The Pittsburgh Penguins appear to be on the brink of a significant overhaul, likely entering the official phase of their rebuild. This transition may have begun with last year's trade of Jake Guentzel to the Carolina Hurricanes. After failing to secure a playoff series victory since 2018 and missing the playoffs in the last two seasons, the Penguins have indicated a shift in strategy, making budget-friendly additions during the 2024 offseason. These acquisitions could serve as trade assets while also facilitating the acquisition of future draft picks—most notably through the Kevin Hayes trade. The team has not made any major signings, entering the current season with considerable unused salary-cap space while not taking meaningful steps to enhance competitiveness. The 2023 offseason welcomed Erik Karlsson, marking a final attempt to contend before the recent downturn became clearer.

Following a lackluster start to the current season, with a record of 6-9-1 and a troubling 7-1 home loss to the Dallas Stars, the Penguins solidified their focus on the future by trading veteran center Lars Eller to the Washington Capitals in exchange for a fifth-round pick and a third-round pick, which will not be utilized until the 2027 draft. Reports from Pittsburgh suggest that nearly all players on the roster, excluding captain Sidney Crosby, are available for trade. However, executing these trades may prove challenging, potentially resulting in minimal returns. To understand the team's current predicament, it is essential to review how they reached this point. After seventeen successful years in the NHL, a decline was anticipated as core players aged. While the decline in performance among Sidney Crosby, Evgeni Malkin, and Kris Letang is apparent, it has not solely stemmed from natural progression in age; critical miscalculations have contributed as well.

Mistakes in player management and roster construction have accumulated. The Penguins appeared to possess a solid foundation as recently as the 2021-22 season, with Crosby, Malkin, and Letang still performing at a high level, strong five-on-five numbers, and depth on the roster. Nevertheless, the team faced detrimental goaltending issues during the 2020-21 and 2021-22 seasons, leading to a cycle of repeating mistakes by retaining the same goalies without a thorough change in strategy. Previous general managers, such as Jim Rutherford, made important contributions to the team's achievements, including two Stanley Cup victories. However, his final years were marked by hasty roster decisions devoid of a cohesive plan, particularly a misguided focus on countering Tom Wilson rather than sticking to the speed and skill that characterized the team’s earlier success. Following Rutherford's abrupt resignation, Ron Hextall's tenure failed to achieve desired outcomes, visible in his mismanagement during the Seattle expansion draft and questionable trades. Current general manager Kyle Dubas has been tasked with balancing a competitive team around Sidney Crosby while looking to the future. Dubas’s attempts have met with limited success; significant moves have not yielded the expected benefits and have resulted in more challenging contracts. The pipeline of talent from the past five years has shaped the current roster, and a quick fix is unlikely.

Sidney Crosby remains the sole player likely to be untouchable in trade discussions, with his full commitment to the franchise underpinning his status. Absent a direct request from Crosby to be traded, any departure seems improbable, especially given his recent contract extension. Crosby's awareness of the current direction of the franchise suggests a long-term outlook on his part, and speculation regarding his exit due to the team's struggles appears unfounded.

The Penguins face significant hurdles in making trades, with more than half the roster prohibited from movement due to contracts. Key players, including Evgeni Malkin, Kris Letang, Erik Karlsson, and Bryan Rust, hold complete no-movement clauses, while several others possess limited or modified no-trade clauses. These restrictions complicate negotiations, although they do not render trades impossible. Malkin is likely to remain in Pittsburgh alongside Crosby due to the duo's legacy, while Letang, although he shares a similar sentiment, could entertain a change due to concerns about his performance relative to his contract. Pettersson is poised to become a free agent after this season, making him a probable trade candidate. Although not a game-changer, he represents a rental asset with some value.

Karlsson, seeking a Stanley Cup to cap his Hall of Fame career, might welcome a trade. However, his $10 million annual salary for the next two seasons limits the list of potential suitors. The Penguins may need to absorb a considerable portion of his contract or find creative ways to facilitate the move. Jarry's contract further complicates matters, rendering him nearly untradeable given his performance and remaining years on the deal. Other players, such as Rakell, Accairi, and Graves, are also likely to require the Penguins to retain salary to facilitate trades.

Players with the potential for straightforward trades without salary retention or trade clause issues include Drew O'Connor, Anthony Beauvillier, Matt Grzelcyk, Blake Lizotte, and Jesse Puljujarvi. However, Eller has already departed, and Beauvillier and Grzelcyk were intended as short-term acquisitions to increase value for potential future trades. Beauvillier’s performance might yield a late-round draft pick, while Grzelcyk's struggles diminish his trade appeal. O'Connor, despite a slow start, could provide value to any interested teams due to his previous scoring prowess and favorable salary cap hit. Nevertheless, current trade expectations should temper reality, likely mirroring Eller’s return. While the Penguins are positioned to begin selling, transforming the franchise is fraught with challenges and unlikely to yield immediate rewards.