sacrifice himself and waive his no-move clause to help with the impending rebuild.

Meanwhile, if Letang chose to retire, his salary would still count towards the Penguins' cap (since he's over 35), putting the team in a more significant bind than they already are. However, for example, if he allows his contract to be moved to a team desperate to reach the cap floor, there's a solid chance he would yield a decent return.

Although no one is talking about it, the Penguins will be a completely different team in five years, and barring a miracle retool, they will not be in the conversation as potential Stanley Cup contenders.

Considering Pittsburgh won't move Crosby unless he requests it, the decision to break up the trio comes down to Malkin and Letang, with Malkin's legacy trumping Letang's, leaving the defenseman as the odd man to help jump-start a rebuild.